Working with a Mentor

Last updated February 27, 2023

A common challenge I’ve heard is knowing how to get the most out of mentor relationships. Sometimes the relationship quickly fizzles because the mentee doesn’t know what to ask to get useful advice. Below is a brief description of what I have found to be effective when I work with my mentors.

Come prepared with a problem

I like to think of a problem that I’m currently working on (something abstract, not super specific/technical), and then use that as a sort of “case study” to talk through the problem with the mentor. I try to use problems that I can summarize in a sentence or two, so the mentor can get up to speed quickly.

Depending on the mentor and how close they are to the work, the conversation can be as general or specific as need be, but keeping it general is actually a good thing, as it keeps the discussion focused on strategies for solving the problem, rather than solving the problem itself.

Some sample problems I’ve used (or are similar to ones I’ve used) in past discussions:

• How do I balance prioritizing delivering new features against component health work?
• How do I balance long term deliverables against short term deliverables?
• One of my team members isn’t responding to my feedback, how do I handle this situation?
• [Component I own] is unmaintainable, how do I decide when to rebuild it? Do I rebuild it entirely, or piecemeal?
• When I suggest something, sometimes people just accept it or take it as fact. How can I encourage people to challenge me and tell me I’m wrong?
• When should I buy a product off the shelf vs build something myself? What if the product off the shelf is expensive to integrate and doesn’t solve every feature we want?
• [Service I depend on] isn’t very reliable. How much effort should I expend in trying to get the owners to fix it vs improving my service’s resilience to outages of that service?

Observe how the mentor approaches the problem

The goal is to understand how the mentor would approach and frame the problem, and use that to learn strategies for problem solving.

I’ve also had good luck with using the same problem as a prompt with multiple different mentors, and seeing how different people would approach the problem. What’s similar, what’s different, what pieces resonate best with me and what do I want to adopt as part of my personal way to tackle this?

Some things to keep in mind as you discuss:

• What questions does the mentor ask? This may help guide you to a behavior you have or an assumption you’ve made that’s limiting how you think about the problem.
• How do they think about or frame the problem? I have found some mentors will redirect me, telling me the problem isn’t what I think it is, it’s actually something else. I love it when they do this, because it helps me think outside the box and shows me a new perspective I never would have found on my own.
• Solving the problem would be a nice bonus, but is not part of the goal of the exercise. (Most of the problems I use don’t actually have a clear cut solution anyway).