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Rise of the Resilient Manager with Lara Hogan

Episode 33

​​Are you a resilient manager? Do you want to become one? In this episode of Programming Leadership, Marcus and his guest, Lara Hogan discuss what it means to be a resilient manager. She will discuss some effective management skills and thought processes. She will also introduce us to the idea of the manager Voltron.


Show Notes

  • New manager care packages @1:00​
  • Becoming a manager is scary for different reasons for everybody. @5:10
  • Management skills are the same across the board. @9:15
  • At every stage of management, you start over with the same new feelings, new fears, and lack of internal barometer of success. @12:06
  • It’s okay to get comfortable and confident in what you know, but remember you’re going to encounter new things. @14:01
  • Build out your manager crew of support, a manager Voltron. @15:19
  • Your Voltron should include people inside your company and people outside your company. @20:13
  • Manager dens- where you can experience coaching, mentoring, and a safe space, Vegas rules session. @23:57
  • Mentoring is sharing advice and perspective; coaching is helping someone come to their own conclusions. @25:56
  • Coaching is what helps people grow. @26:26
  • What are you optimizing for? @30:24
  • Resilient management has to do with making sure your bucket of energy is healthy. @35:01
  • When thinking about being cut out for management, it’s about given the context, responsibility, and people you work with, does this work for you? @36:52
  • Showing is better than telling. @39:41



Announcer:  Welcome to the Programming Leadership podcast where we help great coders become skilled leaders and build happy, high performing software teams.

Marcus:  All right, welcome to this episode viewers, and I am exceedingly excited to have Lara Hogan on with me today. Lara, welcome to the show.

Lara:  Thank you so much. I’m tickled to be here.

Marcus:  Lara is the best-selling author of her new book Resilient Management, which I have to say has just set Twitter on fire for me, at least [inaudible 00:00:42].

Lara:  I’m so glad to hear it.

Marcus:  Yeah. But before we go there, I also saw you talking about something really intriguing on Twitter, and I am just dying to hear about it. Can we just dive into that just for a minute?

Lara:  Yeah, I’m guessing you are talking about these new manager care packages.

Marcus:  Yeah, exactly.

Lara:  Yeah. Cool.

Marcus:  What is that?

Lara:  Oh, okay. So a while ago, I started to think to myself, new managers, these poor, new managers, you know I’m writing a book for them, I’m coaching them, I’m going through these workshops with them. And I realized, there’s this mix of emotions, it’s like, they’re so excited about this new role, and also terrified as they should be, right? Like it’s exciting to have this new opportunity, new sets of skills to develop, but also, it’s a lot of responsibility, and people get no training.

Lara:  So I was sensing that there was like an opportunity for me to support them in like a slightly different way than I have been. So normally, the way I support managers is like writing and coaching and those kinds of things, but like I am not their manager. How can I help managers who care about this stuff, support the people who report to them in like a little bit of a new way. So I partnered with this company called Small Packages.

Lara:  So Small Packages is a care package company, historically, actually, they’ve just done care packages for women. But I approached the founder, Julie and I said, “Hey, Julie, I have an idea for a care package. Maybe you might not be interested in this at all, because it’d be for everybody, not just women. But like, what if we made a care package for new managers?” And she… Oh, it’s just been a dream developing this thing. And I wasn’t sure how it was going to go. But it’s gone great. The launch… We’ve been live for about a month and it’s just been intense. It’s wonderful.

Marcus:  Okay, so, can you tell us what’s in the box? Or is it a secret?

Lara:  Yeah. No, it’s not. I even did an unboxing. Like, a nerd.

Marcus:  Perfect. We’ll get a link and we’ll put that in the show notes.

Lara:  Perfect.

Marcus:  I hope it’s on YouTube or something like that.

Lara:  It’s on Instagram. Totally. Yeah.

Marcus:  Here we go.

Lara:  Okay, so there’s a bunch of like the tools side so that people feel like they can hit the ground running. And then there’s the care packagey side, so like the stuff to help them celebrate and also relax a little bit. So on the tools front, there is the book Resilient Management. There’s a bunch of tools that I’ve actually developed specifically for this care package, and I put them in a little beautiful folder called new manager toolkit which you can also buy separately from the care package and that includes a manager Voltron card to help you figure out your network of support as you grow.

Lara:  The first one on one questions I developed to help onboard yourself onto the team. A bunch of stuff about handoffs, how do you hand off direct reports from an old manager to you, just tons of like tools and worksheets and stuff to help you hit the ground running. So that’s like the tool kit support side. Then there’s like the caring side so we actually included a bunch of tea, sunshine tea to help you feel like happy and chilled out, aromatherapy oils and Eucalyptus aromatherapy oil, a cookie, a donut cookie to help people feel like they’re celebrating, right?

Marcus:  I was hoping there’d be a donut. Yeah.

Lara:  Of course there’s a donut in there, you know a little merit badge that says kept going because we got to celebrate the fact that this yeah. It’s just… It tickles me. And then to cap it all off, Small Packages in every box they actually include a custom letterpress card. And Julie hand writes the note from the sender to the recipient.

