If you’ve spent any time in HR or people leadership over the past few years, you’ve felt it: culture is getting harder to maintain, harder to measure, and harder to influence. Remote and hybrid work didn’t create the challenge, but they exposed something we can’t ignore anymore.
The truth is simple:
Culture is not set in an all-hands meeting or fixed by the next engagement initiative. Culture is built — or eroded — one conversation at a time.
And the people having the most conversations inside your organization are your managers.
Which is why one data point from Gallup’s State of the Global Workplace 2025 stopped me in my tracks:
Only 27% of managers globally are engaged at work — the lowest engagement of any group.
If our managers are stretched thin, unclear, and unsupported, the ripple effects show up everywhere else. Engagement drops. Psychological safety erodes. Conversations become transactional. Feedback gets delayed or avoided. Teams try to collaborate while missing the human context that makes collaboration possible.
We tend to talk about culture as if it’s abstract.
But most of the culture problems leaders describe — misalignment, low accountability, burnout, lack of connection — can be traced back to the same pressure point:
Managers don’t feel equipped to lead the human side of work.
And that’s something we can fix.
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The Real Culture Bottleneck: Everyday Manager Conversations
When I talk with HR leaders, they’ll often say:
“We want managers to coach. We just don’t know how to help them do it at scale.”
And they’re right to worry about scale.
Most HR teams support hundreds — sometimes thousands — of employees with a team that’s too small to meaningfully intervene in every moment that matters.
Meanwhile, managers are responsible for:
- clarifying expectations
- giving feedback
- navigating conflicts
- supporting wellbeing
- fostering psychological safety
- connecting work across teams
And the environment they’re doing this in isn’t easy. According to Gallup’s 2025 data:
- Global employee engagement fell to 21% in 2024.
- Manager engagement dropped three points, the biggest decline of any group.
- 70% of a team’s engagement is attributable to the manager.
We cannot meaningfully improve engagement without improving the manager–employee relationship.
And the relationship lives inside conversations — not in programs, policies, or perks.
Feedback Is the Single Highest-Leverage Skill (And the Most Underdeveloped)
In our research across thousands of employees, we found something both unsurprising and concerning:
Only 15% of employees said they receive helpful feedback that supports their growth. 70% said they receive none. The remaining 15% said the feedback they get is unhelpful or vague.
That mirrors what broader feedback research shows. For example:
- Only 1 in 5 employees gets feedback weekly, even though about half of managers believe they give it often (Gallup).
- 32% of employees go more than three months without feedback from their manager (Workleap, via Peaceful Leaders Academy).
- When employees receive meaningful feedback, 80% report being fully engaged, regardless of how many days they’re in the office (Gallup).
- Employees who receive daily input from their manager are 3.6x more likely to feel motivated to excel (Gallup).
And here’s the part that still surprises a lot of leaders:
Even imperfect feedback is dramatically better than no feedback at all.
Why?
Because silence creates ambiguity.
Ambiguity erodes trust.
Harvard’s Amy Edmondson defines psychological safety as “an absence of interpersonal fear” — a climate where people can speak up, make mistakes, and share concerns without fear of punishment (Harvard Business School Online).
This is why I often say:
If you want to change your culture, start by helping your managers give feedback that’s timely, human, and grounded in context.
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Connection Doesn’t Come From Forced Fun — It Comes From Understanding
One of the misconceptions I hear most from leaders is:
“Our teams need more connection. Let’s schedule more fun.”
And while the intention is good, the outcome is predictable.
People are overwhelmed.
Another trivia event is not the thing they’re asking for.
What they do want is something simpler:
Connection that is integrated into the work itself.
Especially in remote and hybrid environments, people want to understand:
- what their teammates actually do
- how they prefer to communicate
- how they make decisions
- what motivates or derails them
- how to collaborate without friction
Research on psychological safety and thriving cultures consistently shows that when people feel included, respected, and able to contribute, engagement and performance rise (EdStellar; Civility Partners).
People don’t want to bond around the work with disconnected activities.
They want to bond through the work — by doing it better together, with more clarity and less friction.
That requires a mindset shift I call:
⭐ Relational Curiosity
The Human Skill That Will Define Team Health in the Next Decade
Relational curiosity is the practice of approaching differences not with judgment or defensiveness, but with a posture of:
“What strength is this person bringing? What perspective am I missing?”
This is not soft or fluffy.
This is psychological safety in action.
When relational curiosity is present, teams are:
- more innovative
- more inclusive
- better at leveraging diverse perspectives
- more resilient under stress
Psychological safety research shows that diverse teams outperform homogeneous ones only when people feel safe to speak up, disagree, and take risks (Harvard Business School Online; Workplace Options Psychological Safety Study).
When relational curiosity is absent?
We see what we’re seeing in society:
Polarization trains people to treat different perspectives as dangerous rather than valuable. That mindset walks right into work the next morning.
