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.

Why Just-in-Time Learning Needs to Be More Than Content Availability

Of the 5 Moments of Need — the learning framework introduced by Bob Mosher and Con Gottfredson — the first two, Learn New and Learn More, are considered good matches for traditional learning approaches like classrooms and content [2].

The remaining moments are more fragile. When someone needs to put their learning into practice (Apply), solve an unexpected problem (Solve), or internalize a new way of doing things (Change), most people won’t turn to a learning management system… Each of these three Moments of Need requires advanced L&D strategies that go beyond content libraries.

Moment 3: Help Learners Apply Classroom Learning

What is it?

According to the Harvard Business Review, after receiving training from L&D, only 12% of employees use new learnings in their jobs [3]. The infamous “Forgetting Curve” suggests that by the time an employee walks out of a classroom, across campus, and to their desk, they will have lost 42% of the information they received.

Go to lunch?

By the time they return, the information loss grows to 56%. By the next day, the typical employee only retains about a third of their training. [3] This is why the Apply moment is so challenging, and why the Just-in-Time concept is so attractive.

What does good look like?

A really good strategy for Apply would enable employees to learn in the flow of work, based on their real, experienced context, and these learnings would be personalized to each learner.

What does the market look like?

A look at current offerings shows that most platforms that claim “Just-in-Time” are an evolved version of the eLearning strategy from the 90s. Yes, it is excellent to have courses available, and the switch to micro-learning formats may help employees digest more focused content. Sometimes these platforms offer integrations, but rarely so that employees can actually engage with learning in the tools they use every day.

Personalization looks more like red sauce offerings at the grocery — you can pick Chunky, Sage, or Meat Sauce. In fact, in many cases, these personalizations are simply a learning track, each for Individual Contributors vs. Managers.

What Needs to Happen Instead

Co-founder Kirsten Moorefield has repeatedly told the Cloverleaf product team, I don’t want users to spend time on the platform, I want them to get insights inside the tools they use every day. L&D Practitioners find that when they invest in human skill training for employees, Cloverleaf helps conquer the Forgetting Curve by providing true Just-in-Time learning in Slack, Microsoft Teams, and Email.

As a team of one supporting 2,000 employees, Cloverleaf’s coaching tools have empowered our leaders to develop their teams without constant hand-holding. It’s scalable, personalized, and impactful. — Dr. Erin Meyers

Cloverleaf learnings actually matter to employees because

• They are short and impactful (driven by more than 7 years of internal refinement),
• They are context-aware (Cloverleaf’s algorithms sync with users’ calendars and activity to deliver coaching on the most relevant teammates each day), and
• They are personalized with the most individualized model of human personality available (Cloverleaf’s support across more than 12 industry-leading assessments enables unmatched depth of understanding).

As a result, learning doesn’t just get delivered—it gets used.

Cloverleaf helps turn new knowledge into daily action, accelerating leadership growth and reducing skill decay across the organization.

Great Coaching Can Lead To A High-Performing Culture

🟢 Self-awareness that leads to action.

Leaders need more than just insight into their strengths, biases, and blind spots—they need to know how to apply that awareness in real interactions. Coaching ensures that self-awareness isn’t just theoretical, but something leaders can actively use to make better decisions and foster stronger teams.

🟢 A focus on building strong teams.

Coaching isn’t just about making a leader better—it’s about helping them bring out the best in others, develop talent, and build trust. When leaders are supported through coaching, they create environments where people feel heard, valued, and empowered to perform at their best.

🟢 Actionable feedback, not vague theories.

Effective leadership coaching offers practical, real-time insights leaders can apply immediately—not just high-level concepts about leadership. The best coaching doesn’t just teach theory; it helps leaders navigate the complexities of managing people, giving feedback, and driving change in the moment

🟢 Scalability and consistency.

Coaching should be continuous, relevant, and available to every leader—not a one-time experience for a select few. When coaching is integrated into daily work, it becomes a consistent driver of growth, rather than an occasional intervention.

The impact is real. One study found that for every $1 spent on coaching, companies saw a return of over $7. Coaching doesn’t just develop better leaders—it leads to smarter decisions, stronger teams, and better business outcomes. When leaders are equipped with the right coaching, they reduce costly mistakes, improve retention, and create cultures of accountability that drive long-term success.

Impactful leadership coaching strategies realize it isn’t just about developing individuals—it’s about changing how leadership happens in an organization. When development opportunities are embedded into daily work—instead of separate initiatives—the effects of coaching start to drive real, lasting change.

