Offering Support As An Adviser

You’re an adviser to numerous companies, including Stitch Fix. You’ve surely had many coaching conversations, being an adviser. What strategies have you found to be most successful in coaching others and what does not work?

The biggest strategy is listening. I think a lot of times when you’re brought in as an adviser, very low risk for you. You’re just more there to contribute your experience and point of view to help push the business forward. And I’m lucky to say I’ve advised a lot of great companies, Stitch Fix included, a baby food company that I like, called Yumi, and many others. And really, my job is to listen to what they have to say, and then give them a perspective based on what I’m hearing. Allow them either.... So it’s either me reflecting what they’re saying, and giving like a little shine to that and or a little push them along on the journey. Or it can be like, “Well, this is what I’m hearing. Here’s what I think you need to do based on what you’re telling me.” But then I always asked them, “What are you not telling me? What are you not telling me that can help me on the decision making for you?”

And so I think for me, I’ve been blessed to have so much experience in corporate America, where I can leverage that, to help these founders, these companies see around corners, because I’ve done it in some pretty complex organizations, to the point where I see something that’s happening at Stitch Fix where I’m just like, “That’s not as big or as prominent as you think. And here’s the three routes, or here’s the three options that you can take to get out of the situation. Because here’s what I did at Nike, here’s what I did at Snapchat, etc.”

So, it’s mostly listening. That’s the biggest strategy. And the advice that I give to a lot of these companies is: you don’t have all the answers, you’re on your journey, but bring people like me around you to help you see around corners, to help you understand certain issues may not be as big as you think, certain issues, you may not think are big issues are actually big issues after all.

And what has not worked, either things that you’ve tried in coaching others or things that people tried in coaching you? What doesn’t work so well?

In advising, telling people what to do. It’s not your job to tell people what to do when you’re an adviser or a board member. It’s your job to support. And I think a lot of people don’t understand that when they’re an adviser or board member. They think that it’s their job that you’re like the say. “You’re going to do this and you’re going to do that and like, that’s a bad decision, here’s what you’re going to do.”

Again, that’s a very archaic thing to do from like the 1960s, and I think we’re moving way past that. It’s your job to say, here’s what I’m seeing and here’s what I have seen before, and here’s what you could do.