What's the Best Way to Find a Mentor?

This article is part 3 of our “Women in the workplace” collection. In February, I had the opportunity to interview professional women from different races, backgrounds, ages, countries,  experiences and industries. 

We spoke candidly about our challenges, frustrations, failures and successes - and how they can help you on your career journey. 

We made the editorial decision to anonymize each woman so that they didn’t have to worry about self-editing. This helped us bring you the rawest response to each question. Each article is focused around a theme: you can read it as a stand alone or as part of the collection. 

No one builds a successful career alone. We construct it on the experience and expertise of the people in our field and the discoveries already made. 

That’s why the importance of having a mentor - someone who’s walked the path you’re on and can help you avoid the traps they fell into - plays a prominent role in career columns, podcasts and business development books. 

What’s tricker to understand - and put into practice - is finding a mentor. Finding someone who can help you grow - without it feeling like a one-sided relationship. 

When I asked professionals this question, I didn’t get the clear-cut answer I was (not so) secretly hoping for. Instead, I got a wide range of perspectives with a little something in there that can work for you. 

Let’s start with one you may not hear often. 

From getting assigned a mentor to paying for one

When K. worked in corporate - for companies like IBM and Walmart - she had different mentors.  Some worked out. Some… well, you’ll find out shortly. 

When she started freelancing - and then went on to start her own business - the nature of finding mentors suddenly changed. 

At IBM they assign you mentors… and I think about this a lot: What’s in it for the other person? And when I think about it for a mentor I’m like “Literally. What’s in it for them?”

So now I’m of the mindset that I should pay everyone that mentors me. I think they should be compensated for their time. And if someone is not being paid for their mentorship they may be willing to get coffee with you once in a while but I really don’t see what’s in it for them except maybe a sense of gratitude but really… What’s in it for them? 

They are doing you a much bigger favor so I don’t know what the heck they get out of it. So I’m going to pay for mentorship from here on out. 

Are assigned mentors a good idea?

Working at a big corporation comes with certain benefits. In theory, you can tap into the experience of the people around you and skip a part of the learning curve. 

At her first job after college, K. experienced the reality. 

When I worked at IBM I was assigned mentors. I was in this Blue Spark Rotational Program and I had a Blue Spark buddie. They have you try a marketing role for like 2 months and a sales role for 2 months etc. And then at the end of the year they place you somewhere. It’s like an insane waste of money. It’s so weird. 

I had a Blue Spark Buddie. And she was really great and she gave me a lot of great advice. I would slack her and stuff. 

And then I had another mentor, like a VP mentor who I met with once for 20 minutes but she was way too busy to have time for me. 

And I honestly felt bad just reaching out to her. But she was interesting just because I talked to her for 20 minutes and I was like “Wow. You are the most professional sounding person I’ve ever met. That just gives me something to aspire to.”

And then my third mentor...was this guy who was my regular. He was two regular notches above me but we weren’t on the same team or anything because it was important to them to have mentors from different places. Actually when I think about it, the way they set the program up is really good. There’s just an underlying flaw in what does that person get? You’re basically asking them for a favor every time you reach out to them. What’s in it for them? I don’t know.

I had to dig deeper into the idea of paying for mentorship because it’s something I struggle with. When K. mentioned it, I got this uncomfortable feeling in my gut… So I had to dig deeper because here’s the thing:

Over the last couple of years, I’ve paid a hefty percentage of my earnings for training and mentorship. And as a result, my business has grown in ways I couldn’t imagine. It helped me skip a couple of years of struggling to figure things out for myself.

And yet, despite that, the concept still feels a bit weird to me. That’s why I had to ask K. how she decided to seek out mentorship and make the decision to pay for mentors in the first place. 

I think getting into the [entrepreneurial] world… It’s a lot more normalised. Also the whole starting your own business thing? People in that entrepreneurial world just understand what I’m talking about. 

Also when you’re in the mindset of running a business you understand that money comes in and out. That it’s like an exchange. The second I started… there’s so many different things to pay for. There’s like 20,000. Which one should I fucking do?

Before I sought out J. - one of my mentors -  I worked with A. It was very specific. I had the courses and the books but I had this understanding that I needed feedback from someone and I had no way to get that. And I needed to pay someone. And I had no manager. 

But in a space with so many options, how do you prioritize? How do you find what you need? 

I used to read books on how to get a mentor because I didn’t understand how it works. So now I’ve actually… for the last few days I’ve compiled a list of people I’m going to approach for critiques. My goal is to work with A. one-on-one for the whole year and then bring in various people for critiques. People who offer it as a service. 

And then I’ve got a shortlist of other people where it’s not a service specifically but I respect what they do and I would like their input. 

K. approached mentorship with incredible discipline. She analyzed her experience, identified key areas for improvement, found the people who could help and made a plan. But she didn’t always see mentorship this way:

That’s one of the things that’s really changed how I view mentorship for me and the advice that I probably give to someone else... Before when I was looking for a mentor… Like I loved Tim Ferris and Seth Godin. And I was like “What if Tim Ferriss or Seth Godin were my mentors?”

But now I’m like, “I wasn’t trying to become them and I don’t know what they can offer me.”

