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?
by Robyn Bolton | Oct 6, 2025 | 5 Questions, Customer Centricity, Innovation, Tips, Tricks, & Tools
For decades, we’ve faithfully followed innovation’s best practices. The brainstorming workshops, the customer interviews, and the validated frameworks that make innovation feel systematic and professional. Design thinking sessions, check. Lean startup methodology, check. It’s deeply satisfying, like solving a puzzle where all the pieces fit perfectly.
Problem is, we’re solving the wrong puzzle.
As Ellen Di Resta points out in this conversation, all the frameworks we worship, from brainstorming through business model mapping, are business-building tools, not idea creation tools.
Read on to learn why our failure to act on the fundamental distinction between value creation and value capture causes too many disciplined, process-following teams to create beautiful prototypes for products nobody wants.
Robyn: What’s the one piece of conventional wisdom about innovation that organizations need to unlearn?
Ellen: That the innovation best practices everyone’s obsessed with work for the early stages of innovation.
The early part of the innovation process is all about creating value for the customer. What are their needs? Why are their Jobs to be Done unsatisfied? But very quickly we shift to coming up with an idea, prototyping it, and creating a business plan. We shift to creating value for the business, before we assess whether or not we’ve successfully created value for the customer.
Think about all those innovation best practices. We’ve got business model canvas. That’s about how you create value for the business. Right? We’ve got the incubators, accelerators, lean, lean startup. It’s about creating the startup, which is a business, right? These tools are about creating value for the business, not the customer.
R: You know that Jobs to be Done is a hill I will die on, so I am firmly in the camp that if it doesn’t create value for the customer, it can’t create value for the business. So why do people rush through the process of creating ideas that create customer value?
E: We don’t really teach people how to develop ideas because our culture only values what’s tangible. But an idea is not a tangible thing so it’s hard for people to get their minds around it. What does it mean to work on it? What does it mean to develop it? We need to learn what motivates people’s decision-making.
Prototypes and solutions are much easier to sell to people because you have something tangible that you can show to them, explain, and answer questions about. Then they either say yes or no, and you immediately know if you succeeded or failed.
R: Sounds like it all comes down to how quickly and accurately can I measure outcomes?
E: Exactly. But here’s the rub, they don’t even know they’re rushing because traditional innovation tools give them a sense of progress, even if the progress is wrong.
We’ve all been to a brainstorm session, right? Somebody calls the brainstorm session. Everybody goes. They say any idea is good. Nothing is bad. Come up with wild, crazy ideas. They plaster the walls with 300 ideas, and then everybody leaves, and they feel good and happy and creative, and the poor person who called the brainstorm is stuck.
Now what do they do? They look at these 300 ideas, and they sort them based on things they can measure like how long it’ll take to do or how much money it’ll cost to do it. What happens? They end up choosing the things that we already know how to do! So why have the brainstorm?”
R: This creates a real tension: leadership wants progress they can track, but the early work is inherently unmeasurable. How do you navigate that organizational reality?
E: Those tangible metrics are all about reliability. They make sure you’re doing things right. That you’re doing it the same way every time? And that’s appropriate when you know what you’re doing, know you’re creating value for the customer, and now you’re working to create value for the business. Usually at scale
But the other side of it? That’s where you’re creating new value and you are trying to figure things out. You need validity metrics. Are we doing the right things? How will we know that we’re doing the right things.
R: What’s the most important insight leaders need to understand about early-stage innovation?
E: The one thing that the leader must do is run cover. Their job is to protect the team who’s doing the actual idea development work because that work is fuzzy and doesn’t look like it’s getting anywhere until Ta-Da, it’s done!
They need to strategically communicate and make sure that the leadership hears what they need to hear, so that they know everything is in control, right? And so they’re running cover is the best way to describe it. And if you don’t have that person, it’s really hard to do the idea development work.”
But to do all of that, the leader also must really care about that problem and about understanding the customer.
