#MenteeGoals Prepping for a mentoring relationship

Resources and advice for a successful partnership

Nick Caldwell
Jan 13, 2019 · 5 min read

There are so many benefits to having a mentoring program within your company. In my past roles at Reddit and Microsoft, employee mentoring programs helped me rise through the ranks, pick up soft skills, and give back to the next generation of leaders. Nowadays I’m at Looker and we’re in the midst of spinning-up our first mentoring program. Exciting stuff! I thought I’d jot down a few tips for future mentees at Looker and beyond. Without further ado…

Don’t wait for a “mentoring program.”

Yes, it’s great if your company has one but they aren’t common at startups and smaller companies. Mentoring programs take effort to establish and run, so if your company doesn’t have a formal one don’t sit around and wait for the launch.

Instead, take charge! It’s important to realize as early on in your career that managers or the company are not primarily responsible for your career, you are! Fortunately, there are many avenues for getting mentoring nowadays. Of course, start with looking for internal opportunities by reaching out to peers or managers you respect within your organization.

But in our ever-connected world, you shouldn’t be afraid to look outside the walls of your company for support. Recently, the most impactful mentoring program to me has been participating in a /dev/color squad. Squad members hold each other accountable for achieving clearly stated career goals, while also offering group mentorship and networking opportunities. Plato is another organization to check out, it’s teeming with experienced leaders looking to offer their insights in a one-on-one or presentation style format. Spend an afternoon searching and you’ll find that mentoring comes in all shapes and sizes.

Most of these 3rd party programs have participation fees. Don’t be shy about asking your manager to cover the cost. Even if your company doesn’t have a formal mentoring program it almost certainly has an underutilized employee development budget. If not, consider going out of pocket. Trust me that there is no better return-on-investment than investing in yourself. Also, non-reimbursed educational expenses are tax deductible which help take away some of the sting from your wallet.

(Note: One program I would recommend against is LinkedIn Career Advice. While the idea sounds good on paper, in my experience the response rate and follow-through are much lower than using offline connections to find a mentor.)

Have a plan.

Nothing is more awkward than having a mentee with no set agenda or goals in mind. Without structure, there’s a risk that mentoring sessions become more like social time or therapy. Mentoring isn’t therapy. Mentors will feel frustrated if your direction changes every month because you are trying to “find yourself.” They’ll feel most engaged when they are helping move your career forward in a tangible way.

The absolute best tactic to avoid this problem is to use the first session to establish the parameters of the relationship. How will your mentorship start/progress/finish. I highly recommend setting a time limit for the relationship at or around three months. That’s just long enough to set and achieve a few near term goals. Agree on the goals: could be a promotion, learning a new skill, building your network, etc. Come prepared for each session with a list of questions and discussion topics. Leave each session with a list of action items to follow-up on. Treat your final meeting like retrospective. What worked, what didn’t? Should the relationship formally continue? Are there other mentors you could be referred to?

If you’d like a starting point, First Round Capital has a very simple template for structuring mentoring sessions which provides surprising value. Check it out here.

It’s not just about you.

Mentoring isn’t a 1-way street, it’s a super-highway. For the mentee, this means synthesizing advice from multiple sources: mentors, books, training, etc. For mentors this means understanding that a mentee won’t always listen.

Also since mentoring isn’t a 1-way street, you should find ways to help out your mentor by:

  • Providing information and insights about the industry, company, or your organization. As a mentor it’s always interesting to learn the full context of the problems a mentee is dealing with.

Elevate to sponsorship.

Although this post is about mentoring, in my opinion sponsoring beats mentorship every time. A lot of people don’t know the difference between a mentor and a sponsor. A mentor is someone you go to for advice and free coffee. A sponsor is someone, usually higher up in the organization, who gives you opportunities. All of my biggest career moments came from sponsorship opportunities. These were people who wanted to give me the chance to do something bigger and in return I did my best to make them look smart for taking the bet!

Mid-way through your mentorship you might consider switching things up. About half of my sponsorships came from simply repurposing the standard mentorship coffee meeting. But instead of asking for career advice, I talked about my work history, explained my aspirations, and then asked, “What would you do if you had an extra pair of hands?” You’ll be amazed at the opportunities that arise when you ask that question to the right person.


When you’ve made it, remember to give back. Leaders make new leaders, so set aside the time to become a mentor yourself!

rock on

P.S. If you enjoyed this read, please clap, like, or reshare. I appreciate the support and more folks get read the article too!

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store