Now I have this very specific thing. I want to level up at one skill in particular and I can find someone who can mentor me in that skill. I think that is the best kind of mentorship there is. These ill-defined relationships where you meet for coffee to talk about your career progress, I don’t really get that.

Unless you are… I guess you are treating your mentor like a college counselor or like a guidance counselor. I’ve never found that kind of relationship very beneficial. I think I need to go internally for what direction my career is going in. I don’t need that told to me externally. 

But if I want to level up at a skill, I want to find people who are great at that skill who can give me advice. So that’s how I see mentorship now.

One mentor does not rule it all

That’s another big thing that I think is important. Having a variety of mentors.

I’ve heard that before- like you’ve got your 5 people or whatever. I think it’s true in a lot of ways. And it’s also like a life philosophy- I don’t think your should rely on one person for everything. I’d rather have like a roster of people giving me critiques… 

I think there’s just so much advice out there even if your mentor is a really smart person and you get on really well, not every piece of advice they give you is going to be right for you. 

It’s just getting… triangulating opinions where you can just sort of filter. I’ve also read some articles. There’s like 5 traits that super successful people have. They work hard, work on acquiring skills, they meet people, those sorts of things.

One thing that I didn’t see coming is that successful people seek feedback constantly. 

And so that was like… I have these other 4. But I hadn’t done this one as much. And I’d seen this in a few different Harvard Review Articles and stuff. And then I was like, I need to seek feedback almost constantly.

Because before I was afraid of seeking it out. What if I get bad advice? But I just think you need to seek advice all the time and then just get really good at filtering what is good and bad. Because I think there’s a lot of bad advice and bad feedback out there and you just get better at understanding it. I think so that’s my perspective.

Finding mentorship when you switch career paths - especially if you are going from a corporate job to running your own business or diving into a brand new career trajectory- can be confusing. And not having that support can lead to an overwhelming feeling of isolation.

Alone in the corporate world

That’s how C. felt when she worked at corporate. She felt alone. Isolated. And - despite being one of the most capable people I’ve ever met - without the inherent power of someone who feels confident in what they do. So I asked C. how she overcame this. How she got out of that tough spot. 

It took 10 years. It was 100% me working it through. It took a lot of pain and isolation, and I would say some rejection. Because I always felt alone. My life generally has just been alone. 

I’m a big person at checking myself. Like “I feel this and I fully feel it but wait… Does that make sense? Is that fair? Why is this other person’s reality different?” And if you take the time to listen, you can realize you’re missing pieces of a bigger picture because you’re so engrossed in your own world. 

So yeah… I don’t really know if there was a cookie cutter process of me finding my way. And I wouldn’t say there was a mentor. 

I actually believe pain is a big gift. So is loneliness. I welcome pain all the time and maybe that’s something that always helps me grow. Because that’s the whole point of even living. Grow, change, experience… So whenever there’s an opportunity for pain, I’m pretty quick to jump on it to see how I can change from it. 

I had to dig deeper. Pain avoidance - often linked to loss aversion and the intensity with which we feel it - is a common cognitive characteristic. Our internal neurological drivers make us try to avoid pain at all costs. 

Yet C. actively sought it out. And she used it to work through the challenges at corporate and start a successful New York marketing agency.

I had to find out if this was something she learned along the way or if it was an integral part of who she is. 

My mom’s a single mom and we’ve always been kind of happily in some kind of pain. We living-room-hopped together until she saved up enough to find us a place. But we were really happy... so maybe it’s how I was raised. 

My mom’s so strong and she never boasts. She’s also very feminine and cute. Society trains us to not see those people as strong but she is the strongest person I ever met. She’s been through so much but she remains soft. It’s amazing. 

It’s bizarre to me when other people don’t like pain. Because clearly it brings you a result of change that’s positive. And it balances out to make sure you see the good. So pain is really good, you know? 

Some kind of middle ground

Unlike K. and C., A. has pretty successful experiences with mentorship in the corporate world. She sees it as a two way street: a relationship that both people benefit from and can draw on. 

So I asked her what advice she had for anyone looking to build a relationship with a mentor. 

I think there’s probably some upfront work of who you think a good person could be. That could be somebody that’s doing a job that you’re interested in. Or maybe they have a life experience that’s similar and you think it may be helpful to bond there or… Those are probably good places to start. 

Or maybe they are just the best possible option. I don’t know. Scoping who you think the best bet would be is probably the best way.

And then I think it’s truly fair to reach out and start the conversation over coffee and maybe have a few questions that you may want to ask. 

If it’s someone you’ve worked with before, maybe you want to start by asking them some brief feedback or ask them questions about themselves (people love to talk about themselves) and let them know that you’re like “Hey. I really admire what you’ve done here and I’m interested to maybe one day be in a role like yours. I would love to pick your brain occasionally as I navigate through certain situations. Is that something you’d be ok with? You know, maybe every couple of months we grab a bite and maybe talk about things.

A.’s approach is the polar opposite of K.’s. Her underlying assumptions about the relationships - and the way they work- is starkly different. 

Yet both approaches work. Both professionals are building meaningful, rewarding, well-paid careers in the spaces they carved out for themselves. 

It turns out, there isn’t a single way to find a mentor. And there’s no consensus on what to do or how to do it. Instead, focus on what you need to learn. Who do you admire? Who can you learn from? Who can you help in return? And just take it from there...