Weird, right?

No, it’s not because I’m a closeted workaholic who gets a secret thrill every time I turn on my computer to get some work done. Although that could be true, too? 🤔

I don’t even use my personal laptop all that often these days—except to write or work on the occasional side gig.

It’s the stickers, silly

I have adorned my laptop with stickers—lots and lots of stickers.

I have stickers from trips my wife and I have taken over the past few years—to New York and Japan, Provincetown and Whidbey Island, Snoqualmie Falls and Solvang.

There are stickers that reflect my matcha habit, Seattle Storm fandom, PNW location, and affinity for sea otters. Because who doesn’t love sea otters?

And there are stickers full of pride and rainbows and love.

So yeah … it makes me smile to see it. My laptop tells a story of who I am, where I’ve been, and what’s important to me.

A relative newcomer

I’m fairly new to the sticker game. I never even thought about adding stickers to my laptop until I got to Amazon in 2021.

Before that, I worked in education and used my institutionally provided work laptop for everything, personal and professional.

Despite using it personally, I also viewed it as the property of my institution—something I was expected to care for but ultimately return in the same condition I received it. Unharmed. Unmarred. Sticker-less.

On the rare occasion I saw someone with a sticker-adorned laptop, I was envious of their carefree application. Their ability to express themselves with abandon.

It never occurred to me that I could do it myself.

And then I arrived at Amazon, where nearly everyone had a laptop full of stickers. How many stickers you had—and which ones—were a point of pride.

Stickers were currency. Every team, every initiative, every affinity group had stickers. We wanted to find the best stickers. We wanted our team to have the best stickers.

I’m still ridiculously proud of our SBAI sticker (we pronounced SBAI like “spy”—thus the cute spy-guy). Everyone wanted that one.

Make it yours

I love seeing stickers on other people’s laptops. There’s something wonderful and humanizing about it.

We can get lost as people in the world of work. We’re numbers, cogs in the corporate machine, easily replaceable (or so we’re told).

Stickers are a form of self-expression … and control. What you choose to put on your computer is entirely up to you. There are no rules. No one telling you what belongs where—except you.

So tell me: What’s your take on laptop stickers? What do your stickers (or lack thereof) say about you? Post a pic in the chat—I’d love to see your sticker game!

Bonus read: Two years ago, almost to the day, I wrote this piece about authenticity and professionalism. Whether you’re expressing yourself through stickers or a dashiki, please keep on being you.

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“AI adoption isn’t a technology problem,” it’s a …

• Strategy

• Leadership

• People

• Change

• Operating model

• Organizational design

• Training

• Behavior / habit formation

• Value realization

• ROI

• Trust

• Data

• Governance

… problem.

No kidding. We’re just figuring this out now? 🙄

I mean, seriously … anyone who has ever been responsible for, part of, or in the general proximity of a major technology project knows that the technology is always the easiest part.

So I’m kind of lol-ing every time I see this shared as some newfound insight—like it’s new in the world or just started occurring with AI.

It’s not, and it didn’t.

I’ve said it before and I’ll say it again:

But also …

In this case it is a technology problem, too. AI is wonky and imperfect and still very much in its infancy.

If you’re at all familiar with technology adoption curves, you’ve probably seen Gartner’s hype cycle. If I had to place AI on that curve, I’d say we’re currently fluctuating between the Peak of Inflated Expectations (and whoa, are they inflated!) and the Trough of Disillusionment, and likely will be for a while:

This is normal. It’s following a well-documented and established pattern for technology adoption.

We don’t always know how long it’ll take for any particular technology to traverse this curve, but we know it almost always will.

The bottom line

AI will not save the world nor will it be our demise.

It will persist, however, and one day in the not-too-distant future we will not know a world without it embedded in every aspect of our lives.

Until then, stay focused on the fundamentals—strategy, leadership, and people—while remaining open to the possibilities that a new technology can create.

Bonus read: As we shape what this new technology will become, it is more important than ever that we consider whose voices and perspectives are leading that charge.

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(You know what they say: “Go big or go home.” They really embraced that sentiment. 😳)

Let me know if this scenario sounds at all familiar:

Sometimes the project is even “successfully” completed but instead of thanking you, folks are calling it an unmitigated disaster. No one is happy.

I’ve seen this play out time and time again. It’s even happened on teams I’ve led. And it’s not limited to IT projects or corporate environments, although I’ve certainly seen plenty of it in both. Sadly.

This week’s example came courtesy of my condo’s homeowners association.

Their mistake

The mistake my HOA—and the team in the example above—made was informing their community rather than engaging them in the process.

They told us the project was important. They told us work was happening.

But they waited until they had a final, fully-baked solution before bringing anything to the community for approval.

There were no options presented. No opportunity for input along the way. No transparency in the process—or even a defined process at all.

There was a very proud showing of “look at all the work we’ve done and the decision we arrived at” couched as an opportunity for feedback. And then they were “butt hurt” (as any proud GenXer would say) when that feedback didn’t go their way.

With 100 homeowners and over half a million dollars on the line, this outcome shouldn’t have come as a surprise.

Their mistake was not bringing the community along with them in the process. And it’s a mistake that plays out all too often with our professional communities and projects, too.

Laying blame …

When this happens, there are two ways we can respond as leaders.

The first is to blame our stakeholders. It’s surprisingly easy to do, particularly in environments with any sort of organizational divide or politics (so basically, every org).

It becomes “us versus them” and “they” don’t …

• appreciate us or the hard work we do

• understand or value our expertise

• want what’s best for the organization

Or in my HOA’s case, it was that “the community isn’t ready” for the project.

