Facing Change: Why Curiosity Beats Fear Every Time
Recently, I came across an idea from Chip Conley that captured perfectly what it feels like to navigate big life shifts. Chip described midlife as a subtle but profound transition—from focusing on your external identity (“ego”) to exploring the internal truths (“soul”) that really define you. It’s about shifting from what you’ve built on the outside to discovering what’s been quietly growing on the inside.
This resonated deeply with me because right now, many of us are facing another big shift, driven not by age, but by technology. AI is changing things rapidly, sparking curiosity for some—but fear for many others. It’s tempting to look at AI and wonder what might be lost rather than what could be gained.
But the truth is, whether it’s midlife transitions or technological revolutions, change always forces a decision: Do we retreat into what’s comfortable and known, or do we lean into curiosity and growth—even when that feels uncomfortable or risky?
For me, the answer has always been clear. And it starts by consciously choosing curiosity over fear.
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Midlife: Perfect Time to Start Over (Yes, Even if It’s Scary)” 🫣
When I was in my early 40s, I did something that felt completely counterintuitive at the time—I left a stable corporate career in Audit to start a tech company. It wasn’t just a career pivot; it was a total mindset shift.
I went from a predictable role where my experience and credentials largely shielded me from rejection, to an environment where I faced multiple rejections from investors and potential customers nearly every day. It was humbling, frustrating, and sometimes painful. But more than anything, it was an education in vulnerability.
Chip Conley talks about something called “The Striver’s Dilemma”—the irony that midlife success can become its own kind of trap.
By the time you reach your 40s or 50s, you’ve often built an identity around external markers: your job title, your expertise, your reputation. These become the uniforms you wear—comfortable, reassuring, but also limiting.
You start to believe the idea that to be successful means to avoid failure at all costs. Unfortunately though, your life gets smaller, your world less interesting, and your growth stalled.
I felt this dilemma deeply when I made the decision to become a beginner again. Stripping away the professional identities I’d accumulated over two decades wasn’t easy, but the alternative—settling into comfortable stagnation—was far scarier.
Midlife, I realized, wasn’t a time to cling tighter to what I already knew. It was the perfect moment to learn something new, even if it meant occasionally feeling foolish or uncertain. Especially if it meant those things.
Why Embracing Beginnerhood Makes AI Less Intimidating
There’s something Chip said that really stuck with me: “The key to a great second half of life is putting yourself in situations where you’re a beginner—where you’re learning again.”
When we’re young, being a beginner is just part of everyday life. Kids don’t worry about looking silly or being bad at something—they just dive in. But as adults, especially successful adults, we avoid beginnerhood because we’re afraid of embarrassment, failure, or appearing incompetent.
Yet here’s the truth I’ve discovered firsthand: actively choosing to be a beginner again is incredibly powerful. It frees you from the pressure of needing to have all the answers. Instead, you get to ask questions, experiment, and explore new ideas without needing to immediately be the best at them.
Right now, as AI rapidly reshapes our world, we have another clear choice. We can shrink back into fear, worrying about what this technology might disrupt or take away—or we can embrace beginnerhood again, leaning into the excitement of discovery.
Personally, I’m fascinated by what AI might unlock, rather than what it might replace. I’m diving into prompt engineering, learning how AI can amplify creativity, improve decision-making, and transform leadership development and team dynamics—the areas that matter most to me professionally. It’s humbling. Sometimes it’s challenging. But above all, it’s energizing and meaningful.
In other words, I’m choosing learning over fear—again.
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What the Early Days of the Internet Taught Me About AI
I remember vividly being an undergrad in the late 90s, fascinated by the rise of the internet. Everything felt exciting, uncertain, and full of possibility.
There were browser wars between Netscape and Microsoft Explorer, debates about how the internet would be searchable (Yahoo versus Google), and wildly different bets on e-commerce, from niche retailers like Pets.com to Amazon’s ambitious “one marketplace for everything.”
Back then, I desperately wanted to graduate quickly and jump into that arena because I could sense how pivotal that moment was. It felt like history was unfolding right in front of us, and I wanted to be part of shaping it.
Today, we’re standing at another inflection point—this time driven by AI—and I feel the same familiar excitement. There are plenty of unknowns and, yes, reasons to feel nervous. But I see even greater potential. AI isn’t just another tool; it’s a chance to rethink how we lead, collaborate, and build companies in deeply meaningful ways.
Instead of worrying about “holding onto sands in an hourglass,” I’m grateful to be building something at this transformative moment. I hope others see this time the same way—as a rare opportunity to shape the future, rather than simply react to it.
Take a look below at what we’re building at Cloverleaf.
How Curiosity Becomes a Competitive Advantage in Leadership
We don’t often talk about curiosity as a leadership skill. It’s usually framed as a personality trait—something you either have or you don’t. But I’ve come to see it differently. Curiosity is a discipline. It can be practiced, expanded, and even reawakened—especially if it’s been buried under years of expertise, routine, or responsibility.
Scott Shigeoka, in his book Seek, makes the case that curiosity isn’t just a nice-to-have. It’s essential. And research backs him up.
Studies show that curiosity correlates with better problem-solving, stronger relationships, and even longevity. Peter Drucker, one of the most respected management thinkers of all time, used to pick an entirely new subject to study every two years—something completely unrelated to his work. Why? Because he believed curiosity was fuel for his creativity and clarity.
And yet, in many work environments, curiosity is quietly squeezed out by efficiency. The question isn’t “What’s possible?”—it’s “How fast can we get through this meeting?”
But if you’re a leader trying to navigate change—whether it’s brought on by technology, shifting markets, or generational transitions—you don’t just need efficiency. You need to ask better questions. You need to be open to being wrong. You need to create space to explore.
Curiosity isn’t soft. It’s not fluffy. It’s a leadership edge.
Your Best Chapter Could Still Be Ahead
The older I get, the more I believe this: growth doesn’t stop when you hit a certain age—it just changes form. It stops being about climbing ladders or collecting titles and starts becoming about curiosity, meaning, and contribution. But you only access that kind of growth if you’re willing to get uncomfortable again. If you’re willing to be a beginner.
That’s the invitation in front of all of us—especially right now. Whether you’re navigating midlife questions about identity, or trying to make sense of how AI will reshape your work, the instinct to hunker down and cling to what you know is real. But so is the opportunity to lean in, get curious, and build something new.
I’ve found more creativity, energy, and meaning in these past few years than I ever expected—not because I had it all figured out, but because I gave myself permission to not know, to explore, and to learn forward.
So whether it’s launching something new, diving into AI, or picking up a hobby that reminds you what it feels like to be joyfully bad at something—my hope is that you won’t choose fear.
Choose learning.
Your best chapter might still be the one you haven’t written yet.
The Problem with Taking Management Advice from Reddit
I know what you’re thinking—”the internet” gets a lot of things wrong about, well, a lot of things. And yes, that’s true. But there’s also something genuinely valuable about peeking into the collective mind of the masses—even when we don’t agree with their opinions, or sometimes even find them tolerable.
Recently, I found myself tumbling down an internet rabbit hole. It started innocently enough, sparked by a passing comment from a colleague in a recent meeting. We’d been discussing management styles, and she casually mentioned something she’d read on the “r/managers” subreddit (here’s the link, if you want your own rabbit hole adventure: r/managers).
My first reaction was curiosity, but after spending a bit too much time exploring this online advice, my general takeaway was less excitement and more concern.
Sure, there was the occasional gem of useful insight, but overwhelmingly I encountered perspectives shaped by frustration, bitterness, or experiences with terrible bosses.
To sanity-check my own reaction, I fed the subreddit link into ChatGPT and asked for a summary of the most commonly shared management wisdom from this corner of the internet. And—no surprise here—the top two insights distilled from the collective mind were these:
- Managers exist primarily to solve problems: As one poster succinctly put it, “My biggest surprise as a new manager was realizing how much people depended on me to sort out their problems.”
