We turn it over in our head. We ask a few more questions. We look for one more data point. We check with another person whose opinion we respect. We wait for the timing to feel right.
And still, we hesitate.
We tell ourselves we need more information. More time. More certainty.
Indecision usually grows from very human places. Fear of being wrong. Fear of being blamed. Fear of choosing a path that can’t be undone. Fear of embarrassment.
Add decision fatigue to the mix and postponement starts to feel reasonable.
Meanwhile, the cost of waiting accumulates quietly. Teams stall. Momentum fades. Confidence erodes. What began as a thoughtful pause turns into drift.
Most leadership decisions are made without perfect information. Progress rarely waits for certainty.
So, what is our hesitation really telling us?
Sometimes, it’s a clear no. A request pulls us away from what matters most. We don’t like what we see, but we’re not sure why. Maybe a partnership doesn’t sit right with our values. In these moments, extended thinking isn’t searching for clarity. It’s searching for a way to explain our decision.
Other times, we hesitate because the decision stretches us. It introduces uncertainty. It raises our visibility. It asks more of us than we feel ready to give. Growth decisions usually feel uncomfortable before they feel right.
At some point, the data stops improving and the waiting stops helping.
Start small. Take a step that tests the decision rather than locking it in. Forward motion reveals new information…something thinking alone can’t.
A decision that turns out to be wrong isn’t failure.
It’s feedback.
And feedback points us toward our next decision.
“Whenever you see a successful business, someone once made a courageous decision.” — Peter F. Drucker
Photo by ChatGPT’s new image generator, which is way better than prior versions of the tool.
Ideas and wisdom often arrive with familiar roots.
My views on leadership come from my lived experiences and lessons I’ve learned from great builders and thinkers like Andrew Carnegie, Peter Drucker, Tom Peters, Ken Blanchard, Marshall Goldsmith, Zig Ziglar, Stephen Covey, Jack Welch, Seth Godin, Jeff Bezos, Gary Vaynerchuk, Tim Ferriss, Jocko Willink, James Clear, and countless others.
I’ve also worked with amazing managers and mentors over many decades, including a few who taught me what not to do.
Since I find myself often returning to these lessons, I thought it would be useful to write them down in a list for easier reference.
Leadership Foundations
1. Leadership begins in your mind long before it shows up in your actions.
2. Self-awareness is a leader’s first and most enduring responsibility. Know how your actions land, then lead on purpose.
3. Character outweighs credentials over the long haul.
4. Integrity compounds like interest. The longer you hold on to it, the more it grows.
5. Values are the compass that keep you on course when circumstances shift.
6. Humility is the strength to put others first.
7. Influence comes from trust, not job descriptions.
Vision and Direction
8. A leader’s vision must be big enough to inspire, but clear enough to act on today.
9. Clarity reduces fear. Ambiguity fuels it.
10. Momentum builds when people see the destination and believe they can reach it.
11. Vision is not just what you see. It’s what you help others see.
12. The clearer you are about the goal, the less room there is for fear to grow.
13. Purpose is the map. Storms are just temporary detours.
14. Belief in the destination turns small steps into powerful strides.
15. Every action should feel like part of the same bigger story.
16. Sometimes waiting is the boldest move you can make. Strategic patience is powerful (and extremely difficult).
People and Relationships
17. The right people in the right roles multiply results beyond what you can imagine.
18. A culture of respect will outlast a culture of urgency.
19. Listen like the person speaking might hand you the missing puzzle piece.
20. Pass the applause to others but keep the accountability close to your chest.
21. Trust is invisible, but when it’s gone, everything feels heavier.
22. Relationships need regular deposits of attention, not just withdrawals of effort.
23. Helping someone else win creates a tailwind for your own success.
Decision-Making
24. Good decisions blend facts, values, and the courage to act.
25. The first idea is often just the trailhead. Walk farther.
26. Energy without wisdom burns out. Wisdom without energy gathers dust.
27. Choose the option you can defend in the daylight and live with in the dark.
28. A quick, small decision can open doors a perfect plan never reaches.
29. It’s easier to fix a wrong turn early than to build a new road later.
30. Never cash in tomorrow’s credibility for today’s convenience.
Resilience and Adaptability
31. A setback is a classroom, not a graveyard.
32. Flexibility is a skill, not a personality trait. Practice it.
33. Change is the proving ground where talk becomes action. Priorities sharpen, assumptions get tested, and leadership shows up in decisions, owners, and dates. If nothing changes (no decision, no owner, no date) it was only talk.
34. Adapt your tactics, but never your core.
35. The best views are earned with effort you once thought impossible.
36. Challenges test your limits so you can discover you’re stronger than you ever imagined.
37. Sticking with it usually turns “almost” into “done.”
Growth and Learning
38. The best questions are the ones you don’t yet know how to answer.
39. The moment you stop learning, you stop leading. Sometimes before you notice.
40. Pride blocks the front door to growth. Curiosity leaves it wide open.
41. Ask for feedback before circumstances force it on you.
42. Teach your knowledge, always remembering that your actions teach your values.
43. Every conversation nudges someone closer to, or further from, their best self.
44. Failure carries lessons that success hides. Corollary: High water covers a lot of stumps.
Impact and Legacy
45. Success without significance is empty.
46. The influence you have on people’s lives will outlast your achievements.
47. Your legacy is written in the lives you touch, not in the titles you hold.
48. Leadership is something you borrow from the future. It must be returned in good condition.
49. The most meaningful titles are the ones people give you, not the ones on your nameplate.
50. Think in decades when deciding what to plant today.
51. Your success is multiplied when others stand taller because of you.
52. The best proof of leadership is when growth continues without your hand on the wheel.
53. Leave every place and every person better than they were when you arrived.
Communication & Culture
54. Say the quiet part kindly and clearly. Clarity without kindness bruises. Kindness without clarity confuses.
55. Stories travel farther (and faster) than memos. Stories move people. Memos inform them. Stories turn intention into action.
56. Consistency in small signals (tone, timing, follow-through) builds culture faster than slogans.
57. Meetings should create movement. Reserve live time for decisions and collaboration. End with owners and dates. If it’s just a podcast, send an email. If only two people need to talk, make it a call and give everyone else their time back.
58. Celebrate progress out loud so people know what “right” looks like.
59. Honesty scales when leaders go first. Name the hard thing and show how to address it.
60. Culture forms around what you tolerate as much as what you teach.
Execution & Accountability
61. Strategy stalls without a calendar. Put names and dates on intentions.
62. Start now. Ship one useful thing today. Ride the wave of momentum that follows.
63. Priorities aren’t what you say first. They’re what you do first.
64. When everything is urgent, nothing is important. Choose the one thing that unlocks the next three.
65. Inspect what you expect. Review, refine, and recommit in frequent loops.
66. Own the miss publicly and fix it quickly. Speed heals trust.
67. Scoreboards matter. People work smarter when progress (or lack thereof) is visible.
Faith, Purpose & Centering
68. Quiet time isn’t empty time. It’s where courage and wisdom refuel.
69. Purpose steadies the hands when the work gets heavy.
70. Gratitude turns pressure into perspective.
71. Servant leadership begins by asking, “Who needs strength from me today?”
72. Hope is a discipline. Practice it especially when results lag.
Leading Through Change & Uncertainty
73. Name the uncertainty. People handle the unknown better when it has boundaries.
74. Trade predictions for scenarios. Prepare for several futures, not just your favorite one.
75. Replan without blame. The map changes when the terrain does.
76. Communicate more than feels necessary. The vacuum of silence fills quickly with speculation.
77. Keep experiments small and reversible, so learning is fast and affordable.
78. Endurance is contagious. Your calm can be the team’s shelter in a hard storm.
Coaching & Talent Development
79. Grow people on purpose. Make development a standing agenda item.
80. Coach with questions that build judgment and ownership.
81. When you delegate the result, delegate the authority to achieve it. Authority and responsibility should be in balance.
82. Set intent and boundaries. Agree on check-ins. Then step back so the team can step up.
83. Size stretch work to the person’s readiness. Provide the right challenge, real help, and visible sponsorship. It’s okay if they reach the result by a different route than yours.
84. Build a bench before you need one. Succession begins on day one.
Supportive Organizational Behavior
85. Make it safe to disagree. Invite the view that challenges yours.
86. Credit ideas to their source. Recognition fuels contribution.
87. Write agendas as outcomes, not topics.
Systems Thinking & Process
88. Correct the mistake and improve the system that allowed it.
89. Turn recurring work into checklists and rhythms so excellence is repeatable. Then automate it.
90. Map the flow of work end to end. Prune any step that adds no value. Unblock the rest.
91. Measure what matters. Review it at a pace that improves the work.
Stakeholders & Customer Focus
92. Start with the customer and work back to today’s priorities.
93. Define success in customer outcomes, then align processes, metrics, and rewards.
94. Close the loop by telling people what changed and why.
Conflict & Courageous Conversations
95. Address tension early while the knot is small.
96. Separate the person from the problem. Aim at the issue, not the identity.
97. Put the real issue (the skunk) on the table. Agree on facts before you debate fixes.
Energy & Well-Being
98. Protect time for deep work and recovery so decisions are sharp.
99. Model healthy boundaries. Your example sets the team’s norms.
100. Choose a sustainable pace over heroic sprints. Consistency wins the long game.
Leadership is a skill to be learned and practiced over a lifetime. It grows through steady reflection, small improvements, course corrections, and new discoveries. These reminders pull us back to what matters when life and work get noisy.
Whether you lead a company, a classroom, a project, or a family, your influence reaches far beyond the moment.
The truest measure of leadership is the people we serve and the leaders they become.
Photo by Marcus Woodbridge on Unsplash – I love the idea of a lighthouse showing the way, standing firm and steady especially when the waves are their scariest.
Your mood when you wake up. Waking up on the wrong side of the bed is your choice. You alone decide how you’ll approach each new day.
Your morning routine. What’s included or excluded? How much time are you providing for yourself in the morning? Are you rushing, or welcoming the day at the pace of your choosing?
The tone of interactions you have with others. Are you smiling when you’re talking (whether in person or by phone)? Are you looking for faults in others, or the good in others? The energy you bring is your choice.
Your career choice. Unhappy at work? What are you doing to change it? Are you changing your situation, or just complaining. Not sure if you should work in your chosen profession? What are you doing to figure it out? If this profession isn’t for you, what concrete steps are you taking to prepare to work in another profession? You decide all of it.
Whether you choose to manage your day, or let it manage you.
The places you visit and frequent.
Your hobbies. Do you even have a hobby, or are you too “busy” for anything that brings you joy or peace outside of work?
Your friends. Are they lifting you up or bringing you down? Jim Rohn said, “You are the average of the five people you spend the most time with.” Choose wisely.
The organizations you choose to join or support.
This list only scratches the surface.
It’s easiest to let someone, or something, else make the decisions for you. But remember—choosing not to decide is a decision, and you own it.
So, what kind of day will you have? What kind of life will you live?
“We must strive to exit our tomb of pessimism.” I heard this phrase echo through the Cathedral during the Easter Vigil homily, a little over a week ago.
As Catholics, we celebrate the resurrection of Jesus Christ every Easter…His triumphant exit from the tomb, three days after his crucifixion.
In a much smaller way, we have a daily invitation to cast off our heavy shroud of negativity. To exit our tomb of pessimism.
To break the shackles of hopelessness and redirect our thoughts toward a brighter horizon.
If everything great begins with a thought or an idea, imagine channeling this power toward an optimistic future, filled with amazing possibilities.
It’s easy to stay in this tomb of our own making, looking through the bars at all the people out there who are clearly happier, more successful, and have all the things we yearn for.
The truth is none of them matter. They have no impact on us…except to show us some possibilities, some ideas, and some pathways that worked for them.
We have the power to rewrite our own narrative, to pivot our lives toward a more hopeful outlook. The choice is ours alone.
Escaping the tomb of pessimism demands courage and resolve. It requires us to confront our deepest fears and insecurities, to challenge the status quo of negativity that has held us captive and kept us comforted for so long.
Yet, it is only by confronting these challenges that we can find the promise of transformation. Only through the struggle that we can discover a new sense of purpose.
Will you remain ensnared in the confines of pessimism, or will you seize the opportunity to step into the light, and walk away from your tomb of pessimism?
There isn’t a human being on this planet who can carry an entire organization themselves…
Whether you run a Fortune 500 company or a one-person shop, your ability to delegate will be the difference between success and failure. Delegation may be to an employee or a trusted vendor.
Delegation allows you to multiply yourself. It also provides an opportunity for your direct reports to grow within your company.
Right about now, you should be nodding and saying, “Obviously, Bob, tell me something I don’t know!”
So, you understand the importance of delegating. Awesome!
Consider these questions about what you’re delegating, based on the way some managers and company owners I’ve worked with over the past 35 years view the topic:
When you delegate, are you focusing on your schedule, or on your direct reports’ growth?
Do you view delegation as the art of offloading tasks you don’t want to do, or tasks that are better suited to the expertise of one or more of your direct reports?
Do your direct reports own a specific role or job that’s critical to your organization, or are they merely one of your assistants, waiting for a list of today’s tasks to come from you?
If you draw a flowchart of how your organization functions, how many of the process lines route through your head where some type of decision or approval takes place before the process can move to its next step?
How many employees do you have waiting to talk to you? Do you feel empowered by how long the line out your door is each day?
When faced with a crisis, or a short-term deadline, do you pull back all that you’ve delegated so you can do everything yourself to make sure it’s right?
When you delegate the responsibility for a task to an employee, do you trust them enough to also delegate the authority they need to own that task? If not, why not?
I worked with a manager many years ago who told me how great it was that he had a line of people waiting to see him every time he came back to his office. He said it was the first time he had felt important in his life. Wrong answer, Mr. Important Guy!
I worked with another who told me that, “These people (referring to pretty much everyone in his department) don’t work well under pressure. Whenever we have a tight deadline on a deliverable, I usually stay late and get it done myself. That way I know it’s right.” Wrong answer, Mr. Martyr!
There isn’t a human being on this planet who can carry an entire organization themselves…even though many try. Sometimes, they even fool themselves (and others) into thinking they do it successfully.
The power of any organization comes from its ability to properly delegate, multiply its talent, and foster employee growth. By the way, sometimes the cost of that growth is allowing your employees to make mistakes, or to successfully complete a task in a different way than you would have.
Get delegation right, and everyone wins. Get it wrong, and your employees will stop learning. Their motivation will wane and your organization will ultimately fail.
The accounting definition of goodwill describes it as the established reputation of a business, quantifiable by taking the fair market value of the tangible assets of a company, subtracting that amount from the full purchase price, blah, blah, blah.
The accounting definition is important, but the goodwill I’m interested in is your personal goodwill, which is measured with the answers to these questions (in no particular order):
Do you have a personal reputation as a good person?
Are you a person who can be trusted?
Are you reliable?
Do you work with others based on honesty and integrity first, above all else?
When people describe you to others, do they do so fondly or derisively?
Are you a person who people want to be around?
Do you repel people, or gather people?
Do you have a track record of acting fairly in all situations?
Do you serve others first?
When the proverbial chips are down and everything is going wrong, can others rely on you to rise above the chaos, identify root causes, and get to work solving the problems?
Are you known as the person who runs from trouble?
Are you the one who looks to blame rather than solve?
The answers to these questions will matter more to your long-term success than any college degree or career accomplishment you may achieve.
Your actions and attitudes will show people your answers more vividly than anything you say.
