Leading in uncertainty: wisdom from 12 leaders
After a whirlwind of travel and executive-conference-room-moments, our team finally had a moment this week to pause and reflect. And to breathe in a little inspiration. One of my inspirations was to re-read a series of interviews I did last year with 12 senior leaders who have consistently navigated difficult moments in their organizations with grace and optimism. I thought I would share a synopsis of those interviews here…
The leaders represent an eclectic mix of businesses and passions, from leading the people function of the top tech firm in the world, to building a modern American house of fashion brands. All have successfully navigated intensive growth and transformation in the most competitive markets in the world.
I had asked them not about the big strategic questions facing their companies, but about what they have learned about themselves on their leadership journeys. What is their source of power? How do they know they’re making the right decisions? What do they wish they’d known 10 or 20 years ago? Even down to how they take care of themselves physically.
I was struck by eight themes that kept surfacing. I’ve provided a glimpse into these themes below. And of course, thank you to my fellow leaders for sharing your wisdom:
Susan Sobbott, Former President, Global Commercial Services at American Express | Tim Brown, CEO, IDEO | Beth Comstock, Former Vice Chair at GE | Denise Pickett, Chief Risk Officer, American Express |David Butler, Chief Growth Officer, Kids II | Lew Frankfort, Chairman, Coach | Michael Rubenstein, President, AppNexus |Victor Luis, CEO, Tapestry | Cathy Salit, CEO at Performance of a Lifetime | Beth Jacob, SVP and Chief Customer Success Officer, SPS Commerce | Matt Dixon, Founder and CEO at Purple Patch | Lori Goler, VP of People and HR at Facebook
1. Step away — and sleep — to give your unconscious time to make connections.
I know it seems like the unsexiest of management topics, but I can’t tell you how many times sleep and rest came up. Most of my interviewees had a practice of “stepping away” and letting a problem steep in their unconscious, trusting that they would make connections if they let things alone. As Susan Sobbott put it: “There is magic in diverting attention to something completely different. Just churning on a roadblock is not going to remove it. Less is more here. Stopping work on a roadblock actually can illuminate the remedy.”
Some did this with a walk outside. Some slept on it. Some simply compartmentalized. “I’m not one of these people that has to be aggressively productive with every minute of my life,” Tim Brown says, “I actually think it gets in the way of some of the good things that I do, that if I’m constantly productive, then I don’t give my brain a chance to reflect and synthesize and process. As a creative person, that’s all pretty important.”
“If I’m constantly productive, then I don’t give my brain a chance to reflect and synthesize and process.”
The latest neuroscience findings are adding more and more evidence to support this practice, especially in the role of sleep, where new connections are sorted through and formed. Thus the mythology of sleep in leadership contradicts its actual role and benefits. Western business culture prides itself on sleeping less as evidence of a strong work ethic. But I found that for the leaders I’ve worked with, a good night’s sleep is not just necessary, it’s also in some cases seen as a way to activate strategic thinking and creative juices.
For Beth Comstock it’s certainly true:
“More and more, I’ve come to appreciate the role of sleep. It’s actually part of my process.”
“More and more, I’ve come to appreciate the role of sleep. It’s actually part of my process. I’ll think, I’ll iterate, I’ll beat it up in my head, and then I deliberately ask myself a couple of questions: What are two things that are turning here that I don’t have clarity on? Then I position those two things in my head. Literally, I’m going to sleep on it. When I wake up I say, ‘Okay what clarity do I have about that problem?’ It’s not like, ‘Eureka! Here is the answer.’ But I do find clarity. It’s kind of like giving your brain a filing or a synthesizing assignment.”
2. Focus on finding the right questions, over the right answers.
Tim Brown had a lot to say about this, but the notion that questions should be the starting point for leading in uncertainty came up in different ways in almost every interview. For some, it was the idea that “strategy is defining the right questions,” which is harder than it sounds.