- Document everything, especially during tough conversations: Or as another member emphasized, “Document, document, document—every meeting should end with paper in hand.”
Now, to be clear, this advice isn’t factually incorrect—problem-solving is indeed part of a manager’s job, and of course, documenting conversations can be important. But seriously? These are the absolute best insights we can come up with?
👉 Nothing about being a great listener or genuinely understanding the strengths of your team members?
👉 Nothing about fostering a growth mindset, inspiring your people to reach greater heights, or creating a safe environment built on trust and vulnerability?
I know—I shouldn’t be surprised by what I found from “the internet,” of all places. But the uncomfortable reality is, many managers—especially new ones—are relying on sources like Reddit for daily advice.
Which brings me to a critical realization: as L&D and talent management professionals, we’ve clearly got some important work ahead of us.
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🥴 Reddit’s Most Upvoted Management Advice Misses the Point
When the best wisdom Reddit has to offer managers is “solve your team’s problems” and “document everything,” we’ve got some real issues.
First, there’s the idea that managers should always have the answers—that every problem must somehow funnel upward until it reaches a boss who magically solves it. This misconception isn’t just unhelpful, it actively undermines the potential of both the manager and the team.
Here’s the truth: some of the most effective management moments come when leaders admit openly they don’t have all the answers. It’s precisely this vulnerability—being comfortable enough to say, “I don’t know, let’s figure this out together”—that builds trust, empowers people, and unlocks creativity.
I’ve heard repeatedly from L&D leaders that one of the biggest obstacles managers face in providing meaningful feedback or coaching is their fear that they can’t advise someone without being the technical expert themselves. But the reality is, great coaching doesn’t require domain expertise; it requires curiosity, empathy, and the skill to ask insightful questions.
Second, while documentation of tough conversations isn’t bad advice per se, placing it among the two most crucial things for managers to do sets a troubling tone.
When the first instinct in a difficult conversation is, “I’d better document this,” it subtly encourages a defensive mindset, putting distance between manager and team rather than building trust. Yes, documentation has its place, but if we’re prioritizing paperwork over authentic connection, we’re missing the point entirely.
If this is the dominant message being consumed by new managers online, then it’s no wonder many workplaces struggle to create genuinely healthy and productive environments.
👉 Where is the advice on fostering a culture of listening?
👉 Where’s the guidance on how to recognize your team members’ unique strengths and intentionally put them in roles that let those strengths shine?
👉 Why aren’t we talking about the transformative power of psychological safety, growth mindset, or learning from failure?
The silence on these critical aspects of leadership isn’t just disappointing—it’s dangerous. It leaves managers navigating blindly, armed only with tactics that reinforce hierarchical, top-down management. And it risks perpetuating precisely the kind of leadership failures that drive people to Reddit in frustration in the first place.
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Why Are Managers Turning to the Internet Instead of Their Organizations?
I get it—Reddit is accessible, fast, and feels authentic. You can post a question anonymously and within minutes have real-world anecdotes and advice from others who’ve been in your shoes.
But this raises a bigger, more concerning question: why are so many new and even experienced managers turning to random corners of the internet instead of their own organizations when they face management challenges?
One big reason is that most companies haven’t figured out how to support managers beyond initial training sessions, which often amount to little more than a few webinars or a binder full of “best practices.” Far too many organizations are still treating management development as a once-a-year event rather than an ongoing, daily need.
But managing people isn’t something you figure out in a workshop and then master overnight. It’s messy, complicated, and personal. It’s full of situations that require nuance, immediate guidance, and tailored advice. And when managers find their internal resources outdated, unhelpful, or simply nonexistent, they naturally go elsewhere—right onto the very internet forums where misinformation and misguided perspectives flourish.
We can’t ignore this reality.
If managers keep seeking help from Reddit rather than from qualified, strategic internal resources, companies risk a culture where poor management habits become the norm, not the exception. And that sets everyone up for frustration, burnout, and diminished performance.
Managers Need Contextual Support, Not Outdated Training Binders
This isn’t just a minor annoyance; it’s a critical gap that’s hurting teams, companies, and even careers. Because let’s be honest: management development can’t rely solely on delivering binders full of theoretical models and tips on “giving effective feedback” every few months. Those resources quickly become shelf decor rather than real solutions to real-time problems.
When managers hit a wall—when they’re not sure how to deliver tough feedback, handle friction between team members, or motivate someone who’s struggling—they don’t have days to wait for the next L&D session. They need immediate support that’s specific to their unique challenges, right there, in the moment.
This immediacy matters because management isn’t about generalized scenarios; it’s personal. It involves actual people, real emotions, and specific personalities. Effective guidance should feel tailored and timely—not abstract or generic. Without that, managers default to whatever quick advice they can find, no matter how flawed or incomplete.
Yet most traditional resources completely miss this. They’re slow, one-size-fits-all, and frequently disconnected from the actual daily reality managers face. If we’re going to genuinely equip managers to lead, we’ve got to offer something far more responsive and personalized than just another PDF or outdated training binder.
Managers Need More Personalization To Effectively Lead Their Team
Great management is deeply human. It’s about genuinely understanding the people on your team, what drives them, and what frustrates them—then creating conditions where they can thrive. And let’s be clear: this kind of nuanced understanding doesn’t come from vague, one-size-fits-all advice you pull off Reddit or Google. It certainly doesn’t emerge from training materials that gather dust on a shelf.
Instead, effective management demands personalization. It requires knowing things like: Does Jenna respond better to direct feedback or gentle coaching? Is Marcus motivated by public recognition or quiet, private acknowledgment? And when conflicts or tricky situations inevitably come up, what’s the best way to approach each individual on your team?
But here’s the problem—new managers don’t typically come equipped with these insights. And when they’re left to figure things out on their own, the result is often guesswork, stress, and mistakes that erode trust. That’s why meaningful management support must be context-driven and personalized—offering guidance specifically tailored to real people, real teams, and real moments.
When managers have immediate access to targeted, practical advice, suddenly they’re empowered. They stop guessing and start confidently leading. And that shift—away from generic, surface-level advice towards deeply relevant, personalized guidance—is exactly what management advice should be all about.
How To Close The Gap Between the Problems Managers Face and the Coaching They Actually Need
This gap between what managers actually need and the standard advice they typically get is exactly why we built Cloverleaf Coach.
It isn’t just another chatbot offering surface-level tips. Instead, Cloverleaf provides personalized coaching that’s genuinely insightful, informed by validated assessments and the unique dynamics of your team.
It’s like having an expert coach sitting alongside you—helping you navigate challenging situations, difficult conversations, or team friction, right at the moment you need it most.
Imagine you’re about to give tough feedback to a team member. Instead of just “documenting it,” you can ask Cloverleaf Coach specifically how best to approach that particular person based on their personality, work style, and the context of your relationship.
Rather than guessing or worrying you’re doing it wrong, you get immediate, practical guidance tailored precisely for that interaction.
Or perhaps your team is feeling disconnected or unmotivated. Instead of Googling generic advice about motivation, Cloverleaf Coach can proactively guide you toward what will resonate with each team member, leveraging their strengths to reignite engagement.
This is the kind of immediate, context-rich support that elevates managers from merely reactive problem-solvers into truly effective leaders who build trust, confidence, and empowered teams.
Because let’s be honest—managers don’t have time to sort through a flood of generic advice when they’re in the thick of a management challenge. They need real solutions, personalized and precise, exactly when it matters most.
Managers Deserve Better Support Than Resorting To The Internet
Ultimately, the fact that so many managers resort to Reddit for help isn’t just disappointing—it’s a sign that something’s fundamentally broken in how we support leadership development. It reminds us just how much work remains for those of us tasked with preparing managers to lead effectively, empathetically, and confidently.
We need to set a higher standard, raising the bar for management development so that leaders don’t feel their only option is random internet advice.