The opportunity is that work can be the place where we help people practice a different pattern:
- pausing before assuming motive
- asking about strengths instead of jumping to labels
- considering that someone else’s “difficult” behavior might simply be a different wiring
And managers are the ones who can normalize this — if we give them the tools.
The Problem With Most AI Coaching Tools (And Why Managers Aren’t Using Them)
A lot of AI coaching tools in the market today promise to “coach” employees or managers.
But when managers actually try them, they quickly discover one of two experiences:
1. Endless Open-Ended Questions
Lots of:
- “Tell me more…”
- “What happened?”
- “How did you feel?”
- “What else could you try?”
This can help someone process, but most managers are already time-poor. They don’t have the capacity for a long, text-based coaching session after a full day of meetings.
2. Generic Advice
- “Schedule more regular 1:1s.”
- “Recognize your team more often.”
- “Build trust through transparency.”
Good ideas in general — but:
- not contextual,
- not personalized to the manager,
- not personalized to the team,
- and not really coaching.
Managers don’t need another chatbot in a separate tab.
They need insight — about people, patterns, and dynamics — delivered where they already work.
This is where Cloverleaf’s approach is intentionally different, and where it complements the argument my co-founder Darrin makes about AI coaching and traditional leadership training in this article on AI coaching vs traditional management training.
We built our AI Coach on a simple belief:
Managers don’t need more content. They need better context.
Context about:
- how each person on their team is wired
- how those people tend to interact under stress
- where friction is most likely to show up
- how different personalities hear and interpret feedback
Cloverleaf’s AI Coach is grounded in:
- validated behavioral assessments
- real teammate relationships and org structure
- real team dynamics
- real, in-the-moment situations
So instead of generic guidance, managers get insight that sounds like:
“Before your 1:1 with Michael, remember he prefers time to process. Ask one open question, then give silence — he’s more likely to share what he’s really thinking.”
Or: “You may interpret Jenna’s direct tone as frustration, but her profile shows a high preference for efficiency. Try acknowledging her clarity before diving into the issue.”
Those aren’t scripts. They’re perspective-shifting nudges — the kind that change how a manager handles the next 10 minutes.
And those small shifts, multiplied across conversations, become culture.
If you want to see how this looks specifically for leaders and people managers, we’ve outlined it in more detail on our AI Coaching for Managers & Leadership page.
The Future: AI That Connects Systems — Not More Systems
One thing I believe strongly: AI is not going to succeed by adding more systems to our stack.
It’s going to win by connecting the ones we already have.
I don’t think learning management systems disappear overnight, but I do think the way we use them will radically change. As several analyses of performance management and future-of-work trends point out, learning and coaching are moving toward continuous, just in time, in-the-flow experiences rather than one-off events.
Instead of: “I need to have a tough conversation next week — let me go hunt for a 45-minute ‘difficult conversations’ module.”
We’ll see:
- a short, relevant nudge appearing in the tools managers already use
- personalized to their wiring
- personalized to their employee’s wiring
- tied to the real situation they’re facing, in that moment
That’s AI not as event-based training, but as ongoing support.
Learning delivered in the flow of work, not outside of it.
Coaching delivered in context, not in theory.
And that’s when “culture work” stops being a program and starts being a lived, daily experience.
How Organizations Can Start (Without Overwhelm)
I tell leaders the same thing I’ll tell you here:
You don’t need to fix everything at once.
You just need to start where it matters most.
1. Start with your managers
They are the cultural force-multipliers.
2. Help them give better feedback
Not annual, not quarterly — but timely, small, human feedback.
3. Equip them with context, not just content
Templates don’t change behavior.
Insights do.
4. Integrate learning into the tools they already use
If it’s not happening in the flow of work, it won’t happen.
5. Build relational curiosity into your culture
This is the skill that will define the next decade of teamwork.
Culture Isn’t a Program. It’s a Pattern.
Organizations often look for culture to be something big — a strategy, a rollout, a bold initiative.
But culture is small.
It’s human.
It’s the accumulation of tiny moments that compound into trust.
The data is clear: managers are overwhelmed. Engagement is declining. Psychological safety is fragile.
But the opportunity is equally clear:
If we give managers the tools, context, and insights to navigate everyday conversations with clarity and curiosity… culture gets better. Teams perform better. People feel more connected and more seen.
And the research supports this over and over:
- psychological safety is the foundation of high-performing teams (HBS, 2024)
- engaged managers produce engaged teams (Gallup, 2025)
- meaningful feedback increases motivation and trust (Gallup, 2023; Workleap, 2021)
- work-integrated connection drives engagement (TeamOut, 2024)
Culture is built in conversations.
One conversation at a time.
One moment of relational curiosity at a time.
One manager at a time.
That’s where the real work is — and where the real transformation happens.
If you want to explore how Cloverleaf supports managers in these everyday moments, I’d love to show you.
Not in a “replace your managers” way. In a “give them the context they’ve been missing” way.
👉 Request a demo and see how insight-based, behaviorally grounded coaching can change the way your managers lead — one conversation at a time.
