How to find a mentor and build a rewarding relationship

Having a career-building framework is more critical and has more facets than you might realize

I have come to believe there is one really powerful career-advancing mechanism that isn’t explored nearly enough – and that is finding quality mentorship. Judging from your many questions, you’re thirsty for content in this area, so I’ve decided to do a deep dive. This newsletter is a companion to my Skip podcast episode on mentorship.

Whether you’re seeking a mentor or want to be one yourself, figuring out how to identify the right people and then build and handle that relationship – to gain the very most out of it – can be complicated. People tend to have a rudimentary vision of what mentorship is, but today it comes in all shapes and sizes and is more accessible than ever. What's lacking is a modern framework to take full advantage of the many mentorship resources out there. Overall, I believe that if you’re putting thought into mentorship, it signals you are serious about moving your career forward, which is exciting!

To cover this topic, I’ve created a set of hypothetical scenarios, each with a question and my detailed response. The content is sorted into two overarching categories. The first is how to navigate mentorship resources, including those you can pay for, the free ones, and the many available communities and content. The second category is how to be coached and determine if you’re being coached well. This includes a mix of tips and tricks for deciphering what to lean into and what to avoid as you go add these critical career resources.

So here goes.

NAVIGATING MENTORSHIP RESOURCES

#1: Isn’t my manager and my company enough to guide my career?

“My manager is really experienced, and we have a great relationship. And I am fortunate to work at a company with a learning & development program. But every year I feel like I’m not doing enough to advance my career.”

There was once this assumption that an employee’s success and a company’s success were symbiotically aligned. This may have been mildly true a couple of decades ago – when tenures were longer, technology wasn’t speeding everything along, and remote work didn’t exist. But that’s not the case anymore. Tech roles are far more diverse, roles last only a few years, and changing environments are additive (and even required) to have an elite career.

Meanwhile, a company’s primary objective was, and is, to drive value for its customers, which in turn drives its growth. Perhaps your growth, supplemented by internal development programs, may help a company achieve its goals, but it won’t always. So if the needs of a company, or even a manager, deviate from yours, guess whose needs they’ll favor. A company is betting on itself. And you need to bet on yourself.

This “bet” involves seeking out a broad range of skills beyond just the role you’re in. This means not outsourcing your career to a performance ladder, including a manager and their feedback. Yes, hear the feedback, but tying your success and failure to a specific manager’s specific goals will hem you in. Instead, advocate for yourself and do some exploring outside that bubble.

Naturally, you might ask, “How do I get started in finding the right resources for me, if they aren’t provided by the company?” Let’s address this in the next set of questions.

#2: How can I network to find mentors?

“I am not in a position to spend money on paid resources. I’m trying to hustle and reach out to people, but my LinkedIn requests go unanswered. My friends aren’t that experienced, and the few leaders I do know aren’t that interested in helping. What can I do?”

Mentorships generally fall into two categories, each driven by an incentive. There are coaches who are trained and paid (the incentive) to guide you; they provide structure and keep you accountable. If you want or need firm direction, this option is the way to go. Advisors, meanwhile, are typically untrained and free; they have some pre-existing connection with you, which is what incents them to help.

As an example, I don’t take payment for helping folks. But I do help people I know or people who come through a trusted referral. It’s almost needless to say, but an email sent to a complete stranger will likely go unanswered. Instead, stick with people who have a reason to invest in you and cheer for you. So who are these people? I’ve drawn up this list based on my experience:

• Former managers: Every manager will one day become a former manager – this is why, if you’ve made a solid connection, it’s important to keep in touch even after you’ve gone your own ways. These people know your work and will likely stay in your industry, and they will remain a bit more senior. What’s nice is that a former manager has some detachment from wherever or however you are currently working so they can speak more freely with you.

• Dotted-line managers: These folks know your company but have some distance from your project. They might work in another team or even a different function. As a manager, this person is thinking at that slightly higher level of development, which can be really helpful. Find a few of these folks and touch base periodically to learn their perspective on your work and seek advice on how to progress.