It’s not enough to gather people occasionally into classrooms or webinars, hoping the information sticks. Real-world management requires daily, personalized guidance that meets managers exactly where they are—facing real people, in real-time situations.
At Cloverleaf, we believe managers deserve better, more insightful coaching that actually helps them lead their teams. Not generic tips, not dusty training manuals, and certainly not overly simplistic advice sourced from anonymous internet forums.
Because when managers have access to personalized, context-rich support exactly when they need it, teams thrive, organizations improve, and managers themselves become confident, capable leaders.
The Great Coach Paradox
You’re delivering real transformation.
Leaders walk out of your sessions with clarity they didn’t have before. Teams shift. Cultures start to take root. The feedback is glowing. “You really changed how I see myself.” “That session moved the needle.” “We need more of this.”
But despite the impact, you’re still chasing the next contract.
Not because you’re underperforming. Because the coaching industry is mostly familiar with a business model that wasn’t built for how executives actually buy coaching services.
You’ve followed the playbook:
- Post consistently on LinkedIn
- Sharpen your niche
- Build a funnel
- Ask for referrals
- Host a webinar
It’s not bad advice but it’s solving the wrong problem.
Most advice assures that visibility leads to demand. That if your your branding is on point, or if you have a polished website, clients will come.
But not all visibility is equal.
Social visibility might build awareness. You can be visible as a thought leader—and still be invisible as a solution when a problem hits.
Social posts and personal branding might earn attention. But coaching decisions don’t usually happen while someone scrolls LinkedIn.
👉 They happen in conference rooms after tough feedback.
👉 In 1:1s where a leader admits they’re stuck.
👉 In team meetings where conflict flares up—again.
Those are the moments when coaching is needed. And unless your value is visible in that context, you won’t be the one they call.
Executive buyers aren’t hiring based on who’s posting the most. They’re hiring based on who can solve the thing that’s breaking right now. And in those moments, content isn’t what earns the call, embedded presence is.
So when the next leader, team, or organization hits a moment where coaching could help?
They don’t think of you. Not because you’re forgettable but because your value disappeared the moment the session ended.
Meanwhile, the coaches who are getting those referral calls have figured out how to make their impact visible between sessions. They’ve built systems that keep their insights present when decisions are being made and budgets are being allocated.
That’s the paradox, and the opportunity.
Great coaches aren’t struggling because they’re not good at what they do. They’re struggling because they’re competing with an outdated playbook against coaches who’ve moved to a different game entirely.
This article is not another marketing checklist.
It’s a strategy for how successful coaching businesses actually grow:
- One that doesn’t depend on creating more content
- One that doesn’t require more hours or more hustle
- One that turns your insight into a system—so your presence sticks, your value scales, and your best work becomes your best marketing
Because once your coaching becomes embedded in the daily rhythm of work, referrals become inevitable.
Get the High Impact Coach Crash Course to see how to build a coaching business that delivers more value, serves more clients, and grows more revenue without burning you out.
What Keeps Coaches From Landing Executive Clients
You’ve seen the lightbulb moments. You’ve helped leaders find their voice, navigate transitions, repair trust. The client impact is real.
So why does business growth still feel like a guessing game?
More than likely, it’s not a skills gap. It’s a systems gap, specifically, a visibility gap.
A disconnect between the transformation you create, and how that transformation is remembered, shared, and scaled across the organization.
While most advice is focused on more marketing tactics, other coaches have focused on using systems that make their transformation visible and scalable. They’re not necessarily better coaches, they just understand something about how coaching businesses actually grow that most advice completely misses.
Here’s what’s really going on:
A. The Visibility Trap
Most advice starts here:
Post more. Build your brand. Optimize your website. Define your niche.
This is not bad advice, it’s just not complete. It overlooks that coaching is a relationship to be embedded. It assumes that decision-makers are primarily scanning content feeds, looking for their next coach.
They’re not.
They’re solving urgent problems:
A team that’s unraveling after a reorg
A VP who just got promoted and is struggling to earn trust
A high-potential leader who keeps burning out their team
In those moments, executives don’t care who posted the best leadership quote on LinkedIn.
They’re asking their network: Who can help fix this—and fast?
And most visibility tactics don’t match the moments when buying decisions actually happen.
A well-crafted post might build awareness. But it doesn’t help when a leader turns to HR and says, “We need someone to help this team—fast.”
Because that moment doesn’t happen in public. It happens behind closed doors. In conversations about performance. Tension. Risk.
And unless your coaching has left a visible trail—something that shows up in team interactions, leader behavior, or business results—you’re not top of mind when it counts.
You might get compliments on your insights. But compliments don’t close contracts.
The coaches who do get those calls? They’ve made their presence durable. Their work doesn’t disappear after the session—it stays active inside the team:
In language people repeat
In frameworks teams adopt
In nudges that guide behavior every day
When the next team needs help, they’re not asking “Who do we know?”
They’re saying, “Let’s bring in the person who helped them.”
B. The Referral Reality That No One Talks About
Here’s the stat that should change how you think about business development: Referrals account for 80% of coaching business, yet most strategies don’t actively generate them.
Even worse? Traditional coaching models make referrals harder to earn.
Because your best work happens in private. In confidential 1:1s. Behind closed doors.
The person who brought you in might get a check-in or a progress report. But they don’t experience the change as it happens. They don’t see the tension defused, the clarity sparked, the shift unfold.
And the people around the leader? They might notice something’s different, a steadier presence, a sharper perspective. But they don’t know what caused it.
So when someone asks, “Know anyone who can help this new director?”—your name doesn’t come up. Not because you weren’t effective. But because your impact never became part of the story they could tell.
Your coaching left no visible trail. You delivered the value. You just didn’t deliver it in a way that could be remembered, repeated, or referred.
Compare that to coaches using embedded coaching platforms:
👉 Insight shows up in team meetings—not as theory, but as action.
👉 Language you introduced gets quoted in project updates.
👉 Frameworks you taught shape how decisions get made and feedback gets delivered.
By the time someone says, “We need help,” you’re not just remembered, you’re already part of how the team works.
When referral moments happen, they don’t need an introduction. They’re already in the conversation.
C. What Executive Buyers Interested In Coaching Actually Need
Here’s the truth most coaches never hear:
You’re not just competing with other coaches.
You’re competing with:
Consulting firms that embed behavioral change systems
Internal L&D programs with dashboards and metrics
Platforms that promise scalable development and proof of ROI
These buyers don’t just need to believe you’re effective. They need to prove it to a CFO, a CHRO, or a skeptical board.
They’re looking for:
Behavior change is measured across teams
Engagement data they can report upward
A model that scales across functions and roles—not just individuals
The coaches landing long-term contracts can make their results visible, measurable, and scalable.
They need evidence that your approach creates lasting change—and that it can scale beyond the individual sitting in your sessions.
The coaches winning larger contracts and multi-year relationships aren’t just better at delivery. They’re better at making their delivery demonstrable in ways that analytical buyers can measure and other executives can witness.
🔁 What This All Adds Up To
Coaching works. But it rarely spreads because most coaching models are built for individual impact, not for replication and scalability.
The coaches who crack the growth code understand this: Every engagement has to do two things:
1. Transform the client (which you’re already doing)
2. Create visible proof that transforms the business case for your next engagement
Scale Your Coaching Business Without Adding More Hours
The Positioning Strategy That Gets Coaches Referred
When exactly does coaching get hired? It’s not when someone is randomly browsing your website or reading a clever post. It’s when there’s pressure, a moment of risk, conflict, or urgency.
Clients don’t hire coaches. They hire help for the moments when something’s about to break.
And yet, most coaching offers still sound like this:
“I coach executives.”
“I work with high-potentials.”
“I help leaders lead.”
These are too vague to be memorable. Too generic to be referred. And too disconnected from the real-world situations that make coaching a business priority.
A. Define the Moment, Not Just the Market
Most advice online tells you to define your niche by role, industry, or demographic:
“I work with VPs in tech.”
“I coach women in healthcare.”
