I’m leading a strong senior team—smart, experienced, and committed. But they’re not holding one another accountable. Issues linger longer than they should. Conversations get softened—or skipped altogether. And feedback that would help… comes too late to matter. These are good leaders. They care. So I’m struggling to understand what’s getting in the way—and what to do about it. #AskingForaFriend
Dear Friend,
I'm so sorry you're dealing with this and you are right to be concerned. Sadly what you're experiencing is frustratingly common.
In fact, it’s one of the most common—and expensive—patterns I see when I'm brought in by senior teams to help them build a more Courageous Culture.
On the surface, it looks like a feedback issue.
But underneath, it’s something more subtle: These conversations feel too risky.
Why Accountability Conversations Feel Risky For Your Senior Team
Your leaders are constantly (and often unconsciously) weighing:
“Will this damage a relationship I need to get results?”
“Am I seeing the full picture—or stepping into something political?”
“Is this worth the potential friction?”
So instead of being clear, they calibrate.
They soften the message, or put it in the diaper genie. They wait for a better moment. Or convince themselves it’s “not a big deal.”
And then a few predictable things start to happen:
Small issues don’t stay small. Workarounds replace real solutions. Frustrations go underground instead of getting resolved.
You start seeing more alignment meetings… and less actual alignment.
There’s another dynamic at play too.
By the time someone reaches a senior role, a few quiet assumptions often take hold:
“They should already know this.”
“I shouldn’t need to coach someone at this level.”
“My job is to stay focused on the big picture.”
So feedback gets deprioritized.
Not intentionally. But consistently.
The Impact on Your Culture
And when leaders do step in—without a shared approach or enough practice—it often lands one of three ways:
Too indirect to be useful. Too blunt to be heard. Or too late to matter.
So they back off the next time.
Now here’s where this becomes a culture issue:
Your senior team isn’t just managing performance. They’re modeling how leadership works here.
So when they hesitate…
That hesitation travels.
Down into their teams. Across functions. Into how problems get raised—or avoided.
Before long, you don’t just have a few missed conversations.
You have a pattern:
- People waiting instead of addressing
- Leaders guessing instead of clarifying
- Teams working around issues instead of through them
And the cost shows up everywhere—speed, engagement, retention, results.
So what shifts this?
Shared vocabulary and approach. Shared commitments. Modeling the way.
Investing in Your Senior Team's Ability to Have the Tough Conversations
The shift happens when your senior team builds three things—together:
Confidence – so they address issues earlier, not later
Competence – so feedback is clear, specific, and useful
Courage – so they’re willing to consistently say what needs to be said.
And this is the part many organizations skip:
They try to cascade feedback expectations… without first aligning and equipping the people at the top.
The most effective executive teams we work with take a different approach.
They go first.
They build the skill together. They practice. They create a shared standard for how feedback happens.
And once that happens, everything downstream gets easier:
Conversations are quicker. Expectations are clearer. Accountability feels normal—not personal.
If your senior team is struggling with this, the fastest way forward is to help them build the skill—together, and then teach it to their teams.
Because when your senior leaders experience what good looks like—and practice it together
They don’t just support a feedback culture.
They model it in a way that sticks.
Related: Scaling Success Starts With Principles, Not Replication