Lara hogan

Lara Hogan

Co-Founder Wherewithall

Lara is the former VP of Engineering at Kickstarter, co-founder of Wherewithall, a company that coaches and levels up managers, and author of the new bestselling book, Resilient Management.


You can be an amazing developer, but a terrible manager. We chat with Lara Hogan, former VP of Engineering at Kickstarter, co-founder of Wherewithall, a company that coaches and levels up managers, and author of the new bestselling book, Resilient Management, about her background going from web developer to manager, why becoming a manager isn’t necessarily a promotion, and some of the most important skills people need to not only be good managers, but in any supporting role.

Show Notes


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[00:00:05] SY: (Music) Welcome to the CodeNewbie Podcast where we talk to people on their coding journey in hopes of helping you on yours. I’m your host, Saron, and today, we’re talking about managing with Lara Hogan, former VP of Engineering at Kickstarter, co-founder of Wherewithall, a company that coaches and levels up managers, and author of the new best-selling book, Resilient Management.

[00:00:25] LH: I think knowing the ways you want to grow is the best thing you can do to unlock your manager relationship.

[00:00:32] SY: Lara talks about her background going from web developer to manager, why becoming a manager isn’t necessarily a promotion, and some of the most important skills people need to not only be good managers, but also be good supporters of managers after this.

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[00:02:11] SY: Thank you so much for being here.

[00:02:13] LH: Thank you so much for having me back.

[00:02:15] SY: So let’s start with your background. Tell us a little bit about how you got into tech. 

[00:02:18] LH: So I originally, I mean, one could say I got into tech when Neopets was originally around. I know you hear this all the time.

[00:02:27] SY: Yeah.

[00:02:28] LH: And I had a couple of pets and I needed like a little guild. I don’t remember what those were for, but there’s like an HTML tutorial on the website, but eventually I did it more for real. So I had an internship working for an HTML newsletter company, later basically became a front end developer, self-taught, and rose up the ranks eventually to work at companies like Etsy and as you said Kickstarter.

[00:02:50] SY: Which are some pretty big companies to work for. You were an Engineering Director at Etsy, you were VP of Engineering at Kickstarter, which one was your first management role?

[00:03:01] LH: Oh, it was even before then. So I managed at a company called Dyn. They do DNS believe it or not. It’s not that helpful to know a lot of things about DNS except when it really counts.

[00:03:11] SY: Yeah. What it counts though would really counts though. It can hurt sometimes. Yeah.

[00:03:17] LH: Yeah.

[00:03:18] SY: Yeah. What is DNS stand for?

[00:03:21] LH: That’s a great question. I feel like it stands for Domain Name something, but now I’m completely flanking on that.

[00:03:26] SY: Yeah, but it’s a thing that helps us with domain names.

[00:03:29] LH: It’s like a phonebook for the internet.

[00:03:31] SY: Yeah. Okay. So you were a web developer at Dyn and then you were a user experience manager.

[00:03:38] LH: That’s correct. Wow, you dug deep in that bio. I really appreciate it.

[00:03:42] SY: We do our homework. So what was the biggest difference between being a web developer and then being a user experience manager? What was that jump like?

[00:03:51] LH: For me, the jump was more substantial than I thought it was going to be. At first, I thought it was like, “Okay, I get to do the things that I’m doing every day, shipping code, making the website better, thinking about that user experience and now I’m just going to do all the same things, but like help to tell some more people like what they could be working on every day.” False. Totally wrong. In fact, I was so wrong that one of the people who reported to me started giving me the silent treatment after one of our projects. I don’t even really remember why at this point. I just remember he and I had a very different understanding of what my role was and I needed to really like start to ask more questions of the managers who I reported to, to be like, “Okay, what am I getting wrong here?” Like clearly I’m doing something. Well, silent treatment aside, like I want to make sure that the people I’m working with are happy and healthy and I can support them. And so fundamentally, the difference that I didn’t realize at first was management isn’t about like amassing power and like affecting change and about having more influence. It’s way more of a support role usually.

[00:04:59] SY: Interesting. Okay. So you try to amass all this power and kind of make an impact and that didn’t really work. Did you ever hit your stride as a UX manager?

[00:05:08] LH: Eventually, I think that engineer and I both agreed like this probably wasn’t a great fit for the two of us and he went on to move to a different team with a different manager and I ended up being able to hire some folks. And the folks who I hired were hungry for the kinds of work that we were able to do at Dyn. There’s something unfortunately like really ambiguous about when a team is in a flow versus when a team’s not in a flow, like what are the different pieces’ parts that can help you get to that flow, which I do cover a little bit in the book.