It’s easy to say words like honesty, integrity, trustworthiness, or empathy. The real test is how you act and what you choose to do, whether or not other people are watching.
Show me a team of people who don’t value their own personal goodwill or that of their teammates, and I’ll show you a team that fails 99 times out of 100.
The most important choices you’ll make in life are the ones that either add value to, or take value away from your personal goodwill.
Choose wisely. Your happiness and success depend on it.
With the advent of the internet, and then smartphones, we’re able to access the outside world on-demand from just about anywhere. The flipside is that the outside world can access each of us just as easily.
Friends and colleagues can send us an email or text at any time. They can use a selection of apps to “ping” us from across the world with information, photos, articles, or project status updates.
And, although rare these days, people can even call us on our smartphone…trust me, it still happens.
In all these instances, the expectation is that we’ll be fully accessible, and ready to respond immediately to any and all issues, questions, or opportunities that come our way.
An immediate-response, immediate-judgment, immediate-decision-making model of interaction is the new norm. We train our brains to quickly scan complex situations with the goal of rendering snap decisions that we can provide as part of our response(s).
There’s just one problem: creating this speedy-response capability eliminates the one thing that many decisions (especially complex and long-term decisions) require: TIME
Time and space are exactly what we need to make our most effective decisions.
Time to absorb information at our own pace.
Time to immerse ourselves in a new situation before being forced to judge it or make decisions about it.
Consider the person who gets a new job. This new job is going to be amazing. It’s what they want to do, and it pays a lot more than their last job.
It’s normal to visualize all the ways to be successful in the new job. It’s normal to think of how to spend the new-found money.
It’s also normal that once the work starts, the new job won’t be as amazing as it seemed. After the first week, the job and the people at the new job may seem like a nightmare.
Or, the new job is as amazing as it appeared and the people are awesome. But the work is highly technical and challenging. Doubts can creep in about whether it’s a good skill set fit.
The truth is, in the first week (even the first month) of new things like jobs, relationships, or workout routines, we don’t know enough to judge. We may think we know. We don’t.
This is where the power of the “90-Day Rule” shows itself. What is the 90-Day Rule? It’s something I made up that says for the next 90 days, I’ll immerse myself in the new thing (job, workout routine, etc.) without any preconceived judgment, without any pressure to decide, and without any thoughts about alternatives.
If I’ve decided to do this new thing (after days, weeks, months, sometimes years of contemplation), I’m going to give it at least 90 days before judging it.
In the new job example, consider how freeing a 90-day moratorium on judgment will be. You’re not judging the new people. You’re not judging the new company. You’re not judging your ability to perform in the new job. You’re not even judging the commute.
No judgments means you can focus on what it takes to be as successful as possible in the new job. All the energy you would have focused on making judgments and other distracting decisions is channeled fully into the most valuable tasks.
What about all that new money you’re earning at this new job? What if you give yourself 90 days before spending it on all that new stuff? Have a nice dinner to celebrate the start, and then wait 90 days. You’ll have plenty of time to spend all this new money on the 91st day. What’s your hurry?
When was the last time you gave anything 90 minutes before passing judgment? It’s time to give important decisions at least 90 days before passing judgment.
You’ve decided on this course of action. Let it play out. Give it room. Let it breathe. See where it goes.
What do I know? I know that I don’t know much, even though I know a lot.
Consider everything you know…
All the things you’ve learned since you were born.
All the things you’ve forgotten…in the last five years.
The capital of Vermont. Montpelier. I remember that one from 5th grade, even though I’ve never been to Vermont or Montpelier. I like the way it sounds, and the word Montpelier always makes me think of potato peelers.
“I” always comes before “E,” except after “C” and in weird words like weird.
Over ninety-eight percent of the population of Australia lives within 25 miles of the country’s coastline. I learned that from a tour guide. I assume it’s true.
Now, consider everything you don’t know.
Like, how to sew. Or, how to find top dead center on a Volkswagen engine. What about the method for calculating the orbital decay of a satellite? The percentage of nitrogen and oxygen in our atmosphere?