4 Principles That Make Leadership Coaching More Effective?

Coaching is about helping leaders apply new learning and discovery to improve team dynamics, decision-making, and workplace culture. But for coaching to drive lasting impact, it has to be personalized, relevant, team-centered, and continuously reinforced.

Let’s break down the key principles that make leadership coaching effective.

1. Personalization: Coaching Should Be Tailored to the Leader and Their Team

No two leaders—or teams—are the same. Coaching should be customized to individual strengths, leadership styles, and team dynamics rather than following a generic framework.

How Personalization Makes Leadership Coaching More Effective

✅ Self-awareness is At The Core Of Better Leadership

Leaders who understand their own tendencies, strengths, and blind spots can make better decisions, communicate more effectively, and create environments where people thrive.

• Behavioral assessment platforms with tools like DISC, MBTI, or Enneagram help leaders understand their natural tendencies, communication styles, and decision-making patterns.
• Strength-based assessments (like CliftonStrengths®) highlight what energizes leaders, helping them maximize their potential.
• When assessment insights can be layered, even better! Leaders get a multi-dimensional view of themselves and their teams—leading to more targeted coaching and better results.

✅ Leadership Coaching Should Adapt to the Team, Not Just the Leader

Leadership isn’t just about self-improvement—it’s about building strong teams. Coaching should help leaders:

• Recognize and adapt to different working and communication styles within their team.
• Navigate team dynamics more effectively, building trust and collaboration.
• Lead in a way that aligns with their team’s strengths—not just their own.

When leaders and teams can both be part of the coaching process, the impact is deeper and longer-lasting. Assessments are just one tool that can make coaching more personal, actionable, and relevant—leading to stronger teams and better leadership at every level.

2. Contextual Relevance: Coaching Should Happen When It Matters Most

Leadership isn’t learned in a vacuum. Leaders need coaching in the moments where leadership skills are required—when they’re giving feedback, navigating conflict, or making tough decisions.

⏳ Why Timing Matters in Leadership Coaching:

Often, coaching opportunities happen out of sync with the actual leadership challenges the individual is facing. A one-hour session weeks before or after a tough conversation doesn’t help a leader navigate it in real time.

Leaders need coaching in the moment, when decisions are being made, feedback is being given, and challenges arise—not weeks later when the details are fuzzy.

Leaders don’t have time to dig through notes from past coaching sessions. They need quick, relevant guidance when they’re about to have a one-on-one, handle a conflict, or make a big decision.

Digital coaching tools can integrate coaching insights directly into platforms like Slack, Outlook, Gmail, and team dashboards, so leaders get nudges right when they need them—not as an afterthought.

Instead of hoping leaders remember what they learned in a coaching session, automating coaching nudges makes insights part of their daily workflow, helping them adjust, improve, and lead better day in and day out.

Why Centralizing Your Assessment Strategy Matters

Many organizations invest in assessments, but their impact is diluted when insights, costs, and usage are scattered across multiple tools, vendors, and teams. Without a cohesive, scalable strategy, assessment data remains isolated, underutilized, or forgotten—limiting its potential to drive real behavior change and increasing unnecessary costs.

A centralized approach ensures assessments aren’t just one-time exercises but become ongoing coaching tools that shape leadership, teamwork, and culture—while optimizing investment and eliminating hidden costs.

The Benefits of a Unified, Scalable Assessment Strategy:

✅ One dashboard for all assessments → No more managing multiple platforms or tracking down reports.

✅ Layered insights for deeper understanding → Combine multiple assessments for a multi-dimensional view of individuals and teams.

✅ Automated coaching in the flow of work → Deliver insights where and when they matter—inside Slack, Outlook, Gmail, and team meetings.

✅ Cost efficiency & transparency → Consolidate spending, eliminate redundant vendor contracts, and negotiate better pricing with a centralized platform.

When assessments are centralized, layered, and continuously reinforced, they become more than just static personality insights. They evolve into dynamic coaching tools—actively shaping leadership, improving collaboration, and driving measurable growth across an organization while reducing wasteful spending.

Layering Multiple Assessment Learnings Creates A Rich, Dynamic Platform

Most assessment platforms are limited in functionality by isolated frameworks to understand people—whether it’s personality, communication style, or strengths. But people are multi-dimensional. No single assessment can capture the full complexity of how individuals think, work, and collaborate.

By layering multiple validated assessments, organizations can create a richer, more accurate picture of their people—leading to better coaching, stronger teams, and more effective leadership development.

One Assessment = Limited Insights. Multiple Assessments = A Complete Picture.

Consider how different assessments contribute unique but complementary insights: