Lessons Learned (over decades)

Time’s 2025 Person of the Year is ‘The Architects of AI’. From the December 11 issue:

“It is the story of how [Jensen] Huang and other tech titans grabbed the wheel of history, developing technology and making decisions that are reshaping the information landscape, the climate, and our livelihoods.”

Every December for the past 19 years, I featured the best lessons I learned during the past 12 months. This year I took a different approach: using AI to create it for me. How? I uploaded everything I’ve written since 2004 – 353 articles, columns and blog posts – and asked ChatGPT to find the 65 best lessons. Seemed like a good number since I turned that age in June.

These ‘Lessons Learned’ capture patterns that separate good leaders from great ones. Each one is practical, clear, and grounded in everyday moments. Rather than reading them and moving on, print them and compound their impact on your leadership.

Happy Holidays. Merry Christmas. Happy New Year. May 2026 bring peace to the world, an end to uncertainty, and joy to your family, friends and those you work with each day…

People take their cues from you:
How you show up each day tells your team what matters; your steadiness creates their steadiness

Trust is built in everyday moments: Follow-through, consistency, and respect speak louder than any message; small behaviors create big credibility

Clarity reduces friction: Teams move faster when expectations are simple and specific; clear direction beats intensity every time

Listening is how leaders earn influence: When people feel heard, they lean in; give them space to finish, and they’ll bring more to the table

Specific feedback drives real change: General comments rarely help; point to the exact behavior so the person knows what to repeat or adjust

Your presence sets the temperature: A calm, grounded tone lowers anxiety and keeps people focused; others rise or fall to the energy you bring

You don’t need all the answers: Your role is to create the space for others to think; ask questions that pull out their best ideas

Coaching happens in the hallway: Short, timely conversations fuel growth; use those small openings to build awareness and momentum


Preparation replaces anxiety with confidence: A few extra minutes of planning changes the way you walk into a room; confidence comes from being ready

Reinforce what you want to see more of: People repeat what gets noticed; celebrate the behaviors that shape the culture you want

Delegation grows people: Handing off work builds skill and trust; give people the outcome, not the step-by-step

Accountability begins with agreement: People commit when expectations are clear and shared; confirm the finish line before the work starts

What you tolerate becomes your culture: Ignoring issues sends a message; address things early while they’re still small

Curiosity strengthens relationships: Questions soften tension; they help you understand what’s really going on beneath the surface

Your team mirrors your pace: If you rush, they rush; if you stay steady, they find their footing

Slowing your response improves communication: A brief pause before speaking helps others feel respected; it also gives you time to think


Strong questions build strong teams: Questions that push people to think forward create ownership; people rise to what they help design

Simplicity drives execution: Most decisions don’t need complication; choose, align, and move

Recognition matters more than you realize: People want to know their effort is seen; a genuine thank you carries real weight

Involvement increases commitment: Bring people into the process; they support what they help shape

Direct is respectful: Clear, honest communication prevents confusion; avoiding a message usually makes things harder

Leaders who seek feedback grow faster: Inviting input shows confidence, not weakness; it keeps blind spots from becoming real problems

Your energy walks into the room before you do: Optimism and frustration both spread; be intentional about the tone you bring

Conflict isn’t a threat: Healthy teams disagree and stay connected; leadership is guiding those conversations with purpose


Meetings should create movement: If it doesn’t lead to alignment, a decision, or an action, it’s not a meeting; it’s a delay

Great leaders make complexity understandable: People perform better when things make sense; break issues into plain language

People speak up when they feel safe: Psychological safety leads to better decisions; silence is more dangerous than disagreement

Daily habits shape leadership more than big gestures: Consistency beats intensity; small, steady practices build trust

Ownership changes everything: When people generate their own options, they follow through; ask, “What do you see as your next step?”

Culture starts at the top: You can’t delegate what you model; people watch your behavior more than your statements

Lead with strengths: People grow faster when you focus on what they do well; improve the gaps that matter most

Speak to be understood: Skip jargon; clear talk creates alignment and momentum


Focus is a leadership skill: Help people concentrate on what matters most; attention drives results

Capacity must match expectations: Burnout shows up when leaders ignore bandwidth; adjust priorities with honesty

Accountability grows through questions: Asking “What will you do next?” turns ideas into movement; it builds commitment

Appreciation is a performance tool: When people feel valued, they contribute more; recognition is cost-effective leadership

Time with people is never a distraction: Coaching and listening are not extra tasks; they are the core of leadership

Boundaries teach people how to work with you: Consistency builds trust; mixed signals create frustration

Confidence grows from practice: You improve by doing; repetition builds comfort more than talent does

Leaders must challenge their own assumptions: Your internal story shapes your behavior; make sure it’s accurate


Delegating outcomes unlocks creativity: People innovate when they have room to decide how to deliver; trust the process

Leaders model learning: Admitting mistakes and asking questions make others feel safe to learn; this drives improvement

Presence is about attention, not time: A few focused minutes can move work forward more than a distracted hour

Assumptions are expensive: Clarify meaning before reacting; it prevents unnecessary conflict

Reflection is a leadership tool: Taking time to think improves future decisions; reflection turns experience into insight

Decision-making takes courage, not certainty: You rarely get perfect information; move with what you know today

Frontline voices make everything better: The people closest to the work spot issues first; ask them what they’re seeing

Your emotional state shapes everyone else’s: A leader’s mood sets the tone; stay steady when pressure rises


Growth requires discomfort: Stretching skills feels uneasy at first; support people while still expecting progress

Leaders earn respect by owning mistakes: It shows maturity and builds trust; it also gives others permission to learn

Coaching builds independence: Every time you solve a problem for someone, you limit their growth; guide them instead

Emotion often reveals the real issue: Listen for tone, pauses, and hesitations; they reveal what’s underneath the words

Silence is a performance tool: A quiet moment helps people think more deeply; leaders don’t need to fill every gap

Prioritization creates momentum: Not everything deserves the same attention; focus lightens the load for everyone

Clear expectations build confidence: People perform better when they understand exactly what good looks like

Leadership starts with self-management: If you stay grounded, others will too; emotional discipline is a leadership advantage


Gratitude strengthens teams: Thanking people for real contributions builds loyalty and energy; gratitude is simple and powerful

People want meaning, not just tasks: Explain the ‘why’ behind work to create engagement; purpose fuels performance

Better questions elevate the quality of thinking: Shift from telling to asking; it changes the quality of the conversation

Understanding beats assuming: Check for clarity; ask people to restate what they heard in their own words

Consistency is a leadership multiplier: When people know what to expect from you, trust grows; predictable leadership reduces drama

Sustained focus compounds performance: Teams move faster when distractions are removed; clarity of attention drives results

Leaders rise by helping others rise: Your success grows when you develop others; share the spotlight

Undistracted listening builds trust faster than advice: People feel respected when you truly hear them; it strengthens the relationship and the work

Leadership is a daily decision: Each interaction is a chance to reset, influence, and model who you want to be; small choices create big impact

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