We Studied 100 Mentor-Mentee Matches — Here’s What Makes Mentorship Work

We Studied 100 Mentor-Mentee Matches — Here’s What Makes Mentorship Work

Whitnie Narcisse runs First Round's Mentorship Program and has learned exactly what it takes to make mentor-mentee relationships truly transformative.

When First Round launched its Mentorship Program in 2016, we didn’t know what to expect. We’d heard from a number of people in our community that mentorship remained an elusive, missing piece in their careers. Younger people said it was intimidating and difficult to find a mentor. Their older counterparts said they weren’t sure if their advice truly mattered. But everyone said they believed in mentorship’s transformative power. So we set out to fix it.

The task went to Whitnie Low Narcisse, who leads all of First Round’s advisory programs and more. After putting out a call for both mentees (at First Round companies) and mentors selected from tech’s most talented operators, she was overwhelmed by the response on both sides (eventually accepting exactly 50/50 female and male mentees). Then it was up to her to diagnose why mentorship usually goes sideways and design something different:

The feedback was effusively positive, with high demand for another round. Since then, she’s run two more, each one larger and more popular than the last — totaling 100 matches across all three (with a fourth launching this month). Observing this, and hoping to get even better, we wanted to understand what distinguished the most successful mentor-mentee pairs from the pack. What did they have in common? Many people said the experience had changed their careers. What was that secret sauce? We all wondered.

So, Narcisse asked the best mentors. A lot of them. And we’ve distilled the key lessons they shared for you here. Whether you’re creating a mentorship program for your company, looking for a mentor to help you think through challenges, or hoping to make a bigger impact as a mentor yourself, this article is for you. Mentorship can be an incredible career accelerator — here’s how to actually make it work.

How to Find the Right Match

Obviously, out in the world people don’t have the benefit of being assigned a mentor. You have to do the heavy lifting of finding and asking someone yourself. Usually, this means choosing from among a number of more experienced professionals in your life — a former boss, leaders at your current company, someone who has the job you hope to have someday, someone who has provided support, advice or championed you in past roles. All of these people could be good, but they also might not be. Not because they’re untalented or unhelpful — but because they’re not the best match. Asking someone to mentor you is nerve-racking enough. You want to make sure you’re asking the right person.

On the mentor’s side of the equation, if you’ve achieved success and mastery in an area, you’re probably getting inundated with requests for coffee conversations and regular advice. The more mentees you take on, the less help you can be. They key is to choose just a few people who you can invest in and provide a lot of value to.

To nail the delicate chemistry required, eight questions have proven to be particularly telling, says Narcisse — four that mentors should ask, and four that mentees should ask:

For mentors:

For mentees:

“The ideal experience gap is 5-10 years. That far out, the mentor is experienced but can still remember what it felt like to be in their mentee’s shoes."

Depending on which side of the equation you find yourself, ask the relevant set of questions. This can help to pare down the list of people you’d consider working with. Once you hone in on a few who might fit the bill, consider sending them a version of the other list of questions (i.e. if you’re a mentee, send them the list of mentor questions).

They don’t have to tell you their answers. Frame it as some thoughts to consider before entering into a more regular arrangement. It will make you appear and feel prepared — and set strong expectations. It might also disqualify suboptimal candidates who won’t make the investment you’re looking for. If questions are answered positively on both sides, it’s very likely you’ll have a productive match.

Set the Right Ground Rules

As mentioned above, the First Round Mentorship Program sets some firm parameters — and for good reason. We know this might be difficult in less formal settings, but there are some rules that we do think you should apply to create more effective connections. These are geared toward mentees:

Kick off relationships around distinct problems or challenges: One of the best ways to get a lot of value out of a mentor is to present something specific for them to help you solve. It might be seeing your startup through a successful launch, releasing a feature, building out a design team, or managing an underperformer. Note: this does not mean you’re asking them to solve it for you or give you the answer. Rather, you’d love to get to know them and hear their experience on your path to finding a solution or reaching this milestone.

What’s that one thing in your path that you want to overcome or achieve to get to a different level in your career? That’s a perfect place to start with a mentor.

