by Robyn Bolton | Jun 3, 2026 | Leadership, Strategy
“How much did your last 1,000 long-distance calls cost you?”
Juan Enríquez Cabot, Mexican-American academic, businessman, author, and speaker.
Strategy requires making choices. It’s an exercise in trade-offs. It requires prioritizing one thing over another and saying “no” to more things than you say “yes.”
The same is true for life. It also requires making choices, setting priorities, saying “no,” and making trade-offs.
But what happens when you no longer need to make trade-offs?
That’s one of the questions that Juan Enriquez, best-selling author and TED All-Star, posed during his speech “An Uncertain, Scary, Exciting Future.” To illustrate his point, he took us back to the late 20th century when we used to pay for long-distance calls. In the 1970s, long-distance (state-to-state) calls cost a minimum of $3.50 per minute (in 2020 dollars). In the 1980s as industry competition increased, phone companies started offering discounted rates for evening and late-night calls.
I remember my mom talking to my grandma in Pennsylvania for an hour each week and my grandma in California for two hours each month. Assuming those were the only interstate calls made (they weren’t), at a discounted rate of $1.25/minute, those five calls cost $450 in 2020 dollars.
That’s more than 3x what I currently pay for unlimited calls and text.
We used to trade off money, frequency, convenience, and quality simply to stay in touch with family and friends. Now we don’t.
But we’re still making trade-offs.
There are ALWAYS trade-offs
No one likes trade-offs. We’d much rather have everything than just one thing. After all, if you have (or do) everything then when things change, you’re prepared. You’re safe.
But “all of the above” is not an option.
My mom would have been stuck on the phone for hours every day talking to my grandmas if long-distance calls were free. But, because we couldn’t afford the financial trade-off required for daily multi-hour, long-distance calls, my mom was free to live her life untethered from the kitchen phone.
Now, the financial and physical trade-offs of long-distance calls have gone away but we’re still tethered to our phones. Instead, we’re trading away our attention and energy, data and privacy, even our mental well-being for the “convenience” of always being connected and accessible.
What trade-offs are you making (because you ARE making them)?
Look at your business strategy, your team, your daily calendar. What are you trading off? What will you stop doing so that you can invest more in starting or accelerating something else?
If you’re like most executives, you can’t answer those two questions because you choose “all of the above.”
But you did make trade-offs. You’re trading off time spent with friends and family and your physical and mental well-being to do more with less. You’re trading off your business’ future to maximize today’s profits.
There are always trade-offs. The ones you proactively and consciously choose are always better than the ones that creep up on you, promising “all of the above” while taking the things you’d never knowingly give up.
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.
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 | 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?