“I support senior executives.”
But those are static categories. They don’t reflect the trigger that actually prompts someone to look for coaching.
No one hires a coach just because a leader has a certain title. They hire one because that leader is:
Struggling to earn trust after a promotion
Derailing a team with unfiltered feedback
Stuck in a cycle of burnout or conflict
Those are the moments when coaching becomes urgent. And if your offer speaks directly to that moment?
You’re not just relevant. You’re essential.
That’s what we call moment-matching—and it’s what makes your offer stick.
🛠 Before & After: The Power of Specific Positioning
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Vague Positioning:
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Moment-Matched Positioning:
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|---|---|
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“I coach new executives.”
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“I help newly promoted VPs earn trust and lead with confidence in their first 90 days.”
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“I support team communication.”
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“I help leadership teams rebuild trust after reorgs or feedback breakdowns.”
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“I coach high-potentials.”
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“I help high-potential leaders stop burning out their teams and start building sustainable influence.”
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Getting Your Referral-Ready Messaging Right
Let’s say someone in HR or the C-suite hears: We’ve got a director who’s floundering. Know anyone who can help?
Would your name come up?
Only if your offer passes this test:
Can it be explained in a single, clear sentence?
Does that sentence map to a real, recurring leadership moment?
Would it make someone say, “Yes—we need exactly that.”?
If the answer is no, your referral engine is stalling out—before it ever starts.
Great coaching doesn’t get you referred.
Clear coaching, tied to real moments, does.
💬 Try This: Your Referral Sentence Framework
Write your positioning like this: “When [specific scenario], bring in [your name]—because [the result you help create].”
Examples:
When a newly promoted VP is about to lose their team, bring in Terri, because she builds credibility fast and helps them lead without defensiveness.
When a leadership team’s feedback culture is toxic, call Marcus, he helps rebuild safety without sugarcoating the truth.
If your network can’t say this about you, you’re not just missing leads. You’re missing referrals you already earned.
🔁 The Big Messaging Shift
From “I coach leaders” → To → “I’m the coach you call when ___ happens.”
That’s how you move from being a coach on a list to the coach executives contact, not because you marketed harder, but because you matched your value to a moment that matters.
Why Coaching Sessions Don’t Scale And What Coaches Are Doing Instead
You’ve probably heard this from a client: I wish I had your voice in my head during that meeting.
That’s not just a compliment—it’s a signal.
A signal that the real opportunity for coaching isn’t just in the session. It’s in the moments after—when decisions are made, tension flares up, or feedback is received sideways.
But here’s the problem:
Most coaching model’s do not have a solution and leaves too much to chance.
A. The Costly Gap Between Sessions
Here’s how most coaching works:
You meet with a client.
Spark real insight.
Offer clarity, a framework, a next step.
Then two weeks go by.
In the meantime:
That tricky team dynamic resurfaces.
Pressure builds.
The conversation that needed your voice happens—without it.
And the client?
🤨 They’re left to recall what you said.
🤨 Apply it on their own.
🤨 Hope it still fits the moment.
Meanwhile, your advocates gets no signals. No feedback loops. No proof anything’s happening.
Your value fades—not because the coaching wasn’t good, but because it wasn’t present when it counted.
B. How Embedded Coaching Actually Works On Your Behalf
Now picture this:
On Tuesday morning, just before a tense 1:1, your client gets a nudge reminding them that their teammate values directness—but needs time to process conflict.
Later that day, their team receives a communication tip tied to a pattern you’ve been working on together—delivered inside Slack, where they’re already working.
A week later, the sponsor sees a trendline in team interaction data that signals improved collaboration.
✅ No extra meetings.
✅ No added effort.
✅ Just your coaching—working in the background, reinforcing insight in real time.
That’s embedded coaching. And it doesn’t require more sessions. It just requires systems that carry your insight into the flow of work.
C. How Coaching Platforms Makes It Possible (Without Replacing the Coach)
Cloverleaf is built to reinforce you, between sessions, across teams, and inside the daily rhythm of work.
Here’s how:
Real-time nudges that surface in Slack, email, or Teams based on how each person prefers to give and receive communication, resolve tension, and make decisions.
Layered insights drawn from multiple assessments so your coaching is grounded in multidimensional data, not just personality shorthand.
Coaching visibility metrics like nudge engagement and team insights usage to show that your work is sticking and spreading.
Your brand, not ours, keeping you top of mind, while Cloverleaf runs in the background.
Now, you’re not just showing up once a week. You’re becoming the invisible infrastructure for how the team grows.
🧠 The Big Mindset Shift: You’re not the one who has to be in the room. But your voice still can be.
This is how coaches are reaching more executive clients: Using platforms that use systems that scale their presence without scaling their hours.
How To Engineer Referral Growth
Most coaches rely on word-of-mouth but few actually design for it.
That’s the difference between hoping a past client mentions your name, and building a system where your best work consistently leads to new opportunities.
If you want referrals to become a consistent part of how your business grows, you need a system, one that doesn’t rely on being remembered, but on making your impact recognizable and shareable across the organization.
1. Make the Transformation Shareable
Private 1:1 growth won’t scale unless others see it. Not in outcomes alone, but in behavior they can describe.
From happens when:
Coaching language starts showing up in team conversations.
A framework used in one department becomes common shorthand in another.
One employee resolves a long-standing conflict using an insight from a nudge and shares that story publicly.
What to do: Design your coaching engagements to include a common language or toolset that clients can share and reuse. Use team workshops, written takeaways, or embedded nudges to reinforce these behaviors across the group—not just with your primary client.
2. Activate Internal Advocates
Referrals often flow from your strongest internal supporters—especially when those partners help position your coaching as a solution to bigger goals, not just individual development.
When coaching becomes part of leadership development, onboarding, or cross-functional collaboration efforts, it spreads organically.
Together, they can:
Design a high-potential leadership program with embedded coaching
Partner across HR and strategy teams to tie coaching to business goals
Position coaching as part of broader leadership development, not a side offering
What to do: Identify someone who believes in the work and has access to key initiatives. Collaborate with them to bring coaching into broader contexts: a high-potential program, a regional rollout, or a values-driven culture shift.
They don’t need to “sell” you. They need to help others see how the coaching already supports what the organization is trying to achieve.
3. Use Systems That Keep Insights Active
The most effective referral engines don’t rely on coaches asking for introductions. They rely on systems that keep coaching top of mind, even when you’re not in the room.
This might include:
Monthly opt-in sessions or touchpoints for leaders to connect and share stories
Coaching prompts that align to real challenges (e.g., leading a new team, delivering tough feedback)
Peer-led examples of how coaching insight helped solve a real problem
When people are reminded of the coaching—without extra effort—it becomes easier to talk about and easier to share.
What to do:
Create rhythm and structure that keeps your presence active without requiring more meetings. Use tech, not more time, to stay visible.
4. Support the Business Case Without Needing a Sales Pitch
When budget holders need to renew or expand coaching, they need clarity — not just anecdotes.
Even when the impact is real, decision-makers still need tangible support when advocating for renewal or expansion. What they need is simple: clarity they can point to.
Not a new pitch deck. Not another testimonial. Just signals that the investment is working.
What to do:
Give them what they need to tell the story internally:
Who’s using the coaching tools or content regularly?
Where is momentum building across teams or functions?
What behavior shifts are being noticed or reported?
Make the invisible more visible—and the case for continued investment becomes easier to make.
What This Makes Possible
When coaching shows up outside the session, through frameworks, language, or behavior, it becomes easier to notice, easier to talk about, and easier to spread.
You don’t need to chase leads or craft campaigns. You need to design for recognition.
That’s what turns great coaching into a reliable engine for growth.
3 Steps To Land More Executive Coaching Clients
You don’t need another marketing tactic.
You need a model that makes your coaching easy to see, easy to talk about, and easy to refer—without adding more hours to your calendar.