[00:05:39] SY: So you went from user experience manager at Dyn to Engineering Director at Etsy. Was that the next step for you?

[00:05:45] LH: Yeah. So I was hired as an engineering manager. I was actually I think only the second engineering manager that they’d ever hired. Everybody else who was there, they’re like “promoted” into management.

[00:05:57] SY: Okay.

[00:05:57] LH: And just as an aside, I don’t think that management is a promotion, but that’s a story for later.

[00:06:02] SY: Oh, interesting. Okay. We’ll have to come back to that. Interesting. Yeah.

[00:06:06] LH: Yeah. So at Etsy I was hired as an engineering manager and I was hired to work with their mobile web team.

[00:06:13] SY: Okay.

[00:06:14] LH: This is back in the day when like responsive web design was still kind of a new thing and responsive web design is about helping to make sure that your website looks good on a bunch of different screen sizes. So small screens like phones, mediums, like tablets or even like big desktop screens. And so there was already a bunch of people hired and so I was there to help them figure out how to have an impact on the website in that way.

[00:06:38] SY: So you went from manager to director. What’s the biggest difference between those two roles?

[00:06:42] LH: Yeah. And even in between there, I was like a senior manager, like there’s a bunch of levels and at every company it’s really different with those levels, meaning and the difference. The way that I usually try to describe it is you are responsible for a broader and broader like group of people or your area of impact is wider. At the director level, there’s also like a really funny, weird thing that happens where you have to create stability and clarity when there’s usually just tons of ambiguity. As a manager, I could ask my manager for advice, I could ask them for what I should be doing, I could ask them for just direction. When you kind of move up as a manager, more and more you get no direction. You get no advice. You really have to get comfortable swimming in a sea of ambiguity and creating more clarity for the people who report to you.

[00:07:34] SY: Can you give me an example of that?

[00:07:35] LH: Yeah. So there was a time when I was tasked with just, “Let’s reorganize this whole set of the department.” And I was like, “Cool. Why are we doing this?” And I got a bunch of like hand wavy answers and I realized I suddenly like I couldn’t rely on other people to tell me what should be happening or what was right or what was wrong. I all of a sudden had to start to think like, “Okay, who’s going to react in which ways to this? Do I think this is the right move? What’s going to be the best way to go forward? Honestly, is a reorg even necessary?” Those kinds of questions. If I’m in a manager role, I’m just rolling with it. I’m rolling with whatever is being told to me, and a director role, you’re much more responsible for that pushing back or again like creating clarity where there absolutely is none being handed to you.

[00:08:23] SY: And what ended up happening with that reorg?

[00:08:25] LH: It was a mess.

[00:08:26] SY: Okay.

[00:08:29] LH: Reorgs are hard. I’m not sure if I’ve ever been a part of a reorg that wasn’t a mess. If anybody out there is listening and you’re in the middle of a reorg right now, I apologize. I’m hoping it’s for a good reason, but it’s going to be painful regardless.

[00:08:42] SY: Yeah. And then the next step for you is VP of Engineering at Kickstarter. So we went from director to VP. Tell me about the difference between those two.

[00:08:50] LH: So in a VP role, it’s much more like you’re sitting at the table with other executives usually. Sometimes, again, it all depends on the size of the company. So as an example for comparison, as a director of engineering, the organization that I was working closely with, the people who reported to me was about 35 people. And when I was VP of Engineering at Kickstarter, the entire engineering organization was 35 people.

[00:09:17] SY: Wow.

[00:09:18] LH: So, you know, different sized organization, different sized company, it’s why all of these titles frankly are kind of meaningless in between companies. Camille Fournier wrote a book called “The Manager’s Path” and she walked through the difference in each level and kind of what each role means, but there’s a bunch of stuff in there that acknowledges also these titles can sometimes mean different things at different organizations. So at Kickstarter, what I did was a VP of Engineering was I tried to support this group of 35 people to build a management practice, like build more of a management culture. Everybody there was hungry for more processes in like structure around management, but it just hasn’t happened yet, the Engineering Department, and that’s what I knew I wanted to do it at my next company and so Kickstarter was a perfect fit there.

[00:10:06] SY: What does structure in organization look like among managers?

