Management coach Lara Hogan on perfecting the leadership craft

Each person on your team has different needs, responds to feedback in different ways and evolves in different trajectories – and management should always reflect that. Even when you reach the perfect team dynamic – a new hire or budget cut can easily throw things off balance. But no matter how isolating a management position can feel, you’re not going through it alone. And most importantly, as Lara Hogan puts it, you really don’t have to.

Lara Hogan is an author, public speaker, and coach on management and leadership. Over the years, she worked in jobs such as Engineering Director at Etsy and VP of Engineering at Kickstarter, growing emerging tech leaders, demystifying public speaking, and championing engineering management. But it wasn’t until 2017 that her love for coaching led her to co-found Wherewithall, a knowledge service to help managers hone their skills to better support their teams.

In their workshops and trainings, she found herself giving the same advice over and over again, and so she decided to write it all down. Her latest book, Resilient Management, was born out of that. When should you empower and coach your team vs give them specific instructions on what needs to be done? How can you build the resiliency needed to succeed at the job? What does good, actionable feedback look like?

In today’s episode, we sat down with Lara to chat about leading and supporting a team – from learning mentoring and coaching skills to mastering the delicate art of feedback.

If you’re short on time, here are a few quick takeaways:

• Make a plan for one-on-ones based on the person and the context. While some people might need more mentorship, others will just want some feedback or to bounce off ideas.
• Over time, teams can experience some friction, but that’s to be expected. Treat it as a learning opportunity so they can figure out what each person is feeling and how they can work together.
• Most of us default to mentorship – sharing advice on what to do – when supporting others. But coaching – helping people figure out the answer themselves – can be even more valuable.
• Instead of giving prescriptive advice, focus on the recipient and give feedback around their motivations and worries. That way, it’s much more likely to stick.
• The bigger your support network is (in and outside your organization), the more resilient you become as a manager.

If you enjoy our discussion, check out more episodes of our podcast. You can follow on iTunes, Spotify, YouTube or grab the RSS feed in your player of choice. What follows is a lightly edited transcript of the episode.

The craft of managing

Liam Geraghty: Lara, welcome back to Inside Intercom. We’re delighted to have you back.

Lara Hogan: Thank you so much. I am really excited to hang out again.

Liam: For anyone who didn’t hear the episode, which I think was back in 2016, could you give us a little bit about your career journey so far?

Lara: Absolutely. So, back in 2016, I was working as a director of engineering at Etsy. After that, I was the VP of engineering at Kickstarter. And since then, I have been trying to support managers and leaders, usually in the tech industry, as they support their teams. I try to do that via one-on-one coaching, group coaching, and training workshops.

Liam: Today is all about how to be a resilient manager, which is apt, I suppose, because you’ve written a book about it. It’s called Resilient Management. Why did you want to write this book, and what prompted it?

“I realized that I was saying a lot of the same things over and over again about how to be a good coach for someone”

Lara: I was spending a lot of time thinking about what managers need when they enter this role. From my experience as an engineering manager, engineering director, and then VP, I saw a lot of managers enter into this role, myself included, without any training or guidance. It was kind of the luck of the draw. If you had a team of experienced managers who were good at teaching you and helping you and supporting you, then you could level up and understand the difference between the role of a tech lead and a manager. Because, of course, that’s different at so many different companies.

I was trying my best to support folks in these kinds of roles, both folks I worked with directly within the company, and outside of the company, and I realized that I was saying a lot of the same things over and over again about how to be a good coach for someone, how to give good feedback when you’re in this management role, and I realized that, if I was saying it enough times, I should probably write it down. And the book was born.

“Even these very, very experienced leadership rooms are mind blown by the idea that maybe offering their advice or perspective is not the most helpful thing for somebody”

Liam: In the forward to the book, Camille Fourier says, “Management is a hard job that even after years of practice, you can still find yourself coming back to square one.”