We must create value for the customer before we can create value for the business. Ellen’s insight that most innovation best practices focus on the latter is devastating. It’s also essential for all the leaders and teams who need results from their innovation investments.
Before your next innovation project touches a single framework, ask yourself Ellen’s fundamental question: “Are we at a stage where we’re creating value for the customer, or the business?” If you can’t answer that clearly, put down the canvas and start having deeper conversations with the people whose problems you think you’re solving.
To learn more about Ellen’s work, check out Pearl Partners.
To dive deeper into Ellen’s though leadership, visit her Substack – Idea Builders Guild.
To break the cycle of using the wrong idea tools, sign-up for her free one-hour workshop.
by Robyn Bolton | Sep 16, 2025 | Leading Through Uncertainty, Tips, Tricks, & Tools
When a project is stuck and your team is trying to manage uncertainty, what do you hear most often:
- “We’re so afraid of making the wrong decision that we don’t make any decisions.”
- “We don’t have time to explore a bunch of stuff. We need to make decisions and go.”
- “The problem is so multi-faceted, and everything affects everything else that we don’t know where to start.”
I’ve heard all three this week, each spoken by teams leads who cared deeply about their projects and teams.
Differentiating between risk and uncertainty and accepting that uncertainty would never go away, just change focus helped relieve their overwhelm and self-doubt.
But without a way to resolve the fear, time-pressure, and complexity, the project would stay stuck with little change of progressing to success.
Turn uncertainty into an asset
It’s a truism in the field of innovation that you must fall in love with the problem, not the solution. Falling in love with the problem ensures that you remain focused on creating value and agnostic about the solution.
While this sounds great and logically makes sense, most struggle to do it. As a result, it takes incredible strength and leadership to wrestle with the problem long enough to find a solution.
Uncertainty requires the same strength and leadership because the only way out of it is through it. And, research shows, the process of getting through it, turns it into an asset.
3 Steps to turn uncertainty into an asset
Research in the music and pharmaceutical industries reveals that teams that embraced uncertainty engaged in three specific practices:
- Embrace It: Start by acknowledging the uncertainty and that things will change, go wrong, and maybe even fail. Then stay open to surprise and unpredictability, delving into the unknown “by being playful, explorative, and purposefully engaging in ventures with indeterminate outcome.”
- Fix It: Especially when dealing with Unknowable Uncertainty, which occurs when more info supports several different meanings rather than pointing to one conclusion, teams that succeed make provisional decisions to “fix” an uncertain dimension so they can move forward while also documenting the rationale for the fix, setting a date to revisit it, and criteria for changing it.
- Ignore It: It’s impossible to embrace every uncertainty at once and unwise to fix too many uncertainties at the same time. As a result, some uncertainties, you just need to ignore. Successful teams adopt “strategic ignorance” “not primarily for purposes of avoiding responsibility [but to] allow postponing decisions until better ideas emerge during the collaborative process.
This practice is iterative, often leading to new knowledge, re-examined fixes, and fresh uncertainties. It sounds overwhelming but the teams that are explicit and intentional about what they’re embracing, fixing, and ignoring are not only more likely to be successful, but they also tend to move faster.
Put it into practice
Let’s return to NatureComp, a pharmaceutical company developing natural treatments for heart disease.
Throughout the drug development process, they oscillated between addressing What, Who, How, and Where Uncertainties. They did that by changing whether they embraced, fixed, or ignored each type of uncertainty at a given point:
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As you can see, they embraced only one type of uncertainty to ensure focus and rapid progress. To avoid the fear of making mistakes, they fixed uncertainties throughout the process and returned to them as more information came available, either changing or reaffirming the fix. Ignoring uncertainties helped relieve feelings of being overwhelmed because the team had a plan and timeframe for when they would shift from ignoring to embracing or fixing.
Uncertainty is dynamic. You need to be dynamic, too.
You’ll never eliminate uncertainty. It’s too dynamic to every fully resolve. But by dynamically embracing, fixing, and ignore it in all its dimensions, you can accelerate your path to success.