It’s easy to tell ourselves that we’d be able to do amazing things if only it wasn’t for our stupid stakeholders.

… or leaning in

There is another path we can take. We can learn from our mistakes, lean into the feedback, and course correct in real time.

Our HOA could have said: We appreciate the feedback and realize that we need a more thorough review process, so we’re going to come back with a clear plan to address the community’s concerns.

Not “you don’t get it.” Not “you’re not ready.” Not “you don’t want what’s best.”

But rather: “We heard you.” Maybe we didn’t get it exactly right, but we’re going to fix it.

The real problem here isn’t our stakeholders, it’s us. It’s a failure of leadership.

If you find yourself with a stakeholder revolt on your hands, don’t blame them. Take a good long look in the mirror and ask: Where did we go wrong, and how do we fix it?

Cancelling the project is rarely the answer—but course correcting is.

Bonus read: Working with people is the hardest part of leadership, but the only part that really matters.

Cover photo by Slim Emcee on Unsplash

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An investor introduced my CEO to an industry thought leader who, as it turns out, I’ve known for years through a close friend and colleague of mine.

Nearly every call I do with a prospective customer or partner includes some version of the Kevin Bacon game, education edition.

We’re never more than a couple degrees of separation apart.

I don’t think this is unique to education. Big Tech is also surprisingly small—who you know and their perception of you matters more than you think. I’m told many other industries are the same.

With the world being so connected, you would have to be some sort of fool to burn bridges … right? Right?!?

And yet …

I’m seeing some wild sh’t, yall. People lighting up their soon-to-be former colleagues, bosses, and organizations. Publicly, on social media. 🙄

Like burning the house down on the way out the door. Not smart.

Even if you don’t need or want a good recommendation—or don’t care if they trash talk you in the industry—other folks are paying attention to:

• How you show up in public spaces

• The way you speak about people you’ve worked with

• How you handle difference, disagreement, and disappointment

If I’ve learned one thing from my decades in the workplace, it’s this: Past behavior is the best predictor of future behavior.

Let that one sink in.

Burning down one bridge speaks volumes about what you’ll do with the next one—and someone’s bound to take note.

Stay smart. Stay safe. Keep those matches to yourself.

Bonus read: And speaking of bad behavior … here are a couple more thoughts on the subject.

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This is especially true of leadership.

Leadership calls us to act not only when things are easy, but when they're difficult and messy. The true test of a leader is how we show up when the going gets tough.

Case in point: Minnesota Lynx head coach Cheryl Reeve.

In the midst of another uproar about trans athletes in women’s sports¹, Reeve used her position and platform to talk about the importance of inclusion:

She didn’t have to speak up.

No WNBA coach had at that point, and only one other—Golden State Valkyries coach Natalie Nakase—has since then.

But Reeve understands the responsibility that comes with privilege and power. That saying nothing is also a choice.

Her words spoke volumes, but she didn’t stop there. Reeve backed her words with action by wearing a Trans Kids Belong shirt during a nationally televised game.

This is what leadership looks like, y’all.

¹ The conversation around trans athletes in women’s sports is a ridiculous and completely manufactured “issue.” There are fewer than 10 known trans athletes out of 510,000 athletes in the NCAA, and only 0.001% of Olympic-level athletes globally are trans.

If we truly care about protecting women, perhaps we should focus on improving women’s health and reproductive rights, eliminating sexual assault and violence against women, and reducing gender inequity in the workplace? Just sayin’ …

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Sounds like the beginning of a joke, right? 😉

No such luck. It was a very real LinkedIn post I saw the other day—alongside a picture of the happy gathering.

And my heart sank a little bit. Care to guess why?

Go ahead … I’ll wait ….

Who’s in the room?

I love me a good musical, and there’s none quite like Hamilton.

In it, Aaron Burr sings about the Compromise of 1790 and his desire to be in the inner circle and at the table when deals get struck:

If you’re not at the table, how do you know how decisions get made? How can you be assured that your interests are represented?

You don’t. You can’t. And they’re most likely not.

So back to the 160 AI builders. Who do you suppose was in that room?

I wasn't there, so I can't say for certain. But judging from the photo, the room appeared to be overwhelmingly made up of White and South Asian men.

Anyone see a problem with this?

We can’t assume …

We assume that the people designing products and systems understand the people they're designing for. We assume that our interests are being served.

But we’ve seen time and time again what happens when the people who use products and systems are not part of the teams that build them.

I experience a small version of this every single day as a left-handed person. Turns out, the entire world is built for right-handers—something you don’t think about unless you happen to be left-handed.

Don’t believe me? Check out this fun little piece about all the challenges left-handers have with door handles, scissors, watches, kitchen utensils … the list goes on.

This is a minor annoyance I’ve had to navigate my entire life, but the outcome can be so much more insidious than just inconvenience:

• Automated soap dispensers that don’t work for people with dark skin

• Cars that are considerably more dangerous for women than men

• AI that offers disparate salary advice to women and people of color

• Facial recognition systems that lead to wrongful arrests

So, umm, yeah … really bad shit happens when we’re not in the room.

Representation matters

Just the other day, I was editing a post with ChatGPT. I have a project set up for SGNR that includes a year's worth of blog posts and historical chats to create an AI editor that knows me, my writing, and my voice so that it can recommend edits accordingly.

And yet, during an exchange about how I phrased one section, ChatGPT said readers may think to themselves: “Wait, is he arguing against AI?”

Read that again if you missed it.

A year’s worth of conversations. It’s read all my posts. About being out and proud. Taking PTO time with my wife. Reclaiming our power as women.

And it still misgendered me.

