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The Life-Changing Magic of Mentorship: A Conversation


In the early spring of 2021, I was at a professional crossroads. I had just become the engineering leader on a team for which I had been an individual contributor, and I was grappling with just how real I could and should be with my teammates and my leaders.

I would describe my authentic personality as silly, exuberant, jocular and irreverent, and I hadn’t observed many (any?) engineering leaders with this mix of traits during my six years in the technology world. I didn’t quite know if it was okay to be my silly, exuberant, jocular, irreverent self while leading a software team, but I also knew that to constantly mute and bowdlerize my personality would be exhausting, and just one more thing to manage.

I came to understand that my uncertainty around how to be was fundamentally grounded in questions about authenticity. And I’d run up against this before in academia, both with my former colleagues and my undergraduate students.

Around this same time, I was trying to find my way into the orbit of a work colleague whom I had admired and coveted a work relationship with for well over a year. Bree Smith is known by pretty much everyone at my company, if not personally, then at least by name; she manages the facilitation of the (unparalleled) New Hire Orientation that Pluralsight runs every two weeks, and so anyone who starts at the company spends a solid two days getting to know her just enough to know that they want to know her even better.

She’s also the head of our Women@Pluralsight ERG, our Chief Values Ambassador, the first person to raise her hand and ask an executive a tough question during a Town Hall, and someone you can always count on to get vulnerable and real with anyone and everyone during a meeting of any kind.

She’s fucking authentic. I’d always admired that about her. I guess I envied it to some extent.

So, once I stepped into this leadership role and realized that I couldn’t kick the How me can I be? can down the road any longer, I knew who I wanted to talk to: Bree.

Once I made the connection between my current crisis and Bree, I did what any unhinged person with a deep-rooted fear of public speaking does: I volunteered to give a presentation during every New Hire Orientation, every two weeks, because I knew that this way, Bree would be forced to know me, and maybe – just maybe – her authenticity would rub off on me.

Yeah: That’s how desperate I was.

Well, that turned out to be completely unnecessary, because shortly after I volunteered to give this presentation during NHO, the Women@Pluralsight ERG opened the mentee selection round for the upcoming mentorship season. I requested Bree as my #1 choice, knowing that we couldn’t possibly get paired; surely I was one of about a hundred folks requesting her as a mentor.

I mean, you know how this ends, or begins, I suppose: We were matched.

What followed was a truly magical and life-changing mentorship experience. For six months, Bree and I both worked our asses off around this topic of authenticity, this question of How me can I be?, and I’m telling you: She changed me.

Or – rather – she changed how I show up at work. And since our mentorship officially ended, we’ve developed a professional and personal relationship that fills my cup each and every day, and I believe the catalyst for this is the incredible mentorship journey that we experienced together.

The following conversation is an attempt to capture some of the mentorship magic that Bree and I experienced so that others might replicate it in their own mentorship journeys, whether as mentor or mentee.

The Conversation

Kristen: Bree! Hi! Thank you for having this conversation with me in writing. It’s one that we’ve had about a million times via zoom – and a couple times face-to-face – but every time we do, I think, “How can we bottle up our mentorship magic and sell it – I mean, SHARE it – with the world!?” I think this might be a fun way to do that.

Bree: Kristen! Hi! Listen: Of course I think we are just a match made in heaven as a friend and mentor/mentee duo, but I do also believe that it’s because of how we came together and what we have done with this mentorship that has made our relationship so incredible. So if this conversation can help provide some insight to others, I’m all in. And if this just benefits us by creating a written artifact to hold onto forever, that’s also a win for me! In short, I’m thrilled 💖

Kristen: We do have a pretty cute meeting story 🥰 Which provides a really a great transition into the first question I want to ask you. As you well know by now, “Authentic Kristen” is pretty dang effusive – if I love you, I will tell you that I love you. If I admire you, I will tell you that I admire you. During that first meeting we had to begin my onboarding as the new Slack Prez presenter – our very first time meeting one-on-one – I remember telling you that I had just requested you as a mentor for the upcoming mentorship program because I’d been wanting to know you for a long time, and that volunteering to do the Slack Prez was essentially just a way to slide into your orbit.

