How to Be a Career-Changing Mentor — 25 Tips From The Best Mentors We Know

How to Be a Career-Changing Mentor — 25 Tips From The Best Mentors We Know

In the fall of 2016, the First Round team launched our first mentorship pairing effort as a small experiment, with just a few dozen mentors and mentees pulled from across our community. Fast forward more than three years later to last week, when over 400 pairs wrapped up their last sessions together.

After seven cohorts, 981 pairings, close to 2,000 participants (and plenty of hard work from our very own Whitnie Narcisse and Serena Bian) this mentorship initiative we now call Fast Track has become one of the most impactful things we do here at First Round. Here’s a quick rundown of how it works: It’s a 90-day program that matches seasoned advisors and operators — from both within and outside of our community — with the early-stage founders we’ve backed and the rising stars on their teams. The pairs then meet up for in-person, structured bi-weekly sessions.

Although we’ve massively expanded and iterated on the program over the years, our North Star has remained constant: We want to bottle those most powerful “aha” mentorship moments that can change the course of careers, and deliver them to as many company builders as we can.

As we’ve walked that path, we’ve learned plenty about what makes mentorship work — and what causes it to go sideways. We’ve previously shared some of the lessons right here on the Review, covering common concerns for mentors and mentees, such as how to find the perfect match, set the relationship on the right footing and make sure it’s valuable for everyone involved. Yet as the program has grown, mentors have clued us into another area worth sharing more advice on. The question we’re asked most frequently these days is simple and earnest:

How can I be a better mentor?

For us, this inquiry speaks to an eagerness to give back and a desire to make a real impact. Every mentor has experience and wisdom in spades — but it’s not always immediately clear how to most effectively share it. How do you know when to share your own perspective and when to listen? How do you plant the seed of trust, then tend that relationship over time?



1. Save the troubleshooting for later.

If he were to give one piece of advice to mentors taking on similar work, it would be to invest additional legwork in relationship building from the jump. “Don’t dive right into advising and solving problems,” he says. “Mentors are there to provide a safe and neutral space for expression, ideation and vulnerability around challenges — but you’ll only get to the real stuff if you have trust. Establish it first.”

Dana Mauriello is a Small Business Strategy Consultant at Sidewalk Labs (who previously led teams at Etsy), and she also highlighted the need for a more expansive view of mentorship. “My number one takeaway from being a Fast Track mentor is that great mentorship is not about tactical problem solving — it’s about supporting the person holistically,” she says.

2. Loosen your grip on what it takes to make mentorship “work.”

“Once you mentor multiple people, you’ll realize that some partnerships just naturally work because you already have a common approach, while others require more effort on the part of the mentor. But in my experience, mentors need to let go of their ideas of what success looks like,” says Matt Wallaert, the Chief Behavioral Officer at Clover Health. In other words, a “successful” mentor-mentee relationship will look different depending on each pair.

“I’ve had one mentee relationship where I felt like things weren’t really ‘working’ because I hardly talked to them, but they ended up raving about the experience. From their perspective, the mere fact that I was around ‘just in case’ was enough to give them a confident safety net to proceed. My takeaway is that all mentor-mentee relationships can be made to work if the mentor is willing to be flexible.”

3. Figure out what kind of mentor you are and tailor your advice accordingly.

As the former president and COO at UserTesting and CEO and co-founder of a new startup, ‘nuffsaid, Chris Hicken has experience on both sides of the mentorship table. That’s what’s led him to believe that mentors need to get more granular on what type of mentorship they’re serving up.

“I think people need two different categories of mentors: One that’s three to five years ahead of you who’s doing the job that you want to have next and a mentor who’s much older and has already achieved the level of success you’re after,” says Hicken.

Here’s why: “Mentors who are only three to five years ahead can sink into the nitty-gritty tactics and help you tackle the problems currently on your plate. Mentors who are much further ahead in their careers are going to be terrible on tactics. But they can help you peer around corners that you don’t even see coming. They’ll bring a high-level focus to problems that will keep you tethered to your long-term goals. They can also talk to you in a way that others won’t be able to — they can tell you that you’re being an idiot and get you to listen.”

