The Leadership Skill No One Talks About

Let’s talk about something a lot of us avoid like the plague—sharing our failures. I know, it sounds about as fun as a root canal, but trust me, there’s magic in it.

As leaders, we’re often expected to have all the answers, to be the ones steering the ship through calm seas and stormy weather alike. But here’s the thing—no one expects you to be perfect (except maybe yourself). So why not let your team in on a little secret? You’re human too.

Celebrating Wins and Failures: A Leadership Power Move

When I was leading big teams, I made it a point to share what I was working on, whether it was mastering a new skill, negotiating a bigger deal, or just plain taking a risk. And you know what happened? My team started to celebrate with me when I nailed it, and more importantly, they learned with me when I didn’t.

This isn’t just about being transparent (though that’s important). It’s about creating a culture where everyone feels safe to take risks, make mistakes, and grow from them. It’s about building *psychological safety*—that warm, fuzzy feeling that comes from knowing your team has your back, no matter what.

We even had a phrase baked into the entire company’s culture: 

“Fail Fast and Fail Cheap” 

Why This Matters: Imposter Syndrome and Psychological Safety

Ever feel like you’re one misstep away from being “found out”? That’s imposter syndrome, and it loves to thrive in environments where people feel isolated in their struggles. But when you share your journey— chin hairs and all—you’re not just humanizing yourself; you’re reducing that nasty imposter syndrome for everyone.

When your team sees you, the leader, embracing both your wins and your failures, they start to feel like it’s okay for them to do the same. They stop attributing their successes to luck or external factors and start owning them. And let’s be real—if you’re comfortable talking about your challenges, they’re more likely to bring theirs to the table too.

How to Get Started

So how do you put this into action? Start small. Here are a few ways to weave this mindset into your leadership style:

1. Share Your Journey: Next time you’re tackling something new, let your team in on it. And go into detail! Really open up and make them a part of the journey. 

2. Encourage Team Transparency: Make it a norm for everyone to share their own challenges and successes in team meetings. You’ll be amazed at how quickly this builds trust and openness. 

3. Reframe Failures as Learning Opportunities: When something doesn’t go as planned, reframe it as a learning opportunity. Ask, “What did we learn?” instead of “What went wrong?”

By doing this, you’re not just leading a team—you’re creating an environment where everyone feels valued, supported, and, yes, even safe enough to fail. And that, my friend, is leadership at its finest.

Now For A Challenge…

I want to challenge you to elebrate a risk you took—whether it was a win or a flop. Share it with your team and talk about what you learned. Why? Because when you openly embrace risks and learning, you create a culture where everyone feels safe to grow.

Here’s your mission: Pick one risk you’ve taken recently, and discuss it in your next team meeting. This can be something big or small…at work or even at home. Break down what worked, what didn’t, and what you’re taking away from the experience. This simple action can transform how your team views challenges and setbacks.

Let’s make learning from our fumbles the new leadership superpower.

Now go be human! 🙂 

Why Failure is a Gift Worth Celebrating

This month Meredith Kleeman interviewed Denise Dettingmeijer, the CFO of Medical Solutions, and I think you’ll find the results as insightful and inspiring as we did.  This interview resonated SO deep…

Tell us about a noteworthy mistake you made at work, and the lesson you learned from that event. 

The first time I made a financial mistake that was bigger than I was worth, meaning bigger than my salary, happened early in my career. I was new to a job, and new to working in Europe. I was asked to send over foreign currency revenue figures, and being new to the job and to the international markets, I did just that, but it wasn’t the right thing to do.

I misunderstood the use of what I was being asked to do, which made the figures I  sent the wrong figures that ultimately negatively affected the result of a hedging calculation. (Editor’s note: hedging is a risk management strategy that offsets losses in investments by taking an opposite position in a related asset.) 

My boss called me and said, “Denise, you f*#&ed up.” I replied “Yes, I did. Am I fired?” He laughed and told me “You’re going to have to make a hell of a lot bigger mistake than that to get fired.”

My boss asked me to write up exactly what happened, and I ended up writing the new policy for hedging within the company. The company used that policy the entire time I worked there. 

That mistake gave me the power to feel more comfortable making mistakes. I learned that we could fix that mistake, and I learned that when we fixed it it would be better than it was. I also learned that it’s important to give context when you’re asking for things to happen. When I made that mistake, I thought to myself, ‘I should have known that, I should have asked why, I should have understood the context.’ 