• Peers: Look sideways. Look at the people who might share your motivations and your challenges and start having a conversation with one or two. Comparing tips, struggles, and wins can be incredibly powerful in advancing your own growth and development. 

• Friends who happen to be professionals: Don’t forget the personal relationships you have outside the workplace. These folks know you well and have reason to care. No matter their level, you might find that opening up about your challenges with your friends helps you learn and gives you perspective. Mentors often grow very organically from a friendship.

This is a long list and will take planning and time. In fact, managing your career is much like managing a business. And in many businesses, investing in a board of directors will help steer the company, right? So I wouldn’t limit yourself to a single mentor. Piece together a diverse circle of folks, like a board of directors, who can provide advice through what’s undoubtedly going to be a long career with lots of twists and turns. Having this circle will make you prepared for when something does pop up, and its diversity can generate contradictory advice and even tough love.

If you spend just 30 minutes each week over the course of a year in one of these conversations, that’s 50 conversations. In 10 years, that’s 500, across dozens to hundreds of people. This drives professional luck – those serendipitous opportunities – as well as a lot of connection-making, and will build a (sounding) board. What’s golden is that you can help them as well. So start investing now and focus on the long-term opportunity that your existing relationships will enable.

#3: What happens if no one will coach me?

“What do I do if I just can’t find folks to invest with me?” 

As I noted earlier, hopefully most of you are surrounded with potential mentors – you just need to build deeper connections with these colleagues. It’s easy to assume they won’t be interested, but take a chance and reach out. What do you have to lose? But in case you are just starting out, or you just don’t have the ability to connect with many folks, in the past, you were a bit stuck. But of late, the content on social media has exploded. And much of it is good and better yet, free. More and more professionals want to give back, and their vehicle is through professional content – myself included with The Skip. Seek out the content on LinkedIn, Twitter (X), YouTube, TikTok, and podcasts. Most importantly, budget 30 to 60 minutes every week for going through it to pull out those nuggets that could be valuable to you. 

Great content will give you a lot to think about. Ideally you want to combine this with a community of other people who you can chat or meet up with and trade ideas and questions. I built one about three years ago called the Skip CPO group, and we are launching another for high-potential PMs called Skip Stars. Both are small, experimental and invite-only today. But they are safe spaces in which people can authentically connect, drive tremendous learning, and offer comfort as everyone navigates their careers. Though these professional communities may be hard to find, belonging to one can be a great substitute to a personal network. And if you can’t find one, start one! Just as we saw the quality of content increase over the past few years, I hope to see the same for quality communities.

Whether it’s seeking out a professional, poring over content online to extract those nuggets, or becoming part of a community, the bottom line is: Don’t give up.

#4: Which resources should I pay for?

“As a leader, I know what got me here isn’t what gets me there. I also know I need more than my manager and the company. Do I need to approach this more as an art than a science? I am willing to spend money for guidance. How should I think about the available resources?” 

Every person and every level of role has different needs when it comes to career guidance. Senior leaders are in a particularly tough stage. They don’t get a lot of feedback, their development areas are subtle, and advancing is less about collecting knowledge and more about growing soft skills. It’s not what you’re doing, but how you’re doing it. But unpacking the emotional challenges wrapped inside the “how” requires a lot of emotional intelligence, and folks without training might have a harder time providing guidance for senior leaders.

For example, a paid resource will have the training to guide you through a reset after serious burnout, perceived discrimination, or a cultural mismatch within a company. This isn’t trial-and-error kind of help. It’s expertise. This is why, for senior leaders, I think it’s prudent to have a paid professional in your life.

There are typically two paid paths for seeking guidance: executive coaching or therapy. Both can be instrumental in your career. A strong executive coach is professionally trained and works with a broad range of people who are at your level. And might be experts at the dilemmas that exist at your stage of company. While you are encountering a problem for the first time, they might have seen it multiple times and tried out several solutions. Hearing what’s worked for them and applying their lessons to your situation can instantly accelerate your career. Secondly, a good coach can provide structure, keeping you accountable for progress and framing the right questions to make good use of the time and money you are spending.

