Accountability

The Big Kahuna

Todd Sears

08.19.21

All leaders are challenged through failure, and the best ones emerge stronger from it. In this conversation, Todd looks back at some of his own failures, from hiring to broader business whiffs.

Summary:

All leaders are challenged through failure, and the best ones emerge stronger from it. In this conversation, Todd looks back at some of his own failures, from hiring to broader business whiffs.

Thuy

Just about every leader has successes and failures. Is there a single big failure that stands out in your mind and what did you learn from that?
Todd_Sears

Todd Sears

Gosh, I think there are lots.

Thuy

You get to pick one.
Todd_Sears

Todd Sears

Yeah, I get to pick one. I think one of the failures that I had was from a leadership perspective and managing people very differently in an organization like Out Leadership than when I managed in a Credit Suisse or Merrill Lynch, and I'll talk a little bit about that because I think it is important to understand how different it is to be not just the sole proprietor but a founder of an organization, and one of the expectations that I had of employees coming in was that they would be just as passionate about our work as I was and that they would of course be willing to put in all the work, and that I could trust that that would really happen, and what I didn't do was put in the frameworks and the support structures early on in the organization because I was trying to do so many things, right? You're building the plane while you're flying it, and I failed at several hires. I had some turnover that looking back, I would not have liked to have had, but I also didn't hire the right people. It was sort of a failure on multiple fronts. When I brought people in, I expected them to be stakeholders, not employees, but on the front end, I got excited about people. I would, as my mentor Nina said, I'd fall in love with people. I'd say, "Oh, the person's so great," and I want to mentor them and I would hire them thinking that I would bring them along, versus hiring them to do the job that I needed them to do. That was a major failure for me, that cost me, that cost me time, efficiency, and it created turnover, and so it took me four or five years to really get that right, so that I no longer hire people, if I want to have a mentee, great, I'm going to go have a mentee, but my employees are not going to be my mentees, they're going to be my employees and I'm going to expect them to do their job, and obviously, as a support organization as I mentioned, but I don't mentor them in the same way that I would someone else or the people that I hired early on, and that was a costly failure because it obviously takes resources that hire people and if you have high turnover, then that impacts the team culture, but it was a big learning for me and something that I'm glad I learned, I would have loved to not gone through the pain of those failures, but it has made me a better leader and I think it's made us a much more successful company.