Lara:  So we developed this customer service card for the recipient of this box, whether it’s your friend or your report, maybe your manager who knows and so we’ll like write in there the note of support from whoever is sending it to whoever’s receiving it. And it’s just been incredible to see the outpouring of love between managers. I mean I just, it makes me feel so good. Selfishly, this is so satisfying to see.

Marcus:  Oh, it’s wonderful. I feel like under Christmas trees this season, this is going to be …

Lara:  Yes, yes.

Marcus:  Like if you’re not sure what to get your favorite new manager in your life, this sounds like a wonderful gift.

Lara:  I think so. There’s something just so delightful about it, and we never really send each other physical gifts anymore. Everything that we’ve been building is tools that are digital or you know I’m like in person with somebody or coaching them. And it was so nice to build something that was actually like a thing that people could hold and kind of treasure and feel good about.

Marcus:  My mind is just going so many directions right now. So here’s my question. Why do you think it is so terrifying to become a manager? Because I agree it is,

Lara:  Yeah.

Marcus:  Why though?

Lara:  The fear is different for everybody. And I found this when I was writing the Public Speaking book too. The fears around public speaking are so wildly varied a spectrum. And I see this again in management. There’s the group of folks that are scared because of the amount of responsibility resting on their shoulders. They know that they’re responsible for people’s careers and livelihoods and like business objectives, there’s that kind of grouping of fears.

Lara:  There’s a bunch of fears around like, what if I fail? I don’t know what I’m doing. I’m not equipped. I’ve never learned, been formally trained in these skills. That’s a whole bunch of fears. And then there’s also fears like, I don’t even know what this role is. There’s the unpredictability, the uncertainty, there’s plenty of more too.

Lara:  But those are the kind of the three common things I see people just, they don’t know what they’re getting into. They don’t know what they’re signing up for. There’s no way to like dip your toe in slowly, mentoring a little bit, but you don’t really see the heaviness. And then there’s fears around like, you have to keep secrets, right?

Marcus:  Mm.

Lara:  There’s a confidential information that you’re trusted with. There’s hard things you have to do like potentially firing someone. Like it’s all… It’s pretty heavy.

Marcus:  And you can’t just go back oftentimes. It’s not like you can just undo it.

Lara:  Yeah it’s unfortunate that there’s not more of an opportunity at most companies to switch back and forth from that individual contributor path to the manager path. Some companies do support folks going through that. But as you said, there’s no undo button. If you’ve been in the management role, you can’t just like roll back the clock. You just have to move forward, whether or not that’s contained to do it.

Marcus:  [inaudible 00:06:39].

Lara:  Yeah, exactly. Exactly.

Marcus:  So all these fears sound pretty serious.

Lara:  Yeah.

Marcus:  I remember I went through them.

Lara:  Yeah…

Marcus:  But your box sounds pretty light hearted.

Lara:  It’s definitely light hearted, and it’s definitely like, “Hey, I’m acknowledging in equal parts this is big, and I’m here to support you,” meaning whoever’s sending it could be like, “Hey, yeah, you’ve got a right to be scared.”

Marcus:  Yeah.

Lara:  And also, you’re not going it alone.

Marcus:  Yeah, I like that. And when you said tools, of course, I started thinking about spreadsheets, and then I realized it’s a box.

Lara:  It’s a box.

Marcus:  There’s not like a zip drive in there.

Lara:  No.

Marcus:  You’ve actually created things people can keep for years to come.

Lara:  Yeah… Absolutely. And I mean, there’s stuff that I hope that people get a lot of value of, as I say, over time, but there’s obviously the agenda to hand off those direct reports from one manager to another. But there’s also a notepad that I created that helps give you a prompt before each one on one. What do you want to mentor this person on, coach them on, sponsor them for, what feedback do you have to give them?

Lara:  Just to like center yourself before each and every person you need to meet with, just to remember, like, right, I need to support them in these variety of ways. I need to remember to give them positive feedback, too sometimes. There’s just… There’s so much in there. I’m excited for people to get ahold of.

Marcus:  Wonderful. Well, I want to dive into something you mentioned along the way. And that was the idea that oftentimes we take these roles and we get no training.

Lara:  Yeah.

Marcus:  Now, this may sound like a silly question, but I don’t know if it was always this way this idea that companies didn’t train managers, but I agree with you. It doesn’t happen anymore. And I was curious if you had any ideas about why, why the trend is gone away from it.

Lara:  You know what, other industries do train their managers.

Marcus:  It’s like a secret, don’t tell.

Lara:  So yeah. But like what a classic engineering industry thing, right? Like it’s almost like we’re trying to reinvent the wheel when actually plenty of other industries have figured this out. The other thing I noticed actually about engineers, and engineering management as a discipline is engineers and engineering managers think that somehow they’re unique in these management responsibilities. Folks, I’m so sorry. We are not special.

Marcus:  You’re breaking our hearts here.

Lara:  Oh no. I try to be upfront about it because like the book that I wrote, it includes so many management fundamentals and foundational skills I hope that people will build, and my examples in it are all based in the tech industry. But these skills are not unique to management. In fact, every discipline out there, design, product, whatever, everyone’s going to have their own individual contributor examples and the ways that they might implement these skills. But the skills are still the same across the board.

