How to cultivate mentors

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I spent years thinking mentorship had to be bestowed upon me. That if I worked hard enough and got lucky some benevolent titan of industry would grant me the privilege of being their mentee. As you can imagine, I spent many years without any kind of real mentorship.Sure, maybe I had some helpful chats with the head of my department or my boss or someone a bit more senior than me in another department, but I was pretty much going through my career alone. The thing is, you always go further, faster, and to more interesting places if you get help consistently. Learning how to do this will unlock the wisdom and support you're looking for to build an energizing career you love. 

In this episode of the podcast I discuss: 

  • What kind of mentors to cultivate to build a personal Board of Directors
  • How to actually ask them to be your mentor in a non cringe way
  • How to maintain the relationship so it's fruitful for both parties.


Welcome to the career studio podcast, where we boil down the noise and focus on the core concepts, essential for building an energizing career you love. One that is simply an extension of who you are and how you wanna live your life. Anyone can do it. It's just a matter of knowing what to focus on.

Hello. This is the last podcast of the year And it's been a really fun 2023 for me and I get super reflective this time of year and think about, you know, what I set out to do and how I achieved that and what I want to do for the new year. If you are an avid listener of this podcast, you'll know that my word for the year was connection.

And I really think, I've done a great job with that in all areas of my life. So I've, I'm feeling really good about that and I'm mulling on my word for 2024. I have something in mind, but I'm not going to share it quite yet. I will probably do some sort of episode on that in the new year. I hope everyone is gearing up for the final stretch and the pending holidays.

So yes, with that in mind, I wanted to talk about Mentors today, but actually before I dive into that, I just wanted to remind everyone again that I am taking questions to the podcast. So if you have a specific question that you want coaching on, there's something you're struggling with. That you would like me to do an entire episode on, I would love to hear it.

This is an opportunity to basically get free coaching. So you can go to and submit a question. I have a tool there where you can literally record a voice note right in the browser and submit that and I can keep that anonymous. Even if I anonymize it, you can also just submit a question via email. Okay. And that would be

All the instructions for that are on the website So yeah, guys send them in. What I'm talking about today has come from a listener. I don't have audio for this. This was just a text prompt that I received from a former client.

So yes, I really wanted to talk about mentors and cultivating mentors. Personally, I have drawn on a bunch of my own mentoring relationships in the past few months as I have been restructuring my business for growth. And so I thought it would be a really apt one to discuss because it's especially top of mind for me.

I think we all know that mentors are really important. They act like a shortcut to navigating bumps in the road because it's this preexisting relationship that you can call on whenever you need support and guidance. Which will be regularly because we're always reaching hard things. So it's normal to need support. It's normal to ask for support.

And if you already have existing relationships, it just makes navigating hard things or confusing things that much easier. But often when I begin working with people, they really don't have a lot of formal mentors guiding them. Right? There's just no one that they can go to for help and advice in their career where they have that structure in place.

Cause when people come to me, they're lost or confused or bored, they're burned out. So, you know, they're going through something hard. And so in addition to navigating this hard thing, they also have to build relationships. Afresh, which takes time and effort and it just makes navigating whatever you're going through that much harder because there's extra energy that's required to build up and establish a relationship and get the advice that you need.

Okay. So mentors help us make smarter decisions and they help us conserve our energy and they help us just more efficiently navigate our life. So obviously everyone knows that we need mentors, but in my personal experience, I didn't always have the structure that I do now. And obviously in my experience, working with hundreds of clients.

You know, getting mentors, cultivating mentors, having the right people in your life that can feel hard. Okay. And here I wanted to go through what people usually find is hard. So I think there's a belief that mentors have to choose you. I think this was definitely a space I was in early on in my career.

It was like, Oh, you know, I would love a mentor, but you know, that's something where someone really senior bestows upon, you know, a special chosen one, someone who's really bright and really at the top of their cohort and really shining, they get a mentor, right? A mentor looks at them and is like, Oh, I want to mentor you. And so I'm going to set up this relationship and give you my wisdom.

There's kind of like this passive lens to this belief that, you know, you are chosen to be someone's mentor. It's like this, I, I'm not in control of this, which is where a lot of people are in their career and, and in their life in general, right?

Very passive place of, of letting things happen to them or, or waiting for permission. Okay. So this is really normal if, if you've thought this, okay. The next thing I think. Often getting in people's way of cultivating mentors is like, how do I ask, right? It feels awkward to ask someone like, Oh, will you be my mentor?

