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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.

Whitnie Low Narcisse

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.”

There are a lot of areas where knowing someone personally will help them navigate things better. If a mentee is struggling with relationships with executives, hiring decisions, gaps in their skill set, motivating their team — having a more developed sense of who they are as a person will help elicit the best advice for handling it. Personality, introversion, extroversion, how they manage time, and what they enjoy doing will all make a difference. With this information, a mentor can better inhabit their mentee’s shoes.

This also sets a more conversational cadence for all future interactions. “Plant the seed of trust right away with a more personal conversation,” says one of the mentors we interviewed. “It encourages both people to share their challenges — historical and current. It makes everyone human, emphasizes what is shared in common and is more bi-directional. It also breaks down what might be an intimidating power dynamic, and makes you feel more comfortable as peers.”

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.

“You should never be sitting there thinking, ‘Gosh, what should we talk about?’” The exercise of planning makes sure time is used wisely. When communicating this to mentors, consider framing your questions as: “Here’s what I’ve been wrestling with since we last met, can you please think about how you’ve approached this kind of thing in the past?” That way, mentors have time to scan their history and pull out the most instructive examples and tactics.

“You can always depart from whatever agenda has been set if something more relevant or pressing pops up, but the fact that it was created gets everyone thinking and aware of what the big issues are,” says a mentor. “Generally speaking, mentees who put a lot in are able to get a lot out.

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.

“Try not to veer into big, conceptual thinking or conversation,” says Narcisse. “If you take on something huge like how to manage, it’s easy for your time to run out without actually tackling the practical stuff that’s coming up the next week or month. Try to keep things really tied to the decisions that need to get made, or the solutions that need to be found.”

One preventative measure to try: If a meeting agenda is too jam-packed, or if things start with the mentee listing too many concerns, call a timeout and rewrite that agenda. Mentor and mentee should take five minutes to co-create a more realistic and focused punch list. Don’t try to do too much, be ruthless in paring topics down.

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. For example, one sales mentor saw that her mentee had trouble closing deals. The mentor had been in this position before, and knew that it was actually because she was reaching out to the wrong type of customer. But it’s not always negative — mentors can also help illuminate everything you’re doing right and help you visualize opportunities you would have never seen for yourself.

“A lot of people don’t have anyone at their job acknowledging the small, interim successes,” says Narcisse. “Having a mentor to do that is like hanging diplomas or awards on your wall. You’re able to reference them when you need to muster the confidence to do something new.”

Mentors who are good at sharing their wisdom from experience, rather than just being didactic about what to do next, can help their mentees validate whether their assumptions or actions are correct. They can help leapfrog obstacles that won’t matter down the road. They can tell you how the story is likely to end to save you time going down roads yourself.

One of the best meeting progressions Narcisse has seen is:

It’s also recommended for mentors to ask questions like, “Why is that important?” instead of straight up saying something is or isn’t. Or “How do you feel in meetings like that?” This gives mentees the prompt they need to develop their own insights.

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.

“I had a mentee ask about how I would operate internal board meetings, which led to us talking about specific ways to gain buy in from stakeholders — which he needed to do across the board,” says one finance mentor. “Another asked about modeling revenue, which led to us talking about how to work with benchmarks in a number of situations."

Sometimes mentees ask about X but they really want Y — a new way to think about their work. This is an area where mentors can provide pretty unique value.

Consider looking across agendas for your meetings, and any notes you take. What situations continue to emerge? Can they be batched into themes? Is there a type of problem that's giving a mentee more trouble than others? Is it possible to take on all at once? For example, one mentee was having trouble making staffing decisions. Every week, he’d be concerned about filling a different role. His mentor was able to share a framework for easing these types of decisions across functional areas.

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). Mentors have to be able to say, “Yeah I went through that and I failed spectacularly for these reasons,” says Narcisse. “Mentees need to be okay bringing as much actual data with them as possible — candidate pipelines, deal flows, metrics they’re trying to hit, roadmaps. This is what will make mentors effective at tackling real situations. Great trust and respect need to be established immediately.”

