Bootstrapping Mentorships, A Guide

Bootstrapping Mentorships, A Guide

July 12, 2021


This is a set of reflections on the common aspects of mentorship relations that have gone well for me (on both sides of the table). As for my experiences/credentials, I’ve been a mentor to bootcamp students, interns, as well as early stage and seasoned professionals - inside of and outside of the same workplaces. Some of these relationships went well in that the produced accelerated both on both sides of the table, which is ultimately the purpose of mentorship. Others have fizzled out before finding their stride. So these reflections are based on both successes and failures.

Anyone can be a mentor

Wherever you are in your career, there is someone trying to get there.

As an anecdote, a mentee of mine became a mentor herself while she was only in her first year as an engineer. Despite being so early in her career, she was already having impact as a mentor in her own right by connecting with people who saw her as an example of what is possible.

Effective mentorships have an anchor

An anchor is a goal or set of goals that the mentee is motivated to achieve and the mentor is willing and able to provide guidance on.

The exact, specific goals don't have to be known up front, but having a sense of the high level themes is helpful. E.g. are they focused on getting a promotion, learning a specific skill, etc. One of the first steps of a newly formed mentorship should be goal setting to define the specific anchors.

Identifying goals is itself a pretty good goal. Depending on their background (e.g small, scrappy startups) and career stage, your mentee may not have an practice with this style of goal setting, so having someone to guide them through it the first couple times can be very helpful. Defining goals at this stage can then create the anchors for the next phase of the relationship.

Start with expectation setting

The fastest path to failure is to operate based on unclear expectations. Explicit, clear expectations pave the path to success.

For example,

  • “I expect your to drive the agenda of our meets - come prepared with the topics that you’d like my input on.”
  • “You can talk to me about interpersonal as well as <insert job function> challenges.”

Leverage the mentee's existing development plan

If your mentee has already set goals with their manager, then you have a head start. What subset of those goals can you help them to accomplish?

Focus on their goals that align with your skills

Your mentee may have many goals - you don’t have to focus on all of them.

What knowledge, skills, relationships, or past experiences do you have that align with some or all of your mentees goals? If they have goals that don’t line up with your skills, try to point them towards the person or people who can help them along. At that point, accountability rather than execution can be your focus.

Mentoring through differences.

While it can easier to connect with people who are more like you, there can be value in cross difference relationships exactly because of differences in perspectives and experiences - so long as you've found the right anchor.

Anecdotally, one of my mentors while I was considering the switch to management was a staff engineer. If I’d asked my staff engineer mentor how to become a good EM, they probably wouldn’t have the most relevant perspective, given that they hadn’t undergone that journey themselves. But if I ask, how would you as a staff engineer want to partner with an engineering manager to solve X problem, the difference in perspectives becomes an asset.

Keep a shared journal

A mentorship journal is a great place to store the expectations and goals that you’ve committed to along with on going discussion topics.

In general, I find it helpful to have a place to share notes from one-on-one discussions, and that extends to mentorships as well. Use your shared to

  • House the expectations that you've set for yourself and each other
  • House and track progress against goals
  • Jot down action items that you're each committing to over time

This can be as structured or freeform as you'd like - the goal here is to have a practice that works for both parties that allows you both to make sense of changes over time.

Looking to the future

Mentorships don't need to last forever

Once you've helped your mentee to meet the set of their goals that align with your skills and knowledge, it's OK for the relationship to change phases.

You don't have to get them across the finish line, you just have to help them along the way. Maybe they need to seek out another mentor or sponsor for their next phase, and that's OK!

When changing phases, tweak the variables

Even if you decide to continue on to another phase of your mentorship, consider that the ways in which your mentee needs/wants to be supported may have changed. So to may your capacity to support them have changed. Consider tweaking the following variables:


Maybe you were meeting once a week, how about every two week? If you were meeting bi-weekly, consider meeting once a month. The goal is to meet at a cadence in which neither party feels overwhelmed and both parties have had sufficient time to follow up on actions, try things out, and generate new topics.


Maybe you started out with one hour long sessions. Consider condensing to half an hour, etc.


If your 1:1s turn into more of a social event, that may be a sign to change phases or come to a close.

Consider orienting the mentorship around a narrower set of goals.

Forget a mentor, find a sponsor

Read Forget A Mentor, Find A Sponsor by Sylvia Ann Hewlett. TLDR:

If all goes well, at some point, your mentee is going to need someone in the rooms where decisions are made to advocate for them.

Unless you are in a position to make hiring, promotion, compensation, project selection, etc decisions, that probably isn't you. And that's OK - help your mentee to develop a sense of who those people are that are making those decisions. And if you can, help them to cultivate those relationships. If, on the other hand, that is you: congrats; you’re in a position to be a sponsor! Advocate for your people and build out that bench strength.