Jen Dary on Mentoring First Time Managers (Scaling Tech Podcast Ep21)

Aug 15, 2023 | Team Management

Getting promoted into management can be the most exciting and terrifying moment of a person’s career. In this episode, we speak with Leadership Coach Jen Dary about her work training and mentoring managers, and the particularly difficult aspects of being a first time manager.

Leadership Coach Jen Dary is founder of Plucky where she works with individuals and companies to create healthy dynamics at work. She is also host of the BePlucky Podcast, where she interviews managers and engineering leaders about workplace topics that require resilience and perspective. From coaching to consulting, Plucky helps leaders, managers, teams and employees find ways to be successful together. She leads virtual training cohorts for new managers, working primarily in the tech sector but also with tech adjacent companies. She lives in Arlington, Virginia with her husband and young sons.

Are you a first time manager? Are you a “manager of managers” who wants to know how to better mentor your newer managers? Be sure to check out this episode!

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Show notes with links to jump ahead are below

Show Notes from Episode 21 – Jen Dary on Mentoring First Time Managers

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  • Introduction – Manager of Managers and Showing Up
  • 00:00 In the opening quote, Jen shares her advice for how a manager of managers can help their team: “So I think that the best thing a manager of managers could do is to provide stability, show up for the one on ones, hold space for what they’re frustrated with or anxious about, and appreciate what they’re doing well. I mean, this is like ad nauseam feedback, conversation stuff, but don’t only say when things are not well. They also give ‘+1’ to things that are going well so that they know to continue that behavior. And it is possible that they will not confide in you for a while. They might be like, ‘no, it’s all looking good’. It’s all looking good because they don’t want to be seen as an imposter and they don’t want their boss to know that actually they’re really anxious about it. But that’s where the trust building work comes in.”
  • After the opening quote, Arin and David talk about the importance of coaching and how to learn to be a manager since there were not as many resources for new engineering managers when they were in their first management roles. They also reflect on the conversation with Jen and how the conversation covered the “new identity” that a new engineering manager faces. They also reflect on the importance of discussing emotional balance in management, and how that comes out in the conversation with Jen too. Companies need to care about the productivity and the wellbeing of their team members, and managers need to find the balance between maintaining appropriate boundaries with their team while also allowing them to express their concerns and anxities, and what other things may be going on in their lives.
  • Jen’s Journey to Coaching and Personal Struggle
  • 05:18 Arin introduces Jen: “Leadership Coach Jen Derry is founder of Plucky, where she works with individuals and companies to create healthy dynamics at work. She’s also host of the BePlucky Podcast, where she interviews managers and engineering leaders about workplace topics that require resilience and perspective. From coaching to consulting, Plucky helps leaders, managers, teams and employees find ways to be successful together. She leads virtual training cohorts for new managers working primarily in the tech sector, but also with tech adjacent companies. She lives in Arlington, Virginia with her husband and young sons.”
  • Jen’s consulting business, Plucky, is ten years old now. Jen describes her path to coaching. She worked at a digital agency in New York, and was a director of employee development there where she first learned the skills of being a coach, without actually using that term “coaching.”
  • At that time, her personal life changed and she decided to start a coaching business. Jen shared that: “I became a parent, I went on a maternity leave, had some life thinking, and decided, let me try my own thing!” Jen talked about moving from Brooklyn to Berkeley, California, and embraching her role as a coach. Jen also shared her story of having post-partum depression after the birth of her first child, and then later facing brain cancer. These struggles informed her view of coaching.
  • Jen says that “Fast forward six years, then I am diagnosed with a brain tumor in 2016. That was also obviously a big deal. And I had a craniotomy two weeks later, and I just literally yesterday finished writing a memoir about that experience. And it’s about a diagnosis, obviously, and seeing that through and parenting two young kids. But it’s also about Plucky and the risks I ended up taking after that. Because when you’re almost dead, you’re like, well, who cares if no one buys a ticket? Why don’t I try something?”
  • Her memoir on this experience will be published soon and you can sign up for her email list at BePlucky.com
  • Jen’s Approach to Coaching: Adult Development
  • 16:23 Arin asks Jen to talk about the concept of “Adult Development” and how she uses that in her coaching. Jen compares it to childhood development concepts in psychology, but that we don’t talk as much about how your personal development is not automatically done when you become an adult.
  • Jen describes it as: “I was thinking about adult development when my kids were in daycare, let’s say preschool, where it was very normal to have a conversation with a teacher or a pediatrician, about, ‘oh, they’re not walking yet’, you know, this kind of stuff. Childhood development was something that was a constant conversation in the background of their growth, and it wasn’t a problem to talk about.
  • It was like the expected behavior, ‘oh, this living being is going to be evolving and growing, and therefore this conversation is necessary to make sure they’re on track’. Then you graduate high school and people are like, ‘good luck!’ And we are spit out into sort of this assumed adult state that doesn’t allow for the same kind of checking up. And I felt like it was a missed opportunity to assume that we were fully done when we’re 18, or even whatever you want to say 22 if you go to college, things like that. And so my approach to coaching and kind of just handling people in general is the idea that that development continues.”
  • Jen notes how company perspectives have changed over the last decade. Previously companies would be willing to buy you a programming book, but not coaching. That has changed, and companies are often willing to provide funding for employee coaching.
  • The Identity Shift That New Managers Struggle With
  • 20:56 Arin asks “What do new managers struggle with the most and how can we, as more experienced managers, help them?”
