Leslie Bradshaw’s Leadership Lessons | ExCo Insights

In this series, we explore some of the most important lessons and insights from our executive coaches and mentors.

Executive coach and mentor at The ExCo Group Leslie Bradshaw, Leslie Bradshaw, VP of Growth and former board member at Hyper Island, shares her leadership lessons, including the importance of using caution when deciding who to partner with, the advantage of the “try before you buy” approach, and the significance of distinguishing between credentials and hard work when recruiting talent.

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KEY LEADERSHIP LESSONS

The first lesson, which I learned the hard way, is to be careful who you partner with. It can be easy to get excited and think, “This makes sense. We have a lot of shared vision and aspirations.” But as I’ve moved along in my career, I can look back at some of the people I’ve partnered with—both vendors and founders whose companies I joined—and think, “I would not have partnered with these people based on what I learned about them over time.” So now, when I get excited about a possible working relationship after the first or second meeting, I know that I have to dig a few layers deeper to ensure that we do have the same shared values.

I learned that lesson when I was in my early twenties, and I met someone who I really connected with around the future of social media. He had a pretty successful side business, and I joined forces with him and helped operationalize it into a multi-million-dollar agency. But that’s where the similarities ended. Ultimately, I discovered that our leadership styles were very different in terms of how we thought about developing people and encouraging their best work, and I decided the partnership couldn’t continue.

So my approach now is to do pilot projects and “try before you buy” to see how things play out, so I can better understand how someone works and how they think. I’ve also taken on interim roles at a few different companies, as opposed to fully committing right away, and then decided not to go forward with them for different reasons. You really have to “run water through the pipes” to see how things work. You can’t just say, what is your leadership style? How do you resolve conflict? You have to see someone in action.

The second leadership lesson is around the importance of looking for talent beyond the usual pedigrees that people value, such as the fact that someone worked at Google or went to Stanford. I went to a rural high school myself, and most of the people I’ve looked up to, my father included, didn’t go to college. So I look for those people with dirt under their nails and calluses on their hands, and there’s a kind of white-collar, knowledge-work version of that.

Look for talent in the unexpected zip codes and the unexpected schools.

I learned that when I was skilling up my team, and assumed I needed someone with advanced degrees. And so when someone with a JD and an MBA presented their resume, I thought, wow, this looks like someone who knows what they’re doing, so I’ll make this person my head of operations. This person wanted to manage other people, but we were still small and I needed them to do some of the work themselves. Ultimately, I let that person go, and then I promoted our director of operations to a VP role because this person was hard-working. She leaned in and figured out what she needed to know. She came from the middle of the country, from a smaller town, from a college that was lesser known, and she was absolutely the secret ingredient and the unlock to major efficiencies and greater profitability at the company.

Since then, I’ve really insisted on looking for people from community colleges and state schools, and I’ve become skeptical of people who see their credentials as the unlock, as opposed to hard work. I’ve also taught people around me to look for talent in the unexpected zip codes and the unexpected schools. Just because you had access to that brand-name school doesn’t mean that you deserve everything that the name often represents in society.

WHEN I COACH CLIENTS, WE OFTEN TALK ABOUT…

The most common theme is people want to get promoted but feel they don’t have the time to do the extra work needed on top of their current roles. So we will talk about how they are spending their time. And the best force multiplier for scaling yourself is to develop others so you can delegate more of your work to them. That means teaching others how you do your work so they can learn from you. You explain the steps in a particular task, show them how you do it, and give them an opportunity to ask questions. Then the next time, let them do it and be there to ask any questions. And then, once you both feel confident, let them do it by themselves and don’t micromanage them.

That’s been a huge unlock for many of my clients at all sorts of levels, which has also led to excitement from their team. They, too, are learning new skills, which is, in turn, making them better positioned for promotions. It also frees up more time for my clients to think about the big picture and to devote a few more brain cycles, or even full days, to broader questions around strategy.

Another theme that comes up often is helping people think through whether they really want to go down the path of management and leadership. The reason people often go into management is because it usually comes with more pay. But we spend time talking about whether this is really the path they want, why, and what it means to make that shift from individual contributor to manager and leader. Because you lead with your ears—you have to shift from a focus on providing answers to asking questions and shift from being the smartest person in the room to sitting back and passing the microphone to others to draw the best work out of them and excite the team around a vision and a direction.

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