Churchill's Choice: Embracing Honesty and Vulnerability for Leadership Success
- Timothy Fielder
- May 20
- 7 min read
Updated: 4 days ago
Why is it that new, first-time managers, even before they change their email signature for the new role, already think that showing vulnerability makes leaders look weak when one of the strongest leaders in history was honest and vulnerable and rallied an entire nation?
During the heat of World War II, with the Germans attacking Western Europe, squatting in France, and on Britain’s doorstep, King George VI asked Winston Churchill to take office as Prime Minister of England. With his country under severe threat, Churchill needed to make a choice: to present an image of unshakable strength expressing that Britain was invulnerable, even as the situation became bleaker -OR- acknowledge the weight of the crisis and speak openly about the incredible challenges Britain faced. He chose honesty, and in not pulling punches about the gravity of the crisis – a heavy dose of vulnerability in a leader during a dangerously insecure time – and his willingness to shoot straight with British people rallied and united them in a way that a show of false strength could not have. Let’s explore why the courage to be honest and to show vulnerability is true strength.
The whole fury and might of the enemy must very soon be turned on us. . . Let us therefore brace ourselves to our duties, and so bear ourselves that, if the British Empire and its Commonwealth[e] last for a thousand years, men will still say, "This was their finest hour." - Winston Churchill
How Do We Learn That Honesty and Vulnerability in Leadership is a Weaknesses?
Remember how, on your first day of managerial training, they taught you how you should not show any sign of human emotion, especially confusion or doubt, lest ye be known as weak? No? Because it didn’t happen. Not only did you probably not get managerial training (that’s a topic for another post), if you did,
you wouldn’t have been taught that. But, somehow, this message gets baked into our leadership DNA. As if by osmosis, it is something we all seem to absorb.
If we step back and think about it though, from the time we were just elementary school manager wannabe’s we have been bombarded with those images: the grizzled CEO in the movies, barking orders at our screen idols, never smiling or admitting a mistake. Or the coach pacing the sidelines, with angry confidence even when his team is down by twenty points with five seconds left. The message those images taught us? Strong leaders are always in control, always know the answer, and never, ever flinch.
Then there’s that whole “fake it ‘til you make it” mantra people throw around as something positive, but can inadvertently lead to this fear of not being able to keep up the "stiff spine" leader facade. As a new manager, no doubt you are already battling a little dose of “imposter syndrome.” So, admitting you don’t know something feels like you are announcing to the world that you have no idea what you are doing.
And, you didn’t get here without some early career experiences that live rent free in the back of your mind. Maybe you did ask a question in a meeting and got an intense and dramatic eye-roll in return. Maybe you saw how one of your former managers got dressed down by a superior when they fessed up to a mistake. You jotted those little moments away in a mental “How to Survive This Place” file with “avoid vulnerability at all costs” as the first bullet point in the Executive Summary.
It’s no wonder “hide your emotions,” “project unwavering strength,” and “never let them see you sweat” are the playlist in our minds playing on repeat. It’s time for some fresh tunes; those are outdated without a beat you can dance to.
Why Does Being Honest, Vulnerable, and Brave Enough to Say “I Don’t Know” Make You a Better Leader?
Okay, so that old-school playlist is out. But why exactly does this whole "it’s OK to be human" thing actually make you a better leader? It’s brain science and psychology behind it.
Think about it: who wants to work in a place where they have to walk on eggshells and spend energy avoiding mistakes instead of doing work? That is not comfortable or safe. And, according to some in the know psychologists, what teams need to perform their best is psychological safety. That's the belief that you won't pay a price for speaking up, whether it's a brilliant idea, a "wait, what?" question, a genuine concern, or even admitting you totally dropped the ball.
Vulnerability Fosters Trust Through Psychological Safety:
Leaders who have the courage to be a little vulnerable actually build this kind of "safe space." When you're willing to say, "Hmm, good question, I actually don't know the answer to that," you signal to your team that it's okay to not be perfect. In turn, that encourages them to take some risks, ask some "dumb" questions, and be honest about the blockers they're facing. And, what does that lead to? Higher trust, engagement, and creativity, big ideas, improvements, and innovation that wouldn’t exist if everyone was too scared to step outside the box.
The Power of Connection and Empathy:
When a leader shows they're human – flaws and all – it's not just about building trust; it's about sparking empathy, which is like rocket fuel for team loyalty and motivation. Like magic, you're not just "the boss"; you're a fellow human navigating the same chaos.