Sometimes executive coaches are available from your company. As such, they may have access to your manager and peers, and can arrange confidential 360-degree feedback. The insight might be jarring, but it’s potentially eye-opening. And even if your coach isn’t supplied from the company, several employers subsidize the cost of coaches to invest in their employees, especially their leaders, so it’s worth exploring. 

On the flip side, a therapist won’t know the ins and outs of your function or even the industry. But their training allows them to make progress on the deepest of development areas, which are often wrapped up in a person’s identity and values. A therapist can also work through heart-versus-head dilemmas, and the collisions between your personal and professional lives. I have worked with both executive coaches and therapists, and have found their advice far better than any other resource in my development. And for therapists, your health care plan might cover some of these costs. No matter the type of professional, if you have the means, add at least one paid professional to your board of directors for when you need to mentally rewire yourself to get over a hump or to push through a tough time.

GETTING THE MOST FROM YOUR MENTORS

#5: Can everyone be coached?

Everyone can benefit from advice, but not everyone starts with the skills to maximize coaching. That doesn’t mean you can’t learn the skills. Here I lay out a handful of guidelines to ensure you are getting the most out of your mentors. 

One overarching focus should be your efficiency in communication. If you are paying for the resources, you want to spend your money wisely. If you are borrowing time from busy professionals, you’ll only be able to continue your relationship if you are making progress in each discussion. To this end, you should: organize your thoughts ahead of time (maybe even send a concise agenda note before your conversation); pick a specific area of focus (not “Help me with my soft skills,” but “How do I become a better listener, here’s what I have tried”); provide the right amount of context; and be productive during the first meetup to make a second conversation feel worthwhile to the mentor. 

Once the connection is established, have courage to actively listen and adjust based on the feedback. It isn’t easy to openly talk about your shortcomings or mull the hard questions that could admit a flaw. But it’s important. And realize that any mentor has limited context so they might not get everything exactly right. But even if they are partially accurate, it’s worth pondering. For example, maybe they perceive your dislike for a co-worker as impeding your progress. Though, in reality, it’s not your opinion about this person, but your conflicting styles that are holding you back. The words are wrong, but the sentiment is spot on. 

Much of being coached is about gathering signals from a mentor, even if they are in conflict. For instance, if I am giving guidance, I don’t expect you to do exactly what I recommend. Hopefully, you have my voice, as well as those of your larger circle, in your mind when you’re weighing options. Just like you would with a product you’re developing, you should get as much “signal” as you can, process it and see patterns, and make the best decision possible, all in a very thoughtful way. 

Finally, manage the relationships with mentors carefully to ensure that they are long term in nature. I like it when, after each meeting, people summarize the advice right away to make certain that it has been captured accurately. Then, a few months later, when I see an update on progress, I often chime in – and this context helps me stay engaged when a person needs help again. 

#6: How do I get better at being coached?

In my opinion, the biggest cheat code is to get better at being coached is to mentor others. So if you find yourself in mid-to-late career seeking advice, see if you can spend time giving back to the world. The skills to understand a situation, process it, and provide feedback will help you be concise, listen and be heard, and build a relationship. Whoever you mentor will not only appreciate your insight, but you’ll also pick up the rhythm of these types of conversations. You’ll be able to tee up those patterns when it comes to your own situation. In fact, it might even be more career additive to give to the world than finding the perfect mentor yourself.

#7: How do I know the advice I’m getting is good?

This may be my favorite question because a lot of advice I hear and read doesn’t apply to everyone (or in rare cases, is just biased and ineffective). So it brings out a curmudgeonly side of me. Coaching is a skill. It’s one thing to want to be kind and invest in others. That’s great! It’s another thing to really know how to help people move forward in their careers. I think too many companies have created mentorship programs without a lot of thought, and I think many people who have the time and interest think they can just slide into career advising.