Because the dudes building ChatGPT inevitably bring their own experiences and assumptions with them. They likely don't mean to build a biased or exclusionary product—they simply can't see what they're missing.

They assume the world is exactly as they experience it.

We can fix this

As leaders, we have the power to change this. And the responsibility to.

We need to pay attention to whose voice isn’t being represented—whether on a specific project or within your leadership team.

As company leaders, our responsibility is even greater. It extends beyond our own internal teams to ensuring we truly understand and represent the people and industries we serve.

When I was a CIO, there was nothing more irritating than being sold to by a bunch of tech bros who hadn’t spent a single day in a campus role—but were going to “fix” education. 🙄

No matter how smart they are or how good their idea is, they don't know what they don't know. That's why you need people with lived experience in the room.

So the next time you convene 160 builders—or even 16—ask yourself: Who’s not in the room that should be?

Bonus read: When AI isn’t being unintentionally biased it does have the power to accelerate our work. But it requires experience to make it truly useful.

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It’s one that came up often during my time at Amazon. Andy Jassy, then CEO of AWS, first said it in 2017.

Waaaay back in the before times—and by that I mean pre-AI.

Since then, Jassy has become Amazon's CEO and I now work at the intersection of AI and education. But the sentiment feels more relevant than ever.

To AI or not to AI …

Is not the question.

That ship has sailed. AI has been adopted faster than any major technology in recent memory, reaching roughly 39% adoption in just two years.1

Compare that to roughly 5 years for the Internet and 12 years for PCs.

Businesses are betting heavily on AI as a driver of efficiency and growth. You can see it everywhere: job postings now list AI proficiency as a required skill, earnings reports tout AI initiatives, and CEOs blame AI for the latest round of layoffs—because AI is coming for all our jobs, apparently. 🙄

Okay, boomer.

I’m not worried that AI is coming for my job.

It’s true that AI can produce go-to-market plans, sales playbooks, prospecting emails, QBR templates—and pretty much any other asset I regularly produce or use in my role—in a fraction of the time it takes me to do the same.

Some of it is even pretty good … so I use it to support my work.

But not all of it is good. Or right. The problem is AI doesn’t know which is which. (See the recent REI bicycle ad as the latest example of this.)

It doesn’t know my audience. It can’t understand university faculty, staff, and administrators as the wonderfully complicated humans they are. It doesn’t understand institutional politics, competing incentives, or decades of accumulated context.

It doesn’t know what motivates them or how to connect with them.

That requires judgment—the kind that comes from observation, trial and error, conferring with peers, and years spent working in and around this industry.

You have to know when to trust AI, when to ignore it, and how to shape its output into something that actually works.

That takes experience. And there is no compression algorithm for that.

In the weeks to come, I’ll be exploring what this means for us as leaders, for our educational institutions, and for the edtech companies that serve them.

In the meantime, I want to hear what you think:

Hit reply to drop me a quick note or leave a comment below.

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Yesterday the city hosted a Pride World Cup game. Tonight is the Storm’s Pride night. Go Storm—let’s win “for the gays!” 😉

Shortly, my wife and I will be heading to PrideFest in Capital Hill to soak in gay culture and stock up on gaybie gear—hats, t-shirts, and anything else that sports rainbow colors and sparks joy.

My wife and I are lucky.

We have family who love and support us. We work in companies and industries where being openly LGBTQ+ is generally accepted. We live in a city where we can hold hands, kiss on the street corner, and have strangers approach us to tell us we’re a cute couple.

That doesn’t happen everywhere. That doesn’t happen for everyone.

Not everyone feels safe to be out in public spaces … and sometimes it legitimately isn’t safe to be openly queer at home, work, or in the community.

The most important thing we can do as leaders—and as humans—is create a safe space for others to be themselves in our presence.

Because we all deserve to feel truly seen and accepted for who we are.

Happy Pride, y’all.

Bonus reads: As I head out for Pride festivities this weekend, here are a couple of reminders about why DEI and representation (still) matter:

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One spring day in 2024, I mentioned to the woman I was dating that I wanted to revive my blog but never seemed to have time to write. Being a writer herself, she slyly suggested we could write together each week.

One writing date led to another, that woman became my wife, and for the last two years we’ve gotten up every Saturday morning, headed to our favorite local coffee shop, and written.

Because of that, I've published something almost every Sunday for the last two years: 104 posts in all.

I owe her a debt of gratitude for helping me achieve this. And I’m grateful to all of you for reading and supporting my work.

17 years in the making

I first started Some Guy Named Rae in December 2009 but was never consistent about it. From 2009 to 2016 I only wrote 40 posts, sometimes with a year or two between them. And then life got in the way and I stopped for good (I thought).

So when I restarted in 2024, I had two goals:

1. Extend the conversations and lessons explored through 1:1 mentoring to a broader audience (you!), and

2. Do it consistently.

Two years in, I’ve accomplished both.

Some weeks it’s easy. Others, not so much. Sometimes I know exactly what I want to say; other times I’m hunting for a topic to write on.

Some posts seem to resonate strongly—like when I wrote about burnout, layoffs, and the use of the word “guys.” Others, less so.

I’m writing consistently now, but to what end? It’s been a good run, but many days I feel like I’m writing into the void.

What comes next?

Lately, I’ve found myself wanting more:

I don’t know if it’s the monotony of doing the same thing for two years straight. Or my age and the stage of my career.

Or maybe it’s simply a symptom of our times.

In a world of one-sided conversations and AI-generated slop, I want something more … human. Perhaps you do too?

And so, as I head into year three of SGNR, I’m trying to decide what comes next.