Lara: Absolutely. In these workshops I’m giving to tons of different kinds of managers and leaders at different companies, I talk about a lot of the things that I touch on in the book. What I’m seeing is that folks at any experience level still tend to learn something new. For example, mentoring versus coaching. Mentoring is giving advice, sharing your perspective, and suggesting things somebody could try. Coaching is about asking open questions to help someone connect their own dots. And even these very, very experienced leadership rooms are mind blown by the idea that maybe offering their advice or perspective is not the most helpful thing for somebody. It’s awesome to see folks in lots of different disciplines and levels be able to level up their skills in supporting people around them.

Meeting your team

Liam: In the workshops and the book, you kind of walk people through how to create stability, clarity, and trust amongst the group they’re managing. Let’s go through some of those areas. What do you mean when you say managers should meet their team?

Lara: It’s funny, we could talk about so many different aspects of this. Chapter one’s about meeting your team. It’s about understanding who each of these individuals is and what it looks like when they come together to work together, support each other, and give feedback to one another. That first chapter is about understanding them as individuals and what they can do as a group. Everybody’s going to want feedback in a different way. That means people would like to be recognized in different ways, and understanding the nuances of each individual person – their strengths, their opportunities for improvement, the best way for their brains to receive feedback – is going to help us as leaders and managers work with them as effectively as possible.

If you’re like me, you probably try to use the same techniques with every person you work with. And I learned very quickly that that was not going to be successful. Not everybody wants to hang out and talk with me about what their plans are for this sprint, for example. Some people just want to get it done. Some people just want to ping me with questions afterward. Some people love workshopping problems together. Everybody’s different, and it requires us, as managers, to understand what works and what doesn’t with different people.

Liam: I suppose that brings up the dreaded one-to-ones, for new managers, anyway. It could be daunting, and maybe they’re suddenly managing their peers. What advice would you give to people there?

“Have a game plan for each one-on-one based on the person you’re working with and what you know about them”

Lara: Have a game plan. It’s okay if the game plan goes out the window. That’s totally cool. Everyone’s going to look different, but having a game plan ahead of time allows you to make sure this person gets the support they deserve. And again, that’s going to look different for everybody. Someone who’s just recently joined the team is going to need a lot more mentorship from you about how the team works and what’s expected of them. Someone who has just taken on a big leadership project, on the other hand, is not going to need lots of 101 information. They’re going to want to bounce ideas off of you. They’re going to want feedback from you. And they’re going to want you to give them some autonomy in how they’re tackling those projects. Have a game plan for each one-on-one based on the person you’re working with and what you know about them.

That game plan’s going to evolve over time. It should evolve over time. It’s okay to, let’s say, spend a lot of time coaching somebody through a challenge, and then, in the next week, think about how you can sponsor them for a brand new kind of challenge. Or it’s okay to spend a one-on-one listening to them unload and verbally process, maybe even vent, because maybe that’s what they needed at that moment. It’s also okay to say, “No, that’s not going to help us get the most useful outcome.” I want to help equip managers with all these tools. That way, they can figure out which ones might be the most helpful and useful to employees, given the situation.

“Storming is actually a necessary part. We can’t skip over the friction; we can’t skip over working it out”

Liam: When you write about growing your teammates, you mentioned Tuckman’s stages of group development: forming, storming, norming, and performing. This is the storming stage, right?

Lara: It can be, yeah. Anytime you get a group of people together, at first, they’re often in harmony, mostly because people are still feeling it out. They’re trying to figure out what’s going on. That’s the forming stage in Tuckman’s stages of group development. And then, storming is actually a necessary part. We can’t skip over the friction; we can’t skip over working it out; figuring out where our difference is, what’s the misunderstanding, what we each need, what we each expect. That’s going to bring a little friction, and that’s okay. The reason it exists as a stage is for us to work through it and get to how we want to be existing and working together. We need to have a little bit of friction, a little bit of confusion, clashing even, which can look very different in different situations, in order to make it to a more healthy group dynamic.

