This evening, I was helping a good friend sort out their cover letter and resume and I was talking about the pros and cons of her applying for a more senior role or a more junior role at a pretty well-known tech company in San Francisco. The dilemma for her was that the more senior role would require a lot of intense mentorship for her to scale up to perform where the company would need for her to be. The title had the word “senior” in it, which means that you need to be at a high level of understanding of your role, the industry, and how to execute.
As we talked about needing to get mentorship, she told me point blank,
“Austin, I’ve never had mentorship in any of my jobs to date. Have you? How do you find people to mentor you?”
This stunned me. She has an unreal network in Silicon Valley, and access to a ton of people of influence. I’ve asked her for intros or connections multiple times, and had a chance to speak from her network as well. The fact that she hadn’t found mentorship in her career blew me away.
When I look back on my career, I can definitively say that it has been the #1 factor in my career. Put another way, without the massive investment from my superiors at (nearly) every job I’ve had, I wouldn’t have made it this far.
When I think about the above statement, I realize that my own accomplishments have been so dependent on other people helping me unlock what I can accomplish, so I figure everyone around me has something inside that someone in their company, someone with a bit more experience, has the opportunity to unlock. And I think, if finding mentorship is something people can learn how to do for themselves, we can hand more people the tools to grow their careers, and themselves.
What follows is me exploring what has worked in my life to find mentors at every stage of the way.
My principles for finding mentorship are the following.
Align your growth with the growth of the organization
A big reason I ended up, and stuck around, in startups was the upside potential. There were very few other career paths where I could jump into something on the ground floor and align my ability to grow as quickly as the company needed to grow. That’s an amazing exchange of value. Get yourself inside of a company that has benefits directly from how quickly you grow.
This means that at a lot of the roles I’ve been in, I had a lot of risk. If I didn’t grow quickly enough, the company would outgrow me and I would find myself on the business end of an organization that didn’t have as much use for me. However, it also means that so long as I keep up with how fast the company grows, I represent a solid return-on-investment.
And what do you do when you find an investment that continues to pay off as you pour more into it? You keep pouring more into it.
This probably requires a certain risk tolerance, so take that with a grain of salt. My belief has always been that opportunity to grow and stretch myself was the most important compensation, and I’m willing to take on additional risk because I believe in my own ability to figure out what I need to do in order to grow into a given opportunity.
Which brings me to my next point.
Believe you’re worth the investment
Nobody is going to invest in you if you aren’t eagerly consuming their input, which means you have to believe that someone spending time to coach you and guide your progress is worth their time. The only way you can believe this is if you believe you can take their input and use it to make yourself a bit better every day, so you must believe in your ability and willingness to do the work to grow.
But before you get down about whether or not someone big and powerful can contribute to your life, remember the following. People’s egos are fed every time their input changes someone’s life. People who mentor and coach get a massive ego payoff when they see someone take their advice and achieve amazing results. They feel a swelling of pride because they know without their contribution, you wouldn’t have moved as quickly.
Never forget that mentors get a lot of value out of spending time with you so long as you are taking their input and running with it. Full out.
In situations where I received mentorship from people who weren’t bosses, I made a point of doing free work for them, including ghostwriting a couple of small book for someone. I’ve always made sure my interests were aligned with someone who I believed could help me grow.
Another way to put this is to
Honor their contribution
If you think about the way that a solid mentor impacts your life, they are doing nothing short of transforming it. That’s a contribute you should honor like it’s your own family. They’re raising you up to a more full expression of yourself, of what you can contribute, and of who you are in the world. That’s priceless.
I can count on my hand two different times where I lost sight of how to honor that contribution, and in one instance, I effectively burnt a bridge out of sheer immaturity. That’s a mistake I won’t make again.
Mentorship means someone is pouring themselves into you. That deserves the highest respect.
Now we need to think through who your ideal mentors are.
Identify who you look up to and want to emulate
I went through and thought about the commonalities between the folks that have mentored meg, and I think there is an important thread running through all of them. If you are looking for mentorship, it’s important to find someone who you identify with and aspire to be like.
If you identify with someone, chances are they also identify with you, but as a representation of who they were earlier in their career. Identifying with you provides massive motivation for people to invest in you the way that they would have liked to be invested in. They see the road you are on, and remember what it was like to be at the stage you’re at, and they have an innate sense of what will help you get to the next stage.