Marcus:  Why did you feel this was the right time for this book?

Lara:  I was… This is going to sound so ridiculous. I was finding myself in coaching call after coaching call talking about the same challenges. And there’s difference between mentoring and coaching. So in mentoring mode, I am giving advice. I’m sharing my perspective. I’m sharing what I’ve seen work and not work. Like I actually talk about what I think someone should actively do.

Lara:  In coaching mode, that’s not my job. In coaching mode, it’s actually my job to help this other person come to their own conclusions by asking them lots of questions, giving them a space and time to introspect, really being their champion and their cheerleader, giving them feedback, but it’s all about them and their ideas. And there’s not so much of the space for me to be like, here’s the answer. I mean, sometimes I’ll do that, of course, but that’s not my job as a coach. So I was just so, so, so full up on like, the things that were in my brain and like ready to come out of my mouth. It could come out in like workshops, for example. But it was time for me to put down these things on paper so I can also reference them during coaching calls.

Marcus:  This book just came out of the work you were doing.

Lara:  Yeah.

Marcus:  It kind of just got a certain pressure in your head, and it flowed out through your fingers and onto the page.

Lara:  Exactly. Yeah. And that tends to be the way that I write books. It’s just like… I’ve either given talks about it for long enough or I’ve written up blog posts and I’ve kind of honed my thesis statement and I can back it up at this stage. I’ve gotten all the questions that probably will screw me up. So I can like hopefully write something that will be generally applicable and help people not just of overrepresented groups but everybody in our industry who might be struggling with figuring out how they want to show up as a manager.

Marcus:  Why is this… This group of people, these poor managers, as you say, why are they important to you?

Lara:  Oh, that’s a good question. I just identify so deeply with that struggle. I mean, I’ve always loved management. I don’t know, how did you feel about management when you started?

Marcus:  Oh, no. When I started?

Lara:  Yeah, being a manager.

Marcus:  Well, I felt awkward and scared,

Lara:  Yeah…yeah…

Marcus:  And like jealous that I couldn’t code as much anymore. So mostly I did, and I kind of thought it was like, like a programmer plus, plus,

Lara:  Yeah…

Marcus:  Like, a lot of coding with a little bit of light management, which was totally silly.

Lara:  Well, but how could you have known right, management is this black box.

Marcus:  Right.

Lara:  Intentionally so. As a manager, you’re responsible for keeping in your brain confidential information, really tough decisions that you’re making. It’s… Management explicitly needs to be a black box sometimes, not always but often,

Marcus:  Yeah.

Lara:  And I think that that’s a big reason why when we start out as managers, we just don’t know what it’s like. And so I just feel for them, I care about them. And I remember feeling that way, at every stage of management, you know not just as a new line manager, but when I became a manager of managers, and then when I became a VPE. You know it’s… You start over again with the same new feelings, new fears, you start over again with the whole, like, the lack of internal barometer of success. It’s hard.

Marcus:  Yeah. I felt like every transition felt sort of like the first one in some ways. Not exactly, but there’s an old ’80s, Atari 2600 video game called Pitfall of this guy swinging on a rope over a big hole.

Lara:  Yes.

Marcus:  I always felt like that guy’s going through a transition from one role to another, because I was always afraid I was going to fall into that big hole.

Lara:  Yeah, yeah. And like that fear, it’s just… It’s prevailing, like that fear never really goes away. You go through different seasons of it right, but like, you’re always swinging over a new big hole.

Marcus:  You know one thing and I’m curious if you had this experience, I do remember when I started to not fear it as much. And while that sounds really positive, I think there was a time maybe about 18 months in to becoming a tech lead,

Lara:  Mmhm.

Marcus:  Where I was managing eight people where I screwed up.

Lara:  Yeah.

Marcus:  And I kind of thought that wouldn’t happen.

Lara:  Mmhm.

Marcus:  So I fell in or I tripped or whatever you want to call it, but I remember then thinking like, wow, how did I let my guard down?

Lara:  Mm.

Marcus:  Because I gained a sense of confidence that was more from being comfortable than it was from being good.

Lara:  Yeah, that’s real. You probably… Whatever tripped you up was probably something brand new that you hadn’t seen before. I’m going to guess.

Marcus:  Right. Yeah, yeah, it was.

Lara:  And it’s just that’s the part of the deal, right? Like, we get comfortable and confident with known experiences. Then all of a sudden, a new challenge, a new obstacle, a new context comes our way and all of a sudden, we have to start from scratch. I mean, I think it’s actually okay to get comfortable and confident in what you know.

Lara:  It’s not okay to then brazenly walk through the rest of life saying that I’m going to be great at this for forever. It’s going to be healthy to remember that like you’re going to encounter new. This certainly happened to me the first time I had to fire somebody, I was just so out of my depths. I thought I was the kind of manager that communicated really effectively, and all of those tools failed me.

Marcus:  Yeah, well, I remember thinking I was quite an enlightened person as a manager. And if I were being really honest, I think I was a pretty good boss, at least some of the time and then someone would quit,

Lara:  Yeah…

Marcus:  Or something would happen that would really reflect on the actual work I was doing versus my own self perception of it.

Lara:  Yeah.

