The Best Leadership Advice I’ve Ever Been Given

It was a spring afternoon a few years ago. After a walk around the neighborhood that Lessonly calls home, Max Yoder and I sat down and he told me something that I’ve remembered many times since then, advice that has enriched my relationships in life and work.

He told me I’d built up a lot of goodwill at work, that people appreciated and even trusted me, but that I wasn’t using that. At first I didn’t understand: shouldn’t helping people be an end in itself? Of course, but the goodwill you build up from doing good work and helping people can be used to do even better work and to help even more people. Change is hard, but if you believe in a change for the better, you can draw on some of the goodwill you’ve built up to ask others to try something different, to take a chance. Or maybe a teammate is doing something that’s not helping your team, even hurting it. Someone needs to tell them that, and if you’ve shown that person that you care about them and the team, you can be the one to speak up.

Max gave me the metaphor of a battery that recharges over time: if your goodwill battery is always full, you don’t get the benefit of its replenishment. Spend some of that charge when it matters, and trust that it’ll come back. I’ve always been a bit of a people-pleaser, so I like the feeling of my goodwill battery always being at 100% with everyone in my life. But I’m grateful to Max for pointing out the missed opportunities in doing that. He might have thought he was draining a bit of my goodwill battery in pointing that out, but I’ll say this: its capacity grew as a result.

Over the years, this advice has given me courage when I’ve needed it. As a manager on my team, the easiest thing in the world is to focus on making my team happy, and I do. But I sometimes need to have difficult conversations (difficult for me, at least) such as telling colleagues when their work could be better. Remembering that I’ve built up trust and shown I care helps me have those conversations without fear that the person I’m talking to will suddenly hate me. Outside of work, this advice has given me strength in conversations with family, with whom I don’t always agree politically. These are heavy times, and there are crucial conversations that need to happen about the climate, race, justice, and so much more. Those conversations won’t happen on a large scale if they don’t first happen on a small one. Now, I’ve always been “a good boy” and am unused to taxing my family’s patience, but remembering all the trust I’ve built up with them over the course of my life has given me the strength to share my own convictions, even and especially when they diverge from from the beliefs of those I love. And we’ve had some really meaningful conversations as a result.

This advice—to balance making people happy with challenging them to help you make things better—may be obvious to some, but a few years ago it was just what I needed to hear. And so, I want to share it. I hope you find it useful.