I’m not going to stop writing, but I may not publish every week. I want to create more space to explore new ideas and experiment.

I’m thinking about all sorts of things: expanding my focus, trying different modalities, hosting a subscriber discussion board, or facilitating community conversations—to name a few.

What do you want? What would make SGNR more valuable to you?

More conversation? More interaction with other readers? Different topics? Something else entirely?

I’d love to hear your thoughts.

Cover photo credit: Dino Reichmuth on Unsplash

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(The Seattle Storm is definitely my WBB team but I will forever be a San Francisco 49ers fan. Sorry not sorry, Seahawks.)

As I moved from despair over our third quarter meltdown to screaming my lungs out during a remarkable fourth quarter comeback that put us within one point with 50 seconds left in the game, I marvelled at two things:

First, how I’ve become a huge WBB fan over the last three years. I seriously love going to the games and now watch way more basketball than I do football, which has been my one sports love since I was in my early teens. Go figure.

Second—and far more relevant to this blog—is how fascinating it is to watch a game through a business and leadership lens. There are so many lessons we can learn from WBB players, coaches, and the way the game is played.

Here are three I took away from last night’s game:

1. You can have a superstar player, but they still need a strong team around them for magic to happen. Take Paige Bueckers and the Dallas Wings. Paige was last year’s number one draft pick and is by all accounts a generational player. Now in only her second year, she ranks in the league’s top 10 for points and assists per game. Last year the Wings went 10-34 (22.7%)—Paige alone couldn’t carry the team. This year the Wings are off to an 8-4 (66.7%) start. The difference? Paige is now complemented by another first round draft pick, Azzi Fudd, as well as veteran players Jessica Shepard and Arike Ogunbowale.

2. The best players will do what it takes to win—even if that means sitting it out. I assume most professional athletes have a healthy ego. Yet every game I see some of the best players pass the ball when they could have easily taken the shot themselves. And then there’s the near-constant player rotation. Coaches move players in and out of the game like they’re moving chess pieces around a board. This combo of players isn’t working? Let’s try someone else. Too many fouls in quick succession? Take a beat. Having a bit of a shooting dry spell? Out you go. The best coaches make adjustments quickly to change the arc of the game. For the players, there’s (mostly) no ego attached, it’s all just part of doing what it takes to win—because the team winning is what really matters.

3. Coaching matters more than you think. With world-class athletes, you might wonder why they even need coaching. These are elite competitors who know the game inside and out—so why not just let them play? Because, as it turns out, these athletes still need someone to take really strong individual competitors and turn them into a high-performing team. I’ve seen what happens when this doesn’t happen (2025 Storm team 😳). Even the game’s most experienced players need someone who’s thinking about the game strategically and considering:

   1. How to put the right combination of players together on this particular night to beat this particular team.

   2. Who needs a little motivation and who needs to sit this one out.

   3. When to use a time out, and which one to use. When to double down with a challenge. When to throw up their arms and yell at a referee.

   4. What play to call that will put some points on the board and, hopefully, shift the momentum in the game.

Perhaps the biggest lesson of all, though, is to find joy in all that you do. Like we all do when my favorite player, Dominique Malonga, executes the perfect pre-game alley-oop. Enjoy.

Cover photo credit: Lorie Shaull from St Paul, United States - Basketball, CC BY-SA 2.0

Bonus read: For more leadership lessons from the WNBA, here’s a piece I wrote about the Valkyries coach Natalie Nakase.

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The numbers vary depending on the source, but it’s commonly reported that somewhere between 80% and 95% of AI projects fail to deliver any sort of value or return on investment.

Nearly every week there’s news about another AI debacle.

Recently we heard about Starbucks walking away from their AI-powered inventory system after only 9 months. Before that it was the failed AI deals in California’s LA and San Diego school districts.

Is anyone truly surprised by all of this?

AI is just another technology in a long string of advances we’ve seen over the past 50+ years. If there’s one thing I’ve learned over my career as a technology leader, it’s that we should never adopt technology for technology’s sake.

But that’s what we’re currently doing with AI—and to be fair, what we did with virtually every other technology that came before it.

AI is the shiny penny du jour.

When I was at Amazon, we were instructed to use AI and so use it we did—badly at first, and without any clear intended outcome. AI wrote Forte feedback and OP docs, some so nonsensical they were functionally useless. AI chatbots served up (wrong) answers from long-since abandoned internal wiki pages (IYKYK).

I see the same AI charge in many of the colleges and universities I work with now and as a former CIO, it breaks my heart.

Everyone is scrambling to “do AI.”

Every institution I talk to is in some stage of building their AI strategy, drafting an AI policy, establishing AI governance, or piloting AI tools.

We reacted and are still reacting: AI is here and we must do something with it and exert control over it—because who doesn’t love a little governance?

We have an AI “hammer” and we’re hammering away at institutional challenges like nobody’s business.

Even if what they really need is a screwdriver.

AI isn’t the problem.

The technology is good enough. Or it isn’t, depending on who you ask or what you’re trying to do. That’s not really the point.

We’ve got to stop chasing shiny pennies and doing tech for tech’s sake.

For many years I fought back against putting a separate technology priority into my then institution’s strategic plan. Technology isn’t a strategy unto itself. Neither is AI.

The strategy is and always should be an organizational one—one that technology may enable or support.

I have no doubt that AI will be a transformative technology—like computers or the Internet—that will fundamentally change our lives. To get there, though, we must:

• Stop doing AI for AI’s sake, and start getting clearer on the specific business problem we’re trying to solve.

