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If securing a mentorship was hard, I would argue that deepening a relationship with your mentor and knowing how to get the most out of it is even harder.

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I have wasted years of my past mentors’ time by showing up to 1:1s without knowing what to ask, or hoping that they would guide me in getting the best out of their time. The hard truth is that a mentorship is only worth what you put into it – and I didn’t do those relationships justice. This is the first year that I think I am beginning to ‘get it’. Ultimately, an effective mentorship is about sharing what you want, asking the right questions, and deepening the relationship so that you both trust each other. Here are my findings and reflections on the process.

Establish what you want from your mentor

I promise I’ll only say this a few times, but imagine that I’m shouting it from the rooftops: When someone agrees to be your mentor (formally or informally), they do it for a reason. Mentors want to help you. They have no idea how to do that for you or what you need, they don’t know what’s working for you, and they’re trying their best. Share what you want and need; I can guarantee you they’ll be relieved to hear it.

So, first things first, determine what kind of relationship you have with your mentor now, and how you want it to be in the future. The best way to understand the type of relationship you have is to look at what development approaches they’ve used in your past meetings with them. The most common development approaches that your mentor is likely to use are mentoring, coaching, and sponsoring. This is what they look like:

  • Mentoring: shared experiences
    • ‘When I was in your situation I…’
    • ‘You should…’
    • ‘Have you tried…’
  • Coaching: questions and forced introspection
    • ‘What are you optimizing for?’
    • ‘What do you need to succeed?’
  • Sponsoring: actions that make things easier for you
    • Introductions
    • Shared materials
    • Feedback to manager or advocating for your promotion to the approval committee.

From going through the section above, you may now have a clear understanding of what you have, and also ideally what you need, and now it’s just a matter of communicating that with your mentor. Here are some easy phrases to help get the conversation started.

Situation

Phrases to try

Nudging your mentor toward a coaching approach.

Last time when I asked you ..., you …; I’d like to try something new this time. In our next few meetings, I’d like you to coach me instead. Here’s a list of open questions for the style I’m looking for.

Nudging your mentor toward a sponsorship approach.

There are a few opportunities coming up where I could use your help as a sponsor. In particular, I’d like help with …; here are some ideas I had: …! What are you comfortable with? (Feel free to steal ideas from the table in my previous article.)

Wanting more of ... (style, time, etc.)

  • I want to try something new …
  • I have a lot to cover in our next meeting, could we expand it to an hour?
  • Can we make this a regular meeting?

Not getting what you need.

  • Did you get the chance to check out my doc/agenda? That’s okay, let’s use the first five minutes to do that before we talk.
  • That won’t work for me.
  • I could use more of …
  • Next time, can we try …?
  • I’m surprised by that recommendation.
  • I expected something different.

No longer wanting a mentorship with them.

  • Thanks so much. I feel like I’m in a better position now. Let’s cancel our upcoming meetings and schedule ad-hoc. Can I still message you if I need to?
  • I’d like to share feedback with your manager on how you’ve helped me!

Absorb their knowledge by asking the right questions

I once read an article about a programmer who said that they weren’t particularly good at programming but they were really good at asking the right questions. Since reading that and connecting achieving proficiency to the act of asking the right questions, I see the world through a different lens. Maximizing your mentorship is no different; a major component is asking the right questions and pushing yourself to be bold in what you ask for.

Here are some ideas of what you can add to your next 1:1 agenda, increasing in boldness with each section:

Ask about them

  • What does your day-to-day look like? Can you show me your calendar? 
  • How did you get this job? What did you negotiate?
  • Who do you have good relationships with in this company? How did you form them?

Ask for advice

  • What is no one telling me that I need to know?
  • How should I approach my manager about ...?
  • Can I get a gut check here? I just heard … but that doesn’t line up with …; what am I missing?
  • I did … to solve … and it didn’t work. What did you do the last time you tried to solve ...?
  • I’m trying … and it’s hard because …; how have you done this in the past?

