The world beats a path to people who deliver. Join me here and on the People and Projects Podcast for practical insights on leadership & project management.
Chicago
Joined May 2008
- Tweets5.3K
- Following991
- Followers1.1K
- Likes2.5K
I landed late in Baltimore before a keynote.
No driver.
I called the car service. The owner's first answer: "Nobody told me."
A little later, he called back. And years later I still remember what he said:
"Mr. Kaufman, I have screwed up."
Turns out, he'd booked it for the wrong month.
Here's the thing.... The second he owned it, there wasn't much left to be upset about. I told him that in five days nobody would remember this. And I offered to buy the replacement driver a coffee.
I'd love to tell you my first reaction to my mistakes always sounds like his second call. It doesn't. If I'm not careful, it can sound like his first one.
Blame. Justify. Point at the process.
So here's the lesson I keep relearning:
→ When you mess up: don't blame, don't justify. Just own it.
→ When someone else messes up: go low. Help them solve it.
I talked through this on episode 260 of the People and Projects Podcast, "How to Respond When You Mess Up."
Which is harder for you: owning your own mistake, or being gracious when someone else makes one?
YOU MUST DO THE THING YOU THINK YOU CANNOT DO. ELEANOR ROOSEVELT
Today I'm celebrating 25 years of being in business.
But I don’t think it would have happened without one crucial “Yes” seven years before the launch.
Microsoft invited me to present at their annual TechEd conference. It would be in front of 7,500 people. At the time, speaking in front of 10 was enough to make me panic.
Why did I say yes? I have no idea!
But I do know this: those first 5 seconds on stage (the photo in this post) were terrifying. I was doing the thing I thought I could not do.
Seven years later, I launched our company. Since then, I’ve had the joy of helping organizations around the world lead and deliver projects more successfully. Today I’m in front of audiences at least 100 times a year.
I feel a deep sense of gratitude today.
🙏 Grateful to be loving this work 25 years in.
🙏 Grateful for everyone who has been part of our workshops, keynotes, LEAD52, and podcast community.
🙏 Grateful for the conversations we have here each week.
🙏 Grateful to a God with a sense of humor to provide a career path that I love, doing what I most feared decades before.
Eleanor Roosevelt said it well:
“You gain strength, courage, and confidence by every experience in which you really stop to look fear in the face. You are able to say to yourself, ‘I have lived through this horror. I can take the next thing that comes along. ... You must do the thing you think you cannot do.’”
I’ve lived that. My guess is you have too.
👉 What’s something you once thought you couldn’t do, but did anyway?
CONFIDENCE OFTEN ARRIVES AFTER THE ACTION, NOT BEFORE IT.
We often assume confidence is the feeling that gives us permission to speak up, make a decision, or accept a difficult assignment.
But haven't you seen this? In practice, the sequence is often reversed. We act while feeling uncertain. Maybe it doesn't go perfectly, but it goes well enough that the experience becomes evidence that we can handle more than we thought.
I kept waiting before starting a business. I had lots of excuses. I was not fearless when I made the jump 25 years ago this week! But 25 years later, I have nothing but deep gratitude that I moved forward despite the anxiety.
(BTW, if taking the full jump seems too risky, try making the next step smaller instead of waiting for the fear to disappear. I had about 7 years of smaller steps before making the big jump career-wise)
👉👉 What's an example of how you've seen confidence arriving after the action, not before it?
Check out my discussion with Kelli Thompson in episode 440 for more on this.
Long time @evernote paid subscriber.
When cancelling tonight, they didn't ask why.
Makes me wonder how often I miss opportunities to learn.
AI ISN'T THE ONLY THING BEING TRAINED.
Your mind is, too.
Every article you read.
Every news update you consume.
Every conversation you have.
Over time, those inputs shape how you think and how you lead.
I've never been tested for ADHD, but I'm guessing I'd score pretty well. 🐿️
Fred Marshall joined me in episode 513 to talk about his new book entitled Thrive. It's an important read at a time of foundational change in the world around us.
I've actually changed my social media habits since the discussion.
Lesson: Being intentional about what gets your attention may be one of the most practical leadership skills today.
👉👉 What's one thing you do to stay focused when there are so many forces trying to get your attention?
WHEN FEAR GETS LOUD, RETURN TO THE FACTS.
Have you ever noticed that the lead-up to a stressful meeting is often worse than the meeting itself? Not always, but I've certainly seen that pattern before.
It's so easy to get worked up in the days and hours leading up to it. Our minds can quickly produce a list of everything that might go wrong.