“I’m much more interested in questions. So when I don’t know the answer, I look for a good question. Once you’ve got a good question, the answers tend to come — from other people as often as from yourself. The first good question puts you on the road to the next good question and the next good question… ” — Tim Brown
“Planning is a misnomer. It’s really about strategic decision-making. It starts with identifying the right strategic questions about the business. Each time I’ve moved into a new leadership role, I have worked to identify the few strategic questions the organization has to answer, and the decisions we need to make.” — Denise Pickett
For others it was an observation that when your gut is telling you that your team is stuck for no apparent reason, it’s time to step back and ask if you’re solving the right problem. Susan Sobbott explains:
“I turn to the customer, ‘Who are we trying to serve and why? In what way can we serve them? What job are they hiring us to do?’ The key is to eliminate all the noise and then ensure single-minded focus on that objective…[And when you can’t find an answer?] My first thought is, ‘Am I asking the right question?’ Because maybe I’m looking for a solution to a problem that’s not solvable. Maybe there’s a different problem I should be solving. So if I’m trying to go from point A to point B, and I can’t find my way there, maybe I should be looking to get to point C or D. I work to reframe the issue. Then I’ll break it down into smaller pieces. ”
“My first thought is, ‘Am I asking the right question?’ Because maybe I’m looking for a solution to a problem that’s not solvable.”
3. Practice your inner dialogue: Name what you are experiencing.
When asked about managing their emotions, most interviewees reflected on some form of talking to themselves. “I literally say I’m feeling fear, or I’m feeling nervous, or I’m feeling cautious,” said David Butler, “Naming it helps me deal with the state and still be present.”
One or two wryly commented that as they get older they talk to themselves more. The point they were making is that they have learned that by naming the emotion or experience they’re having, they can acknowledge it without letting it control them. They are exercising the power of naming something. They own their emotion. Their emotion does not own them. This was an interesting business reflection on something that comes up in meditation practices. Neuroscience is increasingly teaching us how mindfulness practices like this can help you as a leader shift from a stress response (which can lead you to be impulsive or defensive) to a more intentional response, with lower anxiety.
“I ask myself, ‘Why am I feeling this way and how do I want to handle it?’”
“I’m aware when my blood pressure’s rising or I’m feeling impatient or I’m feeling frustrated. I ask myself, ‘Why am I feeling this way and how do I want to handle it?’ That’s why I talk about self-regulation and thoughtful responses. I listen to my emotions to help me understand — to know on a cognitive basis if my heart’s beating fast or if I’m not actively listening when someone is going on as if they’re a radio. I ask myself, ‘Why am I not listening? And what’s the best way to deal with that?’” — Lew Frankfort
4. Source data, but trust your gut to make a call
To the question “What do you rely on most, data, your gut, or other people?” the frequent response, not surprisingly, was, “all three.”
“When you make decisions, it’s a combination of magic and logic. Logic is the rigor and the knowledge and the analytics. Magic is the instinct and the judgment and the street smarts.” — Lew Frankfort
But as we unpacked that idea, what emerged is that every leader has a threshold where the data falls short of providing 100% confidence — or even 80% or 50% — in a decision. Crossing that threshold is about trusting your gut. One interviewee pointed out that, “You can’t be a leader and not use your gut.” Of course, gut works well only when it’s developed through trial and error, and is held in relationship to relevant data.
For some, this meant going out and seeing for yourself: “My formula is to immerse myself in as much of the subject as possible. I’m a big believer in go see for yourself. I think, yes, you can read a lot. People can give you reports, but you must go see for yourself.” — Beth Comstock
And for others, giving the data some time to seep in so your subconscious can make the right connections:
“There is this magical process that happens with me, where over the course of the days that I’m mulling over the problem, a perspective emerges.”
“I’m a pretty data-driven decision maker. So I don’t make a huge number of calls on instinct or on the fly, which is part of the reason why AppNexus CEO Brian and I are good complements to each other. I go into data-collection mode. I ask questions. I read. I learn. And I find that there is this magical process that happens with me, where over the course of the days that I’m mulling over the problem, a perspective emerges. And it’s usually a perspective that is supportable by the facts and the data that I’ve collected.” — Michael Rubenstein
5. Prototype your way forward.
And when a decision isn’t clear? Make your way forward. The leaders I see who are most successful in ambiguity are those who can take a next step, even when the next step isn’t clear.
