Leaders Archives - Mile Zero

3 Deaths. 3 Lessons. 3 Questions to Survive (and Thrive)

by Robyn Bolton | May 5, 2026 | Leadership, Leading Through Uncertainty, Stories & Examples, Strategy

Sunday morning, my phone blew up. Thirty-three text messages. Most mornings, I have zero, so my first thought was “who died?”

The texts were about a death. Sort of.

Sloan Management Review died (ceased publication) and a group chat filled with academics, thought leaders, and consultants were having an absolute meltdown.

Knowing that my husband, an actual Sloan graduate, hadn’t yet seen the news, I broke it to him gently. “Okay,” he shrugged, not even glancing up from his phone.

This was in stark contrast to his reactions to the demise of Spirit Airlines (howling with laughter at the memes) and the resurrection of Allbirds as an AI company (thoughtful and incredibly technical analysis).

Lesson 1: The Race to the Bottom Never Ends Well

CNN’s headline said it all, “Why did Spirit fail? Too many passengers hated flying it.” To prove the point, the article opens,

“Lousy service, not the Iran war, killed Spirit Airlines. Spirit was doomed to fail because of mismanagement, deep financial problems, and – crucially – its reputation for poor customer service. The spike in jet fuel prices during the war just accelerated Spirit’s inevitable demise.”

If that can be written about your business, you don’t deserve to be in business.

It’s only a matter of time until you’re not.

Lesson 2: Be Patient for Growth and Impatient for Profit

Allbirds raised $348 million when it IPOed in 2021 and, at one point, was valued at $4.1 billion despite never turning a profit. Six years later, its stock price had fallen 95% and it sold its business and IP to a brand management company for $39 million.

How did this happen? There are plenty of theories – it expanded too aggressively into bricks and mortar retail, it made ugly shoes but operated like a fashion brand, its Tech Bro image is no longer aspirational for Gen Z customers – but the fact is that it prioritized growth over profit and that ultimately bit them in the balance sheet.

Lesson 3: Some Businesses are Butterflies

While my colleagues’ alarm was understandable, it missed the bigger picture.

Sloan Management Review (SMR) didn’t die. It metamorphosed.

Yes, the SMR brand is going away, but future ideas, research and findings will continue to be shared through digital newsletters, short-form videos, podcasts, and social-first content.

In effect, SMR is metamorphosing to better reflect how its subscribers consume information. Busy executives don’t have the time to read long-form, dense research articles. They grab information in snippets and soundbites. This change ensures the people who need the ideas the most get them.

3 Questions to Find Your Fate

Do you treat your customers like they exist for your benefit? In other words, are you more focused on value extraction than value creation and delivery? If yes, start planning your business’ funeral and don’t expect anyone to attend.

Do you have a financially and operationally sustainable business model? If no, start planning your funeral but take comfort in the fact that people will attend and may even say nice things about you.

Do you know the unique, relevant, valuable, and hard to imitate reason why you exist? Can you articulate the rare and essential Job to be Done you do for your customers? If no, you’re on life support. When you can answer yes, you’ll be ready to be a butterfly.

One quick caveat

When businesses die, people lose their jobs and that is incredibly tragic. The psychological, financial, and relational impacts of job loss are tremendous, impacting people far beyond the individual laid off. It can take months, even years for people and families to recover and, for some, it never happens.

Creative destruction is real and necessary for long-term economic, technological, and societal growth. But the short-term impact has human consequences that should never be ignored.

Competing Priorities Aren’t a Trade-off. They’re a Test. Are You Passing?

by Robyn Bolton | Apr 28, 2026 | Leadership, Leading Through Uncertainty, Strategy

“Never half-ass two things. Whole-ass one thing.” – Ron Swanson, Parks and Rec

With all due respect to Ron Swanson, leaders today need to whole-ass two things. In a world of constrained resources, you don’t have enough time, money, or people to put against your highest priority, let alone multiple high priorities.

But if you think you must choose between investing in today or the future, know that you’re most likely choosing between killing your company quickly or slowly. That’s what “And, not or,” and it’s required in these three areas.

Development AND Research

“Right now, it’s not sufficient to just keep treading water.” – L. Rafael Reif, former MIT president and current professor of electrical engineering and computer science

“America Is Losing the Innovation Race” screamed the Foreign Affairs article in which Reif detailed evidence that America is falling behind China in electric vehicles, nuclear energy, war technologies, and other areas of critical technology.

