Great Leaders Take Risks
How to Pursue Your Boldest Ambitions in Uncertain Times
You can’t be a great leader if you avoid taking risks. Risk is everywhere, it’s unavoidable! In every new hire, every deadline, and every bold vision there’s always the risk of failure. Avoiding risk is a game you never win: rewards come from taking risks, not avoiding them. Embracing risk is a game you win often: and the more you play, the more skillful you become. Great leaders embrace taking risks in pursuit of a meaningful vision for change. To achieve your ambitions, you too must embrace taking risks.
So why do so many of us spend our days avoiding risks instead of embracing them? We check our messages constantly to reduce the risk of missing something important. We avoid difficult conversations to reduce the risk of conflict. We avoid delegating to reduce the risk of someone else screwing it up. We even take pride in minimizing risk as a measure of our competence—rather than our failure to take the risks that matter.
I see this all the time in my work coaching startup leaders. They spend long hours toiling at their desks, but struggle to squeeze in the work that matters most to them. They focus on avoiding small risks at the expense of embracing big ones—the risks with big rewards attached. Hiring. Performance management. Strategy. Fundraising. Part of the problem with avoiding all risk is that we don’t discern which risks are worth taking. Often the risks that are most important don’t feel urgent until it’s too late.
We avoid these risks because of stress. Our bodies’ natural “fight or flight” stress response tells us we’re in danger: our heart rate increases, our blood pressure rises, chemicals pour into our bloodstream—and often we truly believe these risks are dangerous. But I’ve heard hundreds of these stories from leaders over the years. When we actually name the risks they’re working so hard to avoid, they’re not so scary: usually it’s embarrassment, frustration, or inconvenience. Office work is far from dangerous! Yet the risk feels huge: whether we’re stressing over millions of dollars or a few words in a meeting, somehow it all feels like it’s life or death. That’s the stress response: our bodies reacting like it’s a fire when it’s just a fire drill. We remember that feeling of danger long after the risk has passed—so no wonder we avoid risk instead of embracing it.
That stress can manifest in all sorts of ways, depending on how you’ve learned to cope with it. Some of us let angry outbursts fly in meetings, others carefully avoid saying anything that might cause offense. Some of us give up on working towards our goals, others can’t stop working for fear of what would happen if we did. That kind of obvious, conscious stress is a quick path to burnout. But more often stress is subtle: that false sense of danger sits in the background, quietly guiding us away from risk. So we respond to the easy messages and leave the hard ones for another day. We avoid disagreement instead of engaging with alternate points of view. That’s how we end up working hard all day but never taking the risks necessary to achieve our goals.
You don’t have to be a rocket scientist to realize that risk avoidance isn’t a sustainable strategy in life or in leadership. You can only motivate yourself through stress for so long before you burn out. But the problem with stress isn't just that it’s unsustainable in the long term. Stress also clouds our judgement in the present—and makes us less effective leaders. When every fire drill feels like a real fire, it’s impossible to accurately assess risk. We’re on perpetual high alert from danger! We end up making “safe” choices instead of principled ones, running from risk instead of towards opportunity.
You can’t be a great leader if you avoid taking risks. We avoid risk when we’re stressed because we sense danger—but real danger seldom materializes. Instead that stress reduces our effectiveness in decision-making, communication, and other key leadership skills. It’s impossible to lead well when you’re so worried about risk! Risk is unavoidable. If you want to be a great leader, you must reduce your stress through embracing risk.
Reducing Stress through Embracing Risk
Great leaders know there are lots of fire drills in modern life but very few fires. They don’t ignore their stress—they work through it as it arises. Sure, they still panic like the rest of us when a fire alarm goes off! But they manage their stress in the moment by taking a deep breath and reminding themselves the stakes are seldom as high as they seem. They look for flames, but almost never find them. In minutes or seconds, the feeling of danger is gone.
Great leaders are excited by the possibilities of their work, not terrified of its risks. By facing their stress head on and working through it, they learn to embrace daily risk-taking to pursue their goals. They sleep soundly at night not because they’ve eliminated all risk, but because they trust themselves to handle whatever it brings. They know they’ll be just fine whether they succeed or fail. With practice, you can get there too. But if you find yourself avoiding risk all day, or lying awake in bed at night, chances are your unprocessed stress is the culprit.
“But Kenneth, the danger is real for me! My professional success is on the line! My family’s financial stability and healthcare is hanging in the balance! How exactly am I supposed to ‘work through’ that kind of stress?” OK, let’s follow that train of thought—and check the facts. The way humans respond to danger is calibrated for saber-toothed tigers, not Zoom meetings. So it’s critical to check if our stress levels match the facts before we act on that feeling of danger.
Do you really believe if this job doesn’t work out you’ll never get another one? That your family couldn’t tolerate a temporary reduction in income? Take a moment to envision what would really happen in your worst case scenario. How likely is that scenario? Often our fear of failure is driven by imposter syndrome, not facts.
If your family has serious health issues or little financial safety net maybe there’s real danger there (in the US, at least). But “fight or flight” helps us make fast decisions, not thoughtful ones—panicking still won’t help. In the vast majority of cases the risks are temporary discomfort, not physical danger. Take it from someone who was fired from Silicon Valley five times, spent a year plus finding his next gig, and then told the story on a top 10 tech podcast: you’ll be fine.