Kelli Thompson offers a practical response: name the worried thought, then look for evidence. One of my mentors said it this way: Name the lie, insert the truth.
What's true? What's some evidence? Consider:
-- You have prepared.
-- You understand the project.
-- You were invited into the room for a reason.
-- You may not know every answer, but you can follow up.
Check out episode 440 with Kelli for more ideas (and better sleep the night before the meeting)!
YOUR EXPERIENCE CAN GUIDE YOU.
IT CAN ALSO LIMIT YOU.
We all carry mental maps shaped by family, culture, work, success, and disappointment.
Those maps help us navigate. But a lesson that served us well years ago may quietly become an assumption that no longer fits.
One of my maps that needed re-writing? "It's just easier if I do it myself. It will get done correctly. On time. And it would take too long to get them up-to-speed."
That worked as a first line manager, at least at times. But it held me back going to Director and Vice President. I needed a new map.
Cornelia Choe joined me episode 511 to talk about this and more. One idea is to try asking: If I were new to this situation, which assumption would I be most willing to question?
👉👉 What is a leadership belief you have had to update over the years?
In a world of lame AI assistants, the one used by @SiteGround was truly helpful in debugging a problem. 👏👏
FEAR DOES NOT HAVE TO DISAPPEAR BEFORE YOU MOVE.
I wanted to start a company years ago. But it seemed to scary. So many things could go wrong. No guaranteed salary. No benefits.
So I didn't move. Until it was clear my current job situation wasn't any more certain than making the jump.
I jumped. And I'm so glad.
You don't have to wait for fear to disappear. Cornelia Choe told me in episode 511 that she calls it optimistic fear.
It does not ignore risk or pretend everything will work out. It keeps the danger in view while leaving room for curiosity, options, and useful action.
The next step does not need to be a major commitment. It can simply be one conversation that helps you understand the situation more clearly.
For me, that was starting conversations with people already doing keynote speaking and workshop facilitation. I couldn't believe how generous people were in sharing insights! Suddenly the thing that seemed unbearably risky seemed possible.
👉👉 What's an example of when you experienced optimistic fear in a way that moved you forward?
Ask "What results do I want to buy from them?" Barry Wolfe
Instead of asking “What do I want to pay them to do?” ask “What results do I want to buy from them?”
Barry puts together a case for why that simple shift, from verbs to nouns, can change the way you write job descriptions, give feedback, and align teams.
Check out the discussion with Barry in episode 490 of the People and Project Podcast.
“There is no shortage of good days. It is good lives that are hard to come by. A life of good days lived in the senses is not enough. The life of sensation is the life of greed; it requires more and more. The life of the spirit requires less and less; time is ample and its passage sweet. Who would call a day spent reading a good day? But a life spent reading -- that is a good life.” Annie Dillard
I don't know about you, but 2026 sounds like a sci-fi movie to me! And we're now halfway through the year!
In this quote, Annie has her own definition of what a good life is. But how about this? What's something from the first half of the year that was meaningful to you? I'd love to celebrate with you! Leave a comment below.
In a world filled with marginal vendor support, I am so impressed with @SiteGround . Time and again, they have been super responsive without canned, templated responses. If you've been thinking about changing where you host, I have nothing but high praise for this support team!
Just made a doctor's appointment. They use @elise_ai on the phone and I can confidently say it was the best, almost natural interaction I've had with a voice agent to date.
I actually messed with it a bit to see how it would handle the situation and it was flawless. Well done.
Want better meetings? Here's what I learned from talking with Rebecca Hinds in episode 506:
Return on Time Invested (ROTI).
It’s a simple concept Rebecca learned from Elise Keith: After a meeting, ask participants to rate the meeting from 0 to 5 based on one question:
“Was this meeting worth the time you invested?”
I love this framing because most meeting metrics are surface-level:
-- Number of attendees
-- Whether there was an agenda
-- Whether action items were captured and if people followed up on them
But none of those necessarily tells us whether the meeting actually moved the work forward.
And the truth is, different people often experience the same meeting very differently.
I've seen situations where the organizer thinks, "Great discussion!"
Meanwhile, others are thinking: “That could have been an email.”
Once you get the ROTI rating, here's what Rebecca follows up with: “What could I do as the organizer to improve your rating by one point?”
It's not asking for how to make the meeting perfect. Rather, how can we make it just a little better? (Or as Mike Rognlien likes to say it, How can we make it suck less?)
---
We often evaluate projects based on value delivered, not just activity completed. Maybe meetings deserve the same mindset.
Not: “Did we have the meeting?”
But: “Was it worth the investment?”
