Being a Great Coach with Anjuan Simmons Engineering Coach at Help Scout

Published on Mar 6, 2022

41 min read

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In this podcast, I talk with Anjuan Simmons, Engineering Coach at Help Scout. We discuss how an engineering manager is like a coach. Anjuan has some great advice for aspiring engineering managers. We discuss a key insight between dissatisfaction and satisfaction. He talks about his player-centric approach, unique approach to time management, as well as some great reading recommendations and critical insights.

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Transcript

[00:00] Vidal: All right. Good afternoon today I have with me Anjuan Simmons and thank you so much for coming to ManagersClub.

[00:06] Anjuan: Thank you for having me.

[00:06] Vidal: So that maybe we’d start out, I was looking at your background and currently you’re an “engineering coach,” is that right?

[00:19] Anjuan: Yeah.

[00:06] Vidal: That’s awesome. If you could say a little bit about what an engineering coach does and about your background in management?

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What’s your background and how did you get into management?

[00:19] Anjuan: Sure. So the title engineering coach is very much an artifact of the company that I’m currently working for. And that company is called Help Scout. Help Scout is a company that makes software for customer support professionals. And some of the other bigger names in our category are tools like Zen Desk. ZenDesk is probably the biggest one. We typically go after more small, medium-sized businesses. So we very much play in the SMB part of the market, whereas ZenDesk is more like enterprise huge companies. And so at Help Scout, we use the term “coach” instead of manager.

And so there are coaches in engineering. There are coaches in marketing, coaches in sales. Anyone who manages people is a coach. And the reason that we like the term coach is because that really better describes what we want to do with our people.

And so there are coaches in engineering. There are coaches in marketing, coaches in sales. Anyone who manages people is a coach. And the reason that we like the term coach is because that really better describes what we want to do with our people. And that is to try to help them maximize their potential, but also not really try to force-feed them process or methodologies, but by walking alongside with them helping them to see that a lot of the questions that they have the answers are inside of them.

And that there are things that they can actually dig deep down and get you. That’s how I came to be an engineering coach. That’s what’s my background. I started at Accenture, which is obviously a really big, well-known company. And so I started out in the model of going to clients and working with them on their technology problems.

And that part of my career was very much a big part of how I formed and cut my teeth as a software manager. Accenture was where I first managed a software development team. It’s where I first learned how to implement software at the largest scale. And then I went on to Deloitte another company similar to the first one and continued doing After consulting, I got a business degree. And I started going into the world of startups. And so I started trying to understand, can I take the rigor and the scale of these huge consulting companies like Accenture, like Deloitte, but learn to do it with a smaller team and really focus on one product.

And that’s where I started going through the world of startups. And that’s how I got to Help Scout which is not a startup anymore. I mean Help Scout’s been around for 10 years. But it’s very much has a scrappy startup mentality. And it’s still, what’s considered to be a small technology company. And that brings us to today.

[02:48] Vidal: That’s awesome. I really like that idea of the coach, cause I think there are a lot of similarities between an engineering manager and say the coach of a professional sports team. I like to make those analogies sometimes.

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And yeah, I was looking at your background. You have a very long background in leadership and management, which I’m really interested to share with people. So maybe with that we could start with, what would you say are some of the highlights, of being an engineering leader or coach, and maybe what are some of the low lights or, the things you enjoy don’t enjoy about it.

What would you say are some of the highlights of being an engineering leader or coach, and what are some of the low lights?

[03:19] Anjuan: Absolutely. And you’re exactly right. Oh, how do we use the term coach? We believe that the best coaches were former players. And so if you’re if your coach in the engineering part of the company, you were a software developer, right? You’ve built software, deployed software. So as a coach, we understand that in life we are also able to help them understand not just the bits and pieces of development but how do you think of your career. How do you think about what you want to do? Not just right now, next week, but over the next 5, 10, 15 years.

Regarding the highlights and the lowlights. I think that what I get out of my career and the highlights that I really get jazzed about have always been around helping people do things that they never believed that they could.