[00:10:11] LH: Totally, I mean we’ve been talking about these different levels but like also, again, what each of these levels do, and when you have these teams, I like to think of teams as like the atomic units of an organization who reports to which manager, like sometimes you might have a bunch of people all working on the same project and so they’ll all report to one manager. Other times you’ll have a manager who has direct reports that it’s span a bunch of different projects and those might be what we would call like a Matrix Management Structure. There’s all of these different ways we can organize these people and who they report to and the stuff that they work on. And there’s no one right or wrong way to do it. So a lot of this is thinking about, “What are we optimizing for as a group?” Maybe we’re optimizing for making sure engineers have the same manager for the entire duration of their career or this company to help with like they have that shared contacts, they know all of their history, they can help get them promoted, all that stuff. Sometimes we’ll optimize for making sure a manager has context about the day-to-day inner workings of a project so they’ll probably want to have all the people on that project report to them and not like engineers scattered across different projects. So you can see there are so many different ways that someone could go about it. And again, no right or wrong way. It’s all just trade-offs.

[00:11:31] SY: So it’s interesting that earlier you said that being a manager isn’t necessarily a promotion.

[00:11:37] LH: Right. Yes.

[00:11:37] SY: Tell me a little bit about that because I think that’s kind of the thing most of us believe is how you become a developer and then eventually you get to the next step and the next step is obviously being a manager. So if it’s not a promotion, what would you call it?

[00:11:48] LH: Right. I would call it a transition.

[00:11:50] SY: Okay.

[00:11:51] LH: So for me, promotion indicates you get more of something. You get more clout, maybe more responsibility and that’s definitely true regardless. But like we often think like a promotion means like you have proven that you are operating at the next level in this role. And what’s weird about management is that it's a completely different discipline than engineering. There’s like obviously like overlaps there, but like engineering is one set of skills and management sometimes is like an orthogonal set of skills. There are some things in common like you have to know how to influence the people around you when you’re an engineer, especially a more senior engineer, and when you’re a manager. That goes all the way across. But for example a manager, you might have to communicate out news to your team. And as an engineer, you may or may not be responsible for that thing.

[00:12:42] SY: Yeah.

[00:12:43] LH: As a manager, you’re responsible for a bunch of people’s career progression and like as an engineer, you’re probably not responsible for that at least not directly. Since it’s such a different role and it has so many different skill sets that might be used, that’s why I don’t think of it as a promotion because in engineering, if you get promoted and get promoted and get promoted, you may still not be a great manager, but you’re a fantastic senior engineer.

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[00:14:40] SY: So once you became a manager, however you did get promoted, you went all the way up to the VP level. What were some of the biggest hurdles you face when you are climbing that ladder?

[00:14:49] LH: I kind of hinted at this before, but there’s that thing about making some sense out of ambiguity where all of a sudden there’s no boss to tell you what to do anymore and there’s no one there to really give you that guidance that you’ve probably been leaning on for the rest of your career so far. And the more and more you kind of think about supporting the people around you and helping them build cool things and make it a healthy organization, the more you’re probably going to have to build your own support network from scratch, both inside the company and outside the company.

[00:15:22] SY: Can you give me an example of that? Was there a moment when you felt like, “Oh, my goodness, I can’t rely on what I used to rely on to get this problem solved.”

[00:15:30] LH: Absolutely. So as a manager, there were a bunch of times when I would go to my manager, I’m thinking of one manager in particular, and I was noticing he wasn’t kind of giving me the things that I thought a manager should give me. So at the time, I was like, “My manager should be giving me feedback, giving me advice, giving me an opportunity to like verbally process stuff out loud, like give me some gut checks. Give me some stretch projects to help me grow.” And that’s what I thought my manager should be doing, any manager should be doing, and this manager wasn’t doing any of those things. And so I noticed like, okay, I’m starting to lean on other people around me and I feel weird about it. I feel like I’m kind of going behind my manager’s back and like leaning all these other people. So I had a heart-to-heart with him in which I asked him, “Hey, what do you think a manager’s role is? Can you describe how you picture it?” And he did and he described it as setting executive direction, like creating that forward facing vision and helping us figure out how to get there was really tactical and like totally I can see why he had that definition of what management is, but I needed something else. So I said to him, “These are these things, you know, stretch projects and getting feedback and giving me some space to verbally process stuff. Is it okay if I lean on some other people for that too?” And he was like, “Oh, yeah. Do not come to me for those things.” So I actually had started developing this idea of like a manager crew where instead of just having one manager to support you as you grow and develop, you should build out a crew and the metaphor I use for this is a Voltron. So Voltron comes from like a 1980’s television show, in which a bunch of like lions come together and form a superhero robot thing.