Or it feels like it's not your place to ask, or there might be fear of being rejected. Someone says, I don't have time or I don't want to, I don't like you. You know, it comes from this place so it's inappropriate for me to ask for time. They won't want to give me their time. So this is a headspace you could be in. Very normal. We're going to talk about it.

And then, and then the last thing I think a lot of people don't even know who to ask, right? Like, who should I ask to be my mentor? How do I even think about selecting the right person? And I think this is especially difficult if you aren't clear on your path professionally.

Right. You can feel lost as to who to even go to for guidance. So that's what we're going to dive into today. Basically how to create the opportunity for mentorship, who to ask, how to ask, and then how to maintain the relationship in an ongoing way. Okay. So let me just explain how I think about mentorship.

So first of all, You do not have to wait for someone to bestow the honor of being your mentor on you. You can and should choose who you want in your life, you know, just like friends, right? You choose who you want to be friends with. You meet lots of people and you, you see who you vibe with and you choose those people and you want to think about mentorship in the same way.

And I'll explain this more in a second, but the point here is that. Okay. And then I think the other important point to mention is that while certainly a long term mentor is valuable and is something that you can cultivate in your life, you don't always have to think of mentorship in that way. And I think that this is what gets a lot of people tripped up thinking that it has to be this long term relationship.

And so that's just a lot of weight to put into a relationship that you haven't even built yet. Okay. Thank you. I mean, like everything I teach, these relationships will evolve over time by testing and learning by starting small and seeing what sticks. Long term mentors emerge through short term experimentation, right?

Testing and learning in a relationship to see, is this person going to be a long term mentor? Essentially, as you go through life, you're meeting people. And with every interaction, you can ask yourself, do I want to see more of this person? Do I like the conversations we have? Do I think the advice that they give me is useful?

Essentially, there's a kind of three stress tests to choosing a mentor, bringing a mentor into your life. The first test is, does this person provide the type of guidance that I find valuable, right? So in your career, in your life, you're going to meet a lot of people. The first question is, does this person give me advice that I like?

Then the second test is, are they available to provide that guidance with some sort of regular cadence? Is this more than a one off? Are they available to kind of be with me in an ongoing way? And we can talk about what ongoing means. That'll vary depending on the person. I'll talk about that in a bit. And then the third test is, does this ongoing guidance continue to be valuable as I evolve, as my career evolves, right?

Constantly stress testing the relationships that are in your life to ask yourself. Are these still relationships that I want? Are these still relationships that I need? This is basically what's at the heart of creating a mentor. And of course what you can see is that you can't cultivate mentors if you are not talking to people, right?

You have to get comfortable asking for help and guidance to begin with for whatever it is you are exploring or trying to figure out in your life. Whatever you don't know. Whatever is hard. That's what you want to talk to people about. Right? So make the list of your questions, your fears, your concerns, figure out who can help you answer these questions and get talking. Right?

And if this is hard for you, or if you don't know where to start, go back and listen to episode three. Called: Your people, because so often the issue in our career is that we're not talking to people. We're just, you know, sitting at home stewing on something or thinking about something without actually getting out there and, and asking our half baked ideas to, to other people.

So you have to get out there and talk to people. And once you do that, you can start to have this lens of, was that valuable? Are they available to me in an ongoing capacity? Do they continue to be available to me? This is how you find people that you want to bring into your life. Right. Because in these conversations, as you're trying to figure out your career or your life, some people you're going to click with some people you won't write to and the people that you click with, these are potential mentors.

And of course, you know, all the people that you just work with normally or have worked with in the past, those are also potential mentors and just people generally in your life, family, friends, potential mentors, right? So. Everyone you interact with essentially can be a mentor and it's up to you to decide if you want them to be one or not.

Okay. So let me get a little bit more tactical and in how I explain this, like how do you actually turn a conversation into a mentor relationship? It's not like you have to be super formal and, you know, write them a little handwritten note saying, will you be my mentor? It's basically as follows.

Step one, as I was saying, talking to people about whatever it is you're struggling with that you think can help you. Right. Thinking about who I know? Who am I tangentially connected to who can help me answer whatever the questions are that I have, right? Even if I don't even know what my questions are, what do you need to figure out before you can figure out your questions?