These different modes mean that mentors need to get realistic about the kind of advice they’re aiming to provide. “Don’t try to be that grizzled veteran if that’s not the gap you’re filling for your mentee. You don’t want to serve up career platitudes if they’re looking for targeted go-to-market tactics. Think about what bucket of advice you can provide and then structure your conversations accordingly,” he says. “At this stage in my life, I’m generally the one who’s three to five years ahead of my mentee, so I’m helping them think through tactical issues. Every meeting, they have to bring one problem that we’re going to solve together. If I was filling that role of a much more experienced mentor, I’d probably opt for more loosely structured, meandering conversations.”

4. Be sure to listen for the subtext.

Several mentors emphasized the power of listening to your mentee, spiking out the simple truth as an important lesson that’s crucial to reiterate. But Beth Robertson added a slight twist.

“Mentorship is all about meeting a mentee where they’re at. You have to listen to the challenge that they’re overtly telling you about, all while hearing what they’re actually saying,” Stripe’s Startup Partnerships and Growth Lead says. “Listening for the actual root of my mentee’s challenge, confirming if what I’m hearing is true and then helping them unpack ways to work toward a productive solution via open ended questions has been key for me.”

5. Remember that most of mentorship is getting your mentee to focus on the right problems.

As VP of Growth Marketing, Micah Moreau is charged with driving retention and acquisition across DoorDash’s three-sided marketplace of consumers, “Dashers” and merchants. A role like this one requires intense focus and sharp problem-solving skills, traits that come in handy as a mentor.

“I try to spend 90% of the discussion focusing on the problem — how to define it, how to quantify it, and how to ensure that it is the most important and impactful problem my mentee and I can tackle together,” he says. “In my experience, nine times out of 10 the issue isn’t about finding the optimal solution, but rather ensuring people are focused on the right problem in the first place.”

Sidewalk Lab’s Dana Mauriello also recommends double clicking to make sure that the challenge your mentee brings you is truly a priority. “Why does your mentee feel that this issue is an important challenge to prioritize? What’s the personal impact of this challenge? Asking questions like these in my sessions with my mentee helped us come to the realization that the challenge we were discussing didn’t actually need to be prioritized that highly after all,” she says.

6. Hand down your hard-won context.

As a mentor, Salesforce VP of Sales Dare Olonoh tries to frame his feedback in three categories:

Broad information he’s experienced or observed in his career: “This gives context, so they can gain an understanding of industry norms they haven’t had exposure to yet,” says Olonoh. “It’s easy to forget how confusing and scary certain situations can be the first time you encounter them in your career. I try to normalize those things for my mentees. Take the example of external hires filling new roles. I’ve had conversations with several mentees whose natural reaction was to start worrying — or have a mini freakout. The reality is that those things happen all the time in a fast-growing company and aren’t personal attacks.”

Personal stories: “I share when I’ve faced similar situations, how I felt emotionally in those moments and how I made decisions,” he says. “It’s important to be as human as possible, which is why personal stories can be impactful. Some of the challenges we face are purely intellectual but most of them are also very emotional. Personal stories are a great way to connect emotionally and help someone feel a little braver.”

Frameworks: “There are different approaches I’ve used to make decisions and communicate my asks in a way that strengthened my relationships with leadership, rather than weakened them,” he says. “One framework I use on a regular basis is the Navy saying of ‘ship, shipmate, self.’ It’s a great mindset for making asks. For example, when asking for a promotion, it helps to talk about what the promotion would mean for the company and your team, rather than focusing on just your needs. That could look something like, ‘I’m excited about where we’re going and would love an opportunity to have a larger impact going forward. I want to keep contributing, and would like to be considered for a promotion to take on this role to help us achieve those goals.”