Now, I’m not saying toxicity is necessary for healthy groups. I’m not saying that a lot of conflict is necessary to lead the team, but I just want to set expectations. If you’ve got some storming, treat it as a learning opportunity, “Okay, let’s figure out what we each need and how we can work together.” I give a couple of examples of tools you can employ to identify that conflict, dig into it and see what folks are feeling.

“What does good, healthy feedback look like?”

Liam: And like you said, obviously not huge amounts of it, but it’s natural that, at this kind of stage, you would have a little bit of friction.

Lara: You got it. Friction can look like, “Okay, let’s get really clear about what our team mission is.” It can look like, “Okay, we’re all disagreeing about what we’re here to do, so let’s figure out that path forward.” Friction can be, “I don’t like how someone’s commenting on the code reviews.” Right? That’s important for us to figure out. What does good, healthy feedback look like? How can we make sure everybody has the skills and tools they need to give powerful, helpful feedback? It could look like so many different things. And again, as you said, it’s a natural part of how we figure out how we’re going to work together.

Leadership hats

Liam: You also talk about these four different hats. Earlier, you mentioned coaching and sponsoring. Can you tell me a little bit about these four hats that a manager may end up wearing during this kind of growth for your team?

Lara: Absolutely. I love to talk about these four specifically because we often combine them under the term of mentoring or managing. But these are four distinct skills that managers, leaders, and, really, anybody can employ based on the situation and the person.

“We’re often taught that our knowledge is the most valuable thing we can share with others, so most of us default to mentorship as a mode of supporting the people around us”

The first one’s mentoring. It’s sharing advice, sharing your perspective. It’s the classic, “Here’s what I would do in your situation,” or “Here’s what I have done in your situation.” As knowledge workers, we’re often taught that our knowledge is the most valuable thing we can share with others, so most of us default to mentorship as a mode of supporting the people around us and helping them grow. I don’t want to knock mentorship, but research has shown it’s actually not the thing that helps people grow. Mentorship helps people get unblocked; it helps people onboard. There’s totally a place for mentorship. But if someone’s onboarded and they’re in a growth moment, trying to stretch their skills, trying to grow new muscles, have new experiences, or grow as a leader, we want to look at coaching, sponsorship, and feedback.

Coaching is asking lots of open questions to help someone figure out what’s true for them, what’s important about this, what their gut is telling them. Those are great examples of coaching questions you can use to help someone figure out for themselves what’s true. I believe everybody has the answers inside themselves already, and it’s my job to help them get in touch with those answers and figure out what’s true for them. It’s super useful when someone is growing that new muscle. If we’re just telling someone what to do, they don’t actually learn that skill in the same way they might have learned with coaching. Those are the first two that are often conflated. When we talk about coaching or mentorship, we use it as an umbrella term, but they’re two distinct skills.

Sponsorship is the one directly correlated to career trajectory. It’s the idea that we’re helping this person get to the next level by giving them opportunities to do visible, valuable work. You’ve probably already had a sponsor in your career, even if you didn’t recognize it that way. And you’ve probably been a sponsor to other people too, even if you didn’t know it at the time. Anytime we suggest someone work on a high-impact project, put them up for running a company blog post, or shout them out in some big group meeting, those are all different forms of sponsorship. And again, it’s the one that’s more directly correlated to people getting further in their careers.

The last one is feedback. We all know there’s good and bad feedback, but we can get better at this. And these four skills can be used in combination. It’s not like you need to only wear one at a time. You can go back and forth between them based on what this person sitting in front of you needs.

Better feedback

Liam: When I joined Intercom, feedback was such an interesting area because I had come from being a freelancer, working for myself, and suddenly, I was in this environment where we really care about giving feedback to help people. But it can take a little bit of getting used to.

“What I like to focus on when I’m teaching folks about feedback is what the feedback recipient cares about. What are they motivated by? What are they worried about?”