[00:17:16] MAN: Ready to form Voltron. Ignite hyper power.

[00:17:22] LH: And so I’m picturing this as like manager who’s like one person’s an arm and one person’s a leg and they all kind of come together to be the superhero manager that I would love to have in my life and maybe that one arm is about giving me good feedback and that one leg is about giving me that space to verbally process. But I think it’s really important for anybody to think about who is in their Manager Voltron of support and add to it over time.

[00:17:46] MAN: Form feet and legs. Form arms and body. And I’ll form the head.

[00:18:02] SY: So you currently coach managers and emerging leaders. That’s what you do all day long, which I assume means that you’re also a good manager. Do you remember a moment when you realize that you were good at this?

[00:18:14] LH: So I joke a lot about those moments when you ask someone a powerful question and it makes them sit back and go, “Huh,” like that painful but excited feeling.

[00:18:26] SY: Yeah.

[00:18:26] LH: We’re like, “Oh, that’s a hard question that they just asked me, but now it’s inspiring all this new thought.” And the first time that happened to me where I asked a question and made them sit back and be like, “Huh,” I was working with someone who said, “I think I really want to be a manager.” And I was like, “Cool. What would you gain from being a manager?” And they were like, “Well, I could change the things around me more effectively.” And I said, “Oh, interesting. I have not found that to be true. What’s like what’s blocking you from enacting that change in your current role?” And they sat back and said, “Huh.” I don’t remember what the reasons they had were, but it was obviously something both internal and external, like maybe they were external factors that they could still overcome or internal factors that they just hadn’t explored before and it was that kind of question, that powerful question that both made me realize like, “Oh, I think maybe I can do this work as a manager and help people go deeper and introspect and explore the shape of the challenges or roadblocks that they’re encountering and come to their own answers.” And later, by the way, I found out that, sure, this is sometimes what managers do but really it’s what coaches do. So for me, being a good manager is actually more about being a good coach.

[00:19:43] SY: Let’s talk about that. What is a coach?

[00:19:45] LH: So a coach is someone that helps you explore any topic, usually work related, to kind of stretch and grow and come to your own conclusions, find your own answers and continue to evolve as a person. So in my job as a coach, I use two tools. One is open questions, those questions that make you go, “Huh, all right,” and reflections, which is like holding up a mirror to someone and helping them introspect or helping me to just say, “Here’s what I’m hearing you say,” you know, is that right to help them take that pause and kind of introspect. So that’s what I have the honor of doing every day and it’s just the best job I’ve ever had.

[00:20:25] SY: And you took this skill, this thing you’re really, really good at and you created a whole company out of it. What inspired you to make a company out of being a coach?

[00:20:33] LH: There was something about how I was coaching people internal to Kickstarter and I really wanted to meet a lot more managers and leaders at other kinds of companies. So Etsy and Kickstarter for example are both mission-driven companies. They’ve both got the same vibe and the same kind of internal structures and hierarchies and that kind of thing. And I read a study about expertise, like how do humans build up expertise, and the study compared firefighters in urban areas to firefighters in rural areas, and they control for the number of fires and number of years in service and all that and they found that firefighters in urban areas were much deeper experts at fighting fires than the ones in rural areas and that was because the diversity of building densities of population densities, of materials, of heights, and there’s something about having a diversity of experiences that you go through that makes you a deeper expert. So I ended up deciding like, “Let me go see if I can work with a bunch of people at a bunch of different companies and see all of the different ways that organizations operate, different sizes, different ages of company, different like political hierarchies, different messes.” And for me, it was really exciting to think about coaching folks in all of those different contexts.

[00:21:51] SY: What were some things you notice just in general? What did you learn from working with people across different fields?

[00:21:56] LH: One of the hilarious things that I learned is like it’s all the same problems.

[00:22:02] SY: Oh, interesting.

[00:22:03] LH: It’s different contexts and different ways you might need to tackle a problem because of that context that you’re in. You know, the people who are around you or what the company cares about, that’s all different, but like the problems are all the same. Usually, it’s like some big changes happened and we don’t know how to navigate it or some conflict is happening between two people or more and I don’t know how to help them stop it. Or this person is behaving in a way that I really don’t like. How can I help them behave a little bit better? It’s all the same problems.

[00:22:39] SY: So you not only worked as a coach, but you also wrote a book about management. What made you decide to write a whole book about this?

