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.
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.
by Robyn Bolton | Mar 11, 2026 | AI, Leading Through Uncertainty, Strategy
Thursday, February 26.
3:35 pm PST – Jack Dorsey said thank you and goodbye to 4,000 people. Block;s profitability was growing, but the promise of “intelligence tools…paired with flatted teams” enabled a fundamental shift in how the company could be run
4:12 pm PST – He posted his farewell announcement to X for the world to read. In it he wrote, “I know doing it this way might feel awkward. I’d rather feel awkward and human than efficient and cold.”
Is there anything more darkly humorous than a CEO trying to avoid appearing efficient and cold when communicating a decision to make the company more efficient and cold?
Only the moment when your boss calls to ask how your plans to grow the business and going and then informs you that the C-Suite wants a plan “to do what Dorsey just did”
Tuesday, March 10.
Time unknown – The agenda of Amazon’s weekly “This Week in Stores Tech” focused solely on investigating why “the availability of the site and related infrastructure has not been good recently.”
More specifically, why, for SIX HOURS, Amazon customers could not access their accounts, view product prices, or complete checkout. That is nearly $300M in lost revenue assuming the outage only affected North America.
All because, after years of cutting headcount and ramping up AI, junior engineers basically vibe-coded production changes..
As best practices and safeguards are yet to be “concretized,” it’s now the responsibility of senior engineers to review all production changes prepared by junior programmers.
How efficient is that AI looking now?
What we lose when we bet on hype, not proof
Researchers at Oxford have documented companies using AI as justification for cuts they had already planned. A January 2026 survey of 1,006 global executives found that 60% have or will make cuts in anticipation of AI’s impact while 29% plan to slow hiring. Only 2% have laid off staff as a result for actual AI-driven results.
Thousands of people are being laid off based on hype, not proof.
It’s reasonable to expect that, one day, AI will live up to the hype and deliver on all the promises promoters are making. But that’s a long-term bet that only pays out if you survive the inevitable crashes in efficiency, revenue, and institutional knowledge.
When organizations swap out people for “intelligence tools,” they lose institutional memory, the subtle, often unspoken, sometimes subconscious knowledge that makes things work. These are the people who understand your clients, your controls, and why past decisions were made. AI can automate workflows. It cannot replicate that knowledge. And once it’s gone, it’s gone.
And the loss continues even amongst the people who remain.
Research from MIT shows that regular AI use reduces activity in brain networks responsible for creativity and analogical thinking by 55%, and the atrophy persists even after people stop using AI tools. You are not trading people for AI. You are trading people for AI while simultaneously reducing your remaining team’s capacity to think creatively, adapt quickly, and catch mistakes. Operations get fragile. Innovation stalls. And when the AI-assisted work fails, as it did at Amazon, there’s no one left to fix it.
The root of growth is never hype
When the call comes down from on high to “do what Dorsey did” it’s hard to counter with cautionary tales like Amazon or reality checks about the state and capability of the organization.
But you can ask questions:
- Are you cutting based on what AI has delivered or what we expect it to?
- How will we ensure essential institutional knowledge isn’t lost?
- If (when) AI-assisted work fails, who fixes it? Amazon’s answers were still on staff. Will ours be, too?
Growth is essential to every organization. But you can’t cut your way to growth.
AI doesn’t change that fact.
It just makes it easier to believe the hype.
by Robyn Bolton | Feb 23, 2026 | Leadership, Stories & Examples, Strategy
Congratulations, you’ve done the hard part required to get buy-in! You asked instead of told, said “I don’t know” out loud, and got genuine buy-in. Your team believes, is engaged, and ready to go. And yet execution is stalling.
What gives?
Activity without Achievement
There’s no doubt that people are working hard. You can see it in their schedules and you hear it in your one-on-ones. But projects are moving slower than they should, decisions that seem straightforward take weeks, and agreements made in meetings are quietly undone. Strategies, buy-in, timelines are powerless against an invisible and unnamed force.
So, you consider your options. A team offsite can provide a helpful rest but there’s no guarantee it sticks when you’re back in the office. Training can help shore up skill gaps, but your team is already capable, so this doesn’t feel like a skill problem. You could reorg but that creates new problems.
Your People Aren’t the Problem
The problem isn’t your people, your team, or even your culture. The problem is the hidden seams between people, teams, and cultures, that create friction.
Because of friction, people hesitate to share information across functional or hierarchical seams. They make assumptions about other generations. They work to achieve individual or functional, rather than collective, goals.
These friction points have been part of your organization for so long that they are accepted as normal. As immoveable and unchangeable as your company’s mission and vision. And because they’re so ingrained, you shift your efforts to things that feel changeable: skills, org charts, and communication plans.
You’re addressing symptoms because the root cause seems impossible to fix.
It’s not impossible.