Here’s how to start building it:
A. Anchor Your Message to the Moments That Trigger Buying Decisions
Take a fresh look at your website, profile, or client pitch.
Ask:
Does this map to a real decision point? Could someone in HR or the C-suite see this and immediately know when to call you?
Would a colleague be able to refer you—without needing to explain what you do?
Does your message focus on the moment coaching becomes essential—or just describe your services?
If your language centers on your identity (“executive coach,” “leadership expert”), shift it. Make it about the problems you solve and the moments that trigger a coaching conversation.
Clear positioning isn’t about clever language.
It’s about making it obvious where you fit, when it matters most.
B. Build a Coaching Offer That Leads Naturally to Expansion
The best offers don’t end with the session. They set up what comes next.
If your coaching creates visible change—and that change gets noticed by others—you won’t need to push for more work. The demand will surface from inside the organization.
Here’s how to structure your offer so it generates new opportunities as part of the experience:
Solve a specific leadership challenge that others are likely to encounter too
Use tools like Cloverleaf to create shared language and surface insight between sessions
End with tangible takeaways—like feedback trends, adoption data, or visible shifts in team behavior
When the value spreads beyond the individual, so do the referrals.
A great offer doesn’t just deliver a result. It invites the next conversation—without needing another pitch.
C. Rethink “Business Development” as Reinforcement
You don’t have to be in sales mode. You do need to be in systems mode.
This isn’t about “selling” more coaching. It’s about structuring engagements so that your work travels further—without chasing new leads.
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Instead of this...
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Try this...
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Writing more content
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Letting your insights show up daily through Cloverleaf nudges
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Starting every pipeline from scratch
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Designing offers that naturally lead to expansion
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Waiting until the engagement ends to pitch the next
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Providing real-time progress signals that make the case for “What’s next?”
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Ask Yourself These 3 Questions:
Where does my coaching create the most visible shift?
How can I stay present between sessions without more effort?
What tools or systems help make that shift repeatable and referable?
If you can answer those with clarity, you’ve already started building a business that can serve executive clients.
🙋 FAQ
Q: Will Cloverleaf replace me or make my coaching feel automated?
A: No. Cloverleaf is a delivery system for coaching. You remain the expert. Cloverleaf simply keeps your perspective present in your client’s workflow, via email, Slack, or Teams between sessions. It’s reinforcement, not replacement.
Q: How do I introduce Cloverleaf without sounding like I’m upselling tech?
A: Don’t present it as an add-on. Make it part of the offer:
“This includes daily nudges and personalized assessments, at no extra charge. It keeps the work moving between our sessions.”
Clients understand this. You’re not selling a tool. You’re providing continuity and context, something most coaching models lack.
Q: I only coach individuals. Does this still apply?
A: Yes, and it makes individual coaching more scalable. Clients get nudges and insights throughout their day, so when they show up to your sessions, they’re already in motion. That momentum makes your time together more effective—and more referable. The impact becomes visible beyond the 1:1.
Q: What if my clients already use other assessments?
A: That’s a strength. Cloverleaf brings multiple assessments into a single dashboard—so instead of disconnected reports, clients get a unified view of how to apply insight. You’re not competing with their tools. You’re helping make them actionable.
Q: How should I price engagements that include Cloverleaf?
A: Build it into the experience. Don’t itemize it as “platform access.” Say: This includes personalized insight nudges, session prep support, and access to multiple assessments. It’s all designed to reinforce growth between our sessions.
This positions you as delivering a complete leadership system, not just a set of meetings.
Q: What’s the best way to start?
A: Start small and strategic. Pick one client or team. Frame a 6-week pilot around a clear challenge—like trust-building after a promotion, or rebuilding alignment post-reorg. Use Cloverleaf from the start, and let the nudges show your value in action.
You don’t need a full-scale launch. You need one engagement that proves you belong in the next one.
Change Isn’t Slowing Down—And It’s Not Getting Easier
Change is no longer episodic—it’s the new normal. Whether navigating team restructuring, leadership transitions, hybrid work shifts, or rapid growth phases, People Strategy Leaders are increasingly tasked with supporting teams through continual disruption.
The expectation: keep morale high, engagement strong, and culture intact, no matter how frequent or turbulent the transitions.
Yet here’s the reality: most managers are neither trained nor equipped to handle the deeply relational side of change. They’re expected to maintain productivity, retain talent, and safeguard organizational culture—but they’re often given training sessions that are difficult to fit into busy schedules or frameworks that are difficult to recall in the real, messy interpersonal dynamics their teams actually face every day.
People Leaders are stuck in reactive mode, stretched thin across multiple teams, stepping in to mediate friction or reinforce trust only after issues bubble up. It feels impossible to proactively guide every manager through each nuanced challenge, despite knowing how crucial these moments are for your organization’s success.
82% of HR and management professionals cite change fatigue as a top challenge.
43% of HR professionals and 30% of managers report feeling overwhelmed by the responsibility of maintaining a positive culture amid continuous change. — Lattice State of People Strategy Report (2025)
The solution isn’t yet another training initiative or a standardized playbook. Those approaches repeatedly struggle because the catalyst to lasting change is more relational than procedural.
The future demands a strategy that deeply personalizes leadership guidance based on the actual people involved, their unique personalities, communication styles, motivations, and stress responses.
Managers need tools that equip them not only to lead through uncertainty but to proactively coach their team with clarity, empathy, and confidence, precisely when and where support is needed most.
While most AI tools in change management focus on automating workflows or analyzing performance data, a new kind of AI is emerging—one that supports the human side of change.
These AI coaches don’t just streamline logistics—they help managers lead people and build relational intelligence. These tools can understand how individuals process uncertainty, give feedback, and react under pressure.
Get the free guide to close your leadership development gap and build the trust, collaboration, and skills your leaders need to thrive.
Why Even Good Change Strategies Fall Short Today
Most change strategies rely on well-intentioned playbooks: standardized communication plans, training sessions, and leader toolkits. While these resources may outline best practices, they’re increasingly outdated in the face of continuous disruption—too generic and rigid to respond to the real-time, nuanced realities teams face daily.
- Training is episodic and slow to adapt. Delivered periodically, traditional training loses relevance quickly, rarely translating into meaningful behavioral change, especially during high-pressure moments.
- Change communications lack genuine personalization. Although uncertainty impacts each person uniquely, based on their personality, communication style, and emotional triggers, most messaging is broad, assuming a one-size-fits-all response.
- Managers aren’t supported in relational intelligence. Leaders are expected to resolve interpersonal friction, rebuild trust, and motivate teams through ambiguity, but traditional methods provide few practical tools or real-time insights tailored to actual team dynamics.
- HR Leaders can’t sustainably fill every gap. Despite their strategic oversight, PSLs can’t realistically manage the nuanced interpersonal challenges across numerous teams—yet they’re often held accountable for maintaining organizational clarity, cohesion, and confidence.
88% of HR leaders say shifting priorities are a top contributor to burnout—for themselves and for their managers.
Managers default to “survival mode,” emphasizing tasks over trust and inadvertently amplifying tension, resistance, and disengagement. Change fatigue deepens, leaving PSLs overwhelmed and isolated, carrying burdens no individual team can manage alone.
The answer isn’t to throw out your existing strategies, but to complement them with something that fills their gaps—tools that equip managers to handle the relational and emotional dimensions of change confidently, proactively, and in the moment.
This is where the next evolution of AI in change management can have the biggest impact—supporting the emotional and interpersonal dynamics that traditional tools can’t touch.
Imagine a manager heading into a team meeting after a major reorg.
👉 A typical tool might offer a facilitation framework or an agenda template.
✅ But an AI coach could do more—it could surface coaching insights tailored to the actual people in the room:
- A heads-up that one team member (who thrives on stability) may need more clarity on next steps.
- A nudge to use collaborative language with someone who’s naturally assertive in group settings.
- A reminder that a typically quiet team member may be internalizing stress and won’t speak up unless invited.