By being honest and open about your own less than optimal moments or areas where you're still learning, you give your team permission to do the same, leading to transparent communication, smoother collaboration (because people aren't afraid to admit they need help), and ultimately, strong working relationships.
Neuroscience Shows Vulnerability Signals Authenticity and Builds Emotional Bonds:
Turns out, our brains are wired for this vulnerability stuff! Neuroscience shows that when a leader shares something real or admits they're unsure, it lights up the mirror neurons in the listeners' brains. And that, my friends, is empathy. So, by being vulnerable, you're making it easier for your team to relate to you on an emotional level, building a stronger bond than any escape room team-building exercise ever could.
Plus, our brains act like BS detectors. We can usually sniff out (see what I did there?) when someone's being fake. Vulnerability, though, screams authenticity. And an authentic leader earns the genuine respect and unwavering trust of their team.
It Is So Counterintuitive! How Do You Do It?
I know what your thinking: “Okay, so brain science backs it up, but actually doing this seems pretty risky.” That showing weakness will lead to chaos and lead to carrying a bankers box to the elevator. I get it, it's counterintuitive. But trust me (and science), it won't. Here's your quick start guide for incorporating vulnerability into your leadership approach:
Acknowledge What You Don’t Know: Instead of pretending you have all the answers (you don't, nobody does), try saying something crazy like, "You know what? That's a great question, and I'm not 100% sure. Let's find out together." Boom. Honesty. Not weakness. It shows you want to learn and value others' input. Plus, it takes the pressure off - you don't have to know.
Share Your Struggles and Mistakes: Nobody expects you to be perfect
(except maybe that boss you had way back when that you don’t want to be like). In fact, trying to fake it makes you seem less relatable. When you mess up (and you will, we all do), own it. "Yeah, I totally dropped the ball on that deadline. My bad. Here's what I learned and how I'm going to fix it." This shows accountability and models learning from errors.
Ask for Feedback: Show you value others' opinions and are open to growth. Ask for feedback. "Hey team, I'm trying out this new approach. What are your thoughts? What could I be doing better?" You’re not admitting you're a failure; you’re showing you want to improve and value their perspectives. Bonus, you might actually get some helpful insights!
Model Vulnerability for Your Team: Your team takes their cues from you. If you're open and honest, they're more likely to be the same. Share a relevant personal story about a challenge you overcame. Talk about a time you learned from a mistake. This creates a culture where it's safe to be imperfect.
Create an Environment That Encourages Vulnerability: Actively start building a space where people feel comfortable speaking up without fear of judgment. When someone asks a question that seems "obvious," don't roll your eyes (we talked about that!). Instead, praise them for asking for clarity. Celebrate learning and growth, even when it comes from mistakes.
Balance Vulnerability with Confidence: Being vulnerable doesn't mean you should spill your deepest secrets or constantly apologize for everything. It's about being authentic and honest within the context of your leadership role. You can admit you don't know something and still demonstrate confidence that you'll find the answer or work through it. You're human, but you're still the leader.
Use Vulnerability to Build Stronger Relationships: When you're open and honest, you build relationships. People connect with authenticity. Sharing your struggles or uncertainties can make you more relatable and build stronger bonds with your team members, and build greater trust and collaboration.
Challenges You Might Face and How to Overcome Them:
Fear of Losing Authority: True authority isn't about knowing everything; it's about leading effectively. Showing vulnerability can increase respect because people see you as genuine and trustworthy. If your authority is so fragile that admitting you're human breaks it, you might have a bigger issue and want to re-evaluate your leadership style anyway.
Fear of Losing Trust: Ironically, the opposite is often true. Trying to be perfect and all-knowing can break trust because people sense inauthenticity. Honesty builds trust. People trust those who are real with them, even when they don't have all the answers.
Cultural Barriers: Some workplaces have a "stiff upper lip" culture. Start small. Find opportunities and lead by example. As people see the positive results (increased trust, better communication), it can slowly shift the culture. You might be the rebel who starts the vulnerability revolution!
Embrace Your Humanity
What a relief, huh? The real power in leadership isn't in pretending to be invincible; it's in the courage to be human. Like Churchill rallying a nation with his honest assessment of a dire situation, your willingness to be vulnerable – to admit what you don't know, share your struggles, and foster a culture of openness – will build stronger, more resilient, and more innovative teams. It might feel counterintuitive, but trust the science, trust your gut, and trust me: true strength in leadership isn't about hiding your humanity, it's about embracing it. Now get out there and lead with honesty. It’s OK to say “I don’t know.”
What are your thoughts on the power of honesty and vulnerability in leadership? What experiences have shaped your view on vulnerability in leadership?
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