I remember each of my five firings vividly, including the wave of adrenaline that hit me as the stress response kicked in. So I know that feeling of danger well: as if my manager were unsheathing a dagger across the conference room table. But in the end, the stakes weren’t as high as they seemed. Mostly it was embarrassing and inconvenient: I had to remain professional through a series of awkward conversations, manage my budget carefully, and switch all my doctors to match my new health insurance (thanks US healthcare system!). Sometimes it took a while, but eventually I got another job—even if it wasn’t ideal. I had some sleepless nights, but after a while I moved on.
When I ask clients to check the facts on their own worst case scenarios, the unthinkable outcome they’ve been avoiding tends to be similar: tolerating temporary discomfort and disappointment before moving on. If they aren’t getting what they need at work, they might have to be brave and ask for it, but they’ll be fine. If they leave or are let go, they might have to find a new job, but they’ll be fine. If they can’t land a job, they might have to move back in with their parents or take on debt, but they’ll be fine. I’ve even worked with leaders on H1-B visas who were unexpectedly let go and had to find work within 60 days or leave the country. Update: they were fine. People are remarkably creative and resilient in the face of life’s challenges. Whatever the risks, we figure out a way to handle them.
That’s not to say there aren’t real consequences! Shit does happen. Companies shut down. People get fired. Money gets tight. Healthcare is expensive. Yet regardless of the circumstances, avoiding risk remains ineffective leadership at work and at home. The stress of desperately trying to avoid disaster hobbles our ability to skillfully balance risk and reward.
We can’t resolve stress by avoiding risk. We resolve stress by embracing risk, and recognizing that we can handle it. We might need a few minutes to take deep breaths, face our fears, and remind ourselves we’ll be OK. We might even need a few hours or days. But when we recognize we’ll be fine no matter what happens, there’s nothing left to stress about. We can just do our best to take the risks that matter—and trust that whatever the consequences, we can handle them.
So allow me to humbly suggest that if you’re stressing about work every day, if you struggle to sleep at night, if you feel powerless to change things, or if that feels like a normal “high performance” work culture to you, then you’re probably not embracing the risks you need to succeed. So stop ignoring your stress and start embracing risk. Take a few deep breaths and check the facts. Remember that you can handle anything. If you want to be a great leader, you must embrace risk—and you’ll learn faster if you do it via experimentation.
Embracing Risk through Experimentation
Great leaders face failure head on. They accept when their leadership style isn’t working and embrace risk by trying something new. They adapt nimbly to the feedback the world offers them, adjusting how they ask for help until they hear “hell yes!” They know they can only achieve their vision if they can recruit others to help.
But it’s a vulnerable moment when we admit to ourselves the way we’re leading isn’t working. If I were a different coach this would be where I sell you my book with The One Right Way to Lead. But when my clients ask me, “Kenneth, how should I be leading? What risk should I take?,” my answer is always that we can’t be sure our decisions are right. Ever. There are no guarantees. Requiring conviction that we’re right before we act is just another way to avoid risk! No wonder we’re stressed if we expect every risk we take to work out.
So when I suggest embracing risk, I don’t mean go on a quest to Mount Leadership to find the Golden Strategy that guarantees success. I mean give yourself permission to try leading in a way that’s calling to you—even if it fails. Instead of requiring conviction that it will work before you try, give yourself permission to try even with the knowledge that it probably won’t. Prove to yourself you’ll be fine either way! Trying and failing is how we learn. In the tech world, we’ve embraced experimentation and “failing fast” for product and marketing, but not for leadership. The risks may feel higher in leadership, but the way we learn is exactly the same.
Sure, you could pick your favorite leadership book and adopt its approach as a shortcut. There’s a lot of great startup leadership advice out there, from Conscious Leadership to Radical Candor to the Mochary Method. But which one will feel right for you? How will you implement them in your specific context? How will you know whether they’re effective for your goals? There’s no way to know for sure until you try! That’s why I don’t align myself with any one leadership style—I prefer to prove what works best for each client.
To support that approach, I’ve developed a process to help leaders discover their own unique leadership style and prove empirically they can achieve their goals with it. By reducing stress and embracing risk, you give yourself the freedom to experiment and find your own path. That’s Ask for What You Want! I’m working on a book that explains in detail how to find that path and achieve your goals using these tools.
With less stress, you'll find the courage to take more risks in service of your vision—and the clarity to understand which risks offer the best returns. Experimentation is the most critical risk we avoid in leadership: we cling to familiar patterns long after they’ve proven themselves ineffective. Ask for What You Want offers the tools to embrace that risk, helping you face what’s not working in your leadership style and experiment your way into a better one—by proving that it works in the real world.
When leaders start embracing risk, they discover exactly how free they are to pursue whatever goals they desire in whatever way they see fit. They work hard because they want to—not because they’re worried what will happen if they don’t. You can lead this way too. So what risks are you stressed about right now? How might you embrace those risks instead of avoiding them? What experiment could you try today? Comment below and let me know, I’d love to help.
Are you a startup founder, CEO, or executive? Ready to take a risk on 1:1 coaching? Let’s chat. You can learn more about me and get in touch at kberger.com.