“So…I want to do a 360. On myself. Live. With the team.”
That’s how it started.
Our CEO had just raised a big round. The business was scaling fast. Like any founder under pressure, he craved real feedback.
Not surveys. Not sanitized updates.
He wanted truth. From his team. In real time.
Cue nervous laughter.
(Mine. I was three weeks in as the new Chief People Officer.)
We all know: live, unfiltered feedback is like handing the mic to your in-laws at your wedding and saying, “Go for it.”
But he was serious. And bold.
So I built a leadership session to make it safe and real. No anonymous forms. No buzzwords. Just one question:
“What’s it like to be led by me?”
But I didn’t ask it directly. Too vague. Too HR-town.
Instead, we started here:
“Which A-players are close to quitting?”
Silence.
Then: “Taylor’s halfway out. She’s been pushing for clarity for months.”
Suddenly, we weren’t talking about people. We were talking about leadership signals.
Next up:
“What toxic behaviors do I accidentally reward?”
Turns out: hero culture was thriving.
Late nights, chaos saves, skipping process = praised.
Consistency and planning = ignored.
“You reward chaos,” one exec said. “We have to break something to get your attention.”
That landed.
We worked through more prompts:
→ “Where do my decisions create unnecessary work?”
(“Your 1am Slacks derail entire teams.”)
→ “What broken promises are breaking trust?”
(“We say quarterly planning matters. Then we blow it up two weeks in.”)
→ “What metrics force people to cut corners?”
(“Time-to-hire. We’re chasing speed and bleeding quality.”)
We didn’t call it feedback.
We called it data.
The CEO didn’t defend. He listened. Asked questions. Said: “Wow. First time I’ve heard that. Thank you.”
The team found their voice, because the questions weren’t personal. They were structural.
Not “You’re exhausting.”
But “What team burnout signs am I missing?”
Not “You suck at communication.”
But “Where do good ideas get sidelined in our team?”
By the end, we had 15+ insights. Not just about the CEO, but how they worked as a team.
That’s the thing: it’s never just about the leader. But the leader sets the tone.
What the CEO learned:
✔️ Late-night brainstorms = chaos, not creativity
✔️ Silence on underperformance speaks louder than words
✔️ “Be scrappy” was read as “skip structure”
What the team learned:
✔️ Feedback can be shared, not scary
✔️ Most pain is structural, not personal
✔️ Honesty is easier when it’s invited
Today, the CEO has:
✅ Paired weekly planning with “do not disturb” time
✅ Started celebrating process, not panic
✅ Rewritten company values with the team
✅ Killed hero culture (with kindness)
And he’s still asking questions.
Because real feedback starts with real questions:
🔹 “Where do we look good but perform badly?”
🔹 “Where does our growth strategy miss the mark?”
🔹 “What quick wins do we overcomplicate?”
Want to hear what people really think?
Give them something real to respond to.
That’s how it started.
Our CEO had just raised a big round. The business was scaling fast. Like any founder under pressure, he craved real feedback.
Not surveys. Not sanitized updates.
He wanted truth. From his team. In real time.
Cue nervous laughter.
(Mine. I was three weeks in as the new Chief People Officer.)
We all know: live, unfiltered feedback is like handing the mic to your in-laws at your wedding and saying, “Go for it.”
But he was serious. And bold.
So I built a leadership session to make it safe and real. No anonymous forms. No buzzwords. Just one question:
“What’s it like to be led by me?”
But I didn’t ask it directly. Too vague. Too HR-town.
Instead, we started here:
“Which A-players are close to quitting?”
Silence.
Then: “Taylor’s halfway out. She’s been pushing for clarity for months.”
Suddenly, we weren’t talking about people. We were talking about leadership signals.
Next up:
“What toxic behaviors do I accidentally reward?”
Turns out: hero culture was thriving.
Late nights, chaos saves, skipping process = praised.
Consistency and planning = ignored.
“You reward chaos,” one exec said. “We have to break something to get your attention.”
That landed.
We worked through more prompts:
→ “Where do my decisions create unnecessary work?”
(“Your 1am Slacks derail entire teams.”)
→ “What broken promises are breaking trust?”
(“We say quarterly planning matters. Then we blow it up two weeks in.”)
→ “What metrics force people to cut corners?”
(“Time-to-hire. We’re chasing speed and bleeding quality.”)
We didn’t call it feedback.
We called it data.
The CEO didn’t defend. He listened. Asked questions. Said: “Wow. First time I’ve heard that. Thank you.”
The team found their voice, because the questions weren’t personal. They were structural.
Not “You’re exhausting.”
But “What team burnout signs am I missing?”
Not “You suck at communication.”
But “Where do good ideas get sidelined in our team?”
By the end, we had 15+ insights. Not just about the CEO, but how they worked as a team.
That’s the thing: it’s never just about the leader. But the leader sets the tone.
What the CEO learned:
✔️ Late-night brainstorms = chaos, not creativity
✔️ Silence on underperformance speaks louder than words
✔️ “Be scrappy” was read as “skip structure”
What the team learned:
✔️ Feedback can be shared, not scary
✔️ Most pain is structural, not personal
✔️ Honesty is easier when it’s invited
Today, the CEO has:
✅ Paired weekly planning with “do not disturb” time
✅ Started celebrating process, not panic
✅ Rewritten company values with the team
✅ Killed hero culture (with kindness)
And he’s still asking questions.
Because real feedback starts with real questions:
🔹 “Where do we look good but perform badly?”
🔹 “Where does our growth strategy miss the mark?”
🔹 “What quick wins do we overcomplicate?”
Want to hear what people really think?
Give them something real to respond to.
