The #1 Mistake You're Making with Your Mentor (And How You Can Avoid It)

Tips and resources on how to make the most out of your mentorship.

Hey folks, Steve here 👋

This week I’m excited to feature a piece from Jordan Cutler, which dives into how you can make the most out of your mentorships.

Jordan is a senior engineer at Pinterest and author of the High Growth Engineer newsletter. I highly recommend you check it out if you’re not already a subscriber.

Without further ado, I’ll pass the mic 🎤 to Jordan 👏

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I’ve had over 15 mentors and mentored more than double that. Being both a mentee and a mentor, I’ve seen a lot of mistakes. And I’ve made even more myself.

Today, I’ll talk about the biggest mistake I made as a mentee. By the end of this, you’ll know what to avoid and what you should do instead.

My Mistake As A Mentee: No gameplan

As a mid-level engineer at Gusto, I was ambitious and wanted to grow and get promoted as fast as possible.

To do that, I heard the classic advice, “Get a mentor” from tons of places—onboarding, my manager, and plenty of resources online.

So I thought to myself, “Alright, time to find a mentor so I can grow faster!” I was pretty active in Slack channels, so there were two people I particularly looked up to, who just seemed to know everything and could answer any question. I wanted them as my mentor.

I sent both of them a message, “I’m so impressed by how much you seem to know about front-end, would you be open to meeting once in a while as a mentorship?”

To my surprise, they both said, “Sure!” I set up bi-weekly 1:1s and brushed off my hands like this:

I thought, “My work is done! Now I get to reap the benefits of getting a mentor.”

But boy was I wrong. I showed up to our 1:1 and started with, “Hey, how’s it going?” which resulted in the conversation going in 1 of 3 directions:

1. They start chatting about things going on in their personal life, and I ask follow-up questions to not be rude.

2. They say “Good,” ask me the same, and I start talking, giving random work updates 

3. They say “Good,” ask me the same, and I start talking about my personal life, and they ask follow-up questions, I assume also to not be rude.

Sometimes, we’d do one or a mix of each of these for the full 1:1 time. All of these conversations had one thing in common: They didn’t support my growth. I let the amazing resources I had in front of me—which was the whole reason for getting mentorship in the first place–go to waste. I was wasting my mentor’s time—and mine.

The repercussions of this were twofold:

1. The meetings fell off - It was easy to take the 1:1s less seriously because it became a session for us to chitchat, so much so that we’d just cancel or reschedule often.

2. We had little time for the important stuff - Because I didn’t proactively plan what I wanted to talk about, we’d fill up most of the 1:1 time with chit chat before realizing there was actually some juicy learning and problems to tackle. One time, we realized this with only 5 minutes left after taking most of the time chatting about our personal life. I had a document that needed a lot of work, but we didn’t get to it because I fell into our default mode of conversation.

Fixing My Mistake

I recently joined Pinterest on a team full of busy Staff Engineers. I realize now that securing a mentor is not enough. To truly learn from them, I needed to put work in, not just take. At Pinterest, I have 2 mentors, like I did at Gusto, but I try to maximize the learning I get for the full time we’re together.

Me with my Pinterest swag after joining

Here’s the step-by-step process I follow:

1. I check my calendar preemptively for any 1:1s

2. I add an agenda ahead of time using a simple “Notes” and “Action items” section format (see below).

3. In the “Notes” section, I write either a challenge, question, update, or win.

4. In the “Action items” section, I add things for me to do based on our previous discussions.

5. Lastly, I tag my mentor in the document ahead of the 1:1, letting them know I added to the agenda. They can freely check out what I want to discuss and have some time to think about or review it.

Now, I pose specific questions like, “What would you do to make this doc better? Do you feel like it’s too long?” Preparing pointed questions like this before our meetings resulted in better, more actionable feedback.  

“Yes, it is too long and will result in the audience being confused. Do this instead.”

With this approach I got the document feedback I needed in time, while also minimizing the lift from their end.

How I Come Up With Topics

You may be asking yourself how to come up with topics when you don’t know what to talk about.

I use a technique called “priming,” where you look at a specific set of things to help you brainstorm. The idea is that you have a high-level set of things to talk about and a set of detailed things to talk about.

Here’s what the priming doc looks like:

Access the full doc here

The high-level topics are:

• Condition: How are you feeling? Green ✅, yellow ⚠️, orange 🔶, red 🚨?

• Challenges: What was difficult recently?

• Growth: What areas do you want to grow? What type of help do you need?

• Goals: How are you tracking on your goals?

• Reflections: Is there anything you wish went better recently?

• Relationships: How are things with your manager and other people you’re working with?

Below those, you can see a detailed list of activities to do, things to ask, or learn from my mentor. I also give this same list to my mentees so they know how they can leverage me effectively. Feel free to contribute to the doc any ideas you have too!

The Results

Using this process, my mentors have said things like, “I appreciate how prepared you are for the 1:1s” and “This was such a productive meeting.” An added benefit is that I have gained the reputation of being prepared–adding yet another benefit to receiving mentorship.

It’s also resulted in consistent face-time and fewer canceled meetings since there’s an agenda, and the benefit of the meeting is clear.

Finally, the agenda “sets the stage,” making it clear what the goals are. Now, my 1:1s usually start with a brief, “How’s it going,” about 2-3 minutes of catch-up, and then one of us saying, “Let’s jump in.”

So here’s the key lesson: As a mentee, the number one thing you must do is go from a passive growth mindset to an active growth mindset. Take advantage of the mentor you have. Come prepared and learn with intention at every meeting. Do that, and you’ll grow faster, achieve your goals, and your mentor will thank you for not wasting their damn time 😂

Don’t Go Off The Deep End 🤷‍♂️

While I am now a big advocate of planning ahead of time and have seen great results from it personally and with people I mentor, there are some tradeoffs.

Here’s the before and after of how I spent the 1:1 time:

Before, I spent about 80% of the 1:1 time on personal conversations and only 20% on work-related growth discussions. Doing that has led to amazing relationships with my mentors. I still have recurring 1:1s with them to this day because of how much we know and care about each other. They have dropped what they're doing to talk in situations where I really needed to speak with them.  This depth of relationship was based on not just talking about work.  So there is value in leaving space to connect on a more meaningful level outside of work topics. 

So here’s my final recommendation, given these tradeoffs:

1. Use the priming doc to consider what’s most important to talk about before meeting with your mentor

2. Have an agenda, but also leave some space. If you’ve chatted about mostly work in the last few 1:1s, and your topics today aren’t urgent, set aside some time to grow a deeper relationship. 

3. I recommend balance. The rule of thumb I use is 80% work-related topics and 20% personal-related topics. 

With balance you can make sure to make the most of your time, their time, and build a great relationship with your mentor in the process.

Thanks for reading,

Jordan Cutler

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Thanks, Steve, for this collaboration and for allowing me to share my story with your readers 🙏

If you’d like more from me, check out my weekly newsletter, High Growth Engineer, where I share real-world examples, stories, and actionable tips. I also feature guests, like Steve!