Since 2015, as China invested in science and technology to develop the capability to produce high-end products at scale, US federal spending on basic research, as measured in real 2017 dollars, has declined.

Even the research that is funded isn’t keeping up. A paper published in 2022 examined nearly 50 million academic papers and patents from 1945 to 2010 and found a precipitous decline in the “disruptiveness” (i.e. makes previous findings obsolete or pushes the field in a new direction) of research across all scientific fields, including a 100% drop in the physical sciences and a 78.7% decline in computer and communications patents.

The funding story is quite different but no less alarming on the corporate side. Between 1964 and 2022, business funding as a source of R&D funds more than doubled but the vast majority of those funds are spent on applied research (13%) and development (80%), not the type of fundamental research that launches a country forward economically or societally.

Operators AND Innovators

“It’s a trap” – MBA student

For two hours, we discussed Netflix’s culture: the no vacation policy” policy, the “act in Netflix’s best interest” expense policy, and the management philosophy that stresses hiring people for their expertise and then trusting them to make decisions.

To me it sounded like a dream. So, when I asked who wanted to work for Netflix, I was shocked when not a single hand went up.

To my students, it sounded like a trap.

And that’s ok. Not everyone wants to face the accountability and repercussions of taking risks, exercising judgment, and making decisions.

Companies need people who want to follow processes, become experts in their fields, and keep the business steady and growing. AND they need people who question processes, explore far beyond their industries, and challenge the business to do better and grow further.

AI AND Humans

“What keeps me up is the fact that so many people are being convinced that they don’t matter anymore.” – Former Canadian Prime Minister Justin Trudeau

When 16,000 jobs, on average, have been lost each month for the past year due to AI, it’s pretty hard to convince a human and they matter.

Yet a growing body of research shows that humans enabled by AI generate new and novel ideas more quickly and cost efficiently than either AI or humans alone. In a battle between 125 “global problem solvers” and one expert in prompt engineering, the latter produced 180 ideas in 5.5 hours at a total cost of $27.01 and none of the ideas were meaningfully different in terms of strategic viability, environmental or financial value, or overall quality than the human-only ideas. At P&G, researchers found that the most innovative ideas were generated by AI-enabled teams and that those teams worked about 12% faster than other teams and AI-enabled individuals.

Ultimately, the companies that succeed won’t be the ones that make the best bets.

They’ll be the ones that learn to whole-ass two things.

Uncertainty, Overwhelm, and the Wisdom of Bull Durham

by Robyn Bolton | Mar 30, 2026 | Just for Fun, Leading Through Uncertainty

We survived the first quarter of the year. Congratulations everyone, job well done.

Did we hope for more than just survival? Of course we did! But hey, sometimes just living to fight another day is a victory and we still have nine more months to hit our KPIs, deliver our OKRs, and nail this fiscal’s BHAG.

So, let’s take a moment to focus on what really matters: Baseball is back!

Along with the hope of the new season, and the warm weather that comes with it, comes an excuse to revisit the wisdom of classic baseball moves. In 2021, I wrote about Moneyball’s lessons in innovation and it continues to be one of the top read posts on my blog.

If you feel overwhelmed by Q1, fear not! There’s no greater source of advice on finding simplicity, solving problems, and leading people than Bull Durham.

When you’re overwhelmed, go back to the basics.

Skip: This… is a simple game. You throw the ball. You hit the ball. You catch the ball.

The Durham Bulls are 8-16 and Skip (the manager) has had enough. He’s tried every tool in his coaching toolkit and the team continues to perform poorly, display a poor attitude, and deliver a halfhearted performance. Overwhelmed and frustrated, he turns to veteran player Crash Davis for advice. “Scare ‘em,” Crash offers and what comes next is one of the greatest tirades on film.

But the greatest lesson here is what comes towards the end of the tirade: a description of the utter simplicity of baseball. There’s no strategy, no competitor analysis, no number-crunching, just a simple explanation of the most basic elements of the job. Throw. Hit. Catch.

It’s easy to get overwhelmed by news, technology, corporate politics, the list goes on. That overwhelm causes us to worry, lollygag, and obsess about what could happen. But when we cut through all that to find the essence of what we do and why we do it, things become remarkably clear and the next steps feel obvious.

Fall in love with the problem. Not the solution.

Zeke: We need a night off just to stop our losing streak. We need a rainout.

Crash: I can get us a rainout.