So I have several key tips when gathering advice:

Be cautious of taking advice from failed (or even highly successful) operators: This may sound harsh, but too many people want to be a coach because they didn’t quite make it as a professional, or think advising will be easier than the day-to-day grind. If your coach hasn’t had a successful career, just go slow and ensure the advice really works for you. Don’t follow blindly. And even if they were successful, recognize that coaching is a different skill than playing. Just because someone has been a professional athlete, that doesn’t make them a great coach across every sport and every position. They were on the team – but it’s a totally different skill to know how to break down the many specific elements of the game and apply it to your game.

Beware of extremists and contrarians: These are the “Quit your job!” and “Money doesn’t matter!” group. They are perhaps toward the end of their career and toying with what they might’ve done differently (“You’re young – take the risk!”). In some ways, I respect this. A sharply counter opinion can blend well into the mix of your board of directors. Yet, if this person didn’t take the risks they’re posing to you, then isn’t that suspect? What is their motivation in giving you this extreme advice? If all the prodding equates to just pushing you out of your comfort zone – without direction – it is more antagonistic than helpful. 

Beware of advice that’s just copying from others: Everyone has a unique career path. If a mentor or coach is assuming that what worked for their friend or cousin, or even themselves, will also work for you, there’s reason to be concerned. An advisor or a coach should personalize their advice, not only follow patterns.

Ensure the coach is listening: I’ve saved the biggest piece of advice for last. Whoever you decide to work with must know how to listen and really want to understand you. I’ll get calls from folks who ask for just 15 minutes – they don’t want to take up a lot of my time, which is thoughtful. But I know that 15 minutes is nowhere near long enough to really dig into this person’s concerns. You don’t want cookie-cutter advice. Any good coach will want details and context to understand your journey and what is going to be best for you. Instead of seeking a quick drive-by from an expert, you’d be better off reading advice on social media even if its not personalized.

#8: Who is in Nikhyl’s career board of directors?

This is a question I commonly get, and I feel fortunate to have a pretty rich set of resources that I can call upon when I have career questions. And sometimes it’s not even a question. It’s just reflection or a matter of touching base. As I mentioned, it’s beneficial to have a diverse board so that you’re not getting only one perspective. 

I’m lucky to include a manager at my current company on my “board,” and the company itself has structured performance reviews. I see this more as job advice than as career advice. I have stayed in touch with three to five executives I’ve worked with in the past and who have superpowers other than my own. I talk with them maybe once or twice a year to swap updates. But I know that they’d be available if I did have a specific need.

Then there are peers. These are people I’ve met and connected with over time, starting at school and extending to colleagues from past companies. I speak with these dozen or so folks a few times a year to hear about some of their big decisions and share what I’m working through. I also have about a dozen friends who are not necessarily at the same level in their career, and we keep each other updated monthly. This is very therapeutic. Speaking of which, I talk with a top-flight therapist monthly to develop language and clarity around whatever I might be going through. Then there are the hundreds of people I coach. How often I see them really depends on their needs – sometimes it’s a few times in a given month, if they going through an important decision, but often it’s just once or twice a year. One side benefit I get from all of these conversations is that they keep me primed on the market, trends, and any unusual challenges out there.

#9: Is Nikhyl available to coach me?

Sadly, I only coach folks I know well or who come through trusted referrals. I’ve also never been paid for my coaching, and I prefer to focus on my craft and help as many people get ahead. One of my main goals is to advance the next generation of leaders who can give back and scale their advice. I think that’s one of the hardest parts – scaling yourself. This is the reason I started The Skip – to write and share as much wisdom as possible.

Wrapping up

In the end, there is no magic bullet to finding a pool of mentors waiting for action. It comes down to organizing your needs and building a board of directors. This requires structure, your time and effort, and considering what money you can (or cannot) spend. Think of this as your mentorship to-do list:

• Ensure you are investing 30 minutes on content and 30 minutes on connection each week.

• For each need, be specific about what you are looking for.

• Connect with people who want you to succeed, starting today and investing in the future.

• Ensure you are being heard and carefully weighing any advice that you receive.

• Help others more than you seek help (which is where community comes in)

• If you have the budget, ensure that you have a trained professional to meet with about work-related challenges.