The Surprisingly Simple Way to Be the Best Mentor Ever

Over the course of my career, I’ve mentored quite a number of people beyond those that I personally managed. This includes formal mentorship programs that I’ve volunteered for, heads of product management, and of course friends and colleagues.

Mentor
Illustration by Camellia Neri

When I first started mentoring others outside of my own team at Gusto, I found it challenging to figure out the right structure for the mentorship. How should I run the meetings? How often should we meet? How can I be helpful given that I don’t actually see the results of their work?

There’s a lot of generic advice online about how to be a good mentor (“let them drive” is a common saying), but not many good answers for these questions at a tactical level.

I’ve found that the best approach to being an effective mentor is surprisingly simple: ask your mentee to walk you through specific situations that they found difficult, and challenge them with thoughtful questions.

A mentor’s toolbelt

More often than not, a mentee will not be somebody that you work with directly. What this means is that you don't have full context around decisions being made in their company or by them, so you really can't critique them or give feedback as you would for somebody that you're directly managing.

As a mentor, you have three basic tools in your belt to help your mentee:

  1. Teach them frameworks / best practices, based on your knowledge and your own experience, that they are looking to learn.
  2. Lend a sympathetic ear, listening to what they have to say and making them feel heard by somebody who truly understands their situation.
  3. Have them walk you through challenges they’re having so you can ask more questions and make suggestions, often incorporating #1 and #2 above in your recommendations.

I've found the last tactic to be the most effective. For example, if your mentee is having trouble with stakeholder management, have them talk about a specific recent example. If they’re having trouble with roadmap management, have them show you how they manage the roadmap today and explain the challenges they’re having. You can then ask lots of questions to gain enough context to make suggestions.

Ideally, your suggestions are in the form of both a framework ("here's a generic way to think about problems like this") and a solution ("one potential way to solve this is __________").

After your meetings, your mentee should take a homework assignment to try to incorporate what they’ve learned into their actual job so that at your next meeting they can share what did/didn't work. You two can then iterate together.

Kicking off the mentorship

At the beginning of the mentorship, I've found it useful to be up front with my approach (described above) to set expectations. Let your mentee know that you want them to drive the partnership, and that what's most effective is for them to bring specific challenges and examples to the table for you to discuss together.

Often people are a little nervous about sharing their struggles, but typically open up once you build rapport and explain why it’s so important for them to bring up tactical examples and situations for discussion.

I’ve also found that some mentees start off a little dubious of my own motivations. Why am I taking time out of my busy day to help? What am I expecting in return? So, I also typically share with my mentee why I’m excited about the partnership during our first meeting.

Generally speaking, my motivation for being a mentor is that I want to practice my own coaching skills and get a lot of personal satisfaction out of helping others, and my only ask is that my mentee be forthcoming with feedback for me about how I can be more helpful, which suggestions worked, and which didn’t.

Meeting cadence

I suggest a meeting cadence that allows your mentee to actually work on things in between sessions. This can vary dramatically depending on both what type of help your mentee is looking for and the seniority level of your mentee.

For example, I had a mentee who was in the first few years of her career and was looking for help with how to approach everyday communication with her manager and peers. She had many opportunities to practice new tactics every day, so we chose to meet every other week so that we could iterate faster.

I also had mentee who had recently been promoted to director of product and was struggling with how to best communicate her strategy and vision to her company. Opportunities for this were largely leadership meetings, all-hands, etc. which do not happen frequently, so we chose to meet every six weeks.

The one exception I’ll stipulate is that you find a mentee with whom you’d like to work through a number of challenges or skills in parallel. For example, one of my mentees wanted help on multiple fronts including long-term roadmap planning, short-term prioritization of his backlog, and many conflicting viewpoints from others in the company. In these situations, meeting more frequently may make sense.

Want to Continue the Conversation?

Being a mentor can be incredibly fulfilling and a great way to practice coaching skills—regardless of whether you’re an individual contributor or manager If you’d like to be mentored by some incredibly talented people at Gusto or be a mentor for some of our up-and-coming stars, you can check out our open roles here.

I’d also love to hear from you. How have you structured mentorships in the past? What’s been useful to you as either a mentor or a mentee? Leave a message here or find me on LinkedIn.