  • Jen responds that “If I had to put it to one concept, I would say they struggle with being liked over being respected. People have a really hard time, especially let’s just take a situation which is very common, which is that you’re promoted from within so you don’t get a new job at a new company. You are an IC (Individual Contributor), maybe a senior IC at that point, and now all of a sudden you’re in charge of the other ICs. This is like triple black diamond level management because they used to be your friends and they used to be your peers. And now you could theoretically fire them or get them more money or you’re responsible for their performance reviews and you see them at angles that you didn’t before. That’s really hard.”
  • Jen talks about how this is an identify shift for the new manager. You have a new identity, a new role in comparison to your friends, and you may not have peers who can help you or who you can confidentially ask for help and support. Jen jokes that she tells new managers “Congratulations, now you have to find new friends!”
  • Arin supports Jen’s point by talking about his experiences as a new manager, and how he turned down his first management offer for the same reason – that he wasn’t sure he was ready at the time to become the boss of his friends and peers. Spoiler Alert: Arin eventually did take the management job and is now the co-host of this engineering management podcast!
  • How to Coach Managers
  • 25:16 Jen talks about how new managers can get coaching from outside coaches and consultants like herself, or from their own manager. A “manager of managers” can be very effective in coaching a new manager because they understand the context of the organization and the specific dynamics of that work and the organization. On the other hand, external coaches can also bring in a new perspective.
  • At this point, Jen talks about the importance of being present for a “manager of managers”, and shares the advice we mention in the opening quote of the episode: “So I think that the best thing a manager of managers could do is to provide stability, show up for the one on ones, hold space for what they’re frustrated with or anxious about, and appreciate what they’re doing well. I mean, this is like ad nauseam feedback, conversation stuff, but don’t only say when things are not well.
    They also give ‘+1’ to things that are going well so that they know to continue that behavior. And it is possible that they will not confide in you for a while. They might be like, ‘no, it’s all looking good’. It’s all looking good because they don’t want to be seen as an imposter and they don’t want their boss to know that actually they’re really anxious about it. But that’s where the trust building work comes in.”
  • 1-1 Management Cards
  • 27:48 Arin asks Jen about the decks of cards that she sells, which provide conversation starters for 1-1 meetings, for mentoring, and for mentoring managers. He shares a few of his favorite conversation starters and asks Jen to talk more about them. Arin suggest these are very important for managers like himself, who often get so focused on delivery tasks that he forgets to step back a bit and ask his leaders bigger questions.
  • “Under the subheader of self care … What are you procrastinating on right now? What would make it easier to get moving on that?”
  • Jen responds that “And the thing is about those questions, and I’m glad you appreciate where they’re coming from, is that sometimes when you’re busy, you’re really just focusing on producing and billing if you’re a client services firm and shipping stuff. And it’s not that that’s not part of your job. It’s just that there’s this invisible data all over the place where you could tell this person is struggling because they just had a baby.
  • Jen continues: “It’s almost like you have these secret glasses you put on, and you understand, well, these two have beef, so I’m not going to put them on the same project right now or whatever. It’s this extra data, extra information that’s just flying around that you could account for, and it will probably mean better work, more efficiency, and better productivity. I also want to be clear and say you’re not a therapist, as a manager, and there is a boundary that you will need to hold at some point and gently refer someone to HR or therapy if it gets to that point.”
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  • Jen’s Coaching Curriculuum
  • 35:56 Arin asks Jen to describe what her coaching calls are like – is there homework? How do you choose topics to discuss?
  • Jen describes how it varies based on the needs of the clients, and what is going on at that moment which they need to discuss. “I always start the session by saying, catch me up. Since last time a little bit, I have a couple of questions, probably following up on what we had talked about. And then I say, what do you want to talk about today? And so it is entirely them driving in terms of content. I don’t have a curriculum per se, but the same stuff comes up all the time, right? Trusting yourself. Is this feedback valid or not? Where do you want to go with your life, your career? How do you handle conflict? Everything lately in a post COVID situation? Are you burned out? Are you okay past burnout? Like, are you healed from burnout? Is your team burned out? Did you go through layoffs?”
  • Jen then talks about how hard it is to do layoffs for the first time as a manager, and all the emotions involved, and she and Arin share stories of the challenges in those situations, especially if you as the manager don’t agree on the nature of the cuts being made. They also discuss the spate of layoffs in 2023 and how some of them feel like companies just taking advantage of economic uncertainties to make layoffs that may not be necessary. This creates complicated messages when some people are let go basically for performance reasons, while others are let go but told it has nothing to do with performance.
  • Management Power Dynamics
  • 43:39 David talks with Jen about the importance of addressing the person and the productivity, and the boundaries that the manager must have with their employees so that they don’t become their therapist. Jen talks about how as a culture we are suspicious of power right now for good reasons, and that managers don’t show their human sides enough to help this situation. Jen talks about how “old school power is like, ‘I’m the boss. You’ll do this.'” But that is different than leadership, and today’s workforce wants to understand the “why” of doing things also.
  • Mentoring and Promotions
  • 51:32 David asks Jen about mentoring and growing developers over time, and how that relates to pay increases. Jen notes that some companies will promote people “based on tenure, like the longer you stay, the more money you get paid. I don’t necessarily think that’s the smartest thing to do, but if you do it, just say it, here’s what happens here.” She stresses the importance of being clear and communicative about what metrics and career paths are used when determining promotions. Also, remember that career path does not only come from your company! There is a lot that people should do for their own career path outside of their job.
  • Conclusion
  • 55:00 The best way to keep up with Jen’s work is to sign up for her email newsletter at BePlucky.com. You can also buy her manager journals and 1-1 coaching cards on the same website. She also posts a weekly video on Instagram at BePluckster. You can also find out more at our links below!

Links from Episode 21 – Jen Dary on Mentoring First Time Managers