Right. Talk to people. Okay. And as you have these conversations, ask yourself, did I like this person? Did I find the conversation useful? If the answer is yes. Okay. Now you have yourself a potential mentor candidate. So you're like, okay, I really enjoyed that conversation. I really clicked with that person.

Their advice was super valuable. I think their advice could continue to be super valuable. So step two, after the conversation, because, you know, let's say this is someone that you've never really talked to before. Maybe you went to college with them and you haven't spoken to them in 10 years. Right. And you reconnected with them because I don't know, they were doing something interesting or whatever.

You're in the same city. So follow up. With an email or a text or whatever is appropriate and thank them and say, you know, I really appreciated our conversation. You know, so great to learn about XYZ. And then you say, I would love to stay in touch as I work on, you know, fill in the blank, whatever it is you're working on.

And if they respond positively, then you have yourself basically an active mentor okay. Step three, when you, and actually let me caveat here. You have to see what their appetite is for a conversation, right? You should say, you know, I would love to stay in touch. You know, could I continue to email you? Or do you think we could hop on another call in a couple months if I have another question and just see what they say?

I had a woman once who wanted me to be her mentor. I'd never met her before. She was like, through a former boss I had. And she wanted, you know, some mentoring about coaching. So she called me and we had a chat. Just, you know, I shared some wisdom with her. And then she said, what she was really looking for was, a weekly call with someone who could mentor her because she couldn't afford to hire anyone right now.

And to me, I didn't have the capacity to do that. You know, I didn't have the capacity to have a once a week call with someone that I didn't really know. Right. And so for me, it was like the frequency, but because she was super clear, I was able to say to her, look, I don't have capacity for that. If you want to email me once in a while, I'm happy to provide some insight.

If you want to have another call like later in the year, I'm also happy to do that. So I was able to then give her my availability. Right. I was happy to be available to her, but I needed it to be in a frequency that was different from what she wanted. You have to feel it out here and, and see what's appropriate and gauge their availability.

Okay. So then the next step, step three, when you have another question that's relevant, you reach out and ask them. And then you see how that call goes. Did the advice continue to be valuable? The cadence can also depend a little bit on their seniority to you usually, like, the more senior they are, you might speak with them a little bit less. Compared to if they're around your same level, but again, you have to feel this out a little bit.

And then step four, you just basically continue to do this as long as it's useful. The more you talk to them, the deeper the relationship becomes, right? The stronger the connection. Equally, you might evolve out of a relationship, right?

Your career goes down a different path. Your needs change. They start doing something different that's just not as relevant to you, right? Just something will change that makes the relationship less useful, and then that person will rotate out of your, you know, mentorship community. Okay. So this is basically it, right?

It's just having conversations with people, seeing whose advice is useful. Ask them if they'd be up for meeting more often, or if you could reach out to them again for a question, see how they respond. And based on their response, you then have a structure, right? Maybe it's exactly the structure you want. Maybe it's less than what you want.

Maybe they say they're not available, but then at least, you know. Right. So that's how you create a mentor. You got to talk to people, you have to see what's useful, and then you have to maintain the relationship. Okay. So, you know, when I'm working with my clients through the course of the program, they talk to a lot of people.

Okay. So they're really expanding their network and they're filling it with potential new mentors. And at the end of our work together, I like to have them reflect and nominate what I call your own personal board of directors. And I think people really like the name of this. It's kind of a cool concept to think of your own who's on your board, but we should all have our own board.

How I think about this is a board of directors should be. A set of people who can provide diverse guidance. Okay. Your board is going to evolve as you evolve. You might change careers and you'll need to revise, as I mentioned before, the mentors in your life. So your board will evolve with you, right? If your career changes, you're probably going to slightly shift who's on your board.

But I have a whole structure for thinking about who is on your board, those kinds of archetypes. And I'm actually going to share it now on the podcast. I'm going to just give all of this away because I think it's a really nice tool. So these are the seats. These are the archetypes I like people to think about. You can have more than one person for each of these archetypes of course. You might not have anyone in the seat at the moment. What I've done here is just try and think of diverse sets of advice and leadership and ways of looking at things so that you can have really well rounded support around you.

The first seat I call the gray hair, and this is probably the classic mentor seat that all of us think about. And this is a person at the top of their field who's more senior than you. Someone who can offer you a bird's eye perspective on your options who has hard one pearls of wisdom to share with you .They likely have a big network to draw on. They can introduce you to people if you need me this has changed throughout my career when I was in advertising.

