How to use a disastrous experience to your advantage, or how I learned to lead a team

It’s about 2001 and I’m facilitating a Diversity Council session at a big New York bank. About 30 of us meet monthly to plan and execute initiatives that will drive our our part of the company to be more inclusive and diverse, and better able to leverage that diversity on behalf of the business. I love this team and this is one of my favorite roles.

Sonia asks if she can present a volunteer opportunity to the team. She introduces a non-profit, Unlocking Futures, that supports at-risk youth in the poorest communities to overcome challenges presented by their environment and lead a life of their choosing. They have demonstrated impressive results.

They are holding a bowl-a-thon fundraiser and looking for captains to recruit and lead a team that will raise the funds to put one young person through their proven, effective and inspiring program.

Two senior executives volunteer, as do I. They each assemble a huge team from their department and spare no expense to outfit everyone with matching t-shirts. I’m junior in the organization and don’t manage a team so I invite a few of my friends and this new guy I just started dating to be my team. Everyone agrees to help sponsor a young person. I share the dates, location and background materials but don’t communicate much else. I am super shy about inviting people to donate to the cause.

A few weeks later I get to the bowling alley for the event. I’m shocked to find that my friends have all bailed at the last minute. Except that new guy who shows up with his promised contribution. Our team falls far short of the goal, contributing about $870 of the expected $3,500. I am completely mortified and slink around the alley all evening, trying give myself credit for at least accepting the challenge but mostly feeling disappointed and embarrassed.

I learned something reflecting on that that experience, besides that that guy was a keeper (he's now the hubs). When I looked, I saw that I wasn’t so present with my team during the fundraising period. I did not check in on how they were doing, if they were having any challenges, or needed help. I did not ask for help myself. I did not confirm a few days before that they would be there.

I decided right away that I would redeem myself the following year. I started having conversations with people well ahead of time and recruited double the amount of members needed for the team. I understood why each team member got involved and what it meant to them. I better explained how the non-profit’s efforts would make a difference and made sure team members met some of the young people who’d been through the program. I checked in with everyone and shared our results weekly so we could see where we were with respect to our collective goal. This time, we raised more than enough to fund a transformational experience for a young person, including an empowering training program and a year of committed mentoring. Yes!

By reviewing the experience and what could be added that was missing from my game the first time, the results were much better on the second try. Two things I took from this:

• To lead a group of people to produce results, you need to be present and engaged with them. I actually knew this intellectually already but here I learned how to do it by doing it.
• Don’t assume you can’t do it and give up. In the past I would have decided I’m not good at this and avoided ever doing something like that again. I think it was good to just give myself some grace and try again.

I did not become a perfect leader of people after this, and I’ll always be working on improving in that area. But I did incorporate these lessons, which made a significant difference in the results my teams have been able to produce.

Where did you get it right on the second or third try?