Personally, I’m a fairly scrappy, entrepreneurial sort of person who focuses on hustle and learning quickly rather than coming from a very formal training background. I’ve usually worked best and received the best mentorship from similar people.
Everyone that really mentored me was either an entrepreneur themselves, or entrepreneurial in their career. They were comfortable with risk, believed in upside, and knew what it felt like to be an upstart with a lot of hustle and drive just looking for an opportunity to prove to the world (and themselves) that they had what it takes to make it in business. These types of people respond well to hustle and effort and drive, and they know the value of investing in people and processes that pay off in the future.
When I interviewed at my previous startup, my final stage involved beers with the founding exec of the SF office. We got to work closely to build the office out, and he’s still someone I call for advice regularly. He had a ridiculous set of startup successes in his background, so it was a bit surreal for me to be casually drinking with him at his local in Menlo Park.
Somewhere around the second beer, we talked about the position and how ambitious its goals were. It struck me that the company could (and I thought should) hire someone with several years more experience than I had for the role, and I went ahead and said so. I wanted the role, but didn’t want to sign on for a job where I wouldn’t be successful.
He responded that he knew that I was a bit junior, but that he knew I was scrappy and he believed that I had a lot of upside as an employee. Meaning, he believed that if he invested in me that he would see me deliver greater and greater results. Now, the “upside” part probably also means that because I wasn’t proven in the role they were hiring for, there was risk in hiring me. However, he was choosing to focus on the potential upside he saw in me.
These entrepreneurial types never really forget what it was like to hustle and seize opportunities, and they respect folks who are hustling to seize their own opportunities. These folks also have firsthand experience about what good mentorship has meant for their careers, and they usually have a strong belief in paying it forward to the next generation of hustlers.
Entrepreneurial types also don’t put as much value on your pedigree or your polish the same way a larger company will. They believe in results and they identify with the underdog, so an entrepreneur is very likely to let you prove your worth early on, and once you have done that, they will pour more fuel onto your fire because they see your efforts as a way to grow their company so your interests are directly aligned. The more you grow in your career, the more their business can grow.
How do you know who you should look to for mentorship?
Spend some time thinking about where you want your career and your life to go.
When your career begins to plateau, what do you want your life to look like? What do you want to be capable of? What experience will you need to have? What skills will you need to develop? How much money do you want to know how to earn? How well do you need to be able to lead teams of people?
Thats a primer on some questions you need to ask yourself regularly in your job. My strategy has been to identify the next question that I need to focus on, and then I seek someone out who can help me answer it.
Right now, I’m working very specifically on my ability to think strategically and then to break strategy down into tactical elements. This means being able to identify a goal for the organization, for example more users, and then choose a strategy that will work to achieve more users, like content marketing, and then break down what are the tactical things that will need to be in place in order to execute on the strategy, like how to produce quality blog posts at scale, having a solid place to publish those posts, and on.
What is the biggest thing you need to work on to get to the next stage of your career? Once you’ve identified that, I guarantee you’ll be able to identify who can help you learn that skill.
Then you can do the next thing, which is…
Explain exactly what you are hoping to grow into out of your next career move
I recommend being straightforward about the mentorship you’d like to receive. I make a point of telling people what I’m good at, and then also explaining what I’m focused on getting better at. This does two things. First, it sets the expectation of what they know you are good at and then what you suck at. No surprises. Then, it allows them to hire you or work with you only under the implicit agreement that those are your strengths and weaknesses, and that you want their help to work on your weaknesses.
When I’ve received mentorship from folks at companies, I’ve often set the expectation early on that I am hungry for growth and guidance, and I like to say upfront that when I’ve been mentored in the past I have taken that investment and poured it back into the company. I’ve always meant it, and I believe I’ve usually delivered.
It sounds counter-intuitive, but being upfront about our weaknesses is liberating for everyone involved. We are able to feel known. And everyone around us knows what they can expect from us, and what they can help us get better at. That is the true definition of community and relationship. Awareness and honesty about our collective strengths and weaknesses that gives us the ability to take care of one another.
Finding mentorship at the end of the day is realizing that other people have shared similar struggles, and that they wanted the same level of help you want to get to the next stage of their life. And empathizing with your mentor is the first step to developing a strong relationship with them.
Hope this helps.