Why? They want a promo code
Why? They think your price is too high
Why? We didn't do market research
Why? We're understaffed
Why? I haven't filled the position
Magic, right?
Well, almost.
7/ The 6th Why
Do you notice what happens as we move through the Whys?
💡 They get specific -> We progress from what happened to what caused it.
💡 And more personal -> Groups narrow to individuals.
There's one more Why & it's uncomfortable.
But that's where the growth is.
8/ Back to our example
Why haven't you filled the position?
❌ Maybe you designed an unattractive role
❌ Perhaps you didn't see the demand coming
❌ Or you are losing people faster than you can hire
These answers are raw & imply something about YOU is causing the issue.
9/ This isn't just about work
I can't get in shape
Why? No time to workout
Why? Day is packed with work
Why? My boss keeps piling on more
Why? B/c I haven't told her no
Why? B/c I can't disappoint her
Why? B/c I need the money
Wait, it's a money issue not a fitness problem?
10/ Now what?
Don't overreact to one mistake. We all make them.
Do watch for patterns of mistakes. These tend to reveal true weaknesses.
Most managers have a fuzzy picture of their people.
They know job titles and recent projects. Maybe some surface-level preferences.
High-performing managers have high-fidelity pictures of every team member.
Here's how AI helps you build them:
THE PICTURE YOU NEED
A complete view includes:
• Capabilities (what they can do)
• Preferences (how they work best)
• Character & Values (who they are)
• Expectations (what success looks like)
• Development goals (where they're headed)
CAPABILITIES: What they can do
Feed AI:
• Performance reviews and peer feedback
• Project outcomes and deliverables
• Examples of their best work
Prompt: "Analyze these and identify their top 3 competencies and 2 growth areas."
Good feedback drives people to change.
Bad feedback drives them out the door.
A simple playbook to get it right 🧵
Clarity
Without clear expectations, all feedback feels like criticism.
- Define what excellence looks like upfront
- Use measurable language that eliminates interpretation
- Provide specific examples that illustrate the standard
Clear is kind. Ambiguity is future resentment.
Contrast
Meaningful improvement requires seeing the gap.
- Highlight the difference between current and desired states
- Use data to size the gap accurately
- Acknowledge progress by measuring distance traveled
The gap isn't a judgment.
It's the roadmap to growth.
- Acknowledge your mistake proactively
- Take full responsibility (no excuses)
- Make amends where possible
- Commit to specific behavior changes
- Ask for the chance to earn it back
You can't erase mistakes.
You can earn back trust.
The "Broken Windows Theory" of Trust
Small violations predict larger ones. Missing deadlines. Showing up late to meetings. Forgetting commitments. These aren't minor issues. They're the first sign of trust erosion. Fix them immediately or watch your credibility fade away.
The top performers all follow the same 5-step oversight system that drives results without micromanaging their teams.
Here's exactly how they do it:
1. Create Clarity
Establish 5 parameters upfront:
• Outcome: What success looks like
• Quality: What signals done
• Method: Agree on how the work gets done
• Timeline: Set clear milestones and deadlines
• Risk: The boundaries for autonomy
2. Preview Your Approach
Calibrate oversight based on:
• How critical the work is
• Their confidence in the person
Then communicate the plan:
• "I'll check in at these specific points..."
• "Here's how I'll measure progress..."
Every company has a North Star metric:
• SaaS: Net Revenue Retention
• Consumer: Monthly Active Users
• Retail: Revenue Per Square Foot
• Manufacturing: Margin Per Unit