• Stop applying AI to our existing jobs and processes, and start doing things that weren’t previously possible—until now. It’s time to completely reimagine our organizations and our work with this new technology, not just do it incrementally better or faster.

• Stop taking a one-size-fits-all approach to AI, and start building an AI toolbox with unique tools and capabilities that are fit for purpose.

• Stop treating AI like a tech problem, and start recognizing that successful technology projects—including and maybe especially AI—require change. People, cultures, and organizations all must change. That’s a big lift. (See also: Change Is Messy.)

It’s still early days.

AI has evolved faster than most new technologies, but is still in its relative infancy. Anyone remember the early days of the consumer Internet?

I do. I was in startups during the Internet boom of the late 1990s (and ironically am back in them once again for this next technological revolution). There was a lot of hype, but the websites were little more than digital brochureware and the business models were generally unsustainable. Turns out “eyeballs” aren’t such a good metric, after all.

Many of those experiments failed—like AI is “failing” now.

We went from the dotcom boom in the late ‘90s to the dotcom bust of the early 2000s, and we learned a few things in the process.

Much like with the Internet, I have no doubt that we’ll look back 20 years from now and not be able to believe that we once learned, worked, and lived the way we currently do.

But until then, we’re likely to see a few more failures—because it’s not just technology that has to change, but all of us along with it.

Bonus read: Not to put too fine a point on it, but things are moving so quickly that this article I wrote six months ago is now basically obsolete—although I did get a couple of things right in it.

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I color code my calendar, so I know exactly where I’m spending my time: customer conversations, candidate interviews, product planning, leadership meetings, team one-on-ones.

In most of these cases, the meeting is the work. As leaders, we often orchestrate and execute through others and meetings are an important part of that. I’ve even written about this before: Meetings vs “Real” Work.

But as is so often the case, two conflicting things can be true at the same time.

Because we also lose something important when we spend our days moving from meeting to meeting. It’s not the minutiae work: time to answer emails, respond to Slack messages, or prepare the next Board deck.

It’s time itself—for thinking, reflection, and learning.

This sort of time feels like a luxury. Blocking your calendar for XX hours per day or week to just … think? Clearly you don’t have enough to do. 🙄

Where leadership happens

The problem is, this unstructured time is where the hard work of leadership actually happens.

Without time, we cannot deeply understand our customers and their needs, or our industry and the ways it’s evolving. We don’t have time to think about how these impact our product, our messaging, our approach.

We cannot craft our strategy—or truly assess the impact of one we already have. We cannot experiment with new technologies. We cannot innovate.

Case in point: I work for an AI company. Although I use AI daily, I still haven’t meaningfully integrated it into my own work processes. Not because I don’t want to or don’t believe it can add value, but because I don’t have time to play with it. Try and fail, and try again.

We all need more (unstructured) time

My colleague Jill Leafstedt recently posted about the new type of role needed in an AI world. I agree with her assessment, including the need for dedicated time to learn:

I would argue this has always been needed for roles at every level, but is now more important than ever—especially for leaders.

But somewhere along the way we over-indexed on productivity to the detriment of everything else. Every available minute gets filled, leaving little room for learning, reflection, or experimentation.

We can change that. We must change that—because if we spend all of our time in meetings, we eventually lose the ability to see what’s coming next.

Now’s the moment to take back what we’ve lost.

We tell ourselves that unstructured time is a luxury—but the truth is, it’s essential to lead.

Cover photo by Aron Visuals on Unsplash

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It’s something I’ve been thinking about a lot lately:

Why so many people no longer aspire to leadership roles. According to a recent Forbes article, 41% of workers have no interest in becoming a manager. Wow.

Why so many managers are voluntarily stepping back to individual contributor roles. Trading the title and salary for more autonomy, greater control, and way less stress.

Why so many leaders are burning out … and then opting out. I saw this play out in real time at Amazon. After a 20+ year career in big tech, one of my former colleagues left to become a high school teacher.

Leadership isn’t right for everybody, for sure. I’ve written before that not everyone can—or should—be a leader. (Read more in Not Everyone Can Lead.)

And for those of us who are called to lead, it isn’t always fun. Worthwhile, yes. Fun? It has its moments, but many days—not so much.

It’s … a lot

I see so many good leaders struggle under the weight of the challenges we are asked to navigate Every. Single. Day:

• Balancing the company’s interests with care for our employees

• Supporting an employee who’s recently suffered a devastating loss

• Driving change while not leaving anyone behind

• Aligning everyone on a clear strategy while determining in real time when to stay the course—and when to change it

• Mediating conflict between two equally valued team members

• Making high-quality decisions with far less information or time than you’d like

• Maintaining composure and calming reassurance through every obstacle—no matter how you actually feel on the inside

• Satisfying the competing needs of customers and board members and colleagues and team members, all at the same time

We struggle not because we’re not smart, capable, or can’t rise to the challenge. We struggle because we care—deeply.

We care about making good decisions and doing the “right” thing (spoiler alert: you won’t always get it right and that has to be okay). We care about our people, their wellbeing, and the impact our decisions will have on them.

The price we pay

Good leaders do really hard things every day, and we don’t give each other and ourselves enough grace for that.

It takes its toll. Physically. Mentally. Emotionally.

Particularly emotionally. It requires a lot of emotional energy to navigate complex situations and conflicting priorities day-in and day-out, year after year—and for some of us—decade after decade.

No matter how experienced or adept we are, there is one thing we cannot overcome: at the end of the day, we are only human.

Thank goodness for that.

Because for all our flaws, more humanity is what we need in leadership right now. But that deeply human work comes with a price—good leaders carry a weight that other people rarely see.

And maybe we should talk about that more often.

