by Robyn Bolton | Jun 17, 2026 | Leadership, Leading Through Uncertainty, Tips, Tricks, & Tools
Up and down New England’s coastline you’ll find lobster (pronounced “lob-stah”) shacks. These weathered wood structures produce the freshest lobster and crispiest fried seafood anywhere, enjoyed on picnic tables as the sun beats down and the waves crash against the rocky shore.
It was at one of these shacks that, many years ago, I learned priceless lesson.
As my friends and I placed our orders, I asked that the head of my lobster be removed before serving. The waitress looked at me like I had nine heads but wrote down my request and returned to the kitchen. A few minutes later she reappeared and announced that the kitchen refused to decapitate the lobster prior to serving.
“I don’t like making eye contact with my food,” I stammered.
She nodded and walked away.
When she returned with our lobsters, they all had heads but one was noticeably different. It was wearing “sunglasses” made of olives and toothpicks.
“Here,” our waitress said. “Now you don’t have to make eye contact with it.”
A short-term “solution”
As VUCA-ness (volatile, uncertain, complex, ambiguous) accelerates, C-suite executives do everything possible to create certainty and construct safety. After all, if the company doesn’t survive the short-term, even the best long-term plans don’t matter.
Evidence of this approach is everywhere:
When these decisions land on your desk, you sigh, knowing they are short-sighted but understanding the rationale. Then, you go implement them, knowing unintended consequences are coming.
Unintended doesn’t mean unpredictable
In fact, because you are on the frontlines of your business, striving to deliver today and build tomorrow, you can predict what those consequences will be:
It’s frustrating to see the problems coming but feel powerless to avoid them.
But what does any of this have to do with a lobster wearing sunglasses?
When you know the Why, you can choose the How
When directives land on your desk, don’t sigh and roll them out. Ask for the Why behind the What.
- Why are employees being forced back to the office? Did productivity decrease? Are mission-critical operations not occurring? Are top-performers leaving for in-person roles?
- Why are experienced people being let go? Is the work being outsourced or has it genuinely gone? Why are you no longer hiring entry-level people? Are they too expensive to train? Is retention genuinely poor?
- Why are innovation initiatives being cut? Is the core business in that much trouble? Do we lack the talent? Are we pursuing growth through other means?
Each directive’s Why is different which means you have more options than you realize for delivering the How. Understanding the outcomes the company needs, reveals options for delivering it while minimizing the unintended consequences.
Don’t decapitate the lobster. Find opportunities for sunglasses.
The kitchen could have easily removed the head from my lobster, but they foresaw the unintended consequences of a disappointing dining experience. When they understood my why, they created a spectacular how.
You don’t control the system so asking “Why?” feels scary, hostile, even mutinous.
You do control your piece of it. You know it better than anyone, so there’s no one better to determine the how.
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 | Dec 16, 2025 | Just for Fun, Leadership, Tips, Tricks, & Tools, Uncategorized
Everybody loves a Top X list. This past week I’ve read the Top 100 Best Comedy Movies of All Time, The 100 Best Episodes of the Century, and the NYT’s 100 Notable Books of 2025. And all this before we’re inundated with the Top 10 lists sports, politics, celebrity news, world news, and whatever other topic a writer can dream up.
Top X Lists are about big things, events that affect everyone or that will be remembered for decades. And while those Macro-moments are what stand out in our memories, they rarely define our everyday existence.
What are Micro-moments?
I first heard of Micro-moments in an interview between Dan Shipper, founder of Every, and Henrik Werdelin, founder of Prehype (and incubator that helped launch Barkbox and Ro Health). According to Werdelin:
Micro-moments for me are things when I’m in flow and things where I’m happy. It can’t be a big thing like having a family. It has to be a very concrete things like I like walking over the Brooklyn Bridge in the morning. It’s just something I get profoundly happy about, right? Or I like being in brainstorm meetings with (other entrepreneurs)
But his list of Micro-moments isn’t just a new-age happiness manifestation, it’s an actual decision-making tool. Werdelin explains:
I was basically trying to figure out what to do next and I was keeping all my options open. I got offered a job to run BBC Digital on the international side and then I got offered a job at a design agency called Wolf Collins who had an incredible CEO.
And so, I ended up having these 30 concrete [moments] where I’ve done stuff and then I started to use that as a way to measure options that would be thrown at me. The BBC sounded like it would be a lot of money, and it was like a cool job, and it would give me, I guess, self-esteem for a second. But then when I looked at what it would entail, none of the Micro-moments would be included so I was like, “ah, probably not for me.”
