Be More Podcast: Cultivating Mentor Relationships with Stephanie Bertmer

Stephanie Bertmer, global leadership development lead at Twitter, discusses how to discover the right mentor for you, and how to develop an effective relationship with your mentor or mentee.


Be More is a weekly one-on-one podcast about how everyone can thrive in the new world of work, hosted by Workday’s Patrick Cournoyer. This week we’re joined by Stephanie Bertmer, Global Leadership Development Lead at Twitter, who discusses how to discover the right mentor for you, and how to develop an effective relationship with your mentor or mentee.

Mentorship is both an art and science. But how do you choose the right mentor? For Stephanie Bertmer, there is no right answer to this question. For her, most mentoring relationships develop both subtly and naturally—it’s not a matter of making a sudden and direct choice.

Steph Bertmer leads global leadership development at Twitter and has held multiple senior leadership roles throughout her career. If you want to learn more about Steph and how to develop an effective mentoring relationship, check out our key takeaways, or read the transcript below.

“In the mentor-mentee relationship, if you are a mentor, your response is important when people are being who they are, sharing their challenges to offer your best guidance or support.”

Stephanie Bertmer

Key Takeaways

  • Steph’s background and career overview. Steph is a first generation college graduate. Over the years she has worked in several different customer service roles, such as Virgin America, where she became a flight attendant. She spent almost ten years at Virgin America progressing through their learning and development department.

    Eventually, Steph decided to move into the tech industry where she worked for Hulu and Snap. Now, she works at Twitter, where she is focused on the growth and development of their senior-level leaders.

  • “I wasn’t looking for a mentor. It happened naturally” Steph admits that she was never actively searching for a mentor, and that they sometimes came from where she least expected. On the other side of that mentor/mentee relationship, she mentors people who are ambitious, quick to learn, and are perseverant.

  • Developing a mentor relationship. As discussed earlier, Steph says that her mentor relationships developed naturally. A colleague of hers missed formal training in the specialty they were in, which led Steph to suggest some professional programs to her. This subtly evolved into a mentor relationship. Steph’s advice to anyone looking to find a mentor is that you need to find a person with whom you can develop a personal connection with, and be your total self.


Steph Bertmer: I think in the mentor-mentee relationship if you are a mentor, your response is incredibly important to when people are being really who they are sharing what their challenges are and that full picture so that you can share your best guidance or support.

Patrick Cournoyer: Welcome to Be More, a podcast by Peakon. This is where everyone at an organization can hear different and meaningful perspectives on how we can all thrive in this ever-changing and constantly evolving world of work. I’m your host, Patrick Cournoyer.


Patrick: This is the last episode of this season of Be More, where we have been speaking to leaders around the world about their personal stories of mentorship. The mentorship process is very special to me. I have made every significant decision in my career with guidance from a mentor. I’ve also learned an incredible amount about myself through mentoring, which is a bit of the story today. Steph Bertmer is joining the conversation to help us wrap up the season.

Steph leads global leadership development at Twitter and has held multiple senior leadership roles throughout her career. Today is a bit of a personal conversation as Steph and I worked together for almost 10 years, and have mentored each other in many unexpected ways. Today’s conversation may be a bit different, a bit personal, and hopefully a bit interesting for you. Steph, thank you so much for joining the conversation today.

Steph: Thanks for having me, Patrick.

Patrick: I have been looking forward to this conversation for a couple of weeks, I have to say, because this one is extra special for me because, Steph, you and I know each other.

Steph: We have known each other for quite some time now. [laughs]

Patrick: We do. We are not only friends, but we were colleagues for many years. We’ll get into that. First, Steph, let’s introduce you a bit to the audience and tell us a bit about who you are, and your journey so far?

Steph: Sounds good. I am a first-gen college graduate. I spent a lot of my time in the customer service industry paying my way through college. One of those customer service roles was for an airline. At the time, it was a startup airline called Virgin America where I worked on the front line, eventually becoming a flight attendant. I have many stories to share there if you’d like to hear some of those. It was there where that was actually a pivotal moment in my career. I actually remember sitting through a training session. It was flight attendant training. I was sitting as a trainee, and I was watching the instructors and I thought to myself, I’m like, “I would love to do that. That seems like a really fun, interesting job.”