Bonus read: As I get ready to go to the third Seattle Storm home game in five days (go Storm!), I’m reminded about the leadership lessons we can learn from outstanding coaches—like the Golden State Valkyries head coach, Natalie Nakase.

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My wife and I didn’t have grand plans—no weekend getaway or fancy dinner, no activities reserved months in advance.

We walked around the lake where we first met and later got married. Had breakfast at a local cafe. Went to a coffee shop and wrote. Enjoyed a sunny, 79-degree Seattle day and each other’s company without any pressure to go anywhere or do any specific thing.

It felt luxurious to walk around without a care in the world at 9 a.m. on a Monday morning, while the rest of the world worked.

Monday, Monday

I can’t remember the last time I took my birthday or other personally important day off. Maybe never?

Even if I had, there’s little chance it would have been on a Monday.

Mondays set the tone for the week ahead. Miss a Monday when everyone else works and you start your week ridiculously behind.

In my current role, we hold our go-to-market team meeting on Mondays. Our weekly all-company stand-up covers plans for the week and on the first Monday (which this was), plans for the month. This particular Monday also included a rescheduled call with one of our board members.

I considered taking Friday off instead. But I didn’t.

A long time coming

It’s taken a long time to get to this place.

I haven’t been one to take my birthday off. And it would be completely unheard of for me to use my precious vacation time to just do nothing.

Heck, I haven’t even been good at truly stepping away from work—not checking email or finishing that last “to do”—when I’m on PTO.

But I’m older now. And wiser. 🙄

Or maybe I’m just tired of it all. Grind culture. Corporate greed that prioritizes profits over people. The “work now, enjoy life when you retire” bullshit we’ve been fed our whole lives.

Who benefits from this? Not you. Not me.

Leadership matters

Over the years I’ve talked to countless colleagues trying to navigate personal situations alongside work. My counsel has always been the same:

1. Your employer does not care about you. Now granted, your boss may, but the company as an entity does not.

2. You should always do what’s best for you, because your company will only do what’s best for them. Don’t believe me? Look at how companies are clawing back employee benefits (gated article) right now.

I know all of this. I believe all of this. And yet I’ve still struggled to prioritize myself.

This is where leadership matters most. As leaders, we can set the example for our team. Normalize life being more important than work. Remove barriers to taking time off. Encourage and celebrate team members living their lives.

That’s what my boss did for me.

He didn’t act inconvenienced that I wasn’t going to be there. He didn’t ask me to complete and share my monthly plan before Monday—in fact, he suggested we just push it to later in the week.

There were no passive-aggressive comments. No insinuations. No guilt.

You’re going to be off? NBD, his response said.

And so I took Monday off and enjoyed a beautiful Seattle day with my equally beautiful wife.

Like it was the most normal thing to do in the world. Because even though it doesn’t always feel that way, it really should be.

PS: Happy anniversary, my love. Here’s to many more to come. ❤️

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(I know what you’re thinking—I must be really fun at parties. 🙄)

There’s general agreement that AI will change the nature of work. Accountants and lawyers, marketers and salespeople, product managers and software developers, school administrators and professors … these roles and so many more will change.

But how? Who the eff knows. There are a lot of theories—and a lot of LinkedIn posts—but no matter how confidently they tell you, no one knows for sure.

Slap some AI on that

We’re in the very early days of a new technology and like so many new technologies before it, we’re mostly just slapping AI on top of existing processes and models.

Remember the early days of the Internet? Company websites were primarily marketing brochures, sans that freshly printed smell. IYKYK.

As a CIO I saw this all the time. We added computers to classrooms but the process remained the same. PowerPoint slides replaced overhead transparencies but nothing else really changed—except the cost to equip and maintain classrooms went up exponentially.

Or my own personal favorite (and by favorite I mean nightmare): we brought in new enterprise systems with amazing capabilities and then spent millions of dollars and years of time making the shiny new system behave exactly like the old one, which had processes designed solely based on system limitations—not actual need. 🤦🏼‍♀️

It’s not new. It’s not unexpected. And it’s totally okay that this is the stage we’re in. We just have to stop pretending that we’re not.

The challenge is moving beyond this stage.

The skills we actually need

Humans are remarkably resistant to change. Organizations even more so. Knowing this, how do we:

• Build more adaptable and resilient companies?

• Create cultures oriented around continuous learning and improvement?

• Enable students and employees to be builders and innovators—creators, not consumers?

This is the upskilling we actually need.

We can’t train someone for an AI-enabled role right now. There are no real models for how those roles will work—and the technology is changing so quickly that anything we teach today could be obsolete within a month.

We need to help our teams imagine a whole new way of working.

Not the current processes and deliverables augmented with AI (this is mainly what I wrote about in Leveling Up With AI). Not a “thinking outside the box” type of exercise. We need to start from a blank slate—asking ourselves, “if this job didn’t exist, how would we design it today?”

That’s extremely hard to do. If it is even possible, it requires at least two things:

• The ability to step outside the role and work backwards from the outcomes it’s meant to drive

• Consistent time and space to experiment with new technologies—and figure out how they help achieve those outcomes

This isn’t a one-time activity. It requires continual reinvention of our work. Who’s got time for that?

I don’t know about you, but I rarely have time to get everything done on my ever-growing list of things to do, much less play with AI to reimagine my role from the ground up. And I work for an AI company.

Our challenge as leaders

As I was writing this blog, I came across a friend’s LinkedIn post talking about an AI conference they’re planning to attend. The conference agenda included this note:

Exactly. As leaders, we must rise to this challenge.