I had a different person then who I have now. I actually have a couple people in this gray hair seat and of course they don't have to actually have gray hair. But yeah, you know, they are more senior to you and kind of at the top of their field. Okay. And if you don't know your path, this can just be someone more senior than you, who has that perspective, that wisdom, right? Someone who's maybe navigated bumps in the road in their career or has navigated career change, just someone who you respect, who kind of has that wisdom and experience. that I like this seat to have, okay, so you can consider who that person or people are for you.

The next seat, these aren't in any particular order. The next seat I call the: you plus two. So you always want to be in touch with someone who's just a bit ahead of you or on a similar path or related path. Okay. Cause they're going to be able to offer you very specific, very tactical advice because they've just gone through similar challenges to you.

It doesn't have to actually be two years. Maybe it's three years, maybe it's four years, but someone who's just a little bit ahead of you and the seat can change often, you know, because your path will shift. For each stage of my business I've kind of had a different person. That's a, you plus two for me, right?

In advertising, it was the people who had, who were just like the next rung on the ladder to me. You know, when I was first training to become a coach it was this woman who had a relationship coaching business and she was selling packages. I mean, now our businesses are totally different and I, we, I don't really speak to her that much anymore, but at the time she just had more of a structure around her business.

And so I used to talk to her about that. And then kind of when I realized how I wanted to structure my business, I was part of this big coaching program. People who were in the program, but who were a bit further ahead than me in the development of their business. Now I've hired a coach to help me restructure my business for growth.

And I actually consider her kind of my you plus two. She's probably a little, she's more than two years ahead of me, but she's kind of at that next phase. Of her business that I'm looking to be in, right? So for me, this has evolved, for you it will evolve, but it's just that person that's a little bit ahead of you.

Okay. The next seat is kind of a fun one. I call it the maverick, and this should be filled with someone who has designed whatever you consider to be an unconventional career, something that is just different than what you've done, okay, someone who can really offer like a different perspective to thinking about your career, who might challenge what you believe is possible, who might push you to explore things outside your comfort zone or look at things in different ways.

You know, I have a bunch of different people. I have a friend who he's had a very varied career. He worked in consulting and venture and now he partly runs a nightclub and he's just an interesting guy. And I like to talk to him about the career decisions he's made. Like really, I have a friend, she's like a career consultant. She is, you know, a senior partner at McKinsey, very, very different career to me, but that kind of wisdom is still valuable to me because she's thinking about her career in a slightly different way. It's a much more structured, maybe traditional career. And me being a coach and an entrepreneur, you know, it's very different from me.

So you could also consider someone like that a bit of a maverick. I also have a friend who has launched a very cutting edge business in crypto. It's like a market data crypto business. She just really sees 10, 20 years into the future. She has a lens that I don't have thinking about business, thinking about the world. So I really value her opinion as well.

So, you know, it's, to me, these are just people that think differently than me. They have different careers than me. It's just good to have those types of people in my life. So I'm not in my own little bubble of coaching. So yeah, so think about who that person is for you. I think what I mean by maverick is just that it's very different from you.

Okay. The next seat I like to consider, I call it the cheerleader. Because everyone needs a cheerleader in their life, right? It's those moments when you need encouragement to keep going or to pick yourself up after a failure.

You know, you want someone who really believes in you, who has your back. One of my best friends is a coach and he's always telling me what he sees as possible for me. He's always telling me how amazing I am and how great I am and I need that, right? I need someone who really believes in me because sometimes I, you know, I get down on myself or I get bored of myself and just to have someone remind you of what you're capable of and who really sees you and champions you is a really nice energy to have.

And sometimes you just need that person to bring in that energy. So, I really think the cheerleader seat is an important one. The next seat I like to think of is the personal life icon. That is what I call it. I could maybe think of a better name. That's what I, that's what I've called it for now. But, you know, I think you're, you are not your career, right? Your career is just a part of you.

And I think it's really important for us to remember that this is not the be all and end all. It's really important to create a rich life, you know, and your career is one part of that. So I think having someone in your life who you think balances their professional life and their personal life in a nice way is important. If you're a parent and you're working, maybe someone who does that balance really well could be an interesting person to put here. Just someone you admire for how they've made time for their personal priorities or integrated their family life into their professional life.

