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 11, 2025 | Leadership, Leading Through Uncertainty
The business press has a new obsession with courageous leadership.
Harvard Business Review dedicated their September cover story to it. Nordic Business Forum built an entire 2024 conference around it. BetterUp, McKinsey, and dozens of thought leaders and influencers can’t stop talking about it.
Here’s what they’re all telling you: If you’re playing it safe, stuck in analysis paralysis, not innovating fast enough, or not making bold moves, then you are the problem because you lack courage.
Here’s what they’re not telling you: You don’t have a courage problem. You have a systems problem.
The Real Story Behind “Courage Gaps”
The VP was anything but cowardly. She had a track record of bold moves and wasn’t afraid of hard conversations. The CEO wanted to transform the company by moving from a product-only focus to one offering holistic solutions that combined hardware, software, and services. This VP was the obvious choice.
Her team came to her with a ideas that would reposition the company for long-term growth. She loved it. They tested the ideas. Customers loved them. But not a single one ever launched.
It wasn’t because the VP or the CEO lacked courage. It was because the board measured success in annual improvements, the CEO’s compensation structure rewarded short-term performance, and the VP required sign-off from six different stakeholders who were evaluated on risk mitigation. At every level, the system was designed to kill bold ideas. And it worked.
This is the inconvenient truth the courage press ignores.
That success doesn’t just require leaders who are courageous, it requires organizational architecture that systematically rewards courage and manages risk.
What We’re Really Asking Leaders to Overcome
Consider what we’re actually asking leaders to be courageous against:
- Compensation structures tied to short-term metrics
- Risk management processes designed to say “no”
- Approval hierarchies where one skeptic can overrule ten enthusiasts
- Cultures where failed experiments end careers
The courage discourse lets broken systems off the hook.
It’s easier to sell “10 Ways to Build Leadership Courage” than to admit that organizational incentives, governance structures, and cultural norms are actively working against the bold moves we tell leaders to make.
What Actually Enables Courageous Leadership.
I’m not arguing that there isn’t a need for individual courage. There is.
But telling someone to “be braver” when their organizational architecture punishes bravery is like telling someone to swim faster in a pool filled with Jell-O.
If we want courage, we need to fix the things the systems that discourage it:
- Align incentives with the time horizon of the decisions you want made
- Create explicit permission structures for experimentation
- Build decision-making processes that don’t require unanimous consent
- Separate “learning investments” from “performance expectations” when measuring results
- Make the criteria for bold moves clear, not subject to whoever’s in the room
But doing this is a lot harder than buying books about courage.
The Bottom Line
When you fix the architecture, you don’t need to constantly remind people to be brave because the system enables. Individual courage becomes the expectation, not the exception.
The real question isn’t whether your leaders need courage.
It’s whether your organization has the architecture to let them use it.
If you can’t answer that question, that’s not a courage problem.
That’s a design problem.
And design is something that, as a leader, you can actually control.
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 | Sep 2, 2025 | Leading Through Uncertainty, Strategy
In September 2011, the English language officially died. That was the month that the Oxford English Dictionary, long regarded as the accepted authority on the English language published an update in which “literally” also meant figuratively. By 2016, every other major dictionary had followed suit.
The justification was simple: “literally” has been used to mean “figuratively” since 1769. Citing examples from Louisa May Alcott’s Little Women, Charles Dickens’ David Copperfield, Charlotte Bronte’s Jane Eyre, and F. Scott Fitzgerald’s The Great Gatsby, they claimed they were simply reflecting the evolution of a living language.
What utter twaddle.
Without a common understanding of a word’s meaning, we create our own definitions which lead to secret expectations, and eventually chaos.
And not just interpersonally. It can affect entire economies.
Maybe the state of the US economy is just a misunderstanding
Uncertainty.
We’re hearing and saying that word a lot lately. Whether it’s in reference to tariffs, interest rates, immigration, or customer spending, it’s hard to go a single day without “uncertainty” popping up somewhere in your life.
But are we really talking about “uncertainty?”
Uncertainty and Risk are not the same.
The notion of risk and uncertainty was first formally introduced into economics in 1921 when Frank Knight, one of the founders of the Chicago school of economics, published his dissertation Risk, Uncertainty and Profit. In the 114 since, economists and academics continued to enhance, refine, and debate his definitions and their implications.
Out here in the real world, most businesspeople use them as synonyms meaning “bad things to be avoided at all costs.”
But they’re not synonyms. They have distinct meanings, different paths to resolution, and dramatically different outcomes.
Risk can be measured and/or calculated.
Uncertainty cannot be measured or calculated
The impact of tariffs, interest rates, changes in visa availability, and customer spending can all be modeled and quantified.
So it’s NOT uncertainty that’s “paralyzing” employers. It’s risk!
Not so fast my friend.
Not all Uncertainties are the same
According to Knight, Uncertainty drives profit because it connects “with the exercise of judgment or the formation of those opinions as to the future course of events, which…actually guide most of our conduct.”
