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Leadership in uncertain times
Making good decisions even when the outcome is uncertain; what to do when the founder leaves; and links you might enjoy.
Farrah Bostic
October 01, 2025
We announced this summer that we’d bring back The Difference Engine’s newsletter. We’ve rebranded it — now called “20 Minutes in the Future”, inspired by Max Headroom (with help from our great friend and author, Joanne McNeill).
This newsletter will arrive in your inbox once a month. If you have questions for us, or topics you’d like us to explore, please drop me a line at [email protected]
As we begin the 4th Quarter of 2026, we’re thinking a lot about leadership. As we work with our clients to reach audiences, build brands, and respond sensibly as economic, political and social conditions change, leadership is a theme that recurs in each strategic challenge.
We believe strongly in the partnership between research and strategy.
Because strategy without research is guesswork.
And research without strategy is noise.
That’s why we do both. We see our role as helping our clients navigate changing business models, cultural trends, economic realities, and other obstacles to growth.
The strongest brands and businesses show leadership — with their own employees, customers and other stakeholders, and within their category and community.
Leadership is about providing the purpose, direction, and motivation to accomplish a clear goal, and it’s about improving the organization.
Data helps leaders decide how to focus that motivation and chart the path to the ultimate goal the organization has set. Still, these kinds of decisions are hard. They won’t always work out the way you hoped, no matter how hard you tried, or how thoroughly you planned, or how creative you were, or how passionate your team was.
Which begs a really important question: how do you know when a decision was good?
I had the pleasure of taking a course on decision-making theory from the late John Orbell, who wrote a wonderful article about Hamlet as a decision-maker under stress. In Hamlet’s case, his choice was not only whether to avenge his father; it was also whether to believe his father’s ghost. And the consequences were huge: he would either save his father’s kingdom from a murderous despot, or sacrifice his immortal soul to the devil.
No big deal.
What Hamlet’s case teaches us is that there is an important difference between risk and uncertainty. Indeed, Orbell wrote in his article, “A decision maker confronts risk when he or she can attach probabilities to alternative states of the world with confidence… Under uncertainty, not only can one still lose but one does not know the odds.”
We live in a time that produces more data, more complexity and higher stakes than ever. This, somewhat paradoxically, leaves many leaders feeling less certain than ever. And when this is the case, we need good methods of decision making more than ever.
Some may think the way to move from true uncertainty to (simpler?) risk is to gather even more data. We’re in the business of helping our clients do that, of course, but sometimes data becomes a kind of addiction, distracting or paralyzing the decision-maker.
A lot of leaders will conclude they made a good decision if the outcome was the one they hoped they’d get (in essence, good outcomes = good decisions). The poker player and decision strategist Annie Duke wrote that, “We equate the quality of a decision with the quality of its outcome, and succumb to the temptation to change our strategy just because it didn’t pay off immediately.” She called this “resulting” — and noted that it’s a bad strategy at the poker table … and everywhere else.
Leaders make good decisions when they follow a good process of decision-making. Of course, this means two things:
You can make a good decision even if you aren’t certain what the outcome might be; and you can make a good decision even if it doesn’t work out the way you’d hoped.
Organizations need incentive structures that reward good decision-making processes at least as much as they reward good decision-making outcomes.
To do this, leaders need to develop a shared language of certainty/uncertainty, so that people understand the degree of confidence about a data point or a potential decision.
They need to adopt systems that prioritize intentionality and integrity — that calculate a “net benefit” for the organization, its employees, its customers, its shareholders, and its community, and is clear-eyed about the necessary trade-offs before the decision is made.
I believe, as my friend and colleague Ron J. Williams, a partner at Co-Created does, that brands should be “customer-aligned”. Brands should do what creates value for their customers, is aligned with their values, and gives them a reason to trust that the brand will keep its implicit and explicit promises to them. Of course, the value a brand creates for customers has to create value for the brand as well — that’s where the alignment piece comes in. Finding that alignment is the job of a good decision-making process, informed by just enough data to take leaders from total uncertainty, to manageable risk.
If you have ideas or questions about decision-making, customer alignment, risk & uncertainty, or want to collaborate with us on good, data-informed decision-making for your team, get in touch!
Meanwhile — what does it mean to lead when the leader leaves?
IN CONVERSATION WITH… KATHERINE LEE, EXECUTIVE STRATEGY DIRECTOR — ATHLETICS
What happens when the founder leaves?
How do brands preserve or recapture the soul of the brand and move forward with clarity and purpose?