[00:22:46] LH: I noticed that I was giving lots of the same worksheets and sharing the same frameworks and asking the same questions across my coaching sessions. And I started to think to myself, “Oh, I think I’ve got like a bunch of stuff that if I write it down it might be helpful to people in all different organizational context in all different roles because again those problems are still the same.” You know, I found myself coaching a lot on giving feedback on how to grow the other people on your team, on how to clearly set expectations, on how to manage like your energy drain when you’re in any kind of leadership role, and just generally like how to weather the storms of change that happened within an organization. And those are fundamentally the stuff that I put in the book.

[00:23:34] SY: So were any of the things you put in the book, did any of them come out of any negative experiences that you have with maybe some of your past managers or even just you as a manager?

[00:23:45] LH: Absolutely. There’s a whole chapter about communicating effectively that I’m hopeful as helpful to anybody in any role about how to approach when big news happens. How do you continue that information flow in a way that’s helpful to the people who are going to hear that news? There’s all sorts of stuff about like picturing how they’re going to feel when they need to hear that, coming up with some talking points to prepare that way you can proactively answer questions, coming up with some potential negative questions that people might ask that you don’t want to get blindsided by so you can actually prepare in advance. These all have come out of experiences that I probably won’t share too much detail about where I definitely, definitely, definitely messed up the communication of some big scary news.

[00:24:32] SY: When it comes to being a good manager, how would you describe that? We talked about being a supportive team member. We talked about being able to break news and being able to kind of grow people’s careers. But how would you describe it as a whole? What is a good manager?

[00:24:46] LH: To me, good management is almost entirely about listening and like processing what you’ve been listening to. So like if I’m there and I’m just thinking about the future or if I’m just thinking about myself or I’m just thinking about the organization that I'm surrounded by, I’m probably not that good of a manager because what’s missing is listening to the individuals on the team that you’re supporting. And without that really core piece of information, like what is each member of this team bring to the table? What are each of their strengths, their weaknesses, their fears, the way that they want to grow? Without all that information, I don’t think you can be a successful manager and listening is the only way to get that information.

[00:25:26] SY: So being a good listener doesn’t sound that hard.

[00:25:30] LH: I know. I know.

[00:25:31] SY: It sounds like a really simple thing, like we learned about active listening when we were younger. We learned about paying attention and being empathetic. So these skills don’t seem very hard. Why is this such a difficult thing? Why is it so hard to be a good manager?

[00:25:43] LH: I know. So it’s funny that you say that we learned about active listening as kids because I definitely learned it, but I didn’t retain it. Most of the people who I talk to, and myself included by the way, we default to what I’m going to call like internal listening where someone else is talking but you’re just hearing the sounds in your own head. Maybe you’re thinking about how what they’re saying relates to you or maybe you’re thinking about the next thing you’re going to say or the next question you’re going to ask. But this isn’t really listening and we do it all the time. So there’s two other things that I recommend that people think about when they’re more actively listening. The first thing is the actual words that the person is saying and what’s hard about this is that means we have to tell our brains to stop thinking. We just need to like take in those words, like absorb those words and process those words before we start responding, which actually weirdly means that there’s going to be a lot of awkward silences in our conversations because we’re going to process what they’re saying before we can actually come up with something to say in response. It’s cool, it feels awkward, but I promise it’s active listening. And then the other thing to kind of take in as data is the whole environment. So what’s their body language like? What’s their tone of voice? What else is happening in this environment if it’s a group setting? Is there an energy buzz in the room? Does everybody look like they’re falling asleep? When the group laughs altogether, that’s like the outside environment energy. Are we in a tiny cramped phone booth? Right? That stuff. And that’s the other data I think is really important to kind of take in when you’re actively listening. So it’s really those things, they’re listening to their actual words, taking it all of that data from the environment and then processing it before you start responding.

[00:27:34] SY: Coming up next, Lara talks about how to listen, how to get feedback, and how to grow and help others grow too after this.

[00:27:51] Command line Heroes, an original podcast from Red Hat that I host is back for its third season and it’s all about programming languages. Here’s a clip from the first episode, telling the tale of Python where I’m chatting with Emily Morehouse, one of five women currently working as a core developer on Python about how the language’s extensibility is the key to Python’s attractiveness.

[00:28:14] EM: When approaching software design, you often will have to take either existing software or other software systems and kind of get them all to work together. And one of the very true values of how you can design software is making sure that it’s extensible.

[00:28:35] SY: It sounds like a no-brainer but not every language has achieved the level of extensibility that Python had right from the start. And the truth is if a language doesn’t have extensibility baked into it, there’s a good chance it’ll end up collapsing under its own weight as it grows.