My first Micro-reactions
- Eye roll: Thank goodness you had a list of Micro-moments so you could avoid the soul sucking horror of running BBC Digital!
- Righteous indignation: Do you have any idea how hard it is out there to find a job? People would be thrilled to have a job that delivers only ONE Micro-moment of happiness?!
- Breathe: What a second. What if Mico-moments don’t determine your role. What if Micro-moments…perhaps…mean a little bit more! (yes, that is a terrible rephrasing of the Grinch’s epiphany)
Micro-moments are more than moments of flow and joy. They’re the moments that make up our lives, relationships, and view of the world. They’re the moments that should be on our Top 10 lists but too often get crowded out by noisier, bigger moments.
They’re also things we can create, design for, and sometimes even control.
What are YOUR Micro-moments?
As the period of end-of-year reflection approaches, think about your Micro-moments. What small, concrete moments that brought you flow, joy, or peace, this year? Where were you? What were you doing? Who were you with? Jot them down
When the new year dawns, go back to your list and get curious. What are the common themes, people, places, and activities in your Micro-moments. Write down what you notice.
As the year kicks into gear and everyone settles back into work and school routines, return to your list and start planning. How might you create more Micro-moments?
Life is made up of moments. Many of them are beyond our control. But some of them aren’t. And wouldn’t it be great to know which ones make us happiest so we can experience them more often?
by Robyn Bolton | Nov 1, 2025 | Innovation, Leading Through Uncertainty
“Is this what the dinosaurs did before the asteroid hit?”
That was the first question I was asked at IMPACT, InnoLead’s annual gathering of innovation practitioners, experts, and service providers.
It was also the first of many that provided insight into what’s on innovators and executives’ minds as we prepare for 2026
How can you prevent failure from being weaponized?
This is both a direct quote and a distressing insight into the state of corporate life. The era of “fail fast” is long gone and we’re even nostalgic for the days when we simply feared failure. Now, failure is now a weapon to be used against colleagues.
The answer is neither simple nor quick because it comes down to leadership and culture. Jit Kee Chin, Chief Technology Officer at Suffolk Construction, explained that Suffolk is able to stop the weaponization of failure because its Chairman goes to great lengths to role model a “no fault” culture within the company. “We always ask questions and have conversations before deciding on, judging, or acting on something,” she explained
How do you work with the Core Business to get things launched?
It’s long been innovation gospel that teams focused on anything other than incremental innovation must be separated, managerially and physically, from the core business to avoid being “infected” by the core’s unquestioning adherence to the status quo.
The reality, however, is the creation of Innovation Island, where ideas are created, incubated, and de-risked but remain stuck because they need to be accepted and adopted by the core business to scale.
The answer is as simple as it is effective: get input and feedback during concept development, find a core home and champion as your prototype, and work alongside them as you test and prepare to launch.
How do you organize for innovation?
For most companies, the residents of Innovation Island are a small group of functionally aligned people expected to usher innovations from their earliest stages all the way to launch and revenue-generation.
It may be time to rethink that.
Helen Riley, COO/CFO of Google X, shared that projects start with just one person working part-time until a prototype produces real-world learning. Tom Donaldson, Senior Vice President at the LEGO Group, explained that rather than one team with a large mandate, LEGO uses teams specially created for the type and phase of innovation being worked on.
What are you doing about sustainability?
Honestly, I was surprised by how frequently this question was asked. It could be because companies are combining innovation, sustainability, and other “non-essential” teams under a single umbrella to cut costs while continuing the work. Or it could be because sustainability has become a mandate for innovation teams.
I’m not sure of the reason and the answer is equally murky. While LEGO has been transparent about its sustainability goals and efforts, other speakers were more coy in their responses, for example citing the percentage of returned items that they refurbish or recycle but failing to mention the percentage of all products returned (i.e. 80% of a small number is still a small number).
How can humans thrive in an AI world?
“We’ll double down,” was Rana el Kaliouby’s answer. The co-founder and managing partner of Blue Tulip Ventures and host of Pioneers of AI podcast, showed no hesitation in her belief that humans will continue to thrive in the age of AI.
Citing her experience listening to Radiotopia Presents: Bot Love, she encouraged companies to set guardrails for how, when, and how long different AI services can be used. She also advocated for the need for companies to set metrics that go beyond measuring and maximizing usage time and engagement to considering the impact and value created by their AI-offerings.
What questions do you have?