And I can think of examples of how I’ve helped people achieve things that they made gotten to later, I was able to help them see you have that in your right now. I remember I was on a consulting engagement at a large financial services company and we were doing support and all my support team was someone who was a great member of my team, but she really loved database.

And she always liked to hang out with the DBA team and learn from them. And so I was like, you know what? I have the ability to affect some of the budget. Let’s try to find time for you to go training in relational databases. Oracle at the time and learn more about that. And she did it. She did the training, did great at it, and eventually, she wound up moving over to that database administrators team.

And so while I had to fill the vacancy left by her spot, I love that I helped her get to something that I don’t think she would have thought she could do before we worked together. One other example was when I was at a startup, and I was at that point the scrum master for that startup team.

And so we had a consulting company that we brought on to help add more engineering oomph to what we could do. We needed to do things faster. And so there was someone based in Mexico who was on that team. So she wasn’t even working for the same company, but I realized she had a love for technology, a love for public speaking.

And so I was like, you know what there’s a conference called South By Southwest in Austin, Texas, where I went to undergrad at UT that has a technology festival every year. And I spoke there before. I was like, you know what? I think we could submit a proposal to work on this together.

And I think we can basically give this talk together. And so she was game for it. We submitted the proposal. It got accepted. And so the first time I met her in person, because she was, again, she was like a nearshore person. So meeting in Austin and we gave our talk and she has gone on to do amazing things about technology and helping women get into the tech.

And it’s all because we worked together on this project for this point in time. And I really love to see her grow. So yeah, doing that stuff, it’s really what I love doing. Some of them that’s fantastic. No, sorry. I interrupted. I think fantastic.

[06:27] Vidal: I think it was great specific examples you’ve given. So like when you’re encouraging people to do something they didn’t believe they could before as you believe in them more than they did in themselves which is absolutely awesome.

[06:39] Anjuan: Going to going on to some of the low lights the obvious one is when you have to make a hard decision to say, this person is not working out and you have to part ways.

And that’s something that I’ve done way more than I’ve wanted to, but I haven’t done it excessively. I think I’ve been very fortunate to have either inherited really strong teams or to have been able to hire them. And I think that the way that I try to navigate that is at the end of the day is helping both the organization and the individual get to a place that’s best for both.

And in many ways, I’ve been able to structure having to part ways with someone in a way that this is a chance for you to go do something where you’re a better fit and the company’s a benefit for you. And I’ve written referral letters, I’ve vouched for these people and helped them get to better places.

And so that’s how I try to make that low light something that could be a highlight. And not again, this doesn’t happen overnight. It’s nothing that often as months and years later but always try to make sure that if I do have to part ways with one of my directs, that I am not just invested in making sure that they separate from the company and a very clean ethical high integrity way but I’m also invested just as a person who cares and making sure that they get to someplace that better serves them.

[08:02] Vidal: I agree. That’s probably one of the most difficult things as an engineering manager to have to do. And it’s great to hear how compassionate you are and in taking care of them all. What would you say are some of the biggest challenges you face nowadays as an engineering leader?

What are the biggest challenges you face as an engineering leader?

I think that as an engineering leader, I always frame engineering around the three typical categories: technology, people, and process.

[08:17] Anjuan: Yeah, I think that as an engineering leader, I always frame engineering around the three typical categories: technology, people, and process. And so I think that out of those, the hardest is the people side, because one, it’s the one that I care the most about, but also it’s the one that has the most subjectivity to it. You can get books and you can go to training about how to build better technologies. You can get certified on AWS or SQL server or this and that technology, react or whatever stack, but there’s no real sort of certification for people. And I would say that some of the biggest challenges is trying to make sure that you have a very crystal clear view of the job that’s to be done for your teams, that you align the people who are going to do those jobs with what’s required, but that you also always have in mind what is the end game for this person, right? Because I know that everyone that I work with, it’s not gonna work with me forever.

And so obviously I’m very much invested in like their today success, but what can I do to also help them with their tomorrow success? So that’s the people side. Going over to process, I would say that’s probably the next, most difficult because the process has to be extensive enough so that people understand what’s expected, but not so heavy that people feel choked by it.

