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.
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 | Jul 23, 2025 | Leadership, Leading Through Uncertainty, Stories & Examples
What does a lightning strike in a Spanish forest have to do with your next leadership meeting? More than you think.
On June 14, 2014, lightning struck a forest on Spain’s northeast coast, only 60 miles from Barcelona. Within hours, flames 16 to 33 feet high raced out of control toward populated areas, threatening 27,000 acres of forest, an area larger than the city of Boston.
Everything – data, instincts, decades of firefighting doctrine – prioritized saving the entire forest and protecting the coastal towns.
Instead, the fire commanders chose to deliberately let 2,057 acres, roughly the size of Manhattan’s Central Park, burn.
The result? They saved the other 25,000 acres (an area the size of San Francisco), protected the coastal communities, and created a natural firebreak that would protect the region for decades. By accepting some losses, they prevented catastrophic ones.
The Fear Trap That’s Strangling Your Business
The Tivissa fire’s triumph happened because firefighters found the courage to escape what researchers call the “fear trap” – the tendency to focus exclusively on defending against known, measurable risks.
Despite research proving that defending against predictable, measurable risks through defensive strategies consistently fails in uncertain and dynamic scenarios, firefighter “best practices” continue to advocate this approach.
Sound familiar? It should. Most executives today are trapped in exactly this pattern.
We’re in the fire right now. Financial markets are yo-yoing, AI threatens to disrupt everything, and consumer behaviors are shifting.
Most executives are falling into the Fear Trap by doubling down on protecting their existing business and pouring resources into defending against predictable risks. Yet the real threats, the ones you can’t measure or model, continue to pound the business.
While you’re protecting last quarter’s wins, tomorrow’s disruption is spreading unchecked.
Four Principles for Creative Decision-Making Under Fire
The decision to cede certain areas wasn’t hasty but based on four principles enabling leaders in any situation to successfully navigate uncertainty.
PRINCIPLE 1: A Predictable Situation is a Safe Situation. Stop trying to control the uncontrollable. Standard procedures work in predictable situations but fail in unprecedented challenges.
Put it in Practice: Instead of creating endless contingency plans, build flexibility and agility into operations and decision-making.
PRINCIPLE 2: Build Credibility Through Realistic Expectations. Reducing uncertainty requires realism about what can be achieved. Fire commanders mapped out precisely which areas around Tivissa would burn and which would be saved, then communicated these hard truths and the considered trade-offs to officials and communities before implementing their strategy, building trust and preventing panic as the selected areas burned.
Put it in practice: Stop promising to protect everything and set realistic expectations about what you can control. Then communicate priorities, expectations, and trade-offs frequently, transparently, and clearly with all key stakeholders.
PRINCIPLE 3: Include the future in your definition of success: Traditional firefighting protects immediate assets at risk. The Tivissa firefighters expanded this to include future resilience, recognizing that saving everything today could jeopardize the region tomorrow.
Put it in practice: Be transparent about how you define the Common Good in your organization, then reinforce it by making hard choices about where to compete and where to retreat. The goal isn’t to avoid all losses – it’s to maximize overall organizational health.
PRINCIPLE 4: Use uncertainty to build for tomorrow: Firefighters didn’t just accept that 2,057 acres would burn – they strategically chose which acres to let burn to create maximum future advantage, protecting the region for generations.
Put it in practice: Evaluate every response to uncertainty on whether it better positions you for future challenges. Leverage the disruption to build capabilities, market positions, and organizational structures that strengthen you for future uncertainty.
Your Next Move
When the wind shifted and the fire exploded, firefighters had to choose between defending everything (and likely losing it all) or accepting strategic losses to ensure overall wins.
You’re facing the same choice right now.
Like the firefighters, your breakthrough might come not from fighting harder against uncertainty, but from learning to work with it strategically.
What are you willing to let burn to save what matters most?
by Robyn Bolton | Jul 8, 2025 | Strategic Foresight, Strategy
You stand on the brink of an exciting new adventure. Turmoil and uncertainty have convinced you that future success requires more than the short-term strategic and business planning tools you’ve used. You’ve cut through the hype surrounding Strategic Foresight and studied success. You are ready to lead your company into its bold future.
So, where do you start?
Most executives get caught up in all the things that need to happen and are distracted by all the tools, jargon, and pretty pictures that get thrown at them. But you are smarter than that. You know that there are three things you must do at the beginning to ensure ultimate success.
Give Foresight Executive Authority and Access
Foresight without responsibility is intellectual daydreaming.
While the practice of research and scenario design can be delegated to planning offices, the responsibility for debating, deciding, and using Strategic Foresight must rest with P&L owners.
Amy Webb’s research at NYU shows that when a C-Suite executive with the authority to force strategic reviews oversaw foresight activities, the results were more likely to be acted on and integrated into strategic and operational plans. Shell serves as a specific example of this, as its foresight team reported directly to the executive committee, so that when scenarios explored dramatic oil price volatility, Shell executives personally reviewed strategic portfolios and authorized immediate capability building.
Start by asking:
- Who can force strategic reviews outside of the traditional planning process?
- What triggers a review of Strategic Foresight scenarios?
- How do we hold people accountable for acting on insights?
Demand Inputs That Challenge Your Assumptions
If your Strategic Foresight conversations don’t make you uncomfortable, you’re doing them wrong.
