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 | 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.
by Robyn Bolton | Apr 22, 2026 | Leading Through Uncertainty, Strategy
“Weeks. Always weeks. Man, the last time I talked months was a million weeks ago.”
Jim Halpert, The Office, 2013
Last week, I spoke to the Chief Human Resources Officer of a tech company about an engagement that would take 2-3 weeks to complete. Her response? “We don’t talk in weeks anymore. We talk in days, preferably hours.”
At first, I wanted to remind her that just because a woman can make a baby in nine months, doesn’t mean nine women can make a baby in once month.
But we weren’t talking about making babies. We were talking about leading a company in a world that feels like it’s changing faster than ever and we’re scrambling to catch up or keep pace. But is speed really the solution?
She’s right. We need to move faster.
An increase in the pace of change isn’t just a feeling. It’s facts:
The World Economic Forum and Bain & Company put it plainly, “What was once a five-year strategic horizon has compressed into a 12-month horizon, while a two-to-three-year plan is now a six-month view. The strategy machinery must spin at a speed no company is used to managing.”
They go on to say that “waiting is not caution – it is abdication.” But as dangerous as doing nothing is, how does it compare to do the wrong thing quickly?
She’s not wrong. But speed isn’t the (whole) answer.
McKinsey’s research begins to answer that question. It found that, of the 70% of large-scale transformations that failed, neither a lack of urgency nor insufficient speed were root causes. Instead, the most common root causes were:
- Setting targets based on incremental thinking rather than bold vision
- Failing to engage the full organization in the change
- Never embedding new ways of working into how the business actually runs day to day
These findings are reinforced by The Project Management Institute’s 2025 global study of nearly 6,000 projects finding that that found that 50% of projects successfully delivered the intended outcomes and create value while only 13% failed. For projects without a clear vision of success, the number are flipped, failures exceeded both successes and projects with mixed results.
None of those failure modes are solved by moving faster. In fact, compressing timelines makes them all worse. Less time to clarify and communicate a vision of success and build commitment. Less time to engage broadly. Less time to make anything stick.
The solution isn’t speed. It’s clarity.
Without clarity, every new technology, every competitor move, every shift in the market feels equally urgent and equally threatening. And when everything is urgent, nothing gets done well. Just quickly.
But when you have clarity about who you are as a leader and why your organization has a uniquely relevant, valuable, rare, and hard to imitate reason to exist, you aren’t overwhelmed when things change. You see relevant choices faster, understand trade-offs better, and move with confidence instead of chaos.
This is why the WEF and Bain report doesn’t focus on speed but on the imperative to treat strategy as a continuous cycle: constantly updated, scanning for signals, recalibrating as new information arrives.
The time pressure you feel is real, but the answer isn’t only to move faster. It’s to root yourself in clarity about who you are and what you do so that when you need to move in days, you already know what you’re moving toward.
Clarity leads speed. Not the other way around.
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.
