How do I manage someone who does good work but misses every deadline?
Stop trying to make feedback comfortable. That's what's making it worse.
Series
Straight Answers
Direct answers to the questions managers ask.
49 pieces
How do I make time for strategic work when I'm drowning in operational stuff?
Your calendar is full of urgent operational work. Approvals, firefighting, meetings about immediate problems. You know you should be thinking strategically: planning, improving systems,
How do I delegate work that I could do better and faster myself?
You're not saving time by doing it yourself. You're spending your career doing work below your pay grade while your team learns nothing.
How do I give someone hard feedback without them shutting down?
You know something's not working. You've been thinking about it for weeks. Finally, you sit them down and say "your work quality has been slipping." They get defensive, you backtrack, and nothing improves. Vague feedback is worse than no feedback.
Should I promote my best individual contributor to manager?
The best individual contributors often make mediocre managers. The skills don't transfer. Being excellent at writing code doesn't mean you can teach someone else to write code. Closing deals yourself is different from building a system that helps five people close deals.
What makes 1-on-1s actually valuable vs. just going through motions?
Most 1-on-1s are status updates dressed up as conversations. You ask how things are going. They say "fine." You ask about their projects. They tell you what you already know from Slack. Thirty minutes later, nothing changed except you both feel like you checked a box.
How do I split my time between my best and worst performers?
Most managers get this backwards. They spend 70% of their time on underperformers trying to fix what's broken, and 10% on top performers who "don't need help." The math says do the opposite.
Is it worth paying to retain someone who got a competing offer?
The reality? Most of the time, if someone's looking, they're already gone. The counter-offer just delays the inevitable while making it more expensive.
When is training people worth it vs. just hiring better?
Most training is a waste of money. Not because training doesn't work, but because you're training the wrong people in the wrong skills. Here's the break-even calculation.
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