You can be detailed in the help you need, and your mentor will know they provided concrete and measurable help. This is far better than asking someone for general or ongoing career advice.

Build in offramps. This goes hand in hand with the rule above. People are much more likely to work with you if they don’t see it as a perpetual commitment. A lot of mentees go in believing that they’ll ask someone to be their mentor, and then that person will ride shotgun with them throughout their career. While this can and does happen occasionally, it’s not always realistic, and your needs are bound to change.

Consider setting a soft deadline on an initial engagement from the beginning: i.e. “Our new feature launches at the end of Q2, I’d love to meet with you every couple of weeks until then.” That way, there’s a natural exit after value has been provided. If you have great chemistry and want to continue chatting after that, that’s awesome. But don’t make it the expectation. You’ll get more enthusiasm upfront and maximize your chance of finding the right lifelong mentors.

Create a schedule — but keep it loose. Choosing a challenge or problem to base your mentorship around sets you up well to ask for a series of meetings. In order for this type of relationship to truly change the way you work, you need some regularity and predictability. In most cases, people talk with their mentors whenever something comes up or they get stuck. In this situation, mentors generally provide an off-the-cuff analysis and advice that may or may not be their best thinking. Regular meetings empower duos to come prepared and make smarter, incremental progress — while getting to know each other better.

The key, however, is to not impose a rigid or unrealistic cadence. Everyone is busy, particularly very accomplished people. Things come up, fires break out. If you're too dead set on a schedule, one cancellation can throw the whole thing off track. Instead, set a loose guideline — like every other week for a quarter, or twice a month for six months — not “every other Sunday” or “every first Tuesday at 6 p.m.” This will sound more reasonable on both sides, and minor rescheduling here and there won’t derail you.

Measure progress every meeting. In the agenda you set (and send ahead) for each meeting, set aside 5-10 minutes at the beginning to talk about what’s happened in the interim. What progress has been made toward the concrete goal you’ve defined? If you had to quantify it, what would you say? Maybe you’re 30% there? 80%?

Having this type of rough metric to share is helpful for both mentors and mentees. It provides momentum and aids in goal setting. For example, you can discuss what would take you from 25% to 40% by the time of your next conversation. This keeps the work and conversation moving forward.

Carve out time to exchange goals. Likewise, at the end of every meeting, you want to designate 5-10 minutes for both people to summarize their immediate goals. The mentee should use this time to review what was discussed during the conversation and distill it into action items — selecting those that can be accomplished by the next meeting.

Perhaps more importantly, the mentee should also use this time to inquire about their mentor’s goals. What’s going on with them at work? What are their short-term objectives? What needs to happen for them to accomplish these tasks? Is there anywhere that you as the mentee can jump in and help? Perhaps you can make a referral or introduction. Maybe you can be a sounding board or second pair of eyes. Just because you have less experience doesn’t mean you can’t give back starting now. This will make any mentor more inclined to work with you in the future, and is a key part of providing positive energy. At the very least, understanding what they’re working on will give you visibility into the job or career you might want to pursue.

The 10 Commandments of Mentorship

Yes, we know that title is cheesy, but there are 10, and they truly should be heeded in order to make mentoring matter. Some are more for mentors, some are more for mentees — but both should keep them all in mind. These battle-tested lessons were fielded by Narcisse from active, successful mentors in our program, including folks like Airbnb Head of Design Alex Schleifer, Eventbrite VP of Communications Terra Carmichael, and Slack ’s first product manager, Kenneth Berger.

ONE: Don't use the word 'mentor'

A little ironic for an article all about mentorship, but nearly all of the mentors we spoke to identified use of the word as the number one reason they were dissuaded or disinclined to talk to someone. It carries some negative connotations with it: it’s a time suck, it implies a very close relationship with someone you may barely know, it sounds like a long-term commitment. Direct asks like, “Will you mentor me?” are a universal turn off.

This type of mentee approach is much preferred: “Hey, I’m trying to get through XYZ specific situation or challenge, and I’ve heard from several people, [NAME WARM, RESPECTED MUTUAL CONNECTIONS HERE], that you might be able to provide some insight or direction in this area. Might you have time to meet for coffee?” Don’t ask for an hour in an initial message like this — instead say 30 minutes. If the conversation is good, it’ll last longer, but throwing out the shorter slot demonstrates emotional intelligence and that you won’t waste their time. Always buy them the coffee.

