Tip
Ada Chen Rekhi had been coaching a seed-stage founder on Zoom for months—brilliant operator, sharp strategic thinking. When they met for lunch in person, the founder showed up dressed like a weekend hangout: old T-shirt, hair in a claw clip, bra straps showing. Ada gave her the feedback: “There’s a gap between how I’ve come to know you as an operator and how you presented at lunch. These are fixable things that might affect how investors perceive you.” The founder’s response: “No one has ever connected the dots for me. I’m about to go into fundraising. This is incredibly helpful.”
Turns out giving hard feedback about unwritten rules is something only experienced people can do.
No one had told the founder because it’s risky. Your manager won’t give feedback on physical appearance—there’s no winning, only liability. HR won’t touch it. Peers won’t risk the relationship. So people navigate entire careers without learning the game mechanics: what “executive presence” actually means, what polish looks like, how people get disqualified for fixable things.
If you’re experienced enough to see these dynamics, give people the hard feedback everyone else is too scared to give. Do it with care: explain why you picked them, show you’re invested in their success, make it about their work not about them personally.
Staying quiet isn’t neutral—it’s selfish. You’re protecting yourself from discomfort at their expense.
You can see these unwritten rules because you’ve been in the room long enough to decode them. You’ve watched careers accelerate or stall on presentation, polish, executive presence. Younger managers are still navigating it themselves—they can’t explain what they don’t fully understand yet. You’re past that. You’ve cracked the code. That’s the responsibility that comes with experience.
Context
Ada Chen Rekhi interviewed 80+ people about coaching and discovered the most valuable feedback was often about “game mechanics” no one explains—how to network, how to present yourself, what the unspoken rules are. This feedback only lands when it comes from someone with authority and earned trust.
For experienced professionals, this is wisdom transfer that matters: you can see the patterns clearly enough to articulate them, and you have the standing to deliver feedback that would be risky from anyone else.