Marcus:  And sometimes the contrast was rather challenging.

Lara:  Yeah, I mean, you are describing in a nutshell, the poor human experience of leaders generally. I see this with managers, right, but like all of a sudden you’re responsible for a whole mess of people or strategy or something, and then you’re feeling good. And then one day you wind up like in that pit.

Marcus:  Yes.

Lara:  Oh, it’s hard. That’s why having like a crew of support around you, I think is so valuable, not just your manager, because your manager is one person, one person who can like give you feedback and one person who can help you level up your skills.

Lara:  But they’re… They’ve got a special set of skills, and that’s just one set of skills. You need a crew to lean on, especially as you find yourself in those pits, either people who have experienced that before you and they can help you dig yourself out of it, or people who know you really well, can give you feedback. Having a good coach in your life can be really important. But I really emphasize this idea of like building out your manager crew of support, which I often refer to as like a manager Voltron.

Marcus:  Voltron.

Lara:  If you imagine a bunch of people assembling together to be your network of support as you grow and it’s going to evolve over time.

Marcus:  I want to take just a moment and thank my sponsor GitPrime. GitPrime has sponsored the show, not just because they’re fantastic people, but because they really believe that leadership and engineering is about people. It’s about conversations. GitPrime is a platform that allows you to have better conversations with people. Yes, it has lots of other benefits, you can probably plan better. You can see metrics about individual performance.

Marcus:  But let’s just take that one idea about individual performance. Whenever I talk with a GitPrime user, and by the way, lots of my clients are GitPrime users, they always tell me how surprised they were at what was really happening on the team. See, it’s really easy for you, as a manager to observe generally how people are working. You can look at PRs, you can look at who’s assigned what tickets.

Marcus:  You as the CLM, the software engineering manager, you get a notion for what people are doing. But there’s always these beautiful surprises about who is really performing well and who’s secretly struggling, about who’s the person that’s saving everybody’s bacon through fixing a lot of stuff behind the scenes, and who is absolutely doing all the PRs. This kind of data lets you move from looking at people as just well, they’re all engineers, and they’re all kind of doing engineering work to seeing exactly where each one of them is strong and has opportunities to grow.

Marcus:  That’s why I love this tool so much. I believe that new and surprising conversations come out of data, that when you can sit down with somebody and start to understand and intuit why things are happening, you’re going to create even better quality of exchanges. By the way, you know here on this show, we talked about the fact that leadership is what keeps people connected to their work and prevents turnover and keeps them motivated. It’s about the relationship. I like to say that GitPrime not only lets you build better software, it lets you build a better relationship with your team members. Start a free trial today at

Marcus:  I think Jason Wong’s post on the first team

Lara:  Yeah…

Marcus:  Kind of smells like that, although I have a slightly different variation on how my first team was created. But if somebody is sitting here listening, and they really want that,

Lara:  Yeah.

Marcus:  What you’re describing, how can they start to assemble that group? How do they even take the first step?

Lara:  It’s so tricky, right? It’s intimidating to think like, oh, how do I add someone to my crew of support? Because I’m going to have to be vulnerable with them. Can I trust them? What if they don’t have time or interest? What if they don’t like me? You know the normal things. So there’s two things I usually recommend to people. The first is to look for cross-functional leaders internal to your company that are at the same level as you. Because often these are the people who will be a really effective first team. Now you brought up Jason’s blog post, which I adore. You want to share with people the definition of a first team mentality?

Marcus:  Sorry, you caught me off guard, which is fine. We’ll just keep this in.

Lara:  Yeah.

Marcus:  I’m trying to remember it now. But the way I remember it was something along the lines of those peers and those people in the company who you support and who support you, and in many ways, those are the relationships which your teams model to work together.

Lara:  Yeah.

Marcus:  Maybe I added that last bit.

Lara:  I like it.

Marcus:  How do you define it?

Lara:  Yeah, that’s exactly right. The way I think about it is like this cross-functional group of peers, maybe not cross-functional, but your group of peers, where you’re prioritizing what they need in your world, which is so counterintuitive. Because when we first become managers, we’re kind of taught implicitly or explicitly, that the people who we should be prioritizing are the people who report to us. So it’s counterintuitive to think like, wait, my first team should be my peers?

Lara:  And this is because this group of people, they’re the ones who you can support and they will support you. You will get additional context from them. You’ll learn about what’s going on in their world. You can see the problems that they’re going through and how they are approaching them. And that’s all going to benefit you as well. And you get to help them, which is by the way, the best way to build a Voltron, that two way helping each other is so, so, so healthy and critical.

Lara:  So there’s so many different ways to do this. Grabbing people for coffee, definitely a way to build a first team. I love to bring in this concept of manager round tables or manager dens in which the same group of like six to eight people get together every other week for some set amount of time. It’s all confidential like Vegas rules, what happens in the round table stays in the round table.

Marcus:  Yeah

Lara:  I learned this from Paloma Medina who used to be the Learning and Development Director at Etsy. It was incredible. My manager den that she put me in, they supported me through my first hard challenges as a manager at Etsy, they helped role play difficult conversations with me. They helped me get gut checks, they took me out to drinks after I had to fire that person, just like the whole nine. And so that’s… It can be such a valuable crew, small crew to lean on as you grow. So that’s, that’s like option A for building your Voltron, which I think is important, but not the whole thing.

