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.
Firing people sucks. The only thing worse is being fired. It is easiest to push the idea from your mind. Ignore it. But in each life, there are moments that matter 100x more than others. Those are worth being prepared for. This is one of those moments. Here's how to be ready:
Watch the Radar
Layoffs rarely surprise.
Internal: Slowed spending? Frozen hiring? Leaders distracted by "secret" projects? Why? They stop the bleeding before cutting deeper.
External: Layoffs at competitors? Fundraising stalled? Ask: How different is your company?
Build a Runway
You'll make better decisions if you're not worried about basic needs. Get on the fast track to saving 6 months of living expenses. How?
Reduce your burn: lower costs from big to small
Grow your income: spin up your side hustle now
Unclear expectations cause 95% of problems at work. The manager is frustrated. The employee is confused. Everyone loses. Here's my simple playbook for managers and employees to get on the same page fast:
If you're the manager:
Setting expectations is your primary job.
If your team doesn't know what you expect, you're failing them. And despite great effort, chances are they're letting you down.
The vicious cycle of frustration builds.
If that's the case, there are only three causes:
1. You're not managing your boss well 2. You're incapable of making a decision 3. You're hoping people will read your mind
I've trained 1400+ managers. They all struggle with delegation. The issue isn't assigning work. It's ensuring the work gets done well without micromanaging. Here's a simple 5-step system for helping your team succeed:
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..."
If I've learned one thing about leading teams the last 25 years, it's that you won't get anywhere without trust.
Here's how to build it (and keep it)🧵
There are 4 types of trust.
Each one build upon the previous:
• Character Trust (integrity)
• Capability Trust (skills)
• Consistency Trust (reliability)
• Connection Trust (relatability)
Skip one and your foundation is shaky at best.
CHARACTER TRUST
• Do what you say you'll do
• Take radical ownership of mistakes
• Be honest even when it's uncomfortable
• Make decisions based on principles, not politics
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.