Give ROTI a try!
𝐇𝐨𝐧𝐨𝐫𝐞𝐝 𝐭𝐨 𝐛𝐞 𝐫𝐚𝐧𝐤𝐞𝐝 𝐚𝐦𝐨𝐧𝐠 𝐭𝐡𝐞 𝐓𝐨𝐩 𝟓𝟎 𝐋𝐞𝐚𝐝𝐞𝐫𝐬𝐡𝐢𝐩 𝐏𝐨𝐝𝐜𝐚𝐬𝐭𝐬!
Since 2009, we’ve been obsessed with one thing: helping our global community navigate the human side of projects and lead with more confidence.
Being recognized as a top global voice in leadership is a testament to the incredible guests who share their wisdom and the listeners who show up every week to grow.
As excited as I am about the last 508 episodes, I can't wait to share the discussions planned for the months ahead!
With over 4.5 million podcasts out there today, the fact that you choose to spend time with us is something I never take for granted. On behalf of the team that's involved with the production, thank you for helping the People and Projects Podcast reach this milestone!
👉👉 Can you think of a guest or episode that you recall as being helpful? I’d love to hear in the comments.
“We were smart people. We had smart people on the team, and we somehow failed miserably.” Stephen Shapiro
In episode 507, Stephen Shapiro talks about a major project failure, and lessons learned from it.
In my experience, projects don't usually fail for lack of intelligence (though it's easy to blame it on that).
Check out the discussion with Stephen about his new book "You’re Not Playing With a Full Deck: Why the People Who Drive You Crazy Are Your Unfair Advantage".
A common mistake I've seen among a lot of project managers (including myself): assuming negotiation only happens during “big” conversations.
Never Settle by @AttiaQ and John Richardson hits the shelves today. Our discussion will show up in episode 514 of the People and Projects Podcast.
After reading their book and talking with Attia, I’m more convinced than ever that negotiation is happening constantly:
-- Trying to gain support from a stakeholder
-- Pushing back on unrealistic expectations
-- Navigating priorities across teams
-- Deciding whether to say Yes or No
-- Working through tension without damaging trust
The book makes a compelling point:
The gap is usually not knowledge. Most leaders already have many smart ideas about communication and negotiation. The real challenge is applying those ideas when emotions, pressure, fear, and relationships come into play.
That’s where this book really shines. It is practical, emotionally intelligent, and grounded in how conversations actually unfold in real life.
I recommend you add Never Settle to your reading list!
👉👉 What's an example of when we're negotiating, perhaps without even realizing it?
Coinbase announced a ~14% workforce reduction this week. CEO Brian Armstrong shared a very direct open letter outlining their shift to a leaner, AI-first organization.
Whether you agree with the approach or not, this feels like a preview of how many high-performing companies will operate going forward:
* AI-Native Talent. How are you actively building skills so you’re seen as fluent in this new era?
* Fewer Layers, Faster Decisions. They’re flattening the org to a maximum of 5 layers. Expect more of this across tech and beyond.
* No Pure Managers. I think it's interesting that he's saying leaders will have 15+ direct reports but must be active individual contributors. That tension has always existed. But the "player-coach" model is worth considering.
Earlier this week, I helped a client use AI instead of hiring me for a traditional engagement. I could fight that tide. We've decided that learning to surf is better and actually more fun.
What stands out to you in Coinbase’s announcement?
This is an email I sent earlier today to all employees at Coinbase:
Team,
Today I’ve made the difficult decision to reduce the size of Coinbase by ~14%. I want to walk you through why we're doing this now, what it means for those affected, and how this positions us for the future.
Why now
Two forces are converging at the same time. We need to be front footed to respond to both.
First, the market. Coinbase is well-capitalized, has diversified revenue streams, and is well-positioned to weather any storm. Crypto is also on the verge of the next wave of adoption, with stablecoins, prediction markets, tokenization, and more taking off. However, our business is still volatile from quarter to quarter. While we've managed through that cyclicality many times before and come out stronger on the other side, we’re currently in a down market and need to adjust our cost structure now so that we emerge from this period leaner, faster, and more efficient for our next phase of growth.
Second, AI is changing how we work. Over the past year, I’ve watched engineers use AI to ship in days what used to take a team weeks. Non-technical teams are now shipping production code and many of our workflows are being automated. The pace of what's possible with a small, focused team has changed dramatically, and it's accelerating every day.
All of this has led us to an inflection point, not just for Coinbase, but for every company. The biggest risk now is not taking action. We are adjusting early and deliberately to rebuild Coinbase to be lean, fast, and AI-native. We need to return to the speed and focus of our startup founding, with AI at our core.