Lara:  Part B is about finding people outside of your company that you can lean on as you grow, which is again, gross and weird. Like networking is like a weird dirty word, right? Like it’s hard for us to figure out, how do I add people to my Voltron? My favorite way to do this is totally ripped off from the former CTO of Meetup, Yvette Pasqua. She did this really sneaky thing that I didn’t realize what was happening at the time.

Lara:  We’d bumped into each other at some event and she emailed me later and said, “Hey, Lara, I know that you run an infrastructure team. I’m thinking about reorganizing my infra team. Can I take you out for coffee and just like pick your brain? Do you have any strong opinions about like reorgs for infrastructure teams?” And I was like, do I ever have war stories and opinions and you know the whole nine, because she guessed accurately, that I would be enthusiastic to talk about my …

Lara:  We love talking about ourselves as humans, right? But she gave me the floor to talk about my experiences, my beefs, my opinions, which is a great way to add someone to your Voltron. That was her way of looping me in. Now she actually had this problem, don’t like make up a problem and then like go and try to talk to somebody about it. Actually have a problem that you want some advice on or help with and then like reach out to someone who may be like a little bit extended in your network and ask them if you could take them out for coffee, ask about that specific thing.

Lara:  Obviously, some failure modes here. Don’t just leave it open ended. Don’t just say like, “Hello, person. I’d love to pick your brain over coffee. Do you have an hour to meet at this place close to my office?” No, that person does not have the opportunity to like take the time out of their day to travel to where you are for some unknown reason. Like we want to get specific, and we want to make sure it’s something that we think that they’re going to care about. We can make it clear why we’re asking them.

Marcus:  Was there a follow-up after that meeting? It sounds like that was the beginning of something, not the ending.

Lara:  Totally. It’s funny thinking about how that all unfolded, that coffee actually turned into drinks when I was going through a really, really tough time at work. So when we got together, and of course, I wanted to talk about infrastructure reorgs, but I had this other pressing stuff on my brain. She gave me the opportunity during that same hangout to share all of the disgusting management stuff I was dealing with. And it was so lovely just to have that space to unload with someone who’s been there, you know.

Lara:  And so that was the beginning. We ended up actually working together. She hired me to be a fractional VP of Engineering at Meetup. So it was like definitely the start of like a … you know we still hang out. We still chat. We still lean on each other. Like we can text each other whenever we have a question or a problem or just want to vent. So definitely you hit the nail on the head. That was the beginning of a really beautiful Voltron relationship.

Marcus:  Mmm… Now, if you’re listening to this, and this sounds interesting to you, it sounds like these are really practical ways that you could start to work with people outside of your network. But I want to go back to the den.

Lara:  Yeah.

Marcus:  Because you mentioned it was brought to you by somebody in L&D at Etsy.

Lara:  Mmhm.

Marcus:  And I think oftentimes, L&D is tasked with these kinds of really neat, beautiful things. But I wonder if that’s the sort of thing that managers could self-organize, that one person could take the initiative.

Lara:  So in my workshops, we’ve actually started to do a manager den, that way I can show the people who attend the workshop what it feels like to be in a small group where someone shares a challenge, they spend half of the time coaching them meaning asking open questions and reflecting. Not giving advice, right? Not just like saying, here’s how I would do it. And then the rest of time actually doing the statements of advice.

Lara:  Then when they have like a 15, 20 minute exercise on what it feels like to have a small group, again, safe space, Vegas rules setting to share their challenges and get help. And then I ask, how might you bring this back to work?

Marcus:  Nice.

Lara:  Because often, we just have never seen that model before, right? We’ve never seen the model of a small safe space where we can lean on each other and like share our challenges and get help from one another. We just feel like a very lonely game management.

Lara:  Now I want to have a really quick plug. My company Wherewithall also facilitates these for other companies. So we will either go in if they’re in New York City or we’ll remotely facilitate these dens that way they can have like a third party perspective doing the facilitation. They don’t have to worry about whether or not there’s a manager in the group, that’s going to be an effective facilitator.

Marcus:  Wonderful. We’ll have to put a link to your company and that offer in the show notes.

Lara:  Thank you.

Marcus:  You know and it really goes along with a hypothesis I’ve been forming, that a lot of times I think management thinks, well, if we need to improve a problem with our people, what we need to do is get training on a topic.

Lara:  Yeah.

Marcus:  And I’m starting to think, and I think you’ve confirmed it for me that all we really need to do is start to talk about it in a safe place on a regular basis.

Lara:  Yeah.

Marcus:  And maybe if we don’t even know what it is,

Lara:  Well said.

Marcus:  That might go a long way towards improving the work experience.

Lara:  Definitely. And there’s a thing that you hit on there, which was about talking about these topics without even necessarily knowing what the topics are in advance. And the talking about I want to dig into real quick. I mentioned this earlier, right. There’s a difference between mentoring so sharing advice, sharing perspective, and coaching, which is helping someone come to their own conclusions.

