The leadership challenge I see more than any other?
Executive leaders who believe they’re giving clear, consistent developmental feedback—while their people quietly insist the opposite.
I hear it all the time from CEOs and execs:
“We hold people accountable.”
“We set clear expectations.”
“I give feedback all the time.”
And then I talk with their direct reports:
“I never get feedback from my boss.”
“The last time she gave me input was during my performance review.”
“I have no idea what he thinks of my performance… I assume no news is good news?”
That gap is real. And it’s costly.
If you struggle with developmental conversations, here are a few simple places to start:
1. Start with the function, not the person.
Ask: What does the organization need from this function?
Are those needs being met? Does everyone agree on what success looks like? Is the performance on track?
2. Then look at the leader.
Not just their outputs—how they show up.
I hear things like:
“He’s invisible to his people.”
“She’s the CRO—she needs to be inspiring this team.”
“He’s so hard to follow in meetings. People consistently tell me they’re confused.”
These are real examples from real executive teams.
3. Review the expectations you’ve actually communicated.
In the last 6 months, what have you clearly articulated—about both performance and behaviors?
Is it written down? Trackable? Consistent?
And the real question:
Have you ACTUALLY said these things out loud?
If it’s not been communicated to them (and recently), it doesn’t count.
Avoidance of these difficult conversations often sounds like:
“It’s not the right time.”
“They’re sensitive.”
“They should already know.”
“I don’t want them to leave.”
Avoidance is still avoidance.
Try these three simple rules for developmental conversations:
- Set clear expectations up front.
- Be timely, specific, and consistent.
- Tell the kind truth.
If you were the one needing development, how would you want your boss to treat you?
Most leaders would say: Respect me enough to give it to me straight.
Your people want the same. And giving them that clarity is one of the most profound expressions of leadership.