These aren’t hypotheticals. They’re examples of how AI coaching can be built on personality science and relational intelligence practices, not just task automation.
This is what it looks like to move from reactive leadership to proactive guidance—in the flow of work, when it matters most.
No new programs to manage. No heavy lift for you or your teams. Just practical, personalized insights exactly when and where they make the biggest difference.
Make Team Development More Impactful
Why Managers Are the Linchpin—and the Risk Point—in Change Initiatives
Managers are on the front lines of change. They’re the ones fielding the unspoken worries after all-hands meetings. They’re navigating tough 1:1s when motivation drops, tensions rise, or trust erodes. In moments of uncertainty, it’s not HR that people turn to—it’s their manager.
And while most managers are capable, few are equipped to coach people through the emotional weight of change. They’re used to delivering outcomes, managing tasks, and keeping things moving. But when relational dynamics surface—conflict, resistance, disengagement—many default to what feels safest: get through the checklist and avoid rocking the boat.
Managers play a pivotal role in executing change management plans, acting as advocates and facilitators who can help reduce friction and increase adoption.
The problem isn’t that managers don’t care. It’s that they rarely have the visibility, support, or tools to handle the emotional and relational side of leadership—especially in fast-moving, high-stakes environments.
They might not notice when someone starts to withdraw. Or they might power through a conversation that actually needed patience and empathy. Even well-intentioned managers can unintentionally damage trust—just by missing the emotional nuance.
And People Strategy Leaders? You often get pulled in to patch it up. To coach the leader. But with so many teams to support and only so many hours in the day, you’re left managing the loudest problems—or the ones already on fire.
That’s why more and more teams are implementing micro-coaching platforms. Not as a new initiative to manage, but as a way to embed leadership support directly into the moments that matter.
The right AI coaching tools can eliminate the relational guesswork that can happen in the midst of managing organizational change. They give managers timely coaching insights—tailored to how each person on their team thinks, communicates, and handles stress—so they can lead more effectively without becoming full-time coaches themselves.
This is how leaders move from reactive support to proactive leadership. Not with more theory. But with in-the-flow, psychometric-powered insights that help managers build trust, reduce resistance, and lead with clarity, every single day.
What Micro-Coaching Means—and Why It Is More Effective In Times of Change
Micro-coaching helps your people lead better, in real time.
It doesn’t require managers to memorize frameworks or master new models. Instead, it equips them with relational awareness in the moments that matter—when trust is built, engagement wavers, or team dynamics get tense.
This isn’t about adding more to their plate.
It’s about delivering the right insight at the right time—so they can lead with empathy, adapt with confidence, and build trust without second-guessing themselves.
Micro-coaching helps managers:
- Adjust their communication style based on how each team member processes stress, uncertainty, or change
- Approach 1:1s, feedback, and friction with confidence, not fear of misfiring
- Strengthen trust through consistent, human-centered interactions—not scripts or generic training modules
And it doesn’t require more meetings, more certifications, or more prep work.
What it requires is real-time, personalized coaching insight—delivered in the flow of work.
Imagine a manager heading into a tough 1:1. Instead of guessing how a team member might react to feedback, they receive a brief, personalized coaching tip:
This individual is naturally sensitive to criticism—start by affirming their contributions, then move into specific opportunities to improve.
👉 It’s a small nudge. But it changes the tone, the trust, and the outcome of the entire conversation.
👉 It helps leaders turn everyday interactions into moments of meaningful interactions.
👉 It helps managers do what People Strategy Leaders have been trying to scale for years: leadership that’s relational, personalized, and consistent, especially in the face of uncertainty.
How To Scale Manager Support—Without Burning Out
People Strategy Leaders already know what great leadership looks like in times of change. The challenge isn’t identifying it—it’s scaling it.
When you’re supporting dozens of teams, you don’t need another playbook or training to administer. You need tools that coach with your managers—automatically, in real time—so you can stop being the only one holding the culture together.
Tools like these embed relational intelligence into daily routines, so your managers get the insight to lead better and have more time to focus on moving the needle on initiatives that matter the most because people have a shared language that lends to collaborative teamwork.
What AI Coaching Can Do
The next evolution of change support is agentic AI coaching that actively understands your people, predicts friction, and gives managers the tools to lead through it. What’s emerging is even more powerful—AI that acts like a real partner to your managers. Not by replacing them, but by coaching alongside them through the interpersonal complexity of everyday work.
Here’s how some AI is already helping teams navigate change management:
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When This Happens…
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How AI Coaching Can Help
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A manager needs to prepare for a tough meeting
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Surface who’s likely to resist change, who needs clarity, and who may disengage silently—based on real personality data
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A teammate is frustrated or feeling misunderstood
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Offer context-specific coaching on how to navigate relational tension, including suggested language and tone
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A manager wants to give better feedback
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Help write, time, and deliver feedback in a way that lands—tailored to the recipient’s personality and preferences
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A leader wants to rebuild trust with someone
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Recommend trust-building actions, guide reflection afterward, and suggest recognition that feels meaningful to the other person
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Someone feels isolated in a remote team
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Offer nudges to stay connected in ways that feel natural to them—without forcing awkward interactions
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A manager wants to help a team member grow
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Suggest skill-building opportunities and communication strategies based on motivation profiles and goals
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A reorg or change initiative is coming
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Analyze team dynamics and predict emotional and relational impact—before the change is communicated
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A team is adopting a new process or policy
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Interpret the rollout through the lens of how different team members will process the change—and how to preemptively support them
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Cloverleaf gives you that structure, without spinning up a new initiative. These tools are already built, already delivering insights, and already integrated into the way your teams work.
Don’t Just Track Participation, Track Progress That’s Invisible to Most Tools
55% of HR professionals say engagement is a top priority, but many lack the tools to support long-term resilience.
Typical change metrics—like training attendance, survey scores, or system adoption—tell you who clicked, checked in, or showed up.
But they don’t tell you the one thing People Strategy Leaders actually care about: Are your people getting better at navigating change together?
That’s the real story beneath the dashboards. Because in times of disruption, what matters most isn’t participation. Its capability:
- Can managers hold trust during tension?
- Can teams communicate clearly through ambiguity?
- Can individuals stay engaged when things get messy?
These are the outcomes that shape culture, not just during a change rollout, but long after.
Not through more forms or status updates, but through behavioral signals embedded into daily work:
- Coaching Tip Engagement: Are managers using relational insights to guide how they lead? (And how often?)
- Insight Search Patterns: Are people looking for better ways to give feedback, repair trust, or solve friction?
- Culture Pulse Shifts: Are teams maintaining alignment, or showing early signs of fragmentation?
Coaching with Insight Is the Manager Superpower for Modern Teams
What makes change hard isn’t the plan—it’s the people part.
Even with the right timeline, a solid comms strategy, and executive alignment, change falls apart when trust breaks down, feedback goes sideways, or people quietly disengage.
Most managers aren’t trained to handle that part.
They’re good at keeping projects on track—but not always equipped to spot emotional resistance, adapt their communication, or coach someone through uncertainty.
That’s why the next generation of leadership isn’t just strategic.
It’s relational.
Managers need insight into how their people think, feel, and work—so they can lead with empathy when it matters most.
Modern change leadership demands:
❌ Less theory.
➕ More traction.
❌ Less one-size-fits-all.
➕ More support that meets people where they are.
That’s exactly what AI-powered coaching in change management is designed to deliver. Personalized guidance, rooted in how their people actually think, communicate, and respond under pressure, surfaced right when they need it.
This is how leadership scales during change.
Not through top-down programs, but through managers who know how to lead with clarity, empathy, and relational intelligence in the moments that matter.
And that’s what your managers need from you now: Support that helps them lead people, not just manage plans.
🙋 FAQ
Q: What if our managers avoid conflict or don’t even see it coming?
A: Most do. That’s why empowering them to be proactive leaders is so necessary. It’s about equipping them with real-time, relational insight—before moments of friction—so they can respond with empathy instead of escalation.