How about the exact weather forecast for a month from now? What your customers will want or need or expect one year, two years, five years from now? The truth is, they probably don’t know either.
I’d venture to say that what we don’t know is “Infinity minus One” larger than what we do know. Sounds hopeless.
But it’s the unknowns that make our little journey interesting. Discovering the secrets of an unknown is the reward for our curiosity.
How does cruise control work?
How and when did someone decide it was a good idea to pick certain red berries, dry them in the sun, then put them over a fire for just the right amount of time (whatever that is), then grind up what’s left and run hot water over it to make coffee?
Where does castor oil come from?
Curiosity and the humility to admit our ignorance, in pursuit of new knowledge is the key to learning.
Understanding that our decisions will never have the luxury of complete or perfect knowledge. We’ll never know everything before making the decision.
In fact, taking that risk and making the (uninformed) decision is another way we learn. If our decision is wrong, we learn from it (hopefully) and make a new decision that is less wrong.
Knowledge is power, and ignorance is bliss. Both are right.
But I believe ignorance can have more power. The power to try. The power to seek. The power to chase the unknown.
What do I know? I know that I don’t know much, even though I know a lot.
Knowing that I don’t know drives me to ask the dumb question(s), to search for answers, to seek the unknown, to leap, to discover, to practice, and most of all, to never stop learning.
I’m often most productive when dodging the thing I’m supposed to be doing.
Here’s a paradox about productivity:
I’m often most productive when dodging the thing I’m supposed to be doing.
I always know when I’m avoiding a task, even if tell myself I’m not. That task that seems undoable, requires multiple synchronized steps, requires difficult decisions, involves lots of other people who may not be “on board,” or the task with a nebulous benefit way out in the future.
It’s easy to dodge these challenging tasks and focus on the simple stuff. That list of to-dos I can knock out in an afternoon.
I know I’m not doing the tough thing, but at least I’m being productive. Nobody can accuse me of being lazy if I just keep moving.
This is the curse of staying busy, while not accomplishing anything.
I can dodge all I want. I can tell myself stories to justify my delay.
It doesn’t matter, the tough task will still be there, waiting.
Here’s another paradox:
When I finally face the tough task, the one I’ve been avoiding, it usually starts to look a lot easier. The next indicated steps begin to show themselves. The unwieldy becomes doable.
The dodge makes the tough task appear bigger than it really is.
It comes down to fear. Fear of the unknown. Fear of the difficult. Fear of embarrassment. Fear of failure. Fear of success (yes, this is a thing).
What if this task is harder than I imagined? What if it owns me? What if I can’t do it? What if someone sees me fail?
The answer to all these questions is, “So what. Get started anyway. Stop dodging and start doing.”
“Knowing what to do is very, very different than actually doing it.” – Seth Godin
If you live to the end of your 90th year, you will have lived 2,838,240,000 seconds…
I heard the term, Time Billionaire, a few weeks ago on the Tim Ferris Podcast (which I highly recommend, by the way).
There are 31,500,000 seconds in a year.
If you live to the end of your 90th year, you will have lived 2,838,240,000 seconds.
Each of us is a time billionaire. We have billions of seconds at our disposal.
To date, I’ve used about 1.67 billion of my seconds. If I’ve slept for a third of my life (wouldn’t 8 hours per night be nice?), I’ve been awake and actively (?) living for 1.1 billion seconds. I have roughly 770 million more active seconds remaining (if I live to be 90).
How many billions of seconds have you used? How many do you have left?
It’s easy to answer the first question, impossible to answer the second one.
One thing is certain. If you’re reading this post, you’ve already used billions of your seconds, and you probably have millions more.
The most important question is: What do you want to do with your remaining seconds?
We decide how we use our seconds (even when we choose not to decide, or let someone else decide for us).
None of us gets a second helping of seconds. It’s worth investing some valuable seconds to consider what to do with the rest of our seconds before they’re gone.
Grandpa Bob Encouraging Leadership 
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