How One Company Resolved the Friction and Tightened the Seams Without Extra Work
When a K-5 curriculum company decided to expand into the Middle School market, they knew they were asking the project team to do something new that was complex, ambiguous, and fraught with high-stakes decisions.
Six months in, the project was breaking down. Decisions that should have taken a day took weeks or months. Work got stuck as different functions weighed in at different times with different mandatory requirements. People hid problems and gave optimistic updates.
The executive who owned the project had seen this before. In fact, she was seeing it in every project team across the entire company. So, she knew that the problem wasn’t the project or the people, it was something much deeper, something that was such a part of the company’s standard operating process that it had become invisible.
So, she brought in someone (me) who could see things differently and together we sought out the seams, naming the moments when friction occurred, and engaging the team in developing and experimenting with solutions.
And we did it all as part of the daily work.
We redesigned hand-offs in real time, experimented with decision-making rules until we found what worked for multiple decision types, and rewarded people for saying “I don’t know.”
Within six months, the project was back on track and engagement and morale were sky-high. Other teams took notice and asked for advice. New products began shipping on time, on budget, and to rave reviews.
Now the Real Work Begins
Where are your seams showing up? A cross-functional initiative that’s losing momentum? A decision that never seems to stick? A team that’s aligned on paper but stuck in execution?
That friction has a name. And it’s findable.
If you’re ready to find the seams and resolve the friction, set up a SeamSpotter Session. It’s a 60 to 90-minute conversation, no prep required, and you’ll receive a written summary and recommended next steps within 48 hours.
If your team is bought in, but execution keeps stuttering, you can fix it. Email me at robyn@milezero.io to get started.
by Robyn Bolton | Feb 16, 2026 | Leadership, Leading Through Uncertainty, Strategy
“None of it worked. When I pulled the executive team back together and asked what went wrong, these executives said, ‘You told us what to do. You never asked us what to do.
“What I should have done is just said, ‘I don’t know.’ And when you say those words, what happens is everybody wants to help you.”
That is how Josh D’Amaro, the newly named CEO of the Walt Disney Company, characterized his defining leadership development moment.
Sound familiar?
Every executive, at some point in their career, has faced this moment. The business is doing poorly, the future is uncertain, and everyone is looking to you for answers.
But few of us learn the lesson that Mr. D’Amaro did. So, we keep telling and wondering why compliance isn’t generating the results we expected.
Compliance and Buy-In are not the same
In our world of “using positive words to describe uncomfortable realities,” we often characterize compliance as buy-in. And that’s a dangerous mistake.
“Compliance,” explains innovation expert Tendayi Viki, “comes from external pressures to follow rules and policies due to fear of consequences. In contrast, buy-in comes from internal motivation where people genuinely view the initiative as valuable and legitimate.”
Compliance is what happened when D’Amaro convened the market and sales executives of Hong Kong Disneyland together and told them “to adjust, build, and set ourselves up for the future.”
When things are not going well and the future is uncertain (and therefore scary) it’s normal to think that, because you are in a role with authority, that you need to have all the answers. But you don’t. Because you can’t. Because no one has the answers.
You need help.
Why Buy-in, not compliance, is required for success
No one is going to help you when they’re afraid. Instead, they’re going to execute orders regardless of their own experiences or judgment, which may be more informed and likely to result in the desired outcome (as was the case with D’Amaro and his team).
But when you ask for help, people help. They feel ownership of both the problem and the solution and seek out creative ideas and alternatives. They work across traditional organizational boundaries, like functions and levels, and they’re more resilient when faced with adversity. Even better for you, they don’t require constant instruction, surveillance, and micromanagement.
Getting buy-in frees you up to do the very thing you want to do: lead a team to a common goal and better future.
Buy-in is NOT another Change Management initiative
I’m sorry to say that getting buy-in is much harder than running the standard Change Management playbook.
Change management gives leaders a structured playbook of communication plans, training schedules, governance milestones. It’s systematic, observable, and leader-driven. And it’s not wrong. It’s just not sufficient to gain buy-in.
Buy-in is individual, nonlinear, and rooted in belief, not process. It forms one person at a time based on trust, relevance, and whether the individual sees themselves in the future state. It happens when one human being trusts the motives and behaviors of another human being.
How to get Buy-In
Earning buy-in requires you to do what D’Amaro eventually learned: invite dissent, share incomplete thinking, and say “I don’t know.” But that’s just the beginning.
You also have to find where things are breaking down internally, the gaps that allowed the situation to grow ever more concerning and dire. And it’s rarely at the obvious boundaries between silos that everyone can see and org charts try to fix.
It’s at the seams: the hidden disconnects between people, decisions, handoffs, and incentives where functions, levels, and priorities intersect. These seams are where compliance lives and buy-in dies. And until you make them visible, you’ll keep mistaking one for the other. But they can be made visible and that changes everything.
Now that you see the difference, where is compliance masquerading as buy-in in your organization?