Lara: I’ve found it’s really useful to talk about the different skills we can employ when we give feedback, and we can choose which one works best for us and the environment we’re in. The way we traditionally give feedback looks like, “Hey person, here’s a thing I’m seeing,” or “here’s a behavior I’m seeing you do, here’s why I think you should change that behavior, and please do this behavior differently in this particular way.” It’s typically a very prescriptive act of giving feedback. We know that it probably won’t stick because in that form, we, the feedback giver, are focusing on ourselves, not the feedback recipient.

What I like to focus on when I’m teaching folks about feedback is what the feedback recipient cares about. What are they motivated by? What are they worried about? What are they most focused on? And how can I translate the feedback I have for them in those terms? Let’s say someone is really steamrolling a meeting that all their peers are in. They’re using up all the time, dominating the conversation, not letting anybody else get a word in edgewise. Bad feedback would be like, “Hey, you’re taking up a lot of time in the meeting. Please use less time,” or “please interrupt less.” In and of itself, that’s not bad feedback, but I want to make sure this feedback is going to land, that this person’s going to hear it and feel motivated to do something differently. And in those examples, that’s not going to do it.

“That’s the goal of the observation part – for us to get on the same page. We’re not at a disagreement point yet because these are just the facts”

So instead, I like to follow what I call the feedback equation. Observation of behavior is the first part: “Hey, I noticed that, in the meetings last week, we spent 25 minutes out of the 30 focusing on your topic.” That’s fact-based, that’s measurable, that’s observable. Those are not my judgments or assumptions. My observation should be, “here’s what’s happening in a fact-based way: who, what, when, and where.” They’ll be like, “Oh yeah.” That’s the goal of the observation part – for us to get on the same page. We’re not at a disagreement point yet because these are just the facts.

Then, describe the impact of this behavior in a way they might care about. It’s not always possible to do this, but when you can, it’s going to make it so much easier for this person to actually absorb the feedback and be motivated to do something differently. I might say, “Okay, we spent 25 minutes at this 30-minute meeting talking about your topic. I know you care about this, and I know you care about your teammates getting on board with it and being excited about it with you.” Right? That’s the impact. “The problem is, at 25 minutes, people are zoned out. No one’s listening. Everybody’s checked out. That’s the dynamic that I’m seeing.” Again, I’m not just saying, “This is bad,” or, “Please do this differently.” I’m saying, “Hey, I know there’s a reason why you’re doing this. I know you care about it. Here’s the impact I don’t think you mean to have.”

“If you’ve nailed the fact-based observation – they’re not disagreeing – and the impact that they care about, they’re already motivated to do something differently”

And the final part of the feedback equation is asking open questions. We’re taught to give a request like, “Could you please keep your updates to five minutes?” or whatever. But instead, let me see if I can ask a genuinely curious, open, coaching question like, “Okay, when you’re in this meeting and you’re giving your update, what are you optimizing for?” I’m putting it right back on them. My goal is for this person to sit back and be like, “Oh, huh, what am I optimizing for?” And to really chew on it. That way, we can figure out what to do differently together. It opens up a two-way dialogue rather than having this feedback be a one-way brain dump.

With this kind of formula, we can hopefully get to feedback that’s going to land and be digested by this person. If you’ve nailed the fact-based observation – they’re not disagreeing – and the impact that they care about, they’re already motivated to do something differently. You don’t need to make a request, right? It’s so hard to give feedback that’s actually going to be heard by this other person, but I promise, with a bunch of practice and thinking about it from their perspective, it can go way easier than the “Hey, I have a request for you” version.

Build resiliency

Liam: That brings us to that whole area of setting clear expectations. What are some of the things people should do to go about that?