[00:28:53] EM: Python has been designed in a very interesting way that allows it to be kind of extensible at its core. You can actually like patch different pieces of the system at run time. So if you want to switch out how modules are imported or you want to switch out your string type or your integer types, Python allows you to do all of these things fairly easily. At the heart of Python’s extensibility is something called C extensions or C modules. And so Python has actually been designed to give you an entry point to other languages, and essentially if you can write a C extension or C module that can then bridge to, I mean, hundreds of other languages, you can kind of hack Python.

[00:29:52] SY: You can find it wherever you get your podcast and make sure to check out the show at

[00:30:03] SY: For managers that you coach, is it simply that they don’t know these steps and you’re kind of educating them and giving them an outline of things to do or is it even when they know what steps they should take they struggle to actually implement it?

[00:30:17] LH: Oh, it’s absolutely both. You know, a lot of us don’t think about how we listen every single day. And so the first step is for me to say, “Hey, here’s this.” I usually call them by the way three levels of listening, Level 1 is that internal listening, Level 2 is more about them and their words, and Level 3 is about their body language and the environment. So I kind of frame it as those three levels and then I say, “Cool. Your homework here is to practice Level 2 and Level 3. And when we meet next, I want to talk about what was hard, what was surprising, what was awkward, what you learned from it, what were the takeaways.” And so usually it’s genuinely that practice, that being able to over and over and over because it takes so much self-management to get good at this. I find myself whenever I notice that I’m in that level one listening the internal to my head listening, I’ve started a practice of saying to the other person when I realize it like, “Oh my goodness. I’m sorry. I’ve been in my whole head for the last 30 seconds. I’m so sorry. Could you please just say it again? I want to genuinely listen to what it is that you’re saying.” And sometimes that’s awkward and usually they chuckle and then they say it again and I really force myself to hear the words that they’re saying.

[00:31:24] SY: Okay. So feedback. Feedback is another really big part of a manager’s job. What is the most effective way to give feedback?

[00:31:31] LH: So I have something I call the feedback equation and anybody can use it. So the feedback equation starts with your observation of someone’s behavior. This is like the who-what-when-where of this person’s behavior. So the example I usually like to talk through is someone is sending me really short emails, like terse emails. It seems like they’re mad at me. There’s only like three to five words in the body. I just want the observation of his behavior, but I can’t include any of my judgments or assumptions, like my observation of this behavior should not be you send me really short emails because that’s a judgment, right? I also shouldn’t say, “It seems like you’re always in a hurry,” also just an assumption, right? My observation would be more like, “Hey, in the last week, you’ve sent me six emails that each contain fewer than five words in the body.” Observation, just the facts, just the who, what, when, and where. Next though we can start to include the impact of this behavior and this is the next part of the feedback equation. So the impact could be, “Does this behavior impact me? Does this the behavior impact their co-workers? What else does this behavior impact?” Usually, we know how it impacts us. There’s a reason why we’re giving this feedback, but the weird thing is the person we’re giving the feedback to, they might not care about what we care about.

[00:32:54] SY: Yeah.

[00:32:54] LH: So it’s really important to take a step back and say, “Okay, what does this person care about? And can I reframe the impact of their behavior in a way that describes like, ‘Okay, they are going to care about this?’” So in the example of the emails, like I might say, “It seems like you’re mad at me all the time and like I care about that,” but they might not care about how I feel about them. But maybe they care about efficiency. Maybe they care about like getting the project done. So I would say the impact of the emails with fewer than five words in the body is that I have to reply to get more context and this adds time to the process. So like it’s going to drag it out over time and I don’t think that’s what you want. Impact. The last part is either a question for them about this behavior or a request for them to behave differently. Now most of us, frankly all of us default to making a request, right? At this point, I can be like, “Could you please write longer emails?” It feels obvious, right? But this doesn’t really help at all. In fact, it kind of shuts down the conversation and it makes it feel like a hard piece of feedback. And frankly, if you’ve gotten this far, if you’ve described an observation that’s truly fact-based and an impact that they already care about, they are already thinking about how they should behave differently. You don’t need to tell them how. So instead, ask a genuinely, curious, open question. My number one favorite open question to ask at this point is, “What are you optimizing for? What do you optimizing for when you write emails?” And I want to genuine know the answer to that. I can’t be loaded, right? I can’t be like, “What are you optimizing for?” Right? And it also can’t be like a leading question, like, “What if you try blah?” Because that’s a request. I should ask something I’m genuinely curious about because that’s going to increase my empathy and it’s going to turn it into a two-way dialogue where we’re going to come to a really good solution together.

