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

Blown Away

I haven’t written much recently. Seems after 20 years of monthly commitment to the craft, I needed a break. Not so much because of ‘writer’s block’ as realizing that most of my recent posts were about the same subject. As our daughter said, ‘Dad, I don’t have a conversation with you anymore that you don’t mention AI.”

Then today I discovered something new – and the writing gods called me to share. It was a ‘you’re kidding me’ moment… about… AI.

Google NotebookLM is one of the best uses of AI I’ve seen. In its own words: “NotebookLM is an AI-powered tool designed to help users comprehend and interact with complex information. Users can upload various source types, such as documents, web pages, and audio files, into separate notebooks to organize their projects.”

After reading that, I uploaded the PDF version of my book – a compilation of my newsletters, magazine articles and blogs that we published five years ago – then I asked NotebookLM to create a podcast that focused on many of the key themes. One minute later two AI-generated hosts discussed my book in a conversational style that is spot-on accurate and comes across as authentic.

If you’re interested, here’s a link to ‘their’ discussion of some of the best stories and lessons learned from Words Flow Through Me. (FYI… when they refer to ‘the source’ or ‘the author’… that’s me.) Enjoy!

Lasting Legacy

Someone I know died last month. I didn’t know him well; he was the founding member of a group of coaches who gather monthly to discuss business and hone skills. He started it some 20+ years ago. I joined in April 2020, at the beginning of Covid. For years they met in person… during my time it’s on Zoom.

My first impressions of this Vietnam Vet were ‘this guy doesn’t have any filters.’ He wasn’t shy to drop a ‘g-ddamn’ or a ‘bullsh*t’ amidst the wisdom he shared in short bursts. He had retired years earlier from an HR career and wasn’t taking on any clients. He had an oxygen tube under his nose. Some months he didn’t attend, because pulmonary fibrosis disrupted his day.

On December 11, 2023, he introduced the group to ‘something new’… an A.I. ‘disrupter’ called ‘ChatGPT.’ After he spoke glowingly of how it would ‘change everything’ including ‘how coaching is delivered,’ I weighed in with: “I don’t see this having an impact before I retire.”

Turns out my analysis might be wrong. I’ve written many blogs about the journey to adapt Large Language Models into my work – and while it has yet to overtake coaching as a discipline, that day indeed might come before I wrap things up.

The coaches group met, as scheduled, this morning… and the entire hour was to share memories of our departed friend. 

One person noted: “A lot of people talk about to never stop learning. He lived it.” Another: “He believed each person must advocate for himself.” Another: “He honored ‘holding space’ with everyone he met. That’s why he started this group and several others, including one for people suffering from pulmonary fibrosis, as soon as he was diagnosed.” One more: “His dad was a doctor in a wheelchair who died when he was a teenager. His brother had special needs and died young. He lost a son in a car accident. Life handed him some tough times… and he never stopped trying to help and mentor others.”

During the past year, he let us know that he was using ChatGPT to convert his notes into prose and poems for when he was gone. Someone asked today, “Did he get to finish that book?” Another responded: “He finished it at 10 o’clock and sent it to a handful of us to read. I spoke to his wife, who said they stayed up until midnight talking, then went to bed. When she woke up in the morning, he had died peacefully in his sleep.”

Bruce Anderson made a big ripple in the universe during his 83 years. 

Ship Shape

Our nearly 27-year-old daughter said recently: “I don’t have a conversation with dad anymore that doesn’t involve his passion for A.I.” I’ll own that. Seems like I’m using ChatGPT every day to assist with things like how to approach potential executive coaching clients, designing a graphic for PowerPoint, or helping calculate the health care costs when I go on Medicare in June. As a starting point for ideas, it’s become an extension of my creative mind thought partner.

Many businesses are rethinking how we work, travel and solve everyday problems. Here are three leveraging A.I. to unlock new business models:

Truck Parking Club. This as an “Airbnb for truckers” that helps long-haul drivers find and reserve parking spots in real time. Parking is a massive issue in the trucking industry, costing drivers time, money, and energy. TPC steps in to match supply and demand dynamically, creating a marketplace where private property owners offer space and truckers secure reliable rest spots. 

Shappi. The logistics startup connects travelers with people who need to send international packages – turning extra luggage space into a valuable asset. Blending trust, efficiency and a gig-economy mindset, Shappi is challenging traditional shipping methods… and helping those who venture from home earn spending money.

Harvey. This A.I. legal assistant helps law firms automate research and draft contracts – and even provide case insights – by reducing mundane tasks and increasing critical thinking time. Harvey isn’t replacing lawyers; it’s amplifying their output by allowing them to be even more efficient and even more strategic, while freeing up time for higher-value client work.

The real value of A.I. isn’t automation, it’s transformation. Much like when leading companies failed to innovate in bygone eras – Westfield buggy whips, Corona typewriters, Fox Photo – the ground is shifting quickly. Don’t bury your head and get left at the (steam engine train) station. Why, our daughter even remembers when we used to go to Blockbuster Video.

Note: Fans of ‘Suits’ likely get the inside joke of Harvey.