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5 Proven Strategies for Leading a Team and Facilitating Growth

November 21, 2025

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Across three decades in corporate and entrepreneurial roles, Jen L'Estrange has learned that leadership is built through intentional choices, humility, and embracing challenging opportunities others avoid. She shares five strategies that shape how she leads her team, navigates risks, and grows a business grounded in trust and purpose.

A trio of business persons conduct a discussion in a brightly lit hallway.
Photo by Entrepreneurs' Organization

After 30 years on my journey through various corporate and entrepreneurial roles, I’ve encountered highs and lows — and learned at least my fair share of life lessons. Following are five pivotal insights that have shaped how I lead teams and foster business growth and development.

1. Do the Job No One Else Wants

My best opportunities have come from work that no one else wanted to do. My first leadership role in IT was turned down by three people before they got to me, and I landed my first role in HR after the entire succession plan had been exhausted. It’s kind of like being picked last for the kickball team at recess, but it’s worked so well for me that now, as we grow our company, we actively look for industries that are underserved in HR. Our work with construction companies and car dealerships is something that most firms won’t touch. But honestly, we only regret what we don’t attempt. 

2. Race the Track, Not the Person Next to You

This took me way longer to learn than it should have. I am hard-wired to compete and early in my career, I spent a lot of time looking around to see who and what was happening around me. It was distracting -- and it probably held me back.

"Creating psychological safety is a business growth superpower. If things go well, my team gets the credit. If things go poorly, I own the loss."

— Jen L'Estrange, EO New York

Once I started a family, I had to learn to identify needs and set clear goals because my race was really about managing my time and being intentional with my priorities. I still struggle to get enough personal time, but I stopped looking around me to see who was next to me. We’re not in the same race.

3. Credit the Wins. Own the Losses

Creating true psychological safety inside an organization is grossly underrated and it’s a business growth superpower. We take calculated risks every day, both in our business and in the businesses that we partner with. We wouldn’t be able to do half the things that we do if my people didn’t feel that I had their backs. If things go well, they get the credit. If things go poorly, it’s my problem to solve. 

Early on in my experience as an employer, one of my consultants said to me, “I’m afraid that if you let me run this engagement on my own, I might screw something up.” I replied, “Listen, it’s not a question of if we screw something up, it’s a question of when. It might be you, it might be me, it might be someone else on the team, but at some point, I promise you, we’re going to screw up. I’ll own that, and we’ll fix it. There’s very little that we do that can’t be fixed if we mess it up. But if we spend all of our time trying to find problems that aren’t there yet, we’ll never move forward -- for our business or for our clients.”

That one conversation changed the whole psychological and emotional profile of my team. Forever.

4. No One Wants To Be Told What To Do

I still struggle with this sometimes, especially in a consulting firm where we’re paid to tell people what to do. I’ve had to learn to first listen to understand and approach issues with curiosity. It’s hard to do because we’re all trained to listen to respond rather than listening to understand. But the truth is that no one wants to be told what to do. We just don’t. And, as a feedback tool, it doesn’t work.

Telling someone what to do strips them of their power and reduces their appetite for calculated risk. Over the years, I’ve learned to listen first, and then ask questions to help the other person see their own solution. Alternatively, I’ll share a similar experience that I’ve had that’s relatable, and use it to guide the person to their own conclusions.

It works so well that I almost never tell anyone what to do anymore. Brainstorming around a past experience changes the conversation to a shared solution, one where they feel ownership -- and are more likely to hold themselves accountable for the outcome.

5.You Can Have Everything Just Not at The Same Time

My journey to entrepreneurship was almost accidental. I had my first child in my mid-thirties after more than three years of fertility treatment. When it was time to return to work, the job that I thought I was going back to wasn’t the job they had for me. I didn’t want to travel as extensively as I had previously, so I resigned.

"My best opportunities came from doing the work no one else wanted to do. We only regret what we don’t attempt."

— Jen L'Estrange, EO New York

It was not a popular move at home, but I had waited so long to start a family; I figured that if someone was going to screw up my kids, it should be me. As much as those years were not as financially rewarding as my corporate roles, I had the flexibility to be with my children, see their milestones, and be part of their young lives.

The company I run now wasn’t even formed until 2015, after two international moves and another baby. We’re in our ninth year now, and I’ve learned so much about how to run a business and how to be a leader. We’ve grown every year and are now a leading consulting firm serving small businesses in the United States.

As my kids become more independent, I am spending more time building the business and am slowly easing back into work travel, but I’m still very intentional about the time I spend with my two boys.

By Jen L’Estrange, an EO New York member who is the founder of Red Clover HR which provides strategic and operational outsourced human resources for small and midsized businesses.