[00:34:46] SY: So another thing that we talked about in terms of the role of managers is that it is their job to grow other people which of all the things we talked about sounds like frankly the most intimidating job that I have to take care of other humans and help them grow as people and in their careers. How do you do that? How do you grow someone?

[00:35:05] LH: There’s four skills that I usually try to tell people about and help them kind of practice. We’ve already talked about one, which is feedback. Feedback is a crucial skill that people can employ to help like level up and grow the people around them. The other three are mentoring, coaching, and sponsoring. So mentoring is all about giving advice and sharing your perspective and like sharing what you seen work and not work. It’s like you’re teaching someone. That’s mentoring mode. Mentoring is really good for helping someone get unblocked and like helping someone on board, like it’s a good problem solving skill to use, but weirdly it doesn’t help people grow. It just helps people get unstuck. So mentoring is one thing we can try to employ once in a while. Most of us default to it, but I recommend people start to practice the other big two, coaching and sponsoring. So coaching, we’ve also talked about a little bit, right? Helping someone introspect, helping someone explore the shape of a problem that they’re dealing with. And so coaching is all about not just like telling someone what to do or giving them advice but sitting back and asking lots of questions to help the other person connect their own dots. And weirdly, this is the one that helps people grow because people are kind of like forming their own connections, right? They’re building those new brain wrinkles themselves. They’re way more motivated to go and do the thing after they’ve developed their own solution. So coaching is the second big skill, and the last one is sponsoring. So sponsoring has to do with feeling on the hook to help get someone to the next level. So that’s like giving them an opportunity, like a promotion or helping them get a conference talk accepted or telling their manager that they’re doing a really good job, anything where you are putting your reputation on the line for this other person and getting them those visible and developmental assignments. That’s what sponsorship is and it is so powerful. Of all of these skills, it’s the one that’s directly correlated to career trajectory.

[00:37:08] SY: So I want to talk about the flip side of managing people, which is actually being managed yourself. What are some things that make someone a good person to be managed?

[00:37:18] LH: I think knowing the ways you want to grow is the best thing you can do to unlock your manager relationship. So like if you show up and you’re like, “I don’t know where I’m going. I don’t know what I want to be working on.” That’s totally cool. Your manager hopefully will be awesome and ask you lots of good, curious questions, but frankly, most managers don’t do this by default. So if you have an idea of how you want to grow and you can describe it to them, maybe that’s, “Hey, I want to gain this new skill set,” like learning this computer language or public speaking or if you want to get an experience, like, “Hey, I would love to learn how to be a mentor to someone. I would love to have an experience being a lead on a project,” or really anything. Having that in mind and being clear about it with your manager is awesome. The other big thing I would recommend people do is tell your manager what you need. Managers are not mind readers. I wish that we were so that we could like help people the way that they want to be helped. But frankly, if something’s wrong, make sure you tell your manager about it. They might not be able to guess. I would hope that they can, but it’s way more important to be clear about what you need from them.

[00:38:31] SY: We talked about listening being a really important part of communicating when you’re a manager. When you are being managed, what communication skills really come into play?

[00:38:40] LH: Still the active listening. I think that’s going to be core to all humans is that active listening skills and I would still also weirdly say that feedback skill, which is definitely a form of communication. I firmly believe in people giving feedback in all directions and that means to your peers and to the people above you. So those are two big communication skills I think are critical.

[00:39:03] SY: That’s so tricky when you’re the one being managed to give feedback.

[00:39:06] LH: Yeah.

[00:39:06] SY: How do you navigate that? I think that the equation certainly helps but even thinking about the courage to give feedback, the confidence to have an opinion, to voice an opinion can be really scary, how do you navigate that?

[00:39:17] LH: One hundred percent. There’s that power dynamic at play, right? If this goes sideways, this person could ruin your job.

[00:39:24] SY: Yup.