What this means
To get there, we are not just reducing headcount and cutting costs, we’re fundamentally changing how we operate: rebuilding Coinbase as an intelligence, with humans around the edge aligning it. What does this mean in practice?
- Fewer layers, faster decisions: We are flattening our org structure to 5 layers max below CEO/COO. Layers slow things down and create coordination tax. The future is small, high context teams that can move quickly. Leaders will own much more, with as many as 15+ direct reports. Fewer layers also means a leaner cost structure that is built to perform through all market cycles.
- No pure managers: Every leader at Coinbase must also be a strong and active individual contributor. Managers should be like player-coaches, getting their hands dirty alongside their teams.
- AI-native pods: We’ll be concentrating around AI-native talent who can manage fleets of agents to drive outsized impact. We’ll also be experimenting with reduced pod sizes, including “one person teams” with engineers, designers, and product managers all in one role.
In short: AI is bringing a profound shift in how companies operate, and we’re reshaping Coinbase to lead in this new era. This is a new way of working, and we need to leverage AI across every facet of our jobs.
To those who are affected
I know there are real people behind these decisions — talented colleagues who have poured themselves into this company and our mission. To those of you who will be leaving: thank you. You’ve helped build Coinbase into what it is today, and I am sincerely grateful for everything you've done.
All impacted team members will receive an email to their personal account in the next hour with more information, and an invitation to meet with an HRBP and a senior leader in your organization. Coinbase system access has been removed today. I know this feels sudden and harsh, but it is the only responsible choice given our duty to protect customer information.
To those affected, we will be providing a comprehensive package to support you through this transition. US employees will receive a minimum of 16 weeks base pay (plus 2 weeks per year worked), their next equity vest, and 6 months of COBRA. Employees on a work visa will get extra transition support. Those outside of the US will receive similar support, based on local factors and subject to any consultation requirements.
Coinbase prides itself on talent density. Our employees are among the most talented people in the world, and I have no doubt that your skills and experience will be highly sought after as you pursue your next chapters.
How we move forward
To the team that is staying, I know this is a difficult day. We’re saying goodbye to colleagues and friends you've been in the trenches with. But here’s what I want you to know as we move forward together:
Over the past 13 years, we have weathered four crypto winters, gone public, and built the most trusted platform in our industry. We’ve made it this far by making hard decisions and by always staying focused on our mission. This time will be no different – nothing has changed about the long term outlook of our company or industry. And most importantly, our mission has never been more important for the world. Increasing economic freedom requires a new financial system, and we’re building it.
The Coinbase that emerges from this will be more capable than ever to achieve our mission.
Brian
POSITIVE THINKING CAN BE DANGEROUS
We often hear that leaders should be optimists, and there is some truth to that. But a former Marine and police officer turned executive coach told me this in episode 494: blind positivity can get you killed more than negativity.
Andrew Wittman prefers Critical Thinking. He uses a matrix of Clarity, Relevance, Accuracy, and Precision. (How can you forget an acronym like CRAP) 😉
It is not about hoping for the best. It is about moving assumptions into the fact column. We need to know where the holes are so we can fill them.
That's straight-up project management wisdom.
“WHEN YOU TREAT YOUR PEOPLE WELL, THEY ARE A BETTER PARENT, FRIEND, RELATIVE.” ASHLEY HERD
If we're not careful, in the world of project management, we can start treating people like resources. We don't intend to. We might even deny it if accused. But I've seen it happen.
And I'm sure I've been guilty of it myself.
How do I know? My wife once told me, "Honey, I'm not your stakeholder!"
Ouch.
Ashley Herd joined me in episode 505 of the People and Projects Podcast. She is the author of a fantastic new book called "The Manager Method." Underlying the message of the book is a theme of how, when we keep our team members in mind, it changes how we lead.
"Treating your people well" does not mean just being nice. It certainly doesn't mean we avoid difficult conversations.
But I've found that when I remember my team has fears, needs, and goals that aren't immediately apparent, it changes the way I interact with them
When they're treated like truly valued humans instead of resources, they'll go to battle with you.
As Ashley mentions, the value spills over far beyond the office. Gallup Chief Scientist Jim Harter reinforced this in our discussion in episode 324: “People with high career wellbeing are more than twice as likely to be thriving in their lives overall.”
Go out of your way to treat people exceptionally well, even during challenging times. It pays off in ways that go far beyond the project plan.
👉👉 When was a time a leader treated you like a "human" rather than a "resource," and what impact did it have on your life outside of work?