Like I said, I was a flight attendant for a short while, and then the opportunity came up for a special assignment. It was an email saying, “Hey, there’s a short assignment where you can come into the corporate headquarters. We do some training facilitation.” I applied and got the role, and really that was a big transition for me into more of the corporate world into learning and development. I spent almost 10 years at Virgin America in a variety of different roles in learning and development and really grew my passion for people and for culture and for growth and development. Like I said, I spent almost about 10 years there.

At the time, Virgin America was in Burlingame, which is in Silicon Valley or close to Silicon Valley. Surrounding Silicon Valley was the Googles, the Facebooks, all of tech. I’d always had an interest. I’m like, “I wonder what tech is like?” Because I’d been in aviation for so long. Finally, I decided to make the move to tech. Over the past several years now, I’ve been in the tech industry at companies like Hulu, and Snap, and most recently at Twitter, but my passion grew for all things people. Moving beyond just development to more things like what are the systems behind that? How does this all come together to create an incredible employee experience?

I had always thought about my career in a very linear way. It was to be a manager, and then be a director, and then be a VP. For me, the North star was VP of people and culture. Early 2020 comes, I get that opportunity, become a VP of people and culture at an ad-tech startup in Los Angeles. It wasn’t three weeks into my role that we went into complete lockdown, COVID really hit. 2020 for me in that role was definitely an adventure. It was navigating getting all of our employees to a fully remote workforce. It was navigating COVID, and really just supporting all of our employees.

It was a difficult year for me. I really took some time at the end of the year to reflect back, and I’m like, “Wow, I am really burning the candle at both ends here.” I’m sure a lot of people in human resources are probably still feeling that well into 2021. I think for me I had to get incredibly introspective. The North star was this title and this fantastic role. I felt like I got there, but I was paying the price for it both from family commitments to my own health. I decided to take a step back and really get deep to understand where my strengths are. What do I love doing? Where does my energy come from?

What I love most about my role was working with our senior leaders or senior executives, working to coach them on their development, working closely with their teams. That led me to Twitter. Now at Twitter, I am in a very focused role where I’m focused on the growth and development for our senior-level leaders and a really focused population, so our women’s leadership programs, programs for underrepresented talent. I couldn’t have crafted a more perfect role. It’s all the things I love into one role in a very focused way. That’s a little bit about my career journey. It felt like it went up. Had to take time and now I’m exactly where I want to be.

Patrick: I love that story and that journey. Did you actively search for a mentor? Did it just happen? On the flip side in your mentor relationships where you’re the mentor, did people seek you out or did it just happen?

Steph: Is that where we get to tell everyone that you’re my mentor? Is it?


Steph: This is the moment. I think for our relationship, it felt like it happened naturally. I wasn’t looking for a mentor. I knew for me, I was drawn to your leadership style. It almost felt like you were a few miles down a path that I haven’t been through, and had little nuggets of what the path ahead could look like. For me, that I found a huge benefit in. It wasn’t or haven’t really actively searched for a mentor. It’s interesting though, but I remember after leaving Virgin, I had expected, these are my own assumptions and expectations, that I would find something else in my next career move. That just wasn’t the case. I wasn’t actively searching for a mentor.

Sometimes they come not out of thin air, but where you least expect them. I think on the flip side, I’ve certainly been in formal mentorship programs and informal. I find myself drawn to mentoring people who are ambitious, who are quick to learn, and who can’t quite see what I feel like I see in them. It’s like, “Wow, you have raw talent.” I think for me those are the types of folks that I’m drawn towards mentoring. What I found recently is that a lot of people reaching out who are also first-gen corporate tech world, first-gen college graduates really haven’t been anyone in their family or close friends circle that has navigated that path. I feel like those folks are drawn to me.