 The agile methodology, when the founders and the people who started thinking about agile, where they met at that ski lodge and wrote the manifesto one of the names that they were going to use, what’s called just lightweight, right? It’s called the lightweight methodology — the lightweight software development whatever. But if a lightweight might be seen as maybe underplaying what they’re trying to do. So they went with “agile.”

But I do the term lightweight because whenever I am in the organization, a big part of my job is to again, have enough process to be useful but not so much process that people feel that it’s too constraining. It’s almost like the founding father who said, I like my government small enough to drown it in a bathtub. I think who said that? So I like my process small enough that you can, that’s maybe a little bit macabre but I do want it to be something that people understand and know, okay. I understand how I fit into this and I understand how it serves me and getting things done. I would say the technology part is probably the part that I don’t worry about as much only because I think that you can figure.

[10:54] Anjuan: Absolutely. Absolutely.

[10:48] Vidal: I agree with you. I think that the people part is definitely the trickier, more non-predictable, and delicate part of the job.

Could you share with us a lesson you learned as an engineering leader?

[10:57] Vidal: In your experience as an engineering leader, maybe you could share, maybe what’s a lesson you learned in your career.

[11:05] Anjuan: Yeah, I think I’ve learned a lot of lessons in my career. I would say that going back to the people part being the least predictable. Last year I had one of my directs leave the company, and this was someone who I one had a good relationship with seem to really enjoy what they were doing. And I didn’t see it coming. So I think the one lesson that you can’t predict people if you lined up my directs and said, pick five of them who are going to quit, I would have never picked him in that five. That was a lesson. And how do I make sure that I have to make bets as an engineering manager, like who my people are, whether they’re going to do, but there’s no guarantee. And you have to be able to roll with the punches. You have to go with the flow. And so that was the lesson that I learned. Now, this person actually nine months later came back to the company and worked with a different team.

He’s actually going to be coming back to my team for a variety of reasons. But again, his initial departure really, really shook me because I thought that I had a really good read on the teammate. And him coming back at least let me know that things weren’t that bad.

The other lesson that I learned is this. The Harvard Business Review published an article that actually started reading recently it’s about motivation and it was written by Frederick Herzberg. So it’s the Herzberg model. The key takeaway from this article is people often assume that the opposite of satisfaction is dissatisfaction and the opposite of dissatisfaction is satisfaction. Meaning if I remove dissatisfaction from my life, then I’ll be satisfied. That’s not true. Actually, the opposite of satisfaction is no satisfaction. And the opposite of dissatisfaction is no dissatisfaction.

So without getting too nerdy, technical, what the article is saying is that satisfaction and dissatisfaction operate on different planes. And so things that are dissatisfying are basically some of the things that we will say are the external parts of the job, right? Like the salary, the office, 401k benefit, my peers, my manager, those are all the external things that if they’re not where they need to be, people feel dissatisfied.

But just because you have a great boss and a great paying salary and great benefits, and you’re working in a great office with, coffee beans you can grind for yourself in the break room and they’d bring in yoga every Wednesday that doesn’t mean that people are going to be satisfied. A lot of people miss that.

A lot of engineering leaders miss that because you focus on these things that yes, reduce dissatisfaction, but do not bring satisfaction.

What brings satisfaction is the next logical question, and I’m glad that you asked, but what brings satisfaction is really around the job itself. And how much do you align with the job? How much do you feel that you can actually grow and hit achievements and be recognized for becoming proficient? Like those things bring deep satisfaction and that’s why you have people leave companies. They have all these things. And really a lot of money that’s been invested in reducing dissatisfaction, but they leave because they’re not satisfied.

And so I think that the engineer who left, who did it come back, I think he was finding he was lacking satisfaction and the forward progression of his career. So he went somewhere and they got that, but I think he found other elements that weren’t where he needed to be and he came back. But I think that the big lesson that I’ve learned, one of the big lessons is as an engineering leader, I have to make sure that I’m mitigating the things that cause dissatisfaction, but I’m also elevating the things that cause satisfaction.

