14 Jan Your Exec Team Looks Aligned. They’re Actually Terrified to Tell the Truth
Recently, one of our coaches was debriefing a session with a senior leader at a fast-growing, mission-driven company.
On paper, it’s a success story: explosive growth, beloved brand, smart executives, sophisticated investors.
Behind the scenes?
The executive team is exhausted, scared to speak honestly, and quietly wondering if it’s worth staying long enough to see a payout.
This isn’t a story about “bad people.”
It’s a story about what happens when psychological safety is treated like a buzzword instead of a core operating infrastructure.
What Psychological Safety Actually Looks Like When It’s Missing
Here’s what our coach described (details changed for confidentiality, dynamics very real):
- The CHRO a human switchboard.
The head of people is supposed to be steering org design, talent strategy, and culture. Instead, she’s spending her days as the intermediary between powerful leaders who won’t talk to each other directly. Founder A doesn’t want to talk to Founder B. The COO only wants to go through the CHRO. Every issue runs through her, which means she’s doing bits of everyone’s job and very little of her own.
- Meetings where everyone nods – and no one agrees.
Executive meetings are full of head-nodding and “sounds good” energy. No one wants to be the one to say, “We can’t do these 200 priorities this year.” So they leave the room “aligned,” then immediately peel off into side conversations to voice their real concerns.
- The meeting after the meeting is where the real work happens.
Leaders are scared to give direct feedback in the room, especially to founders who are known to be emotional, reactive, or even berating in group settings. So they wait until after the meeting and go to the one leader they trust – often the CHRO – to say what they should have said out loud.
- Confused power dynamics at the top.
There are two founders, a strong operator, and a relatively new Chief People Officer. Officially, decision rights live one place; in practice, everyone still defers to the founders. People don’t know whose “yes” actually counts, so they hedge, stall, or try to keep everyone happy.
- Coaching… but no real change.
The company has invested in executive coaching and brought in external firms before. Individual leaders have grown. But the system hasn’t. The same patterns keep repeating because the executive team has never done the hard work together.
From the outside, this might look like “messy but normal” growth.
From the inside, it feels like death by a thousand misalignments.
And this is where “psychological safety” stops being a soft concept and starts becoming a hard business problem.
Psychological Safety Isn’t a Poster. It’s a Permission Structure.
In teams like this, the cost of speaking up feels higher than the cost of staying silent
That’s how you get:
- Strategies that look brilliant in PowerPoint and fall apart in execution.
- A “visionary” founder whose ideas never get meaningfully challenged or prioritized.
- A CHRO who is so busy managing interpersonal landmines that she can’t focus on building the future workforce.
- Quiet contemplation from key leaders: “Is this really what I want to be doing?” – even when a big exit is on the horizon.
Psychological safety isn’t about making everyone comfortable.
It’s about making it safe to tell the truth early – when there’s still time to do something about it.
Why Coaching Alone Doesn’t Fix This
I’m a huge believer in leadership coaching. We do a lot of it.
But when you have:
- founders who won’t talk directly to each other,
- executives who are afraid to push back, and
- an entire leadership team dancing around unspoken power dynamics…
…you don’t just have a leader problem. You have a system problem.
You can coach the CHRO to set better boundaries.
You can coach the founders to be more self-aware.
But until you redesign:
- Who decides what
- How decisions are made
- How conflict is surfaced and resolved
- How meetings are structured and who’s in the room
…you’re putting very expensive Band-Aids on a structural fracture.
What High-Growth CEOs and Founders Need to Do First
If any of this sounds familiar, here’s where to start.
1. Answer the uncomfortable question: Who is actually in charge?
On the org chart, the CEO or co-founder might be “in charge.”
In practice, everyone knows who really sets the agenda and who can quietly veto decisions.
Name it.
You don’t have to flatten every power dynamic, but you do need to clarify:
- Who has final decision rights in which domains?
- Where does the buck actually stop?
- What decisions require true team debate vs. “inform and align”?
Ambiguity at the top is one of the fastest ways to kill psychological safety below.
2. Fix the meeting architecture – it’s not trivial
Bad meetings are not a calendar problem; they’re a leadership problem.
Start with:
- Right conversations, right rooms.
Some conversations belong only with the executive team. Some with the next layer down. Stop “thinking out loud” in front of the whole org and then acting surprised when people feel whiplash.
- Fewer priorities, ruthlessly chosen.
If you leave a meeting with 37 “top priorities,” what you actually have is zero. Psychological safety includes the safety to say, “We can’t do all this,” without being labeled “negative.”
- Real decisions, not performative consensus.
Decide how you decide: vote, CEO call, recommendation + ratify. Then be explicit: “We’ve heard all perspectives; here’s the decision and why. If you disagree, say it now.”
If people still feel they need a side meeting to say what they really think, your meeting design is broken.
3. Put psychological safety on the operating dashboard
If you’re serious, you’ll measure it.
Not just, “Do you feel safe speaking up?” but:
- “In the last month, I’ve disagreed with a senior leader in a group setting and felt respected.”
- “Important decisions are openly debated at our level; they don’t just show up as done.”
- “I understand how and where to escalate concerns without fear of retaliation.”
Track it by team. Talk about it in ELT meetings. Treat it like you would churn, margin, or NPS.
4. Give your CHRO a real mandate – not just emotional labor
If your head of people is:
- running interference between founders,
- absorbing everyone’s frustration,
- and quietly doing the work of three jobs…
…you don’t have a CHRO. You have a human shock absorber.
Clarify:
- What only the CHRO should own (e.g., org design, leadership standards, succession, culture strategy).
- Where founders need to step back and let her lead.
What support she needs – from you – to stop playing traffic cop and start acting like the architect of the people system.
Psychological safety is not about being “soft.”
It’s about building a leadership system where the truth can show up early, decisions can stick, and your best people don’t burn out being the glue that holds everything together.
In high-growth companies, especially those led by strong founders, this work is not optional.
It’s the difference between a team that scales – and a team that quietly starts planning their exit while the company is still on the rise.