Q: How is this different from the coaching tips in our LMS or HRIS?
A: Those systems deliver static, one-size-fits-all content. This is different. These insights are personalized, based on how each person thinks, communicates, and processes change, and delivered in the exact moment they’re needed.
Q: Can this actually scale across hundreds of teams?
A: Yes. It’s already doing so. This isn’t a new system managers have to learn—it integrates into tools your teams already use (like email, calendars, and collaboration platforms), so leadership development happens without overhead.
Q: Is this just for high-stakes change moments, or every day?
A: It’s built for both. Change just makes the stakes visible. But relational dynamics—trust, tension, communication gaps—play out daily. This gives your managers what they need to lead through all of it.
Q: What signals or metrics will we actually see?
A: You’ll see the problems your people care most about solving and how actively they are getting coached, not just whether they logged in. Cloverleaf tracks:
- Coaching tip engagement: Are people acting on guidance in the moment?
- Insight Search behavior: Are managers seeking smarter ways to lead?
- Culture Pulse shifts: Are teams holding alignment, or showing early signs of resistance?
These behavioral indicators give you visibility into growth oriented actions, not just participation.
I’m a big fan of the Hidden Brain podcast by Shankar Vedantam. Shankar has spent his entire career focused on human behavior, and if you’re interested in organizational behavior or leadership development, his work is essential.
The most recent episode, “Relationships 2.0: Become a Better Negotiator,” instantly became one of my all-time favorites—and it’s a must-listen. In this episode, Shankar speaks with behavioral scientist Max Bazerman about how cognitive biases can quietly undermine our ability to negotiate effectively.
What struck me most was Bazerman’s insight that while we often focus on persuading others in negotiation, we rarely examine our own blind spots. We assume we’re objective, rational, or “right”—but our overconfidence and self-centered thinking can lead to outcomes that are far from optimal.
This article isn’t a negotiation playbook. It’s about something more profound: how emotional and relational intelligence shape the way we communicate, influence, and make decisions, particularly in environments where collaboration and alignment matter.
Because let’s be honest—negotiation doesn’t just show up in boardrooms or contract talks. It’s there when you’re aligning cross-functional teams, giving feedback, proposing new ideas, or trying to secure resources. And often, what gets in the way isn’t the other person. It’s us.
Get the free guide to close your leadership development gap and build the trust, collaboration, and skills your leaders need to thrive.
What We Get Wrong About Negotiation
In the episode, Max Bazerman highlights something most of us miss: our most significant obstacle in negotiation isn’t usually the other party—it’s ourselves. We’re often so focused on persuading or winning that we fail to recognize the hidden cognitive biases shaping our own approach.
Bazerman explores how overconfidence and self-centered thinking consistently derail even the most well-intentioned negotiators. We assume our logic is sound, our goals are fair, and our strategy is smart. But when we neglect to account for how our own blind spots distort reality, we walk away with less-than-ideal outcomes—and sometimes, without even realizing it.
One concept he introduces is the “veil of ignorance”—a powerful mindset shift that asks us to consider decisions as if we didn’t know which side of the outcome we’d be on. It’s a way of neutralizing our self-interest and approaching negotiation from a place of fairness and perspective-taking.
Bazerman backs this up with real-world stories, like Robert Campo’s acquisition of Federated Department Stores and Matthew Harrington’s baseball contract negotiations. In both cases, personal bias and lack of perspective led to missed opportunities or fractured deals, not because the negotiators lacked strategy, but because they lacked self-awareness.
This isn’t just theoretical. Research shows that overconfidence is one of the most pervasive decision-making biases in business. According to a 2012 study published in Organizational Behavior and Human Decision Processes, individuals who are overconfident tend to overlook critical information and underestimate risk, two tendencies that are particularly costly in collaborative environments.
And while these examples come from the world of business and sports, the dynamics are just as present in everyday workplace negotiations:
- A manager pushing for budget approval without understanding competing team needs.
- A team member advocating for their project without listening to leadership’s broader goals.
- Or two departments struggling to align on shared priorities because no one paused to ask: “What assumptions are we making?”
If negotiation is about outcomes, then awareness—of self and others—is the most overlooked advantage.
Make Team Development More Impactful
Why Self-Awareness Alone Isn’t Enough
The essence of this episode is clear: it takes both self-awareness and other-awareness to increase our capacity for emotional intelligence.
It isn’t enough to simply understand yourself better, which the traditional behavioral assessment market has done an adequate job of in the past. It requires that you understand yourself in the context of the people you are trying to communicate with in order to effectively sell ideas and achieve the desired outcomes.
This is illustrated in the following graphic.
On the left, we see what most traditional learning experiences focus on—solo development. These tools often provide valuable individual insights, but they are static. They lack the dynamic interplay that happens in real relationships. You learn about yourself, but not how your behavior impacts others, or how theirs impacts you.
On the right is the model Cloverleaf was built around:
☘️ A continuous loop of learning about others and growing with others
☘️ Self-awareness that’s active, contextual, and relational
☘️ Growth that happens not in isolation, but in the actual flow of work and interaction
This distinction matters.
As organizational psychologist Tasha Eurich puts it, People who have high internal self-awareness and low external self-awareness can come across as arrogant or oblivious. In other words, knowing yourself isn’t enough if you can’t see how others experience you.
Most development and assessment platforms deliver data and reports, but rarely provide the context needed to act on them in relationships. That’s why even well-intentioned training programs struggle to create lasting behavior change: the learning doesn’t live where the communication happens.
At Cloverleaf, we intentionally designed our experience to go beyond the individual. Not just to teach people about themselves, but to teach people how to interact more effectively with the people they work with every day.
Turning Insight Into Practice: What Teams Need to Reinforce Human Skills
The challenge isn’t understanding the importance of emotional intelligence—it’s consistently applying it in the messy, fast-moving reality of daily work.
Reading an article, listening to a podcast, or attending a workshop can spark awareness. But unless those insights are revisited and reinforced in real interactions, they rarely change how people communicate, collaborate, or lead.
This is the gap Cloverleaf was built to close. It’s not just a reflection tool—it’s a system designed to bring awareness into moments that matter most.
Consider a few everyday scenarios:
- Before a feedback conversation, Cloverleaf reminds you that your teammate tends to process input more slowly and prefers written reflection before discussing live. So, instead of jumping in during a meeting, you follow up with an email and a plan to talk tomorrow, ensuring the conversation lands more effectively.
- During a project kickoff, you scan your team’s Cloverleaf dashboard and notice one colleague thrives on structure, while another gets energized by open brainstorming. You build a hybrid approach that plays to both styles, avoiding tension and building momentum.
- After a tough meeting, a coaching prompt surfaces on your dashboard: a reflection on how your communication style may have been perceived. It doesn’t just call out a blind spot—it invites you to adapt and grow.
These aren’t afterthoughts; they’re embedded into the flow of work. That’s the point. Emotional intelligence doesn’t live in content. It lives in context.
Research backs this up. According to the Ebbinghaus forgetting curve, we forget up to 75% of new information within six days if it’s not reinforced. But when insights are tied to real-time action—and especially when they involve other people—they stick. That’s the power of social and situational learning.
Cloverleaf doesn’t just help individuals learn about themselves—it helps teams learn with and through each other. And that’s how human skills become real habits.
What Talent Development Leaders Are Asking
These insights from Hidden Brain and Max Bazerman aren’t just interesting for individual professionals—they strike at the heart of what HR, Talent Development, and People Leaders are actively trying to solve:
👉 How do we move from individual learning to meaningful team development?
👉 How do we measure growth in emotional intelligence or negotiation skills, especially when outcomes are relational?
👉 How do we make soft skill development stick, beyond a one-time workshop or LMS module?
These aren’t abstract questions. They reflect the real tension between what organizations say they value (collaboration, communication, empathy) and how they actually support people in developing those skills.