And then my directs, I need to always make sure that I’m probing for that. What are the dissatisfaction items going on with them, but also what are the satisfaction items that they need to really thrive?

[15:05] Vidal: That’s really interesting because yes, a lot of big top-tier tech companies, have amazing food and salary and benefits and all these luxuries so why would anyone ever leave such a place? It’s because of this. So that’s really interesting. I’ll have to check out the article.

What is your approach to hiring?

I wanna ask you about your approach to hiring because now there are a lot of people resigning and switching jobs, and it’s a really interesting hiring market, so what is your approach to hiring?

[15:31] Anjuan: Yeah, the great resignation is real and people are definitely moving around and so opportunity abounds. And so my approach to hiring is very much entrenched in many ways, working at help scout for the past, going on three years they have a great partner in recruiting and just let you know about help scout. We are hiring by the way. And so people who are listening or reading this hit me up. I’m happy to talk to you about what we’re offering. But hiring starts with having a healthy set of places that you go to collect people that are looking for jobs is critical.

Again, I very much partnered with our recruiting function and help scout for that sourcing. And they do an amazing job. Once you understand the pool of people. Again, it’s understanding what is the job. And great hiring starts with great sourcing, but it also starts with great job descriptions. And so one of the things that we do at help scout is be very clear in what the ask is.

We give you a very good view of the role. So let’s say, for example, I’m hiring a JavaScript engineer, right? So we very much describe in the job description or the JD. As we say, which is, this is the role. This is the JavaScript framework that we’re using react. These are the things that we need you to know about software dev life cycles.

But we go beyond that. We give you a flavor of the team that you’re working on. We also say here are things that we want to know about you, right? That you’re curious. That you enjoy learning. That you enjoy working in an environment where you’re fully supported, but you also are given a lot of freedom to move.

And so we very much try to make sure that the job description gives you a great view of what the ask is from a skill and competency standpoint. But also this is the kind of company that we are, and this is why we want you to come and add to our software development team.

And then, so once you have the job descriptions and once you have the sourcing, we very much have a very well-oiled process that we go through. So the recruiting team will have that initial call with the candidate to just learn more about them, get a feel for, okay, beyond the resume and beyond LinkedIn, who are they?

But then they go to what we call it value add, which is that’s where I come in as the hiring manager. And that’s where I also try to understand who is this person? Yes. What degree do they fill what I’m looking for, but do I see this person working with my team? So it’s not just, can you do the technical aspects of the job, but can you be someone who I can see working on my teams?

it’s not just, can you do the technical aspects of the job, but can you be someone who I can see working on my teams?

My teams are extremely important to me. And a big part of my job is making sure that I’m creating not just a bunch of individual people who were close to each other. But a cohesive team that works as a unit. So that’s always a big part of what I try to understand in that value add. Once they pass the value, add they go to a technical screen which is where the engineers in that domain.

So if I’m hiring a Java engineer, Java engineers do that. JavaScript, PHP, whatever. And that’s where they get into the nuts and bolts okay, let’s look really into the technical aspects of this person’s role. At Help Scout, we do a project which is a repository that we make available to you, and we give you some interesting things that we want you to do.

And then that’s also graded, and then after that, if all those things go well, there’s like a final kind of sourcing call where we say, okay, do we think this person should move forward? As a hiring manager, I obviously have the final say.

And then we go into if we want to extend the offer and go from there right then. That is our process. Again, I think it’s lightweight enough for people as they go through it to understand it. But it has enough teeth to make sure that we’re getting into the candidate because I firmly believe that when I hire someone, I’m hiring someone for a multi-year relationship. And so that relationship is something that I very carefully cultivate, even in the hiring phase to make sure that everyone feels good about that person joining our team. And so that, in a nutshell, is my approach to hiring.

[19:31] Vidal: Thanks for sharing those details. Yeah. So you have a very, complete process and I agree with your value-add thing because a mentor of mine always says that software development is a team sport.

What’s your advice for engineering managers who are just starting out?

I think that’s great. What would be your advice for managers who are just starting out? We have a lot of people who listen to ManagersClub who are like new managers and want to get into management.