The Bulls are on another losing streak but this time on the road. As the team bus pulls into another motel and the players gather their bags, they complain about their problem (losing streak), propose an approach (night off) and propose a specific solution (rainout).

When Crash promises a rainout, it’s not because he knows something about the forecast the others don’t. It’s because he understands that there’s more than one way to get a night off. Like breaking into the ballpark, turning on the sprinklers, and flooding the field.

When we fall in love with a solution (rainout) we get stuck. We focus on making one thing happen, when critical dependencies are beyond our control. But when we fall in love with the problem (need a night off to stop a losing streak), we’re able to see less obvious but more likely and effective solutions.

People first. Problem solving second

Larry: [Jogs out to the mound to break up a players’ conference] Excuse me, but what the hell’s going on out here?

Crash Davis: Well, Nuke’s scared because his eyelids are jammed and his old man’s here. We need a live rooster to take the curse off Jose’s glove and nobody seems to know what to get Millie or Jimmy for their wedding present. We’re dealing with a lot of sh*t.

Larry: Okay, well, uh… candlesticks always make a nice gift, and uh, maybe you could find out where she’s registered and maybe a place-setting or maybe a silverware pattern. Okay, let’s get two! Go get ’em.

The Bulls are finally on a winning streak, but off-the-field issue are affecting on-the-filed play and things aren’t looking good. As the players gather on the mound, the team’s Assistant Manager trots out to figure out what’s going on and get the game going again.

After Crash sums up the personal issues, instead of telling the players to be professional, leave their problems at home, and get on with things, Larry focuses on solving the single issue affecting the most people first. It’s only when the players start nodding that he shifts everyone back into work-mode.

Only on Severance can we separate ourselves into work and life modes. Pretending that isn’t the case is counterproductive and toxic. But we can’t let one consume the other because it will ultimately degrade both our professional and personal lives.

As leaders, we need to find the balance between helping the humans grapple with real and personal issues and getting the team (back) on track and doing great work.

Ready to keep playing?

Baseball is a game of survival. A foul tip keeps the at bat alive. A walk keeps the inning alive. A bloop single to score a runner send the game into extra innings.

Winning takes patience and perseverance because the game is rarely won or lost in a single at-bat or inning. Just like you don’t win or lose your KPIs, OKRs, or BHAGs in a quarter.

As we start a new quarter, let’s keep it simple, focus on solving problems, and put people first.

Go get ‘em.

You’re Addicted to AI. That’s by Design.

by Robyn Bolton | Mar 25, 2026 | AI, Leadership, Strategy

“AI is the new cigarette.”

When a colleague said this in the waning days of 2022, days after ChatGPT burst on the scene, she took my breath away. The idea that this miracle would kill us seemed confined to hysterical handwringing foretelling the birth of Skynet.

She was right.

But neither of us knew it was designed to be that way.

Designed for addiction

My friend predicted that ChatGPT would stay free and helpful until usage reached “critical mass,” and then we’d have to pay. Less than three months after its November launch, OpenAI introduced its $20 per month service.

But it’s not the “first one’s free, the next one will cost you” aspect of drugs that makes AI addictive. It’s the design decisions at its core that keeps you coming back:

Purchase Decoupling in which you convert real money into tokens, creating psychological distance between you and your actual spending
Difficulty Curve where skills and benefits accumulate quickly giving you the sense that you’re becoming more capable over time and therefore more committed after progress slows.
Skill Atrophy where every skill you stop practicing because the machine does it for you, quietly disappears.

Even casual AI users have experienced one or more of these:

You get a message mid-chat telling you you’ve used all your tokens and need to come back in three hours even though you’ve paid your monthly $20 fee
You’re prompting in all caps because it’s the only way you can think of to get the LLM to stop hallucinating, while reminiscing about the days when it was a brilliant thought-partner
You’ve relied on AI to outline articles for the last several months, but you need to write in a different style and have no idea how to get started.

And yet, we keep going back.

But it’s not just individuals who are addicted. It’s entire organizations.

Signs that your organization is addicted to AI

Your CFO asks for the total AI spend across the organization. Three weeks and four departments later, the number is three times what anyone expected because the licenses are buried in IT infrastructure budgets, the pilots are expensed as innovation projects, and half the tools were purchased by business units on corporate cards.

The board approved the AI transformation initiative based on the pilot results. Eighteen months later, the pilot case study slide hasn’t changed, headcount has been reduced in anticipation of productivity gains that haven’t materialized, and the team running the pilot has quietly moved on to other work.

