by Robyn Bolton | Feb 2, 2026 | AI, Leadership, Strategic Foresight, Strategy
It was a race. And the whole world was watching.
In 1911, Captain Robert Scott set out to reach the South Pole. He’d been to Antarctica before and because of his past success, he had more funding, more expertise, and more experience. He had all the equipment needed.
Racing him to fame, fortune and glory was Norwegian Roald Amundsen. Originally heading to the North Pole, he turned around when he learned that Robert Peary had beaten him there. He had dogs and skis, equipment perfect for the Arctic but unproven in Antarctica.
Amundsen won the race, by over a month.
Scott and his crew died 11 miles from the South Pole.
When the Playbook Stops Working
Scott wasn’t guessing. He’d tested motor sledges in the Alps. He’d seen ponies work on a previous Antarctic expedition. He built a plan around the best available equipment and the general playbook that had served British expeditions for decades: horses and motors move heavy loads, so use horses and motors.
It just wasn’t right for Antarctica. The motors broke down in the cold. The ponies sank through the ice. The plan that looked solid on paper fell apart the moment it met the actual environment it had to operate in.
The same thing is happening today with AI.
For decades, when new technologies emerge, executives have followed a similarly familiar playbook: assess the opportunity, build a business case, plan the rollout, execute.
And for decades it worked. Cloud migrations and ERP implementations were architectural changes to known processes with predictable outcomes. As time went on, information grew more solid, timelines became better understood, and the playbook solidified.
AI is different. Executives are so focused on picking the right AI tools and building the right infrastructure that they aren’t thinking about what happens when they hit the ice. Even if the technology works as designed, you have no idea whether it will deliver the intended results or create a ripple of unintended consequences that paralyze your business and put egg on your face.
Diagnose Before You Prescribe
The circumstances of AI are different too, and that requires a new playbook. Make that playbooks. Picking the right playbook requires something my clients and I call Calibrated Decision Design.
We start by asking how long it will take to realize the ultimate goals of the investment. Do we need to break even this year, or is this a multi-year bet where results slowly roll in? Most teams have a sense of this, so it allows us to move quickly to the next, much harder question.
What do we know and what do we believe? This is where most teams and AI implementations fail. To seem confident and indispensable, people present hypotheses as if they are facts resulting in decisions based on a single data points or best guesses. The result is a confident decision destined to crumble.
Where you land on these two axes determines your playbook. Apply the wrong one and you’ll either waste money on over-analysis or burn through budget on premature action.
Pick from the Four Playbooks
Go NOW!: You have the facts and need results now. Stop deliberating. Execute.
Predictable Planning: You have confidence in the outcome, but the payoff takes patience. Build a flexible strategy and operational plan to stay responsive as things progress.
Discovery Planning: You need results fast, but you don’t have proof your plan will work. Run small, fast experiments before scaling anything.
Resilient Strategy: The time horizon is long and you’re short on facts. The worst thing you can do is go all in. Instead, envision multiple futures, identify early warning signs, find commonalities and prepare a strategy that can pivot.
Apply it
Which playbook are you using and which one is best for your circumstance?
by Robyn Bolton | Dec 17, 2025 | Press Mentions
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 30, 2025 | Leading Through Uncertainty, Strategy, Tips, Tricks, & Tools
Just as we got used to VUCA (volatile, uncertain, complex, ambiguous) futurists now claim “the world is BANI now.” BANI (brittle, anxious, nonlinear, incomprehensible) is much worse than VUCA and reflects “the fractured, unpredictable state of the modern world.”
Not to get too Gen X on the futurists who coined and are spreading this term but…shut up.
Is the world fractured and unpredictable? Yes.
Does it feel brittle? Are we more anxious than ever? Are things changing at exponential speed, requiring nonlinear responses? Does the world feel incomprehensible? Yes, to all.
Naming a problem is the first step in solving it. The second step is falling in love with the problem so that we become laser focused on solving it. BANI does the first but fails at the second. It wallows in the problem without proposing a path forward. And as the sign says, “Ain’t nobody got time for this.”
(Re)Introducing the Cynefin Framework
The Cynefin framework recognizes that leadership and problem-solving must be contextual to be effective. Using the Welsh word for “habitat,” the framework is a tool to understand and name the context of a situation and identify the approaches best suited for managing or solving the situation.
It’s grounded in the idea that every context – situation, challenge, problem, opportunity – exists somewhere on a spectrum between Ordered and Unordered. At the Ordered end of the spectrum, cause and affect are obvious and immediate and the path forward is based on objective, immutable facts. Unordered contexts, however, have no obvious or immediate relationship between cause and effect and moving forward requires people to recognize patterns as they emerge.
Both VUCA and BANI point out the obvious – we’re spending more time on the Unordered end of the spectrum than ever. Unlike the acronyms, Cynefin helps leaders decide and act.
5 Contexts. 5 Ways Forward
The Cynefin framework identifies five contexts, each with its own best practices for making decisions and progress.
On the Ordered end of the spectrum:
- Simple contexts are characterized by stability and obvious and undisputed right answers. Here, patterns repeat, and events are consistent. This is where leaders rely on best practices to inform decisions and delegation, and direct communication to move their teams forward.
- Complicated contexts have many possible right answers and the relationship between cause and effect isn’t known but can be discovered. Here, leaders need to rely on diverse expertise and be particularly attuned to conflicting advice and novel ideas to avoid making decisions based on outdated experience.
On the Unordered end of the spectrum:
- Complex contexts are filled with unknown unknowns, many competing ideas, and unpredictable cause and effects. The most effective leadership approach in this context is one that is deeply uncomfortable for most leaders but familiar to innovators – letting patterns emerge. Using small-scale experiments and high levels of collaboration, diversity, and dissent, leaders can accelerate pattern-recognition and place smart bets.
- Chaos are contexts fraught with tension. There are no right answers or clear cause and effect. There are too many decisions to make and not enough time. Here, leaders often freeze or make big bold decisions. Neither is wise. Instead, leaders need to think like emergency responders and rapidly response to re-establish order where possible to bring the situation into a Complex state, rather than trying to solve everything at once.
The final context is Disorder. Here leaders argue, multiple perspectives fight for dominance, and the organization is divided into fractions. Resolution requires breaking the context down into smaller parts that fit one of the four previous contexts and addressing them accordingly.
The Only Way Out is Through
Our VUCA/BANI world isn’t going to get any simpler or easier. And fighting it, freezing, or fleeing isn’t going to solve anything. Organizations need leaders with the courage to move forward and the wisdom and flexibility to do so in a way that is contextually appropriate. Cynefin is their map.