Now, be honest: How did that feel to you? That I was seeking out a relationship with you so…aggressively? Was it creepy? Flattering?

Bree: In full candor, I was shocked and impressed. I didn’t think someone would put that kind of effort to get close to me or be able to interact with me in that way. So that was my “shock factor”.

That “impressed” feeling, though, came from a place of acknowledging your commitment to seeing something – or in this case, someone – you wanted to learn from, and then actually doing something about it to get there. How often do we talk around wanting something, dream around it a bit, but don’t take that step to get closer to it? So I was impressed by the commitment and now I’m laughing as I write this because that’s exactly what I have done in the past to those whom I’ve wanted to learn from, as well!

Kristen: Yeah - you’re totally that person, Bree! I love that about you. Most of us really do hesitate to seek out relationships with those we admire or want to learn from, don’t we? That’s been me my entire life. You’re the first person I’ve ever “pursued” in this way – I can’t tell you how many folks I’ve admired from afar and have been too self-conscious and meek and intimidated to approach. And that pattern has actually really held me back in a lot of ways in my life. But when I sought you out, you took me under your wing so readily and provided such positive feedback for that behavior, that I find I’m not hesitating anymore to tell people pretty explicitly, “I think you’re brilliant, and I want to know you, and I want to learn from you.” So thank you for that!

We’ve both agreed that our mentorship relationship was wildly fruitful – moreso than either of us could have even imagined. From your perspective, what made our six months of formal mentorship so productive and impactful?

Bree: I think it comes down to two things: desire and commitment. Let’s break that down a bit: You had a real desire and hunger to partner with me because you saw things that I was doing that you thought you could learn from. But the kicker is that you committed to the follow-through, and committed to the work around what we were focusing on. I'll toot my own horn a bit and say that this commitment was mutual. I was also excited and thrilled over the pieces you wanted to be mentored on, and I take my mentorships seriously and want to commit to the time and energy it takes.

Let’s focus on that commitment piece a little more though: You committed to seeking me out, we both built a really strong foundation on what we wanted out of the partnership, and you followed through on everything we agreed to. We were able to speak really candidly to each other, anchored in respect and trust, and with that I could call you on your bullshit, and you could do the same for me!

Lastly around commitment, I gave you homework or challenges at the end of every meeting, and we agreed that you’d complete them before the next meeting we had. It’s one thing to want to do better – it’s another thing to actually follow through with that want. Even though it was out of your comfort zone, you saw the value in where I was pushing you, and: You. Freaking. Did. It. That to me was why our relationship was (and continues to be!) so “fruitful”. There has been this exchange of flexibility and grace, yet accountability and growth between BOTH of us.

Kristen: Wow, does all of that resonate. I actually remember you asking during our first mentorship meeting – which was all about setting mutual agreements for the upcoming six months – “How do you feel about homework?” And of course, I love homework, and told you as much, and so appreciated the thoughtfulness you took in crafting homework that helped me work through my shit and toward my mentorship goals. And I also really appreciated that you embraced my completing these homework assignments through the writing of mini-essays, which I would agree to post at least 24 hours prior to our sessions, and which you agreed to read before we met. I never missed an assignment, and you never failed to read my mini-essays thoroughly before our session. This took extra time and brain work for you, but you really heard me when I said, “I am so much more expressive and articulate through writing - I’ll get more out of this if I write a reflective response to this question you just posed.”

I want to focus for a hot second on your (continuously! to this day!) calling me on my bullshit. It might help readers to have a concrete example of what that looked like, and the one that most readily comes to mind revolves around my struggles with premenstrual dysphoric disorder (PMDD), and in particular my grappling with the thought of sharing those struggles with my leader. As you know, PMDD knocks me on my ass congitively for a few days a month. My engineering lead role put me in “the public eye” a lot more than I had been before – I was in way more meetings, and I was in meetings every day – and so it became very hard for me to hide during the days that I was suffering from brain fog and ennui. I was constantly worried that my leader would notice and think I wasn’t capable of doing my jonb (side note: why do we do that to ourselves!?), and so despite hearing messages that we should feel comfortable sharing our authentic selves – health issues and all – with our leaders, instead, I tried to diminish my suffering, tried to make an argument that this suffering was nothing compared to what other people are up against in their lives, and so not worth sharing.