// by Adriana Estrada
Each month, I sit down with friends, experts, or colleagues to dive into a topic that’s shaping our respective professional worlds. These conversations spark new thinking, challenge assumptions, and often lead to insights we bring back to our clients.
Recently, I spoke with Katherine Lee, Executive Strategy Director at Athletics, about a topic we have both encountered: what happens when founder-led brands lose their founders. How do they preserve (or recapture) the soul of the brand and move forward with clarity and purpose?
We touched on this subject because we both worked for a brand that lost its founder a few years ago. In an attempt to get its soul back, the company went through multiple rebrands and became increasingly mainstream with every iteration. The cult of personality was diluted; the rallying cry became increasingly irrelevant; and no person or big idea became the brand champion.
So what advice would we give brands that were once shaped by a visionary founder but are now trying to find their footing again? Here are the key themes from our conversation:
1. Identify the Soul of the Brand and Its Touchstones
The brand soul is its essence—the emotional connection it makes with people. The questions to ask are: What problem was the founder solving? What did they believe about their customer? Take Chanel, for example. Coco’s self-determination and ingenuity led to a brand that liberated women from corsets, used menswear fabrics for women, and made the little black dress a symbol of elegance, among other things. When Karl Lagerfeld took over in 1983, the brand was floundering. He brought it back to life by honoring Coco’s values (timeless elegance, rebellion, invention), what her customers loved about the brand, and the recognizable elements (tweeds, pearls, quilted shoulder bag). He invented new ways for audiences to experience and aspire to the brand. He didn’t start over; he built on what was already there. Katherine Lee, Athletics |  |
2. Connect the Past to the Present
 | Staying with the Chanel example, Lagerfeld made Chanel relevant again by bridging past and present. He used supermodels in the 80s, turned fashion shows into cultural moments (who can forget the Chanel grocery store or the iceberg), leveraged technology and social media, and embraced younger, non-traditional, global ambassadors. He stayed true to the brand's soul but refreshed how it showed up. He made Chanel a brand of the future without alienating loyalists. Adriana Estrada, The Difference Engine |
3. Tell the Founder’s Story
The higher the brand sits in culture, the more it needs to become accessible. Telling the founder’s story gives people something to grab onto; especially for those who weren’t around when the brand was born. Share the most memorable part of the story that people can put in their pockets. — KL |  |
| Founder stories are powerful because they’re real. For example, millions of women connected with Sara Blakely’s story of cutting the feet off her pantyhose to create Spanx. That relatable, problem-solving moment built a billion-dollar brand. These stories build emotional resonance and stick. — AE |
4. Keep Challenging the Establishment
| Founders are fundamentally disruptors. That spirit needs to live on. Take Vans for example. Originally a simple rubber shoe company founded by brothers Paul and James Van Doren, it pivoted when James’ son Mark designed a logo for his skateboard and Vans started making shoes for skaters. That’s what catapulted the shoe to new heights and sales. Today, Vans stores still celebrate the Venice Z-boys with black-and-white photos hanging above the new styles. I love that they keep challenging what people know about the brand…but keep the old styles in play. — AE |
5. Update the Value Proposition
A key component to keeping a founder brand moving forward is to find the shared value with the people it’s trying to speak to. If a brand was spectacular at building community with people who consider themselves rebels, does that value proposition resonate for new audiences? Do they still care about rebelling? And if so, what are the things that they need in order to say yes to that? Do they need places and spaces to build a community of rebels? Are they looking for freedom? What are they looking to be free from? Brands have an opportunity to find the places where it can be that bridge. — KL | |
6. Inspire Employees with the Founder’s Purpose
Building the brand purpose around a founder makes people feel like getting out of bed and going to work every day. It's not always sustainable, but the cult of personality can be helpful to move a brand forward and keep it going when people don't know what direction to go in. Employees want to soak in the vibes of someone who has an indomitable spirit. They want someone to follow and breathe the same air as exciting people. And if you have that, that is a huge boon. — KL | |
| A belief system drives internal culture as much as external connection. I think about the Surfrider Foundation’s origin story and purpose—three guys wanted to stop offshore oil drilling in Malibu. That still inspires thousands of staff and volunteers to protect our ocean, beaches and waves. They know why Surfrider exists, and they carry that purpose into everything they do. —AE |
Final Thoughts
Founder energy is powerful. But even when the founder is gone, it doesn’t have to be lost. By honoring the original soul, adapting to cultural shifts, and keeping the mission alive inside and out, brands can remain vital and magnetic for decades to come.
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