[00:39:25] LH: Certainly, that’s important to keep in mind. So I like to sometimes give feedback that doesn’t sound like feedback and usually that starts with asking the person some kind of question to get the thing that they care about or the thing that they’re optimizing for. So I might ask a manager like my manager, “Hey, what are you most worried about right now and what are you most excited about right now at work?” Just a general question like that might give you some more data about the things that they care about. Maybe they care about a big scary project that’s coming down the line or they care about hiring or they care about how the team is doing. Whatever you here in that, take that in and process it and see if you can deliver some feedback to them that has to do with that thing. Let’s say I’m annoyed because my manager only ever meets with me once a quarter and I would like to meet more often. I would ask them that question like, “What are you most worried about right now?” And like let’s say that person says, “Oh, I’m really worried about our ability to get things done as a team. We’re just not shipping enough. I’m really trying to work on that.” I might say, “Got it. Okay.” So you are really, really hoping that we can get better as shipping it as a team. “I’ve got an idea, what if feedback more often so we could like calibrate what we need from each other, what you need of me so that I can make sure that we are executing on the right things?” That’s technically a feedback, but your manager may not know it.

[00:40:50] SY: Yeah, secret undercover feedback. I like that.

[00:40:52] LH: Undercover feedback. That’s basically how to get to know what they care about first.

[00:40:57] SY: What other advice do you have for folks who are being managed?

[00:41:01] LH: A big thing that doesn’t occur to folks that I love to bring up is that your peers are also awesome people to lean on and get to know. When I was the manager of the performance team at Etsy, one of my direct reports started a peer one-on-one calendar where she would get coffees with all of her peers. There were only two other peers in the team. So she started to add other people to the mix too. So she would get a coffee like once a week with the other people in our surrounding teams, and she got to know everybody so well and understand what they were working on and learn from them and get more help with stuff and answer their questions. So I feel like there’s an undervalued thing here about like leaning on and getting to know your peers not just on your team, but even like across the company. It can be really valuable to develop those peer and relationships and get to know each other.

[00:41:51] SY: What can people do who are being managed and don’t feel like they are supportive or don’t feel like their manager is particularly receptive to feedback?

[00:42:00] LH: Yeah. My number one piece of feedback for these situations is to build out your Manager Voltron. So start to think about who else in your midst at the company and even outside the company could give you the support you need that you might need from a manager, especially if your manager is not supporting you in the ways that you need.

[00:42:19] SY: So if you think about the manager and the person being managed as having a really good symbiotic relationship, what does that look like?

[00:42:28] LH: I see that manifesting as having a shared understanding about what’s important to each other. So say I’m a manager and what’s important to me is that the team is feeling really good and what’s important to my teammate is that she is on a track for promotion, like having that shared understanding and helping each other work towards that stuff can be really, really, really beneficial to everybody involved. I think a lot about that like clear communication and like sensitivity to what each other person needs, not so much being sensitive to what your manager needs because that’s not super fair but for a manager to be sensitive to what their direct reports need certainly.

[00:43:10] SY: Now at the end of every episode, we ask our guests to fill in the blanks of three very important questions. Lara, are you ready to fill in the blanks?

[00:43:17] LH: I’m prepared.

[00:43:18] SY: Number one, worst advice I’ve ever received is?

[00:43:22] LH: Oh, my guidance counselor in high school told me I should definitely not take that Visual Basic course because I’ll never need to use it.

[00:43:28] SY: Oh, that was a mistake.

[00:43:31] LH: Yeah.

[00:43:32] SY: Did you take it anyway?

[00:43:33] LH: I did.

[00:43:34] SY: And what made you decide to? Because that’s kind of a tough position because usually the guidance counselor has some power, has a lot of knowledge, has some good advice. What made you decide to not follow that advice?

[00:43:44] LH: There were no other good electives.

[00:43:46] SY: Okay.

[00:43:46] LH: The only other one that was really available was like a stenography course and I was like, “I’m just going to take this.”

[00:43:51] SY: Yeah, good for you. Number two, my first coding project was about?

[00:43:55] LH: Neopets, it was about building out a Lord of the Rings themed guild for my pet.

[00:44:01] SY: Number three, one thing I wish I knew when I first started to code is?

[00:44:05] LH: I wish I knew how much fun the puzzle solving is in coding. I didn’t realize that it was just a bunch of fun puzzles that you get to sit down and chew on for a while.

[00:44:15] SY: Yeah, that’s a good description of what coding is. Yeah. Well, thank you so much for being here and sharing all of your management wisdom with us. Thank you so much.

[00:44:22] LH: Thank you.

[00:44:30] SY: This episode was edited and mixed by Levi Sharpe. You can reach out to us on Twitter at CodeNewbies or send me an email, Join us for our weekly Twitter chats. We’ve got our Wednesday chats at 9 P.M. Eastern Time and our weekly coding check-in every Sunday at 2 P.M. Eastern Time. For more info on the podcast, check out Thanks for listening. See you next week.

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