Lara:  One of the pitfalls about coming together as a cohort and like sharing problems, one of the failure modes that’s potential is for people to just share what they would do, or what they have done,

Marcus:  Right.

Lara:  And make it about not the person with the challenge and make it about everybody else. And that’s actually the hardest part of these dens or round tables is using those coaching skills instead of the mentoring skills, because the coaching skill is actually what helps people grow.

Marcus:  The phrase I hate is, let me tell you what you got to do.

Lara:  Oh, yeah.

Marcus:  And I think every time someone says that to me, I just kind of go well, I’m clearly not going to listen to whatever follows.

Lara:  Yeah.

Marcus:  Yeah. One of the books I’m really in love with right now is William Isaacs’ book Dialogue. And it talks about this idea of a dialogue being a skill, we have to learn to sit in uncertainty. We have to learn to hold inquiry.

Lara:  Mm.

Marcus:  And we are so compulsively wanting to give advice, which comes from us but doesn’t create generative dialogue, like people I think are really hoping for.

Lara:  Yeah. And I think that people often don’t realize that that’s what they’re hoping for. And so I have this workshop, mentoring, coaching and sponsors, we go through these three skills, what are three different? How do you use them? When do you use them? The first exercise I have people do is they’ll get into pairs. And one will share a current workplace challenge with the other, and then explicitly the other person’s tasked with mentoring them, giving them advice, sharing perspective, yada, yada, yada.

Lara:  So we do that, back and forth, five minutes each. Then I teach them about coaching. You know coaching, again, open questions, reflections, not about you, the person with all of the knowledge. It’s about helping the other person come to their own conclusions. So then I have them do the same challenge as before, so share a challenge with the other person, and then explicitly, you’re not allowed to give any advice or in fact, make any statements whatsoever.

Lara:  You are only allowed to ask genuinely curious open questions that start with the word what, and they cannot be leading open questions. It can’t be like, what if you tried, blah? Or like, you know those kinds of like, it’s explicitly just, hey, what’s hard about this, right? What are you optimizing for? What does success look like? What’s the worst thing that could happen? Whatever the thing is.

Lara:  And so then afterwards, we do like a debrief, right? What was the difference? What were the outcomes? You share the same challenge with the same person, what changed for you? And it is… I love this, selfishly as a facilitator, because I can see the light bulb moments happening and these amazing managers are like, oh, I default to mentoring because 95% of us do, and that’s not what helps someone.

Marcus:  Mm…

Lara:  Coaching does, because they’re coming to their own conclusions, they’re going to come up with a better you know solution than you would have, a more creative solution. In fact, best outcome, they come up with a brand new problem statement, because the way that they originally defined it wasn’t even right. So we’re forcing people to go deep, and that’s where the magic happens rather than staying surface level in mentoring mode.

Marcus:  Yeah, we default I think a lot of managers, I certainly did for a long time default to telling.

Lara:  Yeah.

Marcus:  You think that’s what I’m here for, is to do the telling.

Lara:  Right. And that’s… We’ve been told that’s our value.

Marcus:  Right.

Lara:  We’ve been told, especially as engineers, what we have to offer is our knowledge. That’s not actually the most valuable thing. I’m so sorry.

Marcus:  But, but… Okay, but now, and I completely agree with you, but let’s look at a real person who’s listening who says, but you know what, Lara, if I don’t tell, if I’m not leading in that way, it’s going to look like I’m doing nothing.

Lara:  Oh, I know, what a scary feeling, huh?

Marcus:  Right.

Lara:  This is why actually I force people to do this challenge. In fact, if anybody’s listening who’s thinking that, spend the next one on one chat you have in any direction, it could be with a partner, could be with someone at work, someone who reports to you, someone who doesn’t, whatever. Spend 10 minutes, only getting curious, no advice, no statements, nothing except for genuinely curious open question. And also create lots of silence. Like give them room to just unload. I’m so excited for you to see what happens. I genuinely think I can’t convince people by just telling them that this is true. They have to experience it for themselves to see how valuable this exercise is.

Marcus:  I completely agree with you. What’s one of your favorite questions that really cultivates curiosity in you?

Lara:  I actually said it a little bit earlier. My number one favorite question is the, “What are you optimizing for,” question? I use it all the time.

Marcus:  Give us an example. Tell us a story about that.

Lara:  Oh my goodness. Okay, so what are you optimizing for? There’s honestly so many. On coaching calls all the time, someone will be like … Actually, just this morning, I had a coaching call where someone was trying to figure out should they be directive with their teammates? Or should they be more on the empowering end of the spectrum, right? Like they are under pressure to ship this product. They’ve been trying to be empowering, but like oh, they know and this means they end of just telling all their engineers what to do. They’re wrestling with it.

Lara:  So I said, “Okay, let’s take a step back. In this role, what are you optimizing for? In your role as VP, what are you optimizing for?” And then they sit back, and they sit for a moment. This is an important part of coaching, not trying to fill in the silence, just sit back and say, huh, I think I’m optimizing for scaling myself, because I can’t do it all myself. I’m like, yeah, that’s probably true. So like, given that, what’s the right answer here? Being more direct, being more empowering.