Ask for examples of their work

  • Tell me about your last self-review or the one you wrote when you were at my level. Are you comfortable sharing it with me directly?
  • What are your goals for this month?
  • What goals did you set when you were at my level?
  • Would you mind sharing information about your promotion packet (or are you able to get permission to share it with me)?
  • Do you have examples of a good … and why it’s good in your eyes? (E.g. self-review, pull request, architecture document, request for comments, executive summary, post-mortem, engineering blog post, technical retro.)

Ask the hard questions

  • How do you make your work visible?
  • How do you self-advocate?
  • How did you get your last promotion?
  • Have you ever gotten your promotion rejected? What did you do about it?
  • How did you handle a situation where your manager wasn’t giving you what you needed?

Ask for input or favors

  • Can you read my self-review? What should I add and what should I cut?
  • Who should I meet to do …? Can you introduce me?
  • Could you gather feedback about me from my manager?
  • (Link to something.) Can we go over this in our next 1:1 so I can see what I can do better?

There’s no easy recipe for how to pick the questions or how bold to go, but my heuristic is to go 10% bolder than you’re naturally comfortable with and to keep testing your limits. That means sometimes you’ll get it wrong, and that’s ok! Imagine how much value you might have missed out on if you never ran the risk of misstepping!

I’ve recently secured a new mentor. Here’s what my first agenda looked like with them, including the questions I put together for our agenda. I directly sent this in a DM and then added it to a doc to keep track of our 1:1s going forward. (For context, this is someone I’ve known for a year and see regularly in senior meetings, so we’ve had shared experiences and met before, but this is the first time I had an official mentor meeting with them.)

This was for a 1-hour meeting (that became a 1.75-hour meeting) but as you can see, I jumped right in with in-depth questions; taking this risk turned out to be incredibly rewarding. I took the approach of sharing my observations and struggles, and asking for what they saw from where they were sitting. This has given me the confidence to be even bolder in my next 1:1.

Build trust with your mentor

An effective relationship with your mentor goes two ways: you need to trust your mentor and your mentor needs to trust you. Because actions speak louder than words, I’ve found that the best mentorships revolve around positive shared experiences. This can take months or even years to do, but there’s nothing wrong with jump-starting the first step on either side.

One thing you can do to begin the journey of trusting your mentor is give them a small action item or follow-up task at the end of the meeting. This entails agreeing on a deadline and stating anything that the task might be blocking on your side, adding it to the agenda for the next 1:1, and asking for feedback on whether that’s a reasonable task for them. This is helpful for several reasons: it focuses on something small, the expectations are clear, and no one has to remember to bring it up in the next meeting because it’s on the agenda. It’s all built-in. While this might feel like a lot to ask from your mentor, remember that they want to help you. As long as the task clearly ties to your goals, there’s no harm in asking.

To invest in the two-way relationship, there should ideally be moments where you are also building trust with them by taking action items or follow-up tasks – but these are more subtle. The equivalent of an action item or follow-up task as a mentee can take the form of:

  • Asking for homework (and actually doing it) and giving feedback about whether the homework or task is reasonable for you
  • Giving a status update on how a new technique or task is going and adding it to the agenda to talk about in the next meeting
  • Sharing how a problem has improved
  • Sharing feedback you’ve gotten from others in relation to advice they might have given.

If you have a good mentor, tell them exactly what you get out of the relationship and why it’s helpful for you; cite a few examples of what they’ve done that’s had the biggest impact on you, and put it in writing so they can save it for a rainy day. Then go and share it with their manager, too!

What now?

I hope you can reference this article and its counterpart as you find, change, and enhance your mentorship relationships. If you’re up for a challenge, here are three things you can do right now to maximize your mentorship:

  • Set the agenda for your next 1:1 with what you’d like to ask your mentor and send it to them 12+ hours in advance
  • Include a bold question in your agenda
  • Identify homework for each of you that you can plan on introducing 5-10 minutes before the end of the meeting.

Mentoring and being mentored is hard, takes time and patience, and is a lot of work. Two people come into a mentorship with different ideas of what success is and what they need, and ideally, over time, align and evolve together. The clearer you can be about your needs and expectations regarding what you want to invest in the relationship, the faster you’ll get to a point of stability. I wish you the best of luck and hope you get even more out of your mentorships – starting with the next meeting!