7. Skip the instructions — tell stories and share resources instead.

Colin Zima is also a fan of telling stories. And given that he joined Looker back in 2014 (and led data efforts at HotelTonight prior to that), he’s got plenty of yarn to draw on. (Read a few of those stories about how Looker got built here).

“Rather than targeted coaching or giving instructions, I try to surface a similar situation and explain what I did right or got wrong,” he says. “I also try to unpack what I learned about what my boss or colleagues were thinking, or what I picked up from observing how my CEO handled a problem a certain way.”

Zima also thinks mentors should delve into their own startup toolkits to lend a practical helping hand to their mentees. “I share all kinds of documentation, whether it’s job descriptions, product specs, or career ladders. To get even more tactical, talk to how those docs and processes evolved gradually over time and might not match the current stage the other person is at,” he says.

8. Hand out fishing rods, not fish.

Tomas Barreto has previously shared his biohacks for a better career, right here on the Review. This is the mentorship hack the former VP of Eng at Box and Checkr (and current co-founder of Okay) has come to rely on: “As a mentor, I usually try to avoid recommending a solution to a problem, because discussions between mentors and mentees naturally involve information asymmetry and a lack of full context,” he says.

Here are the alternative approaches mentors can explore instead:

Share anecdotes that are similar to your mentee’s experiences, since these are more likely to be remembered and re-applied.

Recommend broad principles that apply to the situation that can be reused in future situations.

Share trade-offs of the different possible solutions to build up the mentee’s toolkit.

What he calls his own personal 50/50 rule: “I spend half of the time in mentorship questions gathering context by asking questions to alleviate the asymmetric information imbalance, and then I also make sure my mentee is speaking for 50% of the time to create psychological safety and maximize adoption of advice,” Barreto says.

9. Give the gift of confidence and validation.

When we asked Jan Chong for her best bit of mentoring advice, she offered up this thoughtful insight: “In my experience, people usually have hunches about what they should be doing to resolve a challenge, but they lack confidence since it’s a new situation. You’ll hear a hesitancy in their voice around what to do next,” says the former Senior Engineering Director at Twitter.

“As a mentor, I always try to reflect back to my mentees what I’m hearing them say. Sometimes just hearing someone who has seen similar challenges rephrase things can provide that clarity and confidence that can take a half-baked idea to a more fully formed plan. Or perhaps you’ll shine a light on a truth that they’ve been avoiding, but deep down already know they need to face,” Chong says.

In other words, mentees often already know the answer already and are seeking out validation, says Andrea Chesleigh, the VP of Product at Boxed (and former product leader at One Kings Lane and Rent the Runway). “I often find that folks already know how they want to handle a situation instinctively and just need me to validate their approach, act as a sounding board and help polish the strategy,” says Chesleigh. “I might also provide a framework to help organize their thinking, but ultimately, being a good mentor is about giving them the tools and confidence in their methodology.”

Beth Steinberg.

Beth Steinberg, talent leader and founder of Mensch Ventures
Beth Steinberg adopts a similar approach. “I usually find people are more on the right track than not. As a mentor, I find my best value is to ask the right questions to reinforce what they already know yet help them reframe the challenge slightly if necessary,” says the founder of Mensch Ventures, a people and talent advisory firm.

10. Help your mentee practice checking for blindspots and surveying stakeholders.

To Vivian Cromwell, framing and perspective are key. After spending more than a decade in engineering at Google, she started her own editorial and travel photography business. She’s also a bit of a Fast Track success story: Her mentee, Labelbox co-founder Dan Rasmuson, valued her insight so much that he brought her on as an advisor to the startup.

For Cromwell, the secret is challenging her mentees to see their situations through multiple lenses. “I ask a lot of questions, especially around how it made my mentee feel and how it made others feel in the office. I want to make sure my mentees have done their homework and gained a comprehensive view of the entire team,” she says. “I sometimes create scenarios for my mentee to practice difficult verbal communications, in which I play the role of the mentee, while they take on the role of one of their team members or peers. Exercises like these can help your mentee develop and practice the habit of seeing things through others’ perspectives.”


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