Would you mentor an aspiring (vs a current) product manager? And how would you want to be approached and asked to mentor them?

I do mentor and coach a number of folks from different backgrounds and at different stages of their career. I typically prefer to mentor folks who are product managers versus folks who may be aspiring to do something or to not really have kind of a clear path forward in life. There are mentors and coaches who are appropriate for those folks as well. I just really enjoy helping people break through their limitations as a product manager, learn how to play organizational politics, for lack of a better word. Learn how to do the things that matter and set themselves up to get promoted and climb the ladder. Strictly just because I think that's where I can add more value.

In terms of the best way to approach a prospective mentor, I'd say come with a well thought out ask. Understand what you want to get out of the mentorship and show that you're willing to do some work. These relationships work best when the mentee puts in the work. People just looking to show up and have someone tell them what to do everyone once in a while don't go far. Demonstrate you'll do the work by doing it before you approach a potential mentor.

Currently, I'm best suited to mentor mid-career product leaders facing challenges I've tackled in the last 5-7 years. For aspiring PMs, I recommend finding mentors with recent experience in entry-level PM roles. They can offer more relevant advice on breaking into the field and building foundational skills. While I focus on mid-career mentorship, I do volunteer with Mentors in Tech for aspiring software engineers. If approached by an aspiring PM, I'd appreciate their initiative, explain my current focus, and offer to connect them with more suitable mentors if possible. I'm open to brief conversations about the PM career path, but for in-depth mentorship, it's crucial to find someone whose experience aligns closely with your current career stage and goals.

I'll start with the second part first. Be direct about what skills you are hoping to develop or share that you are hoping to break into product management, and let the person you are hoping will mentor you know that. Whether you position as a formal request for mentorship, or simply let the person know you respect them and would love advice, the focus should be on establishing the relationship.

For me personally, the word mentor has a higher bar than someone simply asking for advice. If I've never worked with you before, I'd prefer starting a casual series of conversations before giving the relationship a name such as "mentoring". The construct is the same, just the bar feels lower :) - mostly because in a mentoring relationship, I expect the mentee to put in the work to think through what they need, and if I'm meeting someone for the first time, I don't know if they expect to put in the work, or if they expect me to figure out what they need.

I love folks from different disciplines moving into product. At this point in my career, I'm probably best suited to someone looking to transition from outside product into a product leadership role vs. an early career product manager, but I've mentored several folks in the past that want to make this transition and have enjoyed it. Based on research that has been shared with me in the past, a mentoring relationship is most successful if you are within a couple of levels of your mentor -- too much distance, and its hard to get concrete suggestions.