These concepts are part of a broader shift—a move away from static content and solo learning experiences toward something more relational, more integrated, and more enduring. A shift from “training” to practice.
If emotional intelligence, bias-awareness, and better negotiation habits are going to become part of your team’s operating system, they need:
- Reflection prompts that appear when needed, not six months later.
- Collaborative learning experiences that reveal not just how I think, but how we interact.
- Tactical ways to practice, like reframing a disagreement using the “veil of ignorance,” or preparing for a conversation by considering how someone else sees the situation.
These moments are small—but they’re how real change happens. And the more intentional we are in designing for them, the more likely our learning programs will actually lead to lasting behavior change.
Because the truth is, no one develops communication skills in isolation. And no one becomes a better negotiator by just learning to win. They grow by seeing more clearly—both themselves and the people they work with.
What Might Change If You Started With Curiosity?
At its core, this episode of Hidden Brain isn’t just about negotiation. It’s about perspective. And the reminder that success in communication—whether in a deal, a team meeting, or a tough conversation—starts not with talking, but with seeing clearly.
That means noticing our own blind spots. It means pausing before we push our agenda to consider how someone else might see the same situation. It means asking better questions, not just having better answers.
So here’s one to sit with:
Where are my blind spots in how I communicate, collaborate, or lead—and who might help me see them?
If that question resonates with you, take 30 minutes to listen to the episode. Then try putting one insight into practice—not in a high-stakes negotiation, but in your next team conversation.
Relational learning isn’t just a theory. It’s a shift in how we show up. The more intentional we are about incorporating it into our everyday work, the more powerful it becomes.
I recently read the book Super Communicators by Charles Duhigg. This is a must-read for anyone who cares about building people skills in any organization.
It’s a timely topic, given the fast move toward and adoption of AI technologies that is swinging the focus of skill building in organizations away from “hard skills” like software development and accounting, which can increasingly be replaced by AI, to skills that are a unique reflection of our human-ness.
As automation reshapes entire industries, technical expertise is no longer the only differentiator. The skills that will define the next era of leadership and collaboration are deeply human: the ability to connect, to listen, to navigate complexity in conversation. These are the skills AI can’t replicate—and the ones organizations can’t afford to overlook.
LinkedIn recently released its fastest growing skills of 2025, and among the top 10 are skills that directly relate to our ability to communicate and connect with others:
- #2 – Conflict Mitigation
- #6 – Public Speaking
- #7 – Solution-Based Selling
- #8 – Customer Engagement and Support
What do these have in common? They all rely on a person’s ability to read the room, build trust, and adapt how they communicate in real time. These aren’t just traits—they’re skills that can be developed and strengthened.
At Cloverleaf, we believe technical skills will keep evolving, but human connection is the constant that drives collaboration, trust, and performance. And the good news is: it’s not something you’re either born with or not. It’s something you can practice daily.
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What Super Communicators Understand About Human Connection
While there are many concepts, ideas, and resources in Super Communicators, I wanted to highlight a couple that often go overlooked—and that Cloverleaf has been specifically designed to support.
Duhigg’s core idea is simple but powerful: great communication isn’t about being the loudest voice in the room or the most charismatic. Super communicators aren’t born—they’re made. What sets them apart is their ability to prepare intentionally, stay curious in conversation, and create connection through active listening.
These are not vague soft skills. They’re specific behaviors backed by research. And more importantly, they can be practiced.
Our platform helps individuals and teams turn these habits into part of their daily workflow through calendar-based meeting prep, tailored coaching prompts, and reflection tools that support better conversations in real time.
When communication becomes a habit, connection becomes a competitive advantage.
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Preparation: The Underused Power Skill
One key aspect of becoming a super communicator is preparing well for meetings and conversations with others. Duhigg highlights the importance of setting yourself up with a curious mindset—one that’s ready to ask questions and learn before pushing an agenda or selling an idea.
We are well served to do a bit of prep work before a dialogue begins. Researchers at Harvard and other universities have looked at exactly which kind of prep work is helpful.
Participants in one study were asked to jot down a few topics they would like to discuss before a conversation began. This exercise took only about thirty seconds; frequently, the topics written down never came up once the discussion started. But simply preparing a list, researchers found, made conversations go better. There were fewer awkward pauses, less anxiety, and afterward, people said they felt more engaged.
This isn’t just good advice—it’s a repeatable practice. The best conversations start before the meeting even begins.
Cloverleaf makes this prep work easy.
When you connect your calendar to your Cloverleaf account, you receive a daily digest delivered directly to your inbox each morning. It includes personalized insights to help you prepare for the people you’re meeting with—like knowing a teammate prefers direct communication, or that a collaborator is energized by brainstorming. That kind of insight can shape how you approach a conversation and dramatically improve how your message is received.
Great communicators are prepared communicators—and that starts with emotional intelligence and a thoughtful understanding of how others think and interact.
You can learn more about all the great meeting insights and preparation features Cloverleaf offers by viewing our help doc here.
Listening: The Shortcut to Real Connection
It’s not enough to simply prep well for a conversation or meeting. To create meaningful connection—and drive better outcomes—you also need to listen with intention.
Duhigg dedicates a chapter to this idea, exploring the power of asking emotionally resonant questions that build connection. He shares the story of a husband-and-wife research team that brought strangers together to test different theories for forming connection and found:
There was only one method tested that could reliably help strangers form a connection: a series of 36 questions that elicited ‘sustained, escalating, reciprocal, personalistic self-disclosure.’
The key was creating vulnerability that led to emotional syncing—or emotional contagion.
This kind of connection doesn’t happen by accident. It comes from listening not just to respond, but to understand. Super communicators ask questions that invite reflection. They create space for others to feel seen, heard, and valued. That’s what builds trust—and drives real collaboration.
That insight is central to why we added discussion questions as a tool for team building in the Cloverleaf dashboard. Not every prompt is designed to surface deep vulnerability, but they are built to foster meaningful connection. And after reading Super Communicators, we even added a few new ones—see if you can spot them.
At Cloverleaf, we believe connection is built through small, intentional moments. When people feel heard, they engage more deeply with their work, their teammates, and their purpose.
Making Communication a Daily Habit
Super Communicators makes the case that great communication isn’t a personality trait—it’s a pattern of behaviors anyone can build. But even the most powerful insights fade if they aren’t applied when they matter most.
And that’s the real challenge: how do you keep practicing these skills when work gets messy, fast, and unpredictable?
Cloverleaf doesn’t teach you how to communicate in theory—it helps you show up differently in the moments that count. Right before a tough conversation. In the middle of team tension. When you’re preparing for a meeting, and realize the way you like to communicate might not be how they best receive information.
For example:
- After reading Duhigg’s advice on listening, you might recognize a moment in your daily digest where a teammate values emotional insight over data, and suddenly, the tone of your check-in shifts.
- A discussion prompt pops up that mirrors the 36 questions research—not to push vulnerability, but to spark the kind of connection that makes future feedback easier.
- Or maybe you see a coaching tip that reminds you to pause and ask a question instead of jumping straight to a solution.
These are small, human moments. But they’re where communication skills take root. Not in theory, but in practice. Not once, but repeatedly.
Because the future of work doesn’t need more communication training. It needs more communicators who know how to practice what matters—day by day, conversation by conversation.
What Could Shift if You Started With Curiosity?
Communication often breaks down not because people lack information, but because they’re missing perspective. We rush to solve, defend, and persuade. But what if we started with a different goal?
What if the next conversation wasn’t about being heard, but about understanding someone else more fully?
The research in Super Communicators makes this clear: the quality of our communication depends less on what we say and more on how we show up. With curiosity. With intention. With a willingness to prepare, to listen, and to connect.
That’s not just a personal skill—it’s a team advantage. One that deepens trust, strengthens collaboration, and unlocks better outcomes across the board.
So here’s the question this article leaves us with:
What might change in your team, your culture, or your leadership—if curiosity became your default starting point?