From then on I always emphasized the importance of context. I encourage everyone to ask “Why?” I even tell my team to ask five different questions to gain enough information to execute the task. It could be: Why do you need this? What are you going to do with this? Why do you want to know that? I want my team to really dig into what the other party is requesting. (Editor’s note: When arranging this interview, Denise employed her own advice about asking questions to gain clarity, and we’re so happy she did!) 

You might be in the early stages of your career and feel uncomfortable posing these questions to a superior, but as an employee at your company, you have a right to know. In any role you have the permission to engage. I believe we’ll make way better decisions if people feel great about sharing their thoughts and how to do things. 

Now I’m comfortable asking questions and being asked questions back. And I’m a huge fan of letting people make mistakes! I learned from my own mistake that we can fix it and we can work through it. 

What’s a significant conversation you’ve participated in, and what was the outcome?

I find that the most impactful and meaningful conversations occur any time we’re talking about strategy. 

Because I played softball in college, there’s a team aspect to engaging in strategy discussions. I have that mindset of ‘We gotta win!’ And if you’re not here to win, and to bring the company forward and ensure that all of your staff have a viable and amazing job to do, why are we doing it? If the client isn’t satisfied, why are we doing it?

When discussing strategy around growth, we dig into a multitude of questions—where the company’s headed, and what mergers, acquisitions or partners we’ll make. How will we run operations in that context? What are our financial targets?

Those conversations are so impactful because you end up with an outcome of alignment, direction and speed of performance. Or, on the other hand, you end up with a very clear understanding that people don’t align or agree. 

If you enter a conversation about strategy and you think people are on board when they’re not, that’s the worst condition you can be in. If they tell you they’re not on board, that’s a gift too. 

I think any kind of strategic discussion, even among the executive leadership team, is so critical to know who’s in alignment, and who might be agreeing to disagree. Then you can end the discussion by high-fiving to go forward to achieve your strategic aim. 

These conversations are the most thrilling because even if they end up in a redirection or a debate, they’re critical to achieving the company’s goals. I’m in it to win it, because if we’re not changing, we’re not moving forward. 

What makes you feel powerful?

Being a role model energizes me, but that wasn’t always the case. 

Early on in my career, when I was in my 30s, I was asked to join a women’s network and become an operating leader. I declined because I didn’t want to be noticed in that way. I already felt odd enough as a woman working in the finance side of manufacturing, where there were so few women, and I didn’t want the additional scrutiny. 

My CEO at the time called me in and gave me a talking to. He said, “People are watching you, whether you like it or not. You’re a role model, whether you like or not. You can stick your head in the ground, or you can accept it and help people.”

He gave me this great lecture and I walked away thinkng, ‘I don’t want to be a role model. I just want to do my job and be recognized for my job.’ 

But over time, that power of being a role model and knowing people are watching crystallized for me. 

Every time I speak, or give a presentation or an interview, people are watching. They’re watching not just because I’m a CFO, but because I’m the one on the stage, or I’m the one who’s speaking in the interview. 

That knowledge becomes your super power. It reminds you to exhibit all the behaviors that you would love the culture to be. 

There is a lot of stress that comes with it. There are days when people ask “How are you?” and I just want to respond with a sigh. But being able to say, “Good, how are you?” with enthusiasm keeps people moving. There’s a lot of pressure, but it feeds me now instead of drains me. 

I feel like it really changed when I had my daughter. When I had my little girl, I thought ‘She’s not going to battle this world like I had to.’ That’s fuel for me. 

You have to be the role model you want your team and your staff to model. Be the leader you want them to be, be the human you want them to be. It’s everything that they see you as: be the woman, be the female leader, be the professional. I get fueled now by being the best I can be at that role for the people watching me. 

About Denise Dettingmeijer

Denise oversees all financial functions and operations for Medical Solutions, a health care staffing firm. Before joining the team in 2023, Denise served as CFO of Randstad North America and Global Businesses, as well as the Managing Director of Global Finance Transformation. Denise is an active advocate of diversity, equity, inclusion, and belonging (DEIB). She served on an Executive Diversity Council and helped establish several DEIB business resource groups.