Webb’s research also shows that successful foresight systematically explores fundamental changes that could render the existing business obsolete.
Shell’s scenarios went beyond assumptions about oil price stability to explore supply disruptions, geopolitical shifts, and demand transformation. Disney’s foresight set aside traditional assumptions about media consumption and explored how technology could completely reshape content creation, distribution, and consumption.
Start by asking these questions:
- Is the team going beyond trend analysis and exploring technology, regulations, social changes, and economic developments that could restructure entire markets?
- Who are we talking to in other industries? What unusual, unexpected, and maybe crazy sources are we using to inform our scenarios?
- Does at least one scenario feel possible and terrifying?
Integrate Foresight into Existing Planning Processes
Strategic Foresight that doesn’t connect to resource allocation decisions is expensive research.
Your planning processes must connect Strategic Foresight’s long-term scenarios to Strategic Planning’s 3–5-year plans and to your annual budget and resource decisions. No separate foresight exercises. No parallel planning tracks. The cascade from 20-year scenarios to this year’s investments must be explicit and ruthless.
When Shell’s scenarios explored dramatic oil price volatility over decades, Shell didn’t file them away and wait for them to come true. They immediately reviewed their strategic portfolio and developed a 3–5-year plan to build capabilities for multiple oil futures. This was then translated into immediate capital allocation changes.
Disney’s foresight about changing media consumption in the next 20 years informed strategic planning for Disney+ and, ultimately, its operational launch.
Start by asking these questions:
- How is Strategic Foresight linked to our strategic and business planning processes?
- How do scenarios flow from 20-year insights through 5-year strategy to this year’s budget decisions?
- How is the integration of Strategic Foresight into annual business planning measured and rewarded?
Three Steps. One Outcome.
Strategic foresight efforts succeed when they have the executive authority, provocative inputs, and integrated processes to drive resource allocation decisions. Taking these three steps at the very start sets you, your team, and your organization up for success. But they’re still not a guarantee.
Ready to avoid the predictable pitfalls? Next week, we’ll consider why strategic foresight fails and how to prevent your efforts from joining them.
by Robyn Bolton | Apr 15, 2025 | Innovation, Leadership
“The call is coming from inside the house” is one of those classic quotes that crossed over from urban legend and horror movies to become a common pop-culture phrase. While originally a warning to teenage babysitters, recent research indicates that it’s also a warning to corporate execs that murderous business threats are closer than they think.
In the early weeks of 2025, Box of Crayons, a Toronto-based learning and development company, partnered with The Harris Poll to survey over 1500 business leaders and knowledge workers to diagnose and understand the greatest challenges facing organizations.
They found that “while there is a tendency to focus on external pressures like economic uncertainty, technological disruptions, and labor market issues, our research shows the most critical challenges are unfolding within the workplace itself.”
The threat is coming from inside your house.
Here’s what they found and what you can do about it
Nearly 1 day each workweek “is lost to the fear of making mistakes.”
Fear is at the core of all the issues making headlines – burnout, disengagement, lost productivity. It “breeds doubt, prompting individuals to question themselves and others, instigating anxiety, hindering productivity, and promoting blame instead of teamwork.”
Fear is also a virus, spreading rapidly from one person to their team members and on and on until it infects the entire organization, embedding itself in the culture.
Executives and managers are key to breaking the cycle of fear that kills innovation, initiative, and growth. By reframing mistakes and learnings, rewarding smart risks even if they result in unexpected outcomes, and role-modeling behaviors that encourage trust and psychological safety, their daily and consistent actions can encourage bravery and remaking the culture.
70% of people don’t see value in listening to people they disagree with.
Unless you’re employed by Lumon Industries, it’s impossible to be a completely different person at work compared to who you are outside of work. So, it should come as no surprise that most people no longer listen to opinions, perspectives, or evidence with which they disagree.
The problem is that different perspectives and experiences are essential to elements of the problem-solving process. Without them, we cannot learn, develop new solutions, and innovate.
Again, executives and managers play a critical role in helping to surface diverse points of view and helping employees to engage in “productive conflict.” Rather than rushing to “consensus” or rapidly making a decision, by expressing curiosity and asking questions, people-leaders create space for new points of view and role model how to encourage and use it.
87% of leaders lack the skills needed to adapt. 64% say funding to build those skills has been cut.
Business leaders are fully aware of the changes happening within their teams, organizations, and the broader world. They recognize the need to constantly adapt, learn, and develop the skills required to respond to these changes. They can even articulate what they need help with, why, and how it will benefit the team or organization.
But leadership training is often one of the first items to be cut, leaving new and experienced people-leaders “ill-equipped to manage the increasing complexity of today’s workplace, stifling their ability to inspire, guide, and support their teams effectively.”
The solution is simple – invest in people. Given the acute need for support and training, forget big programs, multi-day offsites, and centralized learning agendas. Talk to the people asking for help to understand what they want and need and how they learn best. Share what you can do right now with the resources you have and engage them in creating a plan that helps them within the constraints of the current context.
Answer the phone
Just like that terrifying movie moment, the call threatening your business isn’t coming from mysterious outside forces—it’s echoing through your own hallways. The good news? Unlike those helpless babysitters in horror films, you can change the ending by confronting these internal threats head-on.
What internal “call” is your organization ignoring that deserves immediate attention?