If we want to lead in the age of AI, we need to tackle the very nature of work itself. Our company cultures. How we structure time and measure productivity. The value we place on experimentation and change.

We need to set the expectation that our team members’ roles and work will continually evolve, and we need to provide the tools and space to enable it.

The problem isn’t AI. It never was. It’s getting ourselves—and our teams—comfortable with constant change.

Bonus: I’ve been talking about “thinking outside the box” for a long time, it seems. Here’s a 2013 video where I talk about throwing the box away:

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At some point or another, we’ve all had that person on our team, too. They’re capital-T toxic. They may be actively undermining their colleagues. Gaslighting them—and you.

It can take a while to see it—they’re often good at making you think it’s you, not them—but once you do, you can’t unsee it.

It’s pure poison that will destroy your team if you don’t address it quickly.

One bad apple, indeed.

More insidious apples

There are other types of bad apples—ones less obvious, and in some ways more insidious—because they mean well.

Mediocrity (your underperformers) and martyrs.

They’re not bad people, which makes it all the more difficult to see how they’re silently eating away at your team, rotting it from the inside out.

Mediocrity slowly drains the life out of everything.

Your best people notice what you tolerate. Before long they disengage. Or simply leave.

They don’t want to carry the weight of someone who isn’t pulling theirs. They want teammates who will push them to be better—ones who can help them succeed.

Weaponizing the mission

And then there’s the martyr. Like mediocrity, they don’t look like a problem at first. They’re passionate. Principled. Convicted.

They position themselves as the arbiter of what’s “right” for the company. Everything is framed as protecting the mission. Over time, that becomes a weapon used to shut down ideas, challenge decisions, and undermine others.

The martyr doesn’t build alignment. They quietly create division instead. If you’re not meeting their personal litmus test, you’re not just wrong—you’re a problem.

Mediocrity lowers the bar. The martyr sets a bar only they can meet.

None of these people—not even the toxic ones—wake up with the intent to hurt your team. But intentions don’t matter. Actions do.

All of them will break your culture and your team—if you let them.

Bonus read: Niceness can be an equally insidious culture killer.

No forewarning. No purposeful break. No push to get something out regardless of what else was going on. Just … nothing.

The week prior, I woke up mid-week and found myself so fatigued that I got winded trying to get out of bed—so back to bed I went.

I cancelled most of my meetings but had too many things to do to just rest. So I grabbed my laptop and headed to the couch to quietly work away between short cat naps. Not my most productive time, but stuff got done. 🤷‍♀️

I was sick, but you know how it is—work waits for no woman. (I’ve written about this before, in Out Sick.)

And so it goes …

That’s been the story of my career. Work over pretty much everything else. I’ve always been career-oriented and ambitious. I love my work—and I derive much of my identity from it.

But the reason runs deeper than that.

I have a deeply ingrained and not altogether healthy sense of responsibility. I’ve always believed that you must do all the things you have to do before any of the things you want to do.

Now here’s the key: my “have to’s” have historically related to work, external commitments, and anything expected of me by others. Buh-bye, self-care.

In fairness, I have gotten a little better at this in recent years. But this blog is a commitment I’ve made—to myself and to you—and I take it seriously.

So why didn’t I write?

Alongside my own illness, my dog was having trouble keeping food down. On Thursday, I took him to the vet. They did blood work and gave him some medicine.

On Friday, they diagnosed him with pancreatitis. Special food, more meds. Back to the vet on Saturday morning—things were getting worse.

Saturday evening, we said goodbye to my sweet, nearly 17-year-old pup for the last time. And then I woke up early Sunday morning and flew to a conference for work.

I was a wreck.

I couldn’t write. I couldn’t bring myself to go to the two receptions that I was supposed to attend on Sunday night. All I could do was cry.

My weekend was consumed with grief. And that’s okay. More than okay, actually.

But … work?

I’ve heard for years “No one on their deathbed ever said, ‘I wish I had spent more time at work’.” I’ve even said it to others myself.

But I’ve still lost a lot of really important moments to work.

There’s so much more to life than work. There are birthdays and weddings, spring breaks and holiday concerts. Opening day at the stadium, summer concerts in the park … alongside sleepless nights, high fevers, and mental health days.

These are the real “have to’s.” Prioritize them. Prioritize your children, your significant other, and yourself. Especially yourself.

Work shouldn’t get in the way of life—not the joys, and not the sorrows.

So rest in peace, Obi (Wan Kenobi). You were my constant companion for 16 years—even at work. I will miss you.

Bonus read: I know what you’re saying—now just isn’t a good time to [insert your need here]. Spoiler alert: It’s never a good time. Do it anyway.

I’ve been hearing this a lot lately—especially from mid- to late-career folks leaving (often high-level) roles because they want to do meaningful work with people they like.

We’ve all worked with asshole colleagues or toxic managers—or both. We’ve had enough of the corporate slog, profits over people, and grind cultures. Hard pass.

After working in these types of environments, the inclination is to over-rotate toward niceness, where everyone gets along and pleasantness prevails.

But nice can be every bit as ruinous to your culture. Maybe even more so.

I know nice …

I’ve worked in “nice” cultures. Higher ed is filled with them. And put a higher ed institution in the Midwest or the South and you’ve got a niceness double whammy.

But organizational niceness isn’t all it’s cracked up to be. It prioritizes pleasantness over performance. It masks role misalignment or even incompetence.

It enables toxic behavior to persist under the guise of upholding an organization’s mission, values, or “family.” (Read more in my post Work Isn’t Family)

It’s actually not all that nice, underneath it all.

Let’s not be “nice”

I’m one of those people who left my corporate job because I want to do meaningful work with people I like. But I don’t want to be nice.