[19:54] Anjuan: Absolutely. What I would say is that for managers that are just starting out. It is critical to do two major things.

One, get to know your team.

One, get to know your team. The first duty of a manager is to serve the people on the team that they’re managing. And one easy tool that I’ve started using years ago it’s become more in vogue, but I know that a lot of orgs don’t do it. That’s one on one also called one-to-one.

But this is a regularly scheduled meeting. I think weekly is the best and it should be preferred. You can get away with twice a month, but I highly recommend weekly because that weekly meeting is your opportunity to talk to this person with who you have the responsibility of managing their success and then catching up with them. And like my, and so just to let you know, I have, except for one of my players, I have weekly one-on-ones with all the people who report to me.

And so my one rule is that it’s not a status meeting. I don’t want to get an update on what you’ve been doing. I have many ways to track your status. We have stand-ups. We have weekly meetings. We have all. This is human to human, how are you? What’s going on? How do you feel about the work that you’re doing?

Not the status of the work, but the work in general, and that’s where we’re getting into that. I’m probing for like satisfaction. And Hey, here are some things about the company that you’re going to see happen in the next few weeks that I can make your privy today. I just want to make sure that you understand, what’s coming so that you’re not surprised.

So those one, two ones, again, there for me, there are only 30 minutes. But they are the most valuable 30 minutes that I spend in my week is one of the most with my directs. And that does a few things. It does a lot of things, but a few things that, that are easy to hopefully explain are one you communicate to your directs, that you can.

I’m a busy person. I have a lot of things that I’m responsible for. I’m making time on that busy schedule to totally focus on you. And absolutely, they have my full focus, so I’m not looking at slack. I’m not looking at my phone, I’m eye to eye. And we’re fully remote so it’s all over Zoom. eye to eye over zoom with my player letting him know that I care enough about to give you the one non-renewable resource and that’s my time. But also it’s updating the player on what’s happening within the organization. What’s happening with their team context. And as long as you are giving the direct the opportunity to update you on what’s going on.

It’s very very common when those one on ones are healthy and there’ve been gone for a while, they get into things happening in the players’ personal life that may affect their job performance. And by having that regular cadence, you also give the player the opportunity they pick, because they know that it’s weekly, that it’s something happens oh, let’s say a Monday. And our one-on-one is on a Wednesday. They know that, okay, I’ll bring this up during my one-to-one. And so it’s always giving that place for your directs to know that they can come to you and give you an update on how they’re doing. So one-on-ones are fundamental as a new manager.

The other thing that I would say as a new manager that is critical is to find some way of achieving a team success milestone

The other thing that I would say as a new manager that is critical is to find some way of achieving a team success milestone, right? Because unless you have the privilege and the rare privilege of spinning up a team from scratch and starting to do work more than likely you are inheriting a team that’s already been working, right?

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So they had a manager before you joined them. You’re for whatever reason taking on this team. It’s very important that you interrogate the reality of the teams, a book of business, right? Whatever work that they’re doing and try to figure, okay, what’s close to being done.

What’s maybe can be done, but needs to be nudged along. And you identify something that you can do to show that, okay, we got this done. And for example, when I first started working with the team at help scout one of my teams that I took on that I’m still the coach for I was brought in and they had an extremely complicated backlog, right?

So I’m using Scrum terminology, right? They had a product backlog that was very unwieldy and very complicated. And we had sprints that were in progress and established. But at the time I felt that there was going to be like several weeks, if not months of actually getting something done for this team. And so I worked with the team and established okay, this is something that this is not a huge thing, but it’s something that I think in two more sprints we can get done. And so I really worked with the team to even refine the current sprint backlog, the product backlog focus, the team, negotiate, getting things off their plate.

And then we focused on this and we got it done. We got the work through QA, we got it going across the deployment pipelines into production. Now, why is that important is because as a team, for good or bad, we’re judged by getting things to production to develop value to customers and you do that by getting things to production in general.