Patrick: Interesting that you mentioned that you were in formal mentoring programs. We’ve had many conversations over the past episodes in this season around perspective with formal mentoring programs within organizations. The overall consensus is they’re incredibly difficult to administer and there’s a lot of opportunity basically to make really effective mentoring programs, especially at large organizations.

Some of the leaders that I’ve talked to have said, “I’ve really struggled with putting together a formal mentoring program within my organization.” Coaching is much easier. Coaching is very task-oriented, it’s maybe project-oriented, coaching somebody to a specific goal while mentoring is much deeper or much broader. It’s not really time-bound. It’s more of a longer-term relationship. Were you responsible for administrating a formal–? Oh, you were.

Steph: Yes. I’ve built formal mentorship programs.

Patrick: That’s amazing.

Steph: I think that I had good success with it because it wasn’t left up to chance so it was very structured. I played a heavy role in the facilitation of it both from preparing the mentors and the mentees about what to expect, what mentorship is, how it’s different from things like coaching. There was actually real structure to the program so a beginning, a middle, and an end. I think that’s where the success came from. We gave people guidance on what meetups could look like, what you can talk about, what you can work on. There’s people that naturally hit it off where their mentorship relationship went well beyond the program.

For other folks, it was like, “Thank you for your guidance over the past six months. That was great.” That was it. It’s a bit of an art and science at least from a formal mentorship perspective. I’ve been a part of mentorship programs with external companies, things like an organization called St. Joseph’s Codetalk that’s really focused on giving women technical skills and abilities. I just love that element. Obviously, I’m not an engineer, but it was more of that like, “Hey, how do you actually navigate the tech world?” I found a lot of value in that.

Patrick: Are you a mentor to someone today?

Steph: I am.

Patrick: Has that relationship been a long-term relationship? The question behind the question is we’ve been talking a lot this season about choosing a mentor and really being selective. Again, this is in a non-structured mentorship type program. This is just people finding a mentor for themselves. I’ve had a lot of conversations around how to choose the right mentor for you. Also, the flip of that is as a mentor, how to choose the right person to be the mentee or to mentor because it has to work both ways. Absolutely has to work both ways. You talked about the start of our mentor relationship years ago working together. A big part of that relationship for me was reverse mentoring.

There’s so much that I learned from you through our conversations and our process. Especially at that point in my career, I was incredibly ambitious. To your point, I was thinking about, “Oh, this is the certain role that I want. This is the certain level, this is the certain title that I want.” I remember thinking in many conversations with you around you’re very level-headed, you’re very thoughtful, you don’t rush into decisions. As a mentor, there’s very much the ability for reverse mentorship where you learn so much from the person that you’re mentoring. First off, thank you for that too because you helped me with that quite a bit.

Steph: You’re welcome.


Patrick: If I think about it now, I mentor a number of people now, I have mentors in my career now as well, but I really had to think about what was the right relationship. In the mentor relationship that you are in now where you are the mentor, did it just naturally happen? Was it selected? You don’t have to go into the details about it. I’m just curious about how it came together.

Steph: Maybe this is the pattern here. It started at work actually. It was several years ago. I wasn’t the direct manager of my mentee, but we worked very closely together. I just noticed she was incredibly creative, picked up things very quickly, but didn’t have more of the formal training in the specialty that we have. It just started very subtly like, “Hey, what do you think about taking this course? Or, “Hey, here’s some things that I learned along the way. Why don’t you take these and maybe they can help your work product?”

It started very subtly like that. Then once I had left the company, it just continued on. I feel like why I was drawn to her is yes, absolutely that reverse mentoring. For me, she had that creativity where I am very thoughtful but that fun creative element, I felt like we really balanced each other out. It just also evolved. It started out as a mentorship. It’s part friendship. It flip-flops sometimes.

Patrick: Have you ever had any bad mentoring experiences? If I’m one of them it’s okay.

Steph: [laughs].

Patrick: You can tell the world.

Steph: No. I think really you are my one true mentor. I’ve definitely had unenjoyable experiences where other people have tried to teach me things. It was not consensual mentorship. It’s like, “No, thanks. I’m good.”