So while we can model, calculate, and measure tariffs, interest rates, and other market dynamics, the probability of each outcome is unknown. Thus, our response requires judgment.
Sometimes.
Because not all uncertainties are the same.
The Unknown (also known as “uncertainty based on ignorance”) exists when there is a “lack of information which would be necessary to make decisions with certain outcomes.”
The Unknowable (“uncertainty based on ambiguity”) exists when “an ongoing stream [of information] supports several different meanings at the same time.”
Put simply, if getting more data makes the answer obvious, we’re facing the Unknown and waiting, learning, or modeling different outcomes can move us closer to resolution. If more data isn’t helpful because it will continue to point to different, equally plausible, solutions, you’re facing the Unknowable.
So what (and why did you drag us through your literally/figuratively rant)?
If you want to get unstuck – whether it’s a project, a proposal, a team, or an entire business, you first need to be clear about what you’re facing.
If it’s a Risk, model it, measure it, make a decision, move forward.
If it’s an uncertainty, what kind is it?
If it’s Unknown, decide when to decide, ask questions, gather data, then, when the time comes, decide and move forward
If it’s Unknowable, decide how to decide then put your big kid pants on, have the honest and tough conversations, negotiate, make a decision, and move on.
I mean that literally.
by Robyn Bolton | Aug 20, 2025 | AI, Metrics
Sometimes, you see a headline and just have to shake your head. Sometimes, you see a bunch of headlines and need to scream into a pillow. This week’s headlines on AI ROI were the latter:
- Companies are Pouring Billions Into A.I. It Has Yet to Pay Off – NYT
- MIT report: 95% of generative AI pilots at companies are failing – Forbes
- Nearly 8 in 10 companies report using gen AI – yet just as many report no significant bottom-line impact – McKinsey
AI has slipped into what Gartner calls the Trough of Disillusionment. But, for people working on pilots, it might as well be the Pit of Despair because executives are beginning to declare AI a fad and deny ever having fallen victim to its siren song.
Because they’re listening to the NYT, Forbes, and McKinsey.
And they’re wrong.
ROI Reality Check
In 20205, private investment in generative AI is expected to increase 94% to an estimated $62 billion. When you’re throwing that kind of money around, it’s natural to expect ROI ASAP.
But is it realistic?
Let’s assume Gen AI “started” (became sufficiently available to set buyer expectations and warrant allocating resources to) in late 2022/early 2023. That means that we’re expecting ROI within 2 years.
That’s not realistic. It’s delusional.
ERP systems “started” in the early 1990s, yet providers like SAP still recommend five-year ROI timeframes. Cloud Computing“started” in the early 2000s, and yet, in 2025, “48% of CEOs lack confidence in their ability to measure cloud ROI.” CRM systems’ claims of 1-3 years to ROI must be considered in the context of their 50-70% implementation failure rate.
That’s not to say we shouldn’t expect rapid results. We just need to set realistic expectations around results and timing.
Measure ROI by Speed and Magnitude of Learning
In the early days of any new technology or initiative, we don’t know what we don’t know. It takes time to experiment and learn our way to meaningful and sustainable financial ROI. And the learnings are coming fast and furious:
Trust, not tech, is your biggest challenge: MIT research across 9,000+ workers shows automation success depends more on whether your team feels valued and believes you’re invested in their growth than which AI platform you choose.
Workers who experience AI’s benefits first-hand are more likely to champion automation than those told, “trust us, you’ll love it.” Job satisfaction emerged as the second strongest indicator of technology acceptance, followed by feeling valued. If you don’t invest in earning your people’s trust, don’t invest in shiny new tech.
More users don’t lead to more impact: Companies assume that making AI available to everyone guarantees ROI. Yet of the 70% of Fortune 500 companies deploying Microsoft 365 Copilot and similar “horizontal” tools (enterprise-wide copilots and chatbots), none have seen any financial impact.
The opposite approach of deploying “vertical” function-specific tools doesn’t fare much better. In fact, less than 10% make it past the pilot stage, despite having higher potential for economic impact.
Better results require reinvention, not optimization: McKinsey found that call centers that gave agents access to passive AI tools for finding articles, summarizing tickets, and drafting emails resulted in only a 5-10% call time reduction. Centers using AI tools to automate tasks without agent initiation reduced call time by 20-40%.
Centers reinventing processes around AI agents? 60-90% reduction in call time, with 80% automatically resolved.
How to Climb Out of the Pit
Make no mistake, despite these learnings, we are in the pit of AI despair. 42% of companies are abandoning their AI initiatives. That’s up from 17% just a year ago.
But we can escape if we set the right expectations and measure ROI on learning speed and quality.
Because the real concern isn’t AI’s lack of ROI today. It’s whether you’re willing to invest in the learning process long enough to be successful tomorrow.