And it’s very important early on get that first win out of the way, because the longer you delay that, the longer the team questions are we getting things done? This new manager came on, we still haven’t shipped anything. Your leadership team is also looking at you sideways of saying, okay, you’ve been with them for 30 60 days still haven’t gotten things done. You never want that to be the case. And by, by getting that first win. And that first one may not actually even be getting something to production. I think that’s a great thing to do. It could be something else, but I always try to make sure that as soon as possible, we get that first win, because it’s very important that the team understand that you can win together.

That as the new manager, you’re someone who they can win with. And that usually helps break the seal on the team to say, to put it that way. And it gives you leeway to know, okay, we got done. Let’s figure out how we can do that more together.

[25:46] Vidal: I think this is great. I’m really, I like how you want to have that win with the team during the one-on-ones that you refer to them as players.

So I’m really taking you really like doing this coaching thing, which is really good. And I agree with you. The one-on-ones when I started as a manager, I didn’t really appreciate how useful those meetings would be. And sometimes I’d let my direct skip one-on-ones and I wouldn’t do them very consistently, but I think if you do those well, That is just managers secret weapon, that’s so good.

[26:14] Anjuan: Laura Hogan is amazing. I think I do one on one as well. She is the person who I go to when I want to upgrade my one-on-one. So I shout out to Laura she was a great person to learn more about having great one-on-ones.

What’s your workday like and how do you manage your time, emails, calendar, etc.?

[26:27] Vidal: Awesome. So engineering managers, like everyone, they’ve got a lot to do a lot on your plate. So what’s your workday like, and how do you manage, your time emails, calendar, all the stuff you’ve got to do?

[26:40] Anjuan: Yeah. So to understand my workday, I think it’s important to understand how I manage my work week.

So I tried probably every task management, getting things done, how to manage your work, tool that you can think of, right? Trello boards and JIRA and what I’ve settled on, at least over the past six to nine months is just using my calendar. So what I do every, usually Sunday night, I have my calendar was obviously decorated with many meetings and things that I need to do.

And thankfully, I have a fairly healthy meeting culture at Help Scouts. With my teams where we’re starting to work on, we’ve been working on a big project, so our meetings have expanded a little bit more than I want, but I think it’s still healthy. And so I do see white space in my calendar, right?

So, one of my rules is no white space.

So, one of my rules is no white space. So what I do is I, and I know this sounds counterintuitive. But I have set meetings on my calendar, right? So there’s the, we use objectives and key results at HelpScout. So we have that weekly meeting to review our OKRs. We have a bi-weekly planning session.

We have a triage session we do asynchronously in Slack. So I have all these meetings. So I use my calendar as my task list. So I maintain a list of things that I would need to get done in a given quarter. And so those are things that are things I want to move forward during the quarter. And so I go to my calendar, which is already populated with my meetings and I use that calendar to actually put when I’m going to work on something.

So I have to work on a plan for a mentoring program Monday from 9:00 to 9:30. Then I have to prepare for my one-on-one with my manager from 9:30 to 10 o’clock. And so the idea is that I fill up the white space with my task. Why do I do that? Previous attempts at using tools like Trello, and I had basically a sprint board for myself where I would have cards that were slotted into my tasks and I would drag them from the columns with not starting it, to in progress, to do.

Those systems don’t give you the sense of time, right? Whereas a calendar time is self-evident. So when I’m filling out my weekly schedule, I’m using the calendar to get a sense of what can I do with actual real-time, why I’m using real minutes and hours here. And so by planning my week then I basically worked the plan.

So whenever I start my day, I pull up my calendar and if my day starts with a meeting, then that’s obvious I go to that meeting. But then I go into my task. And I can pull up, let’s see what’s my plan for. And actually looking at it now I put in my calendar not just tasks and meetings, but I have drink water on my calendar.

I have “drink water.” So it’s very micro. Yeah, exactly. And I have. Accessibility training. So I had this training. We’re doing that. We’re all going because we want accessibility to be a first-class citizen at Help Scout. So we’re going through this training about that. I have basically time to spend actually writing.

I have time to spend reading. I subscribe to a number of engineering manager newsletters like Pointer. And so basically my week to answer your question, my day is planned on a weekly basis. And then I use my daily calendar to manage not only, I met my meetings on time, but all of the thinking and the writing, and the reading that I want to do as also just self-evident on my schedule.