You know, someone who's great at setting and communicating boundaries. I have a former client who has structured her life between Long Island and Costa Rica. And yeah, it's very impressive to see. And it reminds me that there's many ways of structuring your life. And for me, that's really inspiring. I don't even speak to her that often, but I think about her a lot when I think about how I want to structure my life and how I want to think about my career and what I want to be available for.

So yeah, think about someone who is thinking holistically, who has that balance that you're looking for, whatever that might be. And last but not least, there's the seat I call the peer coach. So the peer coach is someone that's about your level and you guys would discuss day to day challenges and use each other as accountability partners.

There's a great stat that people who regularly use peer coaching are 65 percent more likely to feel fulfilled at work and 67 percent more likely to report being a top performer. Okay. So peer coaching is a really great structure to have in your life. And note, if you have a peer coach, you're going to be their peer coach too, right? It's a two way street.

You know, I have a handful of coaches who have similar businesses that I talk to every month. When I was in advertising, these people were the peers in my cohort. Okay. So just finding someone that you can relate to is going through the same stuff as you is a really good person to have in your life.

So these are the types of mentors that you can think about, and it's totally in your control to cultivate them and to bring them into your life. So let's just talk a little bit about maintenance and then that's the episode. So the frequency that you talk to these people, as I mentioned before, it kind of depends on the seniority. It depends on their availability, right?

With a peer coach, I'm going to want to be talking to those people regularly. You know, with the gray hair, probably less regularly, but again, you know, this isn't a hard and fast rule. I definitely have peer coaches that I only talk to occasionally and sometimes really senior people I might have a bunch of back and forth with about a topic over a couple weeks and then I don't maybe talk to them for a couple months. Okay.

So again, it just depends on the person's availability to support you and the structure that you guys end up creating together. And I think the last point I want to talk about is around maintenance. And I suppose giving back. Because you know, mentors can enjoy helping you because it just feels good.

Like it feels good to help other people to share your hard won pearls of wisdom. This is scientifically proven, you know, people who you vibe with will want to help you because they enjoy the relationship. And at the same time, you want to make sure that you're supporting your mentor as well. So there's many ways to do this. So that you are kind of maintaining the relationship and it doesn't always feel like a one way street.

You can and should follow them online and when they post something, support them. LinkedIn is a really great channel for this. And if they're on that channel, this is the perfect way to support them by liking their content, by commenting on their content, by sharing, you know, sometimes people in my life will be recruiting. I might share that job with my own network.

You can send interesting people their way or send them business opportunities. You know, I used to work at a company called fast forward. It's a training and coaching company. And the two women that run that, I definitely consider to be in my like gray hair bucket. And, you know, I really respect them and, and. Value their advice. And so I try to send them business when it's relevant, right? When I hear someone is looking for training for their team, I send them to fast forward, right? So in this way, I'm supporting their business as a thank you for them supporting me on occasion.

Right. Maybe there's content that you think they would find interesting, an article that you read, et cetera, send it their way or podcast. Right. So if you're thinking about them, you can send them content, you can send them people, you can support them online. And then this helps it feel more like a two way street.

And then the last piece of advice I'd have here is yes, of course, you know, when you have a question or want support, you can reach out to them. But even when you don't have a need, just updating the people in your life or checking in with your mentors is a really good way to maintain the relationship.

So maybe you get a promotion or you change jobs or something important happens in your life. Just send them an email to say, Hey, like I wanted to let you know, this is what I'm doing. How are you, what's going on with you? Or maybe you're in the same city as them. You know, that's a really good way to maintain the relationship.

So I hope this has been really clear about mentors. I hope this has debunked, demystified getting a mentor. Really, it comes down to having conversations like everything. So much of what I talk about, you have to talk to people. If you're not talking to people, you can't create mentors. So talking to people and seeing who you vibe with, seeing who's advice really resonates with you and then turning that into a relationship. And also understanding that sometimes those relationships will be fleeting. You know, I've had people who were kind of mentors for a couple months and that's it. And then sometimes they'll evolve into longer term relationships.

So, you know, also demystifying this idea that mentors need to be this really senior person who you work with throughout your career. You know, that's just a lot of pressure on a relationship. And I think it often stops people from cultivating relationships at the end of the day. That's what mentorship is. It's just a relationship.

And hopefully I have given you the tools to begin to cultivate your own. Think about who you want on your board. Think about who you can nominate immediately. Reach out to them, connect with them, support them, and you will have more people in your life to support you, which will make everything easier.

Okay, guys, have a great end of the year. Take care. 

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