Spotlight: Josh Gutman

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I wish I had a mentor when I was first starting my career because there was so much that I didn't know I didn't know. For instance, how do you lead teams? What should even be your goal leading teams and how do you set that goal? I remember talking to a four-star general and he asked me how I would know someone is struggling for non-work reasons and whether I had a process that enabled people to check in with me in an honest and open way. That was a really big revelation for me because I realized I can't be an effective mentor unless I could do that with people.

To me, being a great mentor is being the person who someone can come to in order to help them take a step back. There's a lot of things in life that you can optimize for - money, family, prestige, satisfaction - and it's really easy to get narrowly focused on one without testing your assumptions. My goal is to help people widen their field of vision and come up with a framework for evaluating choices in their lives. Of course, we'll have tactical discussions like how to best prepare for an interview, but it can now be informed by the greater context of their decisions.

Ultimately, mentorship is figuring out how to have a long-term relationship with someone. I want to give unique advice to the person and that means getting to know them. I think checking in on a cadence is really valuable because that means you're keeping a continual rapport. That way I can understand their context when we talk because as you know life is dynamic. There will be critical times where we meet much more often and there will be times where they don't need to make as many decisions and we meet less frequently, but it's important to be there for them and be able to give them relevant advice when it really matters.

Hear from other fellows and mentors


Chris Oryschak

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"For me, I really enjoy mentorship of early career people because I was there before. I think the point of mentorship is to give somebody context and viewpoints they don’t otherwise have access to."



Jeremy Navarro

Comparative Literature @Middlebury

"Tyson has been very helpful. He helps me sift through the noise and just focus on what I need to focus on. He also calls me out when I'm making a mistake - we've only been working together for a month, and I feel like I've already made a ton of progress."