Preparing for a New Mentor / Mentee Relationship (or a Great 1-on-1)

A little bit of context…

So, today, I dedicated the vast majority of my schedule to coach and mentor 10 folks via Out of Office Hours, a free mentoring service to help those who want to get into the tech industry.

I signed up because, well, I would have loved to have this type of service when I was younger (even though I was “in” the industry already):

Right now I’m almost half-way through the sessions but I’ve already collected a ton of notes from these new mentees and I wanted to capture a few thoughts for those that might be doing something similar.

In fact, many of these “tips” can be useful to you for any 1-on-1 meeting, whether it’s a personal get-together or a more professional check-in (e.g. Weekly 1:1 Meeting).

But first, here are a few things that went badly:

  1. Mentee didn’t send a confirmation about the meeting time. Always helpful to make sure that, despite an automated meeting invite, to reach out personally.
  2. Was late to the meeting. That’s a big no-no. Time is our most valuable asset and  there’s no other industry where this is more felt and understood.
  3. Spelled my name wrong. Ugh. That just feels… wrong.
  4. Bad audio. A lot of this under your control now so get into a quiet place, not in a public coffee shop, and get some headphones. If the internet is bad, well, then get to a better spot. This goes for in-person meetings as well, of course. Get to a place where you can have an open dialogue and don’t have to yell or whisper.
  5. Didn’t send an agenda or at least an introduction email. Providing context is helpful and saves a ton of time because instead of spending the first 15 minutes gaining context and hearing a long backstory we can just get down to tactical implementations. I share more about this in the VLOG.
  6. Didn’t have an “ask” ready. In other words, the mentee wasn’t sure of their goals for the conversation and outcomes.
  7. Have a backup plan ready for technology to fail. It happens. A lot.

But, in general, I loved having the conversations and was really happy to do it. In fact, I made my VLOG about it today and also shared a few tips on how to maximize the time spent together. Check it:

And, of course, here are the tips below. Remember, these are my personal favorites to ask and to help setup the conversation but many more will do!

It’s super easy to ask…

… and you get amazing answers!

5 Questions to Answer in Preparation for a New Mentor:

  1. Send an intro email, give me context on your background.
  2. Who do you want to be?
  3. Where do you want to go?
  4. How are you going to get there? (Or how do you think you’re going to get there?)
  5. How can I specifically help?

Hope that helps. If you have any questions feel free to hit me up on Twitter or ask me in the VLOG comments! Whoot.