When a mentee is tight-lipped, it can be frustrating for a mentor to read between the lines and give advice based on incomplete information. To alleviate this, mentors should aim to be very transparent themselves upfront, sharing something that highlights their vulnerability or that they are willing to share something fairly sensitive. “You have to be willing to lean in on some personal disclosure,” says one mentor. “Right away share something that went really wrong or that you still regret.”

Remember, nothing engenders trust faster than giving someone your undivided attention. Both mentors and mentees want to feel 100% listened to, like their counterpart is present, and that their time is being wisely spent and valued. Set a loud timer on your phone so you don’t need to have it on the table, and time won’t be a distraction. Remain engaged and committed to bringing your full intellectual horsepower to each meeting, and the trust will follow.

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. Instead, you want to gauge progress by checking in regularly on what a mentee has accomplished between meetings. “The goal is really just making sure that your mentee is executing,” says one mentor. “I calibrate how seriously a mentee is taking things by what they say they delivered between meeting 1 and 2.

At the end of each meeting, mentors should say explicitly: “Okay, you should try to get to ‘X point’ by the time we talk next” — be clear about what that point is and what getting to that milestone means exactly. You don’t want any fudge factor. Then at the beginning of the next meeting, immediately check in: “Where did you net out on reaching X goal we set out two weeks ago?” If not much progress was made, spend time diagnosing why. For mentorship to make a difference, a mentee needs to commit to executing what they say they will.

To set up what can reasonably be done by the next meeting, Narcisse recommends that mentees choose their most pressing challenge and say: “I’m going to tackle this problem. Here’s what I’m thinking I’ll do and why. How does that sound to you?” That way, mentors can help enforce realistic scope. She warns against mentees directly asking mentors what they would do. Replication doesn’t reinforce learning.

Mentees creating agendas should build in time at the start of each meeting to review what was done and how it worked out. For example, maybe they said they’d apply two tactics. What was the outcome? This is where mentors shine — unpacking why things went the way they did.

NINE: Make sure mentors are learning too

Keeping both parties energized about the relationship depends on mutual learning. It’s important for mentors to be proactive about asking questions when they see the opportunity to learn from their mentees — and about connecting the dots after their sessions to see what they might glean that’s relevant to their own work. Mentees can do their part by asking mentors what they want to learn or know more about to see what they can contribute. Here are just a few of the things First Round’s mentors said they learned during their sessions:

Lastly, at the end of a mentoring engagement — or when you reach a milestone like three months — have a check-in where the mentee shares how much of their mentor’s advice they took, how it was applied, where it’s helped and where it hasn’t. It’s a mini post-mortem that yields insight that will help both people get more out of mentorship going forward.

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. You want to socialize important questions, collect responses, and then triage.

You might call this your Personal Board of Directors, and consider treating these relationships the way a company might interact with its board. Narcisse built a personal board of directors for herself over the last several years, and it’s become a major source of insight and strength in her career.

The handy thing is that you can ask your primary mentor for introductions to others in their network who might be able to illuminate different topics, angles or solutions for you. For example, one mentee had three areas she wanted to tackle with her mentor, and one was management. Instead of trying to offer advice himself (as a relatively new manager), he introduced her to a woman who was a tier of leadership above him to provide greater perspective. As a mentor, don’t hesitate to open doors for your most prepared and promising mentees. They’ll always remember you for it, and it’ll reduce their dependency on your point of view.

“Everyone has blind spots, not just those who are less experienced,” says one mentor. “I always ask my mentees to have a couple other mentors who specialize in areas where they need to succeed but where I’m weak. I also have a list of 4-5 folks who I always recommend. It’s also a good idea to ask several mentors the same question to hone in on the right answer or you.”

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.

Across 100 pairs of mentors and mentees, we’ve seen the full range of outcomes. The advice presented above is designed to help both sides make a positive impact on one another. So whether you’re currently applying for First Round’s next mentorship round, or looking to start a similar program or relationship in your own life, keep these commandments and frameworks in mind.

“Making mentorship work for you isn’t easy — even though most of us believe it should happen organically when we’re in the right place at the right time,” says Narcisse. “The truth is, we have to create these opportunities for ourselves. And once we do, we have to treasure these relationships as something rare and precious. I can think of few better professional resolutions as we all head into 2018.”

Photography by Bonnie Rae Mills.

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