And you just totally called me on that bullshit belief. It took months for me to muster the courage to finally share my struggles with PMDD with my leader, but doing so was life-changing, in a way. I mean, especially considering how absolutely wonderful and supportive my leader was when I shared this. I never would have gotten there if you hadn’t had the courage to say to my face, “Kristen, I want to call you on some bullshit right there.”

(And – sidenote – you have this amazing facial tell when you’re about to call me on bullshit. Like, you purse your lips and raise your eyebrows a little bit and I think you might even cock your head slightly to one side, and so I absolutely, one-hundred-percent know when you’re about to do it. Which is why I now always beat you to it by saying, “I know you’re about to call me on some bullshit right now, so just do it, already!”)

Bree: Ha! I’m cracking up over the “tell” of my face. I can’t hide my emotions both in my words and facial expressions. I have known my whole life that poker is a game I will never be successful at! 😉

That being said, although this is very humorous for us, it’s also a great quality of our mentorship relationship to point out! That trust is maintained between us, where you know where I'm standing on any topic with you, and the trust I feel that my candor will be received well and built upon in our discussions.

Kristen: Yes! Mutual trust was so important during those candid, bullshit-toppling discussions.

Okay, my dear friend, I think it’s time to wrap this up, and I’d love to do so by sharing with readers one or two pieces of advice – based on our experience – as they embark on their own mentorship relationships. Here are mine, and they’re pieces of advice specifically for mentees:

First, choose your mentors intentionally. Think seriously about what it is you want to learn, or grow in, or blossom into, and then look around you and see who fits that mold. And then, be honest and effusive with your mentor about why you chose them! That will help clarify for them their “mission”, so to speak, and it will make them feel good, and I just generally endorse effusiveness wherever possible :)

Second, ask your mentor for homework, and then actually do the homework, because it’s the work you do between the sessions that provides the fodder for productive conversation and analysis during your actual scheduled time with your mentor.

Alright, Bree – what about you? What advice do you have for mentors as they move into a mentorship relationship?

Bree: I have several thoughts and advice so bear with me here. I actually want to provide a counterargument to what you are saying around being intentional with a mentor. I think mentorship can be fruitful whether or not you seek someone out for a real specific reason or not. What I'm getting at is: A mentorship relationship can look so different on an individual basis. I think you and I had/have such a successful one both because of the specific needs you were looking for, and because our personalities mesh so well. With other mentorship relationships, there have been very different “vibes”, and yet it’s been such a gift to me, regardless. I have learned something meaningful from every mentorship I have had, regardless of personality alignment, interests, etc. But what makes them all impactful, regardless of “how much” you get out of them has been the baseline of:

✅ Coming in with a need/desire that the mentor can help guide through

✅ Creating a strong foundation in the beginning of the relationship through:

  • Understanding what you want to achieve

  • Understanding how to best work together

  • Sharing how you learn best (i.e., asking the “Do you like homework?” or “Can I call you on your BS?” questions)

  • Deciding what meeting cadence works best, what sort of preparation needs to happen, and how communication will unfold.

✅ Commitment, from both parties, on the relationship. We built that foundation in the beginning so we were ready to do the work, and we committed to doing it – together. You really think I could mentor you on the things I did and not strive to practice it myself? You really think that I could give you homework if I wasn’t open to doing it/had not already done it? You really think I could feel comfortable calling you on your bullshit if I wasn’t asking for the same?

I want to lean into some discomfort here and point out that during this time that our mentorship was forming, my personal life was crumbling in front of my eyes. Between my marriage ending and coming out to my conservative family about my sexuality, I was having to practice what I was preaching to you constantly.

So, the mentorship truly is an exchange. It gets to be a learning experience that mentor and mentee have together, so long as they both show up.

Kristen: I love all of that, Bree. THANK YOU for having this conversation with me once again, in writing, so that we can share what worked for us, in the hopes that it might help others find meaning and growth and connection in their own mentorship relationships.

Oh, and thanks again for helping me figure out how me I can be.

Bree and I somewhat ironically being authentically weird sporting glamorous wigs.


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