“In improv, it’s all about doing the next thing in the scene. You make one move in the scene to discover the next move in the scene, and you must make the next move in the scene to continue the play. I don’t relate to the idea of having the right answers. I see answers as being very fluid — meaning it’s the answer for now. It’s the answer for right now.” — Cathy Salit
And then you build on it, as David, Beth, and Victor explain:
“It’s about really going wide and quickly getting to some sort of prototype, which could be anything, and just iterating on top of that.” — David Butler
“You need laboratories — and I mean it in the broadest sense. You need places where people can start to experiment or test or put different pieces together to start to create structure around the action coming out of the insight.” — Beth Comstock
“If I’m inactive, nothing’s going to happen. And I don’t look at it as getting to a destination. I gain energy by constantly telling myself, it’s just about heading in a direction. And then I become more comfortable with the idea that I can change direction a little bit.” — Victor Luis
6. Don’t be so impatient.
Half the leaders I spoke with, when asked what advice they would give their younger selves, spoke of wishing they’d known to be more patient — with themselves and with their teams. Their advice was something along the lines of “Hey, don’t be so impatient — transformation takes a lot longer than you think, so take the time to bring people on the journey.” The alternative is to live in a state of disappointment and frustration with the pace of change that only diminishes your humanity and your team’s joy and creativity. After all, as one executive noted:
“The journey of transformation is very seldom to a ‘done’ point. It’s just to the next point.”
“Today, I might be helping an organization solve for the problems that we see next. Two years from now, there will be a different set of problems. So we’ll transform. And then, two more years from that moment, there will be something new and we’ll transform again. You have to have comfort with ambiguity and change. The journey of transformation is very seldom to a ‘done’ point. It’s just to the next point.” — Beth Jacob
The cycles of creative disruption have increased in pace (albeit at different rates by industry). So if you’re a 50-year-old CEO today, the odds are increasing that you will oversee more than one organizational transformation in your tenure, if not many. Leading transformation then becomes a competence you need to develop.
7. Relationships, relationships, relationships.
It’s perhaps not surprising that relating to people, and having an emotionally intelligent approach to connecting with the people around you, is a critical capability for all the leaders interviewed.
Some see relationships as their fundamental source of power — as Lori Goler put it, as a leader you only get work done with other people, so without relationships you don’t really have any power. For others, the power of connection was crucially important. That could mean literally walking the corridors and talking to people, or making it a point to ask about someone’s life, not just transacting with them.
“Leaning into a supporting cast can be incredibly powerful,” said Matt Dixon, “People think they have the burden of being an expert in all elements relating to their job; that’s an unreasonable expectation. Very few people are excellent in all elements of their job description. I’ve made it my mission to surround myself in the areas that I’m less skilled in.”
8. Invest in your physical well-being — it supports everything.
Mens sana in corpore sano — a healthy mind in a healthy body — wrote the Roman poet Juvenal to teach his fellow Roman citizens what to focus on in life. Science today tells us unequivocally that physical exercise is hugely beneficial to the brain, and to our overall well-being. I pursued that notion with all the leaders interviewed, and it’s interesting how much of a gap there is between what leaders know to be true — “I perform much better when I’m physically stronger and healthier” — and, in many cases, how they are actually living — “Working out is the first thing to go when things get stressful.”
But as Matt Dixon points out: “Health and fitness are tools in your performance arsenal as a leader, your ability to make decisions—[and not a nice-to-have]”
All agreed that how they feel physically makes a huge difference in their ability to lead and their effect on the people around them. How they invested in physical well-being differed. For some it was taking walks in nature, or yoga. For others it was high-intensity exercise. All, it seems, benefited from exercise as a core habit. Make it your secret priority if you need to, but make it a priority!
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A big thank you to Emily Goldstein who was my partner in crime at SYP in putting an early draft of this together. And to my old alma mater SYPartners, for sponsoring my interviews before I left to start TJALeadership, and for the encouragement to lead and learn about transformation and uncertainty, over two decades.