You eliminated the analyst pool two years ago because AI could do in minutes what they did in days. Now you need to evaluate whether the AI’s output is actually correct, and you’ve just realized there’s nobody left in the organization to check it because everyone who’s done it is gone.

Sound familiar? Your organization is an addict.

Recovery is possible

Addiction can’t be cured, only managed. The same is true for AI.

The road to recovery starts in a similar place: Visibility

Centralize AI spending the way you centralize other business processes AND allow some flexibility by setting strict spending limits and clear decision-making criteria and ownership.
Start pilots with the end in mind by establishing success metrics and scaling plans at the start of the pilot, not when it’s already in process.
Treat certain human capabilities as strategic reserves the same way you’d treat any critical operational dependency. Before automating a function, explicitly document what judgment and expertise currently lives there, who holds it, and what it would cost to rebuild it if needed.

Unlike cigarettes or gambling, we’ve reached a point where we can’t quit AI.

But we can be aware of our addiction and we must manage it.

The first step is admitting that it’s real. And by design.

What Would You Do If You Were Certain?

by Robyn Bolton | Mar 18, 2026 | AI, Customer Centricity, Leadership, Leading Through Uncertainty, Strategy

If you’re uncertain, you’re not alone. According to data from FactSet, 87% of Fortune 500 companies cited “uncertainty” during their 2025 Q1 earnings calls. And while things are definitely a tad chaotic in the world, I’ve started asking my clients, “What would you do if you were certain?”

It’s not an academic thought experiment. It’s a very practical exercise that radically shifts the way the think about and lead their businesses.

An Example That Proves the Rule

Most leaders facing disruption do one of two things: freeze and hope that “this too shall pass” or follow and hope that there is safety in numbers.

Neither is a strategy. Both are knee jerk reactions rooted in fear and communicated in the language and buzzwords of business.

This behavior didn’t start with AI. It happens every time a disruptive technology or philosophy bursts onto the scene. The printing press. The industrial revolution. Microchips. Each time, a new leader and paradigm emerges. How do they do it?

They’re certain.

Not because they’re omniscient. But because they know the answers to three questions

Question 1: Who Are You?

When photography made academic realism obsolete, Picasso didn’t freeze. He didn’t pick up a camera. He created something entirely new. Why? Because he knew exactly who he was. “I don’t seek,” he said. “I find.”

Today’s business icons are no different. Richard Branson describes himself as curious and someone who challenges the status quo. Lou Gerstner, when he arrived at a floundering IBM, declared himself a results man, not a visionary.

These self-definitions aren’t marketing. They’re decisions filters that define what you are and aren’t willing to do, agnostic of events, technologies, and capabilities.

Question 2: What Does Your Organization Actually Do?

Not what you make. Not what you sell. What Job to be Done do customers hire you to do?

Nintendo’s answer has been consistent across 130 years of radical product change: help me have fun with friends and family. From playing cards to the Game Boy, Wii, and Switch, their products changed completely. The Job didn’t.

IBM has done the same. From punch card tabulators to consulting and AI, the Job of helping customers make sense of complex information to run better never change. Amex moved from freight forwarding to credit and debit cards, but it’s commitment to move value securely when direct exchange isn’t an option never wavered.

When you know the Job you do, you stop chasing trends and start making choices.

Question 3: How Do You Move Forward?

You can’t answer this question without answering the first two. When you try, you get caught in the same freeze/follow trap as everyone else.

But when you answer the first two questions, the answer to this one becomes clear. For Picasso and Branson, they create. For Gerstner, he optimized the status quo. For most businesses, the answer is “And, not Or.” They must stabilize today’s business, step into (even follow) the next wave, and invest in creating the new.

Satya Nadella’s transformation of Microsoft is a perfect example. He defined himself as a learner, not a knower. He defined Microsoft’s job as helping people make a difference in their roles. From those two answers, every major move followed logically: maintain Office 365, step into cloud, create quantum computing technology.

None of it was reactive. All of it felt certain.

Your Moment Is Now

Yes, the world is uncertain. You don’t have to be.

Before you close this tab and tell yourself you’ll think about it later, answer the first two questions. You can change your answers later, but you need to start now.

The leaders who navigate this moment won’t be the ones who wait and see or follow the crowd. They’ll be the ones who know themselves and their organizations well enough to be certain.

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