What your leadership team isn’t telling you, and why it matters

On the outside, it can look like your leadership team is running like a well-oiled machine. Meetings go smoothly. People nod along in agreement. No one raises red flags or argues.

It’s smooth sailing… right?

Unfortunately, all that alignment can sometimes be a mirage.

Because the higher you climb, the more filtered the feedback from your team becomes. And that silence can cost you clarity, trust, and traction.

This is what it looks like—and what to do about it.

What isn’t your leadership team saying?

Julia, the CEO of a fast-scaling financial services company, came to me concerned that her executive team was going through the motions.

Revenue was strong, and the “right” decisions were being made, but she sensed something was off.

At her last leadership meeting, Julia told me, “It felt like I was talking to myself. No one speaks up anymore. They looked like they wanted to be anywhere else but here, and they won’t say why.”

The leadership team was under pressure. A recent private equity recap had put the company on an accelerated timeline, and expectations were higher than ever before. Julia, still early in her role as CEO, had already parted ways with a long-tenured COO, sending a clear message that execution, on her terms, was non-negotiable.

However, when I conducted preliminary interviews before their team’s offsite, a more complex story emerged.

They were trying to deliver, but without the psychological safety or clarity needed to do it well.

They were juggling conflicting priorities, shielding their teams from burnout, and making isolated decisions without a shared framework or clear alignment.

In an effort to derisk decision-making (or as she put it, “put the investors’ fingerprints on the murder weapon”), Julia had invited PE operating advisors into meetings with her direct reports. But because she hadn’t explained why they were there or what role they played, it created confusion about who was actually in charge.

As one executive put it, “I don’t know how to dissent without sounding like I’m not a team player. It’s really frustrating.”

What looked like disengagement was actually quiet, careful survival.

Ask yourself: How often do I invite dissenting opinions or uncomfortable truths, and how do I respond when I get them?

Get on the same page with a 360 Assessment

If, like Julia, you suspect your leadership team is holding back, a well-run 360 assessment can be one of the fastest ways for a leader to get clarity on how they’re perceived, where trust is strong, and where it’s starting to fray. This often sparks a leader’s curiosity and motivation to want to change.

For another client, James, a high-performing executive at a growing wholesale insurance firm, the process was eye-opening.

Widely respected and known for staying calm under pressure, James had assumed things were working well.

But his 360 revealed something he hadn’t realized: his team saw him as a curmudgeon (and openly called him that behind his back). No one wanted to challenge his thinking or give him tough news. Moreover, no one felt like they knew him at all.

James thought he was simply being efficient and prioritizing work above all else, but now he understood the opportunity cost of operating on the surface-level.

As we worked through the 360, we paid attention not just to what was said, but to what was missing from his team’s overly-polite feedback.

The vague language and careful tone were signals of a team that respected their leader, but didn’t feel comfortable being fully honest with him.

Ask yourself: What signals might I be missing in my team’s feedback? How can I create more space for honesty?

Create safety for truth-telling

Both Julia and James needed to create an environment where their leadership team could tell the truth, especially when it’s uncomfortable. What Julia and James needed—and ultimately did—was to create intentional space for honesty.

Julia’s team faced intense organizational pressure. Her leaders weren’t resisting change—they were overwhelmed, and holding back their concerns because they had no clear way to surface them.

Together, we created space for the team to name the unspoken trade-offs they were being forced to make: what they were saying yes to, and what was quietly being dropped.

Once out in the open, that information became tools for alignment instead of silent friction.

We also helped the team build new norms around speaking up. That meant introducing language to flag competing priorities without being seen as blockers, and reframing dissent as a strategic asset.

We replaced “Are you on board?” with “What would make this easier to execute?”, a small shift that opened up meaningful dialogue.

Finally, we clarified what execution looked like in this new phase: not reactive speed, but coordinated momentum.

James’ challenge was more relational. While his team respected him, they didn’t feel safe being fully honest.

To rebuild trust, we focused on creating psychological safety, starting with small, intentional changes.

James shifted from a passive “open door” to active invitations for feedback, especially in one-on-ones. He modeled vulnerability by naming uncertainty and sharing the thinking behind his decisions, not just the outcomes.

Soon, he was viewed as a “lovable curmudgeon” by his team.

James also took ownership and began privately tracking signals of progress: moments when someone pushed back, disagreed, or offered unfiltered input. It helped him see progress and identify where silence still lingered.

When you create space for honest conversations—through a 360, executive coaching, or a well-designed offsite—you signal to your team that their input matters and their psychological safety is non-negotiable.

Ask yourself: What does your team need to create a safe space for difficult truths?

If it feels too quiet at the top, don’t assume everything’s fine. Silence is often a signal. Whether your team is quietly triaging trade-offs like Julia’s, or holding back honest input like James’s, the solution starts with making it safe to speak up.

That kind of trust doesn’t happen by accident. It’s built through intentional conversations, clearer expectations, and leaders who model the honesty they want to see. As I like to say to my clients, trust means creating a culture where challenge is welcomed because everyone knows it comes from a shared commitment to the team's success.

The most successful teams don’t avoid hard truths, they know how to work through them together.