Lara: Oh my goodness. I like to think about this as a balancing act. We’ve talked about empowerment skills such as coaching and sponsorship, or being directive and prescriptive. I like to think of it as a spectrum where empowerment’s on one end and directives are on the other. Based on the situation and the context, we might choose to be really empowering when we’re setting expectations, or we might choose to be really prescriptive. It’s going to depend on the people involved, the amount of urgency, who we are as a leader, how people react to us, and just the general context. Even within the same conversation, you might go back and forth between being like, “Okay, here’s what needs to happen,” which is prescriptive, and “all right, how should we go about tackling this?” In the book, I talk about a bunch of different skills we can employ to do either one. But again, coming back to setting expectations, it’s important that we know our audience and the context so we can know how to set expectations effectively.

“People value when managers are thoughtful about choosing between when to empower the team to make decisions versus when to be prescriptive and directive”

Liam: And your team will really appreciate it as well.

Lara: They tend to. They want choice, they want autonomy, and they want clarity about our direction. They want to understand what they’re being measured on. There’s so much to unpack in there. People value when managers and leaders are thoughtful about choosing between when to empower the team to make decisions versus when to be prescriptive and directive about what we’re here to do.

Liam: A lot of the time on this podcast, we’ll end up talking about communication, whether that’s between teams or with customers. But for managers, communicating effectively is so crucial.

Lara: It’s crucial and tough. You just have to get it wrong a bunch, which really hurts. You learn a lot from screwing up a communications plan or using the wrong word in a conversation with somebody. In the book, I walk through a bunch of different ways to approach communicating effectively. Everything from big sweeping changes that might scare folks, like how to approach a reorg, all the way to the tiniest kinds of communication, to the little pieces of feedback we might have or an update we might need to share with somebody. And again, this is going to be dependent on who you are as a leader and the context of your team.

Liam: The book is called Resilient Management, so how should people go about building resilience? It’s especially important as the business world faces economic challenges in times of crisis.

“Who’s come before you, who can you learn from as a mentor or as a coach?”

Lara: I wrote this book before a lot of elections had happened in a variety of countries; before the pandemic; before a bunch of what I would hear in 2022 called “recent unprecedented events.”

Liam: You can say that again.

Lara: Yeah, right. I think we’re all sick of the word unprecedented, and at this stage, we’re also sick of the word resilient. But the skills are still relevant, especially in a manager role, which could feel really isolating. It’s hard to find support systems and people who can help us process what we’re experiencing, what we’re trying to figure out, give us feedback, and help us vent. It’s tough because management is often a solo experience, and there’s also a lot of confidentiality involved. When I wrote the book, I focused a lot on how to build strong network support inside and outside our organization to help us weather the organizational storms we’re going to face throughout our management career.

A lot of it is still relevant today. Who’s come before you, who can you learn from as a mentor or as a coach? Find people who are safe spaces to unload verbally or process events with that are going to keep it confidential. Find people who are politically savvy within the organization that you can learn from. Find people who are going to give you feedback. Have a bunch of different traits you might want to look for as you consider building your network of support.

We often try to lean on our manager to do all those things, but our manager is just one person with one particular set of skills. There’s no way they’re going to be good at all those things. It’s really important to rely on a broader group of people for this kind of support to be resilient as a leader.

Liam: Before we wrap up, what’s next for you? Do you have any kind of plans or projects on the go?

Lara: Yeah, I’ve been working on a video project to take some of the workshops that I do over Zoom and make them into a self-paced video course. A bunch of them are available now, so if folks are interested in learning some of these skills around coaching, sponsoring, giving feedback, and being resilient, there are a bunch of self-paced video lessons with me. You can watch me role-play difficult conversations. There are a bunch of exercises, homework, and tools in there to help people continue to build these skills.

Liam: That’s fantastic. Where can people go to find that?

Lara: Yeah, courses.wherewithall.com.

Liam: Excellent. Where can people go to keep up with you online?

Lara: My email newsletter is probably the best place to find new stuff. It’ll often get transferred over to the blog, if you’re not an email newsletter person. If you go to wherewithall.com, you can find the blog and the newsletter.

Liam: Okay, cool. Lara, thank you so much for chatting with me today. It’s been great.

Lara: It was lovely to catch up.