Dear Ryan,
I’m a COO at a mid-size RIA and I’m at my breaking point. Our CEO is brilliant (I mean that sincerely) but getting him to actually hear feedback has become a full-time job on top of my actual full-time job. I’ve watched good people leave because they felt invisible.
I’ve seen us make the same mistakes two and three times because the post-mortem never really happened. I’ve brought things up directly. I’ve tried putting things in writing. I’ve even recruited allies on the leadership team to echo the same concerns. Nothing lands.
The frustrating part is that he genuinely believes he’s open to feedback. He says it constantly. He talks about psychological safety in all-hands meetings. He just doesn’t practice it. And I don’t think he knows.
I’m not ready to leave. I care about this firm. But I’m running out of ideas and, honestly, running out of patience. How do you get through to someone who doesn’t know they’re not listening?
– Frustrated in the C-Suite
Dear Frustrated in the C-Suite,
First, respect for still being in the fight. Most people in your position have already updated their LinkedIn and started ghosting calendar invites.
But I want to challenge the premise.
You asked how to get through to someone who doesn’t know they’re not listening. Right question, but there’s a harder one underneath it: How do you know you’re not part of the pattern?
Hear me out. In almost every version of this story I’ve encountered, the leader who can’t hear feedback has been surrounded by people who’ve learned to deliver it in ways that are easy to dismiss. Too soft. Too hedged. Too wrapped in reassurance to actually register as a problem. We do it to protect our relationships. We do it to protect ourselves. And eventually it becomes background noise. It’s the organizational equivalent of a car alarm nobody looks up for anymore.
Stevie Nicks once said the band stayed together because they were too stubborn to quit and too honest to pretend. That second part is the one most leadership teams skip.
So try this: Say the hard thing, plainly, once, without softening it. Not in a memo. Not through allies. Directly with eye contact: “I think we have a listening problem on this leadership team and I want to talk about it.”
No preamble. No compliment sandwich.
If it lands, you have your answer. If it doesn’t, you also have your answer. You’ll know you actually tried before you made any bigger decisions.
The leaders who don’t listen aren’t always broken. Sometimes they’re just waiting for someone to stop being polite.
– Ryan
Ryan George is the Chief Marketing Officer of Docupace.