Lara:  He’s like, man, if I’m scaling myself, I can’t just tell them what to do. It’s still going to be me doing it. I need them to come their own conclusions. I need them to develop these skills themselves. That was it. It’s just… The what are you optimizing for question just, it makes us all kind of sit back and be like, what am I optimizing for? Because it could be anything, it could be personal happiness. It could be recovering from burnout. It could be from hitting a stretch goal. It could be from building your skill.

Lara:  Like, we are optimizing for so many different things. I love it. I especially love it during feedback when I’m giving someone feedback about a behavior, because it forces me to be genuinely curious and not make assumptions about why they’re behaving a way that’s driving me up a wall. I get to say, “Hey, when you’re doing this thing, what are you optimizing for?”

Marcus:  I love the question. I’m going to steal it.

Lara:  Do it.

Marcus:  And it also sounds very engineer-y.

Lara:  Yeah.

Marcus:  Which is an added benefit too.

Lara:  Everybody’s optimizing for something and like, we can all sit back and say, oh, yeah, what am I optimizing for?

Marcus:  I think the idea of interdependent pairs, you mentioned the idea of like, two concepts this person in your example was struggling with,

Lara:  Mmhm.

Marcus:  Should I be directive and I’m going to get the words wrong, or should I be supportive?

Lara:  Yeah.

Marcus:  And of course, that’s kind of a binary decision as it’s placed out there.

Lara:  Right.

Marcus:  And when you talk about optimizing,

Lara:  Mmhm.

Marcus:  I feel like it turns it into a slider. We get to put the slider along a spectrum,

Lara:  Mmhm.

Marcus:  And it recognizes that there is… it might be a little farther on one side or the other, but the other one is always in place.

Lara:  Precisely. In fact, in one of my workshops I actually put up on the wall two signs, one says empowerment and one says direction, and then I read out scenarios and I have the whole group stand in a line between those two signs. And I say, “Okay, let’s say a senior leader is speaking over you in a meeting. Where do you fall in this line?” People move up and down it. One of your direct reports comes to you and tells you that they just got another job offer for two times their salary. Do you want to be more directive or more empowering?

Lara:  Like it’s just, you know there’s so many like, there’s no one answer. As you said, it’s a spectrum, right? And we all have a default, like I probably default, but I know I default to the empowering side of the spectrum. So what are the circumstances in which I need to move further towards the being more directive end of the spectrum?

Marcus:  Yeah, I was talking to somebody who went through some leadership training recently and it was around kind of the canoe core personality strengths. And the training talked about how every strength has a shadow.

Lara:  Mmhm.

Marcus:  And that idea that, okay, you’re an extrovert, right? That’s great, but the shadow is you dominate people accidentally, right?

Lara:  Yeah.

Marcus:  And there’s no good or bad, but I think it’s recognizing the shadow that you cast was kind of the point. And I thought that was kind of a nice way to think about it.

Lara:  That’s a beautiful way to think about it. Yeah.

Marcus:  I think your leadership seminar sounds just really amazing.

Lara:  It’s fun.

Marcus:  It sounds like a lot of fun. All right, well, finally, I have to ask Resilient Management,

Lara:  Mm.

Marcus:  What does it mean to be or to have resilience as a manager?

Lara:  Yeah. Oh, management is just so taxing. And it’s taxing for different people in different ways, right? Some of us are taxed because of the amount of talking we have to do all day, some of us are taxed by the amount of like confidential information we have to carry. Sometimes we’re taxed just by the volume of change that we have to weather and defend. You know? Sometimes we’re taxed by top down management, like there’s just so many different reasons why we might be drained in this role.

Lara:  So for me resiliency and resilient management has to do with making sure your bucket of energy is healthy. Given all of the things that are going to drain it, how can we make sure that you are refilling it or stepping away from it if you need to? Because I firmly believe that management roles are not for everybody, and that’s okay. There’s no judgment involved in that. Some of us just happen to be better at some kind of management circumstances than others, right?

Lara:  Like I am really good into firefighting mode, and I’m also really good in long-term planning mode. I’m not as effective. I’m just, it drains me if I’m in the middle, if it’s like both at the same time. Everybody’s different. So for me resiliency had to do with context switching. It has to do with like helping direct reports who are going through a really hard time. It’s having hard conversations, giving hard feedback. It’s communicating effectively. It’s just, it’s so many different skill sets to help you kind of be resilient in the face of all of these organizational storms.

Marcus:  I want to go into something you said because it really piqued my curiosity. I don’t want to misinterpret it. I don’t think you were exactly saying not everyone is cut out for management.

Lara:  Right.

Marcus:  But tell me more, because on the surface, it could be thought of as well, not everyone could be a manager. We’re kind of special. But I don’t think that’s what you meant, so tell me more there.

Lara:  No. So for me, it’s about circumstances and context and the people that you work with. Also, it’s funny, I want to go back to something you said earlier. You talked about being a tech lead with eight people reporting to you. Tech lead, that could mean anything. That could mean management.

Marcus:  It did.