Which is good, because of all the things I’ve been called over the years, nice is not one of them. Direct? For sure. Empathetic? Sometimes. Nice? Nope.

Nice means: “pleasant; agreeable; satisfactory.”

Satisfactory?? Satisfactory is “acceptable, though not outstanding.” Inspiring, right? I’m not aiming for satisfactory—and I don’t want to work with people who are.

I want to work with people who are genuinely good-hearted and incredibly talented, high-performing, and driven to succeed.

I want to work with people who are smarter than me and who make me better simply by working with them—they raise the bar and make me want to up my game, too.

And definitely don’t settle

Working with people you like is not an either/or situation. Genius and goodness are not mutually exclusive.

We do not have to choose between working with a brilliant asshole or a kind but less than competent colleague. If I’m being honest, I’ve worked with both—and prefer neither.

But this is more than just a personal preference. As leaders, we cannot let our organizations settle for niceness.

We may tell ourselves we’re creating a kind, nurturing, and collegial workplace culture, but what we’re actually doing is avoiding hard conversations. Hard decisions.

We’re letting people persist in roles that are neither good for them nor good for our organizations. That isn’t kindness—or leadership.

We’re also sending a very clear message to our high performers. They may enjoy it for a while, but they won’t stay long. No top performer wants to be on the B team.

Hold a high bar

If we want to do what’s right by our people and our organizations, we have to set and hold a high bar for people and performance.

Being pleasant … or agreeable … or satisfactory does not meet that bar. Neither does high performance in and of itself.

Building a team filled with “people you like” might look like hiring people who are:

• Passionate and smart, but humble.

• Unselfish and collaborative, but who refuse to settle.

• Excellent at what they do but are still striving to be better, and will be brutally honest to help others be better, too.

People who want to make an outsized contribution to achieving a team’s mission—and have the capacity to do so.

We’ve all seen the chaos one bad employee can create.

Are we paying enough attention to the damage a “culture of nice” is doing to our organizations?

Bonus read: Sometimes the kindest thing we can do for an employee is help them thrive elsewhere.

“Yep,” was my only response.

If you’ve known me for more than a few seconds, you know that I proudly identify as a troublemaker—and have for pretty much my entire professional career.

OG troublemaker

Waaaaay back in 2009 (now I’m dating myself) I was part of a selective leadership institute for emerging IT and library leaders.

When we registered, we had the opportunity to select ribbons to attach to our name badges—common today, but quite new at the time.

My fellow institute members and I rifled through the ribbon options, contemplating how we wanted to identify ourselves for the two-week experience. The second I saw the TROUBLEMAKER ribbon, my choice was clear.

I haven’t thought about that experience in quite a while, nor have I given much thought to my leadership philosophy recently.

A badge of honor

And then I started listening to Make Trouble by Cecile Richards—because how could I not with a title like that?

She describes herself as a lifelong troublemaker, a a badge of honor that means:

Sometimes it’s “pretty damn awesome,” she says, and “other times it’s scary.” It’s probably a little of both most of the time.

It’s also something we don’t do enough of, because making trouble comes with risk. Political capital. Strained relationships. It could even cost you your job—or your life.

And yet, perhaps now more than ever, we have to make trouble anyway.

As I’m writing this—sitting with my wife on a Saturday morning in our favorite neighborhood coffee shop—people are organizing down the street for No Kings Day.

They, and millions of other like-minded citizens across the U.S., are making a little trouble today. Maybe you are too. Good for them (and you).

Good trouble

Making trouble isn’t only for politics. As leaders, we can and should all be troublemakers, “raising hell” when the situation calls for it.

Like when Costco refused to drop its DEI initiatives. Or when Anthropic stood up to the Pentagon. It wasn’t just the right thing to do; it was good for business. Go figure.

Your form of troublemaking may not be as public as these examples. But it doesn’t make it any less important. It might look like:

• Standing up for equitable treatment of your team members.

• Refusing to do business with companies that don’t have the same values as you.

• Ensuring products are deployed ethically and responsibly.

Because that’s what leadership requires—holding ourselves and our organizations accountable to doing what’s right for our employees, our businesses, and our communities.

So—what kind of trouble are you going to make this week?

Bonus reads: Sometimes there is only one right answer—and we have a responsibility to say so.

The quote came from Cecile Richards’ memoir, Make Trouble, which I’m currently listening to. She attributes the saying to her mother, the trailblazing Texas governor Ann Richards.

It struck me because it’s such a foundational concept, but one that we often forget.

Whether you’re leading an initiative, managing a team, or selling a service—people will act (or not) for their own reasons. Not yours.

It’s not enough to tell them all the benefits your vision, initiative, or solution provides. (And don’t get me started on a features dump. Just—don’t.) Understanding and articulating the benefit to people is necessary, but not sufficient.

You have to understand what motivates them. What compels them to act when they ask themselves, “What’s in it for me?”

As leaders, it’s especially important for us to remember this.

You are not leading if no one is following. And people will not follow just because you tell them to—or because your title demands it. They will not follow unless they have good reason to.

A reason that’s just right for them.

Those reasons will vary, but they often boil down to two things: intrinsic motivators and external incentives. How people view themselves and how they want others to perceive them.

Your job is to discover each person’s reason, understand it, and align to it.

Until then, no one’s buying what you’re selling—whether that’s a product or a vision.

Bonus read: We’re in the throes of March Madness and just weeks away from the WNBA draft—making it a great time to revisit leadership lessons from Golden State Valkyries coach Natalie Nakase.

Cover photo by Rommel Davila on Unsplash