You’re going to get someone to take you more seriously if you can be really granular about what you want to accomplish — it makes them feel like they have exceptional expertise and are being proactively sought out, says Narcisse. Steer clear of broad requests like, “I’m looking for direction in my career…” but don’t get too surgical either, i.e. “I want introductions to these five people…”

To this point, if you’re a mentee sending an ask, you want to be very clear and explicit about why you targeted this person. Do enough homework to briefly explain why you’re looking for guidance relevant to their experience. That way, you don’t have to use the word ‘mentor.’ Instead, you're inviting them to apply their considerable knowledge on something they’ll find intellectually engaging and impactful. That’s how people want to feel — not that they’re taking on an additional obligation.

TWO: Don't treat it like a transaction

If a mentee isn’t careful, this relationship can start to feel pretty one-sided. You sit down with your mentor every so often, buy them coffee or a beer, and then download their wisdom. If you treat it this way, you’re missing out on the gold you could be getting. The best way to prevent this is to use your first meeting to deepen your personal connection. Don’t start with business. Take the time to understand each other’s career paths, goals, hopes, fears, and lifestyle. All of this will factor into how the work itself can be approached optimally, and will highlight issues that might need to be worked through.

“Ask what the person’s life is like outside of work. What’s their family like? How do they spend their time when they’re not working? Where do they live?” says Narcisse. “Where does work intersect with life? Where does it cause worry or stress or inspire enthusiasm? That’s a better entry point into talking about work, and it leaves both people feeling more bought into further conversations.”

THREE: Show up prepared with questions

Every mentor we spoke to said they love mentees to send what they want to discuss in advance in the form of a shared Google Doc (which allows mentors to comment and ask their own questions on what’s been outlined), a slide deck (which forces simplicity), or a checklist.

They highly encourage mentees to treat meetings the way they would 1:1s with their boss, where they set the agenda and own the content of the meeting. Mentors can then read through the day before and come armed with their own questions, more prepared thoughts, and a sense for how they want to contribute.

A good rule of thumb is for mentees to come with one topic they definitely want to address, and a short list of questions (3-5) that will get them the clarity they need on that topic.

FOUR: Don't boil the ocean in every meeting

One of the hazards of mentorship meetings is that there can be far too much to discuss. Very few startup professionals only have one major challenge or problem on their plate. It can be tempting to unpack everything that’s going on lately. This will only limit how deep your conversation can go on the issues that matter most. Be really intentional about picking the 2-3 questions you really want to solve in the space of an hour.

FIVE: Ask your mentor to check your blind spots

Experience gives mentors a different vantage point to see a lot of what you, as a mentee, may not. Ideally, they have been in your shoes earlier in their career. They’ve seen how things play out and can recognize patterns more readily.

SIX: Look for themes and organizing principles

Some of the greatest value a mentor can provide is identifying themes in what their mentee shares and providing broader, organizing principles from their experience that can solve many problems at once.

SEVEN: Be honest and transparent

This is critically important on both sides. If either person feels like they can’t share key information, the relationship won’t work. Everyone has to be comfortable being vulnerable, admitting that they don’t know (especially on the mentor side).

EIGHT: Don't give homework — focus on execution

None of the mentors we interviewed gave homework to their mentees. While it could create accountability, they acknowledge that everyone’s too busy for extra work, and mentees might start dreading going to meetings.

NINE: Make sure mentors are learning too

Keeping both parties energized about the relationship depends on mutual learning.

TEN: Always have multiple mentors

It’s important to have a number of perspectives to bring to bear on the biggest challenges you face. You might not have full-on mentorship engagements going with a handful of people, but it’s good, as a mentee, to have two to three other seasoned operators in your life to consult.

In Summary

We hope this gives you a guide to make mentorship an exceptional tool in your career. Finding the right match and nurturing the connection can lead in any number of directions — to new jobs, new disciplines, and to lifelong friendship. But it requires diligence, preparation and continually asking yourself the questions that will keep you on track with forward momentum.