Lara:  Right. It could mean just being an architect, it could mean being responsible for us hitting deadlines and like delegating out, scoping at work. Like management, it’s so many different things at different organizations with different titles, different responsibilities. People who are in matrix management organizations have a much different job than people who aren’t. So when I think about like being cut out for management, it’s not about whether or not you’re cut out for it. It’s like given the context, given these responsibilities and given the people that you work with, does this work for you? Like are you going to be super taxed at the end of the day? Or are you the kind of person that might thrive or somewhere in between?

Marcus:  Yeah, I think I remember imagining at the company where I got promoted that I wanted to be a manager there.

Lara:  Mmhm.

Marcus:  That there was an entirely different kind of there than I’d ever been in as an employee. And never before at any other company had I looked around and thought I’d like to be a manager here.

Lara:  Mm.

Marcus:  And so, I think that context was everything. And like you said, the titles are so varied, they’re basically meaningless.

Lara:  Yeah.

Marcus:  So I think if you’re wondering if you’re cut out for management, the first question I have is, would you want to be the best kind of managers you see in the organization you’re in right now?

Lara:  Yeah, I love that question. Often when I’m coaching people through their next role or their next, like, do they want to get promoted? Do they want to lead? Do they, whatever? I often ask about the leaders that they admire, both internal to the company and externally, like who are the people that you see you want to be more like, and what about them is appealing to you? And actually, what about that at that company made you want to try out management?

Marcus:  Yeah, I remember being, feeling a sense of respect.

Lara:  Mm.

Marcus:  For example, I remember when I was in my first 90 days probation, I was given the title junior programmer. I don’t know if they still use this title. It’s not particularly as illustrious. But I was given the title of junior programmer and I was meeting with my boss about three weeks in, in a one on one meeting, and the phone rang behind him and I could see on the little LED display, it was the VP of IT,

Lara:  Yeah.

Marcus:  And I just shut up.

Marcus:  I was just like, “Oh, you need to take that? I’ll just step out.” And he just reached back, lifted up the receiver and put it right back down. And he said, “We’re talking. Please continue,” and I didn’t even know what to say, but it was like this incredible moment

Lara:  Interesting.

Marcus:  That I had never experienced before to have a manager prioritize the time we were spending together.

Lara:  Which is fascinating because he was prioritizing his respect for you over his respect for … So it’s not even just about respect. Respect was a huge part of it. But there was something about focus and support in there that seemed like it resonated.

Marcus:  Yeah.

Lara:  Cool.

Marcus:  Yeah. I mean, at the very basics, I was a 26-year-old college dropout, who was a junior programmer, I was the least important person in the department.

Lara:  Yeah.

Marcus:  And yet he made a choice

Lara:  Mmhm.

Marcus:  That our one on one time was going to be between us and interruptions were just not going to happen.

Lara:  The other thing I love about that story is that that demonstrator showed rather than told, right? Like that manager could have said to you like I prioritize you and our time together and our one on ones, and that does not resonate with me. Sometimes it can but most often is the demonstration that really hits home.

Marcus:  Well and I, I can’t tell you how many … I mean, who hasn’t worked for a manager that said, “I’m very supportive and really have your back. And so all you have to do is come and tell me.” And like those sound good, and then the first time you try it, you learn,

Lara:  Mmhm.

Marcus:  Because that’s how you really learn it.

Lara:  Yeah.

Marcus:  Well, Lara, tell us about a manager that you look up to that inspired you.

Lara:  Yeah, oh, I’ve had a… I’ve been fortunate to have a bunch of really great managers, both like direct line managers, and also indirect managers. And the one that always stands out to me actually, you brought up his name earlier, Jason Wong. He’s the one who wrote that first team blog post. Jason was my manager at Etsy, and there were a bunch of seasons that were really tricky. I mean, you can imagine.

Lara:  And the ones that were tricky, not just like organizationally but tricky for me personally, Jason … I should tell you a story. There was one … I’ve got so many stories. He just always went to bat for me in ways that I didn’t even get to see. And whether I found out about that indirectly or later or whatever, like he just … There was one time I was going through an especially hard time and I was really actually worried I was about to get fired, not by him, but for other reasons that we don’t even need to go into.

Lara:  And he sat down with me, and he said, “Lara, I am your sword and I am your shield. Like, don’t worry. I’m here. Like, we’ll go through this together.” And it was just so powerful to know this human who had more responsibility, more clout, more you know seniority, all of these things. This person was ready to stand by my side, no matter what was happening. It was just yeah, speaking of showing rather than telling. It’s really, really powerful.

Marcus:  That is amazing. That is amazing. Lara, thank you for spending the time with us. Where can people find you online? Where can people you know engage your wonderful services?

Lara:  So, you can probably find almost all of my things on Twitter. I’m @lara_hogan on Twitter. I run a company called Wherewithall, so if you Google that and my name, you will definitely find it. But right now I’m getting really into Instagram. So if you look up Wherewithall’s Instagram page, you can see a ton of tips and tricks and tools, worksheets galore.

Marcus:  Wonderful. Thank you so much for being on the show.

Lara:  Thank you.

Announcer:  Thank you for listening to Programming Leadership. You can keep up with the latest on the podcast at and on iTunes, Spotify, Google Play, or wherever fine podcasts are distributed. Thanks to you for listening, and we’ll see you next time.

Announcer:  This has been a HumblePod production. Stay humble.

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