Patrick: That’s actually a very good point because both people in a mentoring relationship have to show up, have to be committed to it, have to want it. It’s work. It takes focus. It takes energy, but both people have to be committed to the success of it. I really believe that because I do think that’s where some of the not-so-pleasant situations happen.

Steph: [laughs] Yes.

Patrick: What do you think about people reaching out to ask for mentorship from somebody that they don’t know, but that they admire or that they aspire to be like? We’ve had some conversations and I’m curious what you think about that. I’ll be really honest, I don’t really know. I’ve never done that personally, but I can maybe see how that could be appealing for somebody, particularly maybe at a certain level within an organization. Maybe a CEO of an organization or somebody who is a senior executive or something where it may be more challenging to find a mentor. What do you think about that?

Steph: The cold reached out?

Patrick: Yes, the cold aspiration is really inspired by somebody and saying, “Hey, I want to learn your ways. I want to learn how you have major success.” Do you think that’s mentorship?

Steph: I don’t know if that’s mentorship in the truest form. I feel like it’s inspirational guidance maybe. That one’s hard. I was thinking about this recently. Even when people just reach out to us for advice or additional thoughts, I think when those work is when you’re really clear about what you’re looking not to achieve, but what you hope to get from the relationship. Is it inspiration? Be really specific with what the task is.

I think very inspirational people, very successful people, I’m sure they get a ton of requests. What do you think about as a really busy, successful person, how you spend your time, where you want to invest your time, and who you invest your time in? I don’t know that that actually works, but I’ve certainly seen it at the more senior levels in the networking groups or people in similar situations or maybe it’s a CEO that you admire. I’ve certainly seen that work, but I’d say at the more mid and junior levels, maybe it gets a little bit harder.

Patrick: The challenge that I see with it is that every relationship that I have had when it comes to mentoring has been based on some sort of a personal connection that I have with the person. I think that’s why mentorship relationships work so well when you can just be your total self. You’re not thinking about impressing somebody or saying the wrong thing or making a mistake. I feel that is so necessary in a valuable and successful mentoring relationship. I don’t know if I would have that with somebody I didn’t know.

Steph: I definitely can see that. Initially, I felt like the common ground for me and the thing that really drew me to you was your career drive. That was something that was personally important to me. When we talked earlier about, hey, my path felt very linear in my mind, I felt like we had similarities there. Initially, as we started getting to know each other, I didn’t always feel comfortable with my mistakes.

Obviously, you saw them happen in real-time, but it was that even though I made mistakes, you showed up, you showed support. I’m like, “Oh, okay, cool. I can be more of my authentic self with Patrick.” I think in the mentor-mentee relationship if you are a mentor, your response is incredibly important to when people are being really who they are, sharing what their challenges are and that full picture so that you can share your best guidance or support

Patrick: I really believe that choosing a mentor based off of– Maybe it’s not even choosing. Honestly, I think it’s the evolution of a mentor relationship. It just happens. For many of the people that I’ve talked to about mentoring, the overall consensus is that these are almost lifelong relationships. They’re multiple years. They’re not time-bound at all and can go six months, a year without speaking to a mentor or a mentee, and then when you revisit or reconnect or have a need or in either direction. it’s like no time has passed or that you know you still have that relationship.

Steph: Yes, absolutely. It’s like a professional friendship. I don’t know how I would describe it. Not from a company perspective. I certainly feel that way as well. It’s just those constant beats throughout a lifetime, really important times. Even not in important times, in the fun times as well.

Patrick: I feel like I say this at the end of almost every episode, but I really mean it. I just feel like I could talk for a long time. I love these conversations. Particularly with you, thank you for everything that I have learned from you over the past, like you said, 10 years or 12 years because I’ve learned so much about myself not only in a professional setting but just in general from our relationship and our mentor relationship. Thank you for that.

Steph: It’s been great to see you and talk to you. Thank you for having me. It’s been a pleasure. [laughs]

Patrick: I love this and I love you joining the podcast and sharing the conversation. Thank you.

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