I take vitamins, right? That’s my day. It’s all on my calendar.

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[30:26] Vidal: All right. I make sense to me because for any task if it’s not on your calendar, when are you going to do it? Especially if it’s like a big task. So wow. But you put everything there it sounds like.

[30:36] Anjuan: Everything’s there. Everything. No white space, right? Every space, at least like working the working day, to be between 8:00 AM. And for me, like 6:00 PM, no white space. And then that gives me a sense of if people ask me to do something else, they’re like, all right, I gotta go to my calendar and I gotta move things around because my calendar plan is my proposal for getting all the things that I need to get done.

So if I have something new, it’s a very easy exercise and says, what do I need to take off my calendar to put this new thing in? And that makes it easier to talk with my supervisor. They asked them to do something. Let me pull up, let me show you my calendar, and let me figure out these things.

What are the things that I will have to take off in order to put on? And then my manager can say, oh, actually, no, actually I’ll come back to you next week. But having that plan in my calendar makes resetting the most valuable work that I’m working on easy to do because it’s all based in time.

[31:32] Vidal: Yeah. Do you use I don’t know, five-minute blocks, 10-minute blocks?

[31:35] Anjuan: Yeah. Okay. I don’t really feel there’s anything more atomic than a 30-minute block is helpful. I think that’s getting a little bit too much, right? So basically the idea is that every block on my calendar has a job and the smallest possible job takes 30 minutes.

Now I may get it done in 15. That’s fine. Then I just usually, drink some more water or do whatever. But the smallest, the most discrete unit is 30 minutes whether there’s 30 minutes or an hour or 90 minutes or two hours. All of those blocks in my calendar, have a job and the goal of what I need to do to make sure that block does his job.

What’s a personal habit that contributes to your success as an engineering manager?

[32:11] Vidal: Got it. Is there a personal habit that contributes to your success?

[32:18] Anjuan: I would say this is one that I’m really proud of. So the one that I just described to you working with my calendar I would say the other personal habit that contributes to my success is always thinking about it, I don’t know if this is a personal habit, but it’s more like a mindset whenever we do something

I always go back to what is the impact on the people involved.

So for example, they give you a very pertinent and timely example. Help Scout is fully remote, meaning that we all work from home or we work somewhere, but not in an office.

And that means that my team I have someone in Vancouver, someone in the New York City area, someone in Brazil, I have someone in Portugal, someone in Spain, like all over the planet. And we had to do nimble timezone management. But twice a year, we all get together in the same place for a retreat.

So the pandemic has unfortunately killed retreats for about a year and a half. So we did virtual retreats. So we had our first in-person retreat after a long break last fall in Park City, Utah actually. It was just lovely. I was able to meet people who I talked to almost every day in person for the first time.

And so we have a fall retreat and a spring retreat, so we’re planning the spring retreat right now. And as we think about the spring retreat and what we want to do, we’re trying to figure out how much did we do, like with team time, how much did we do with playtime? The place we’re staying they have activities at night, they’re amazing activities.

They have like falconry, trap shooting, right? A fun plate of things to do. Like it’s a charcuterie board of delight. And so the question that we’re trying to figure out well is how do we structure the time so that we give people time to, reconnect with each other, to even rest and relax, but also get to business done?

 My question is always what’s best for the people. And I think that one reason that. I’ve been fortunate to be considered a good engineering manager is because of that people mindset. And I’ve been very lucky. I tend to, not to like to brag, but I routinely have people tell me, wow, you were the best manager I’ve ever had. Really enjoyed working with you. And I think that the reason that I’ve gotten that feedback while also having high-performing teams is because of that people-first mindset. And so I think that’s the habit that has been really key to my success as an eng manager.

[34:55] Vidal: That’s awesome. How many people-first mindset, and it sounds like, yeah, people really they picked up on it. They think so. Yeah. That’s awesome.

Share an internet resource, app, or tool that you can’t live without.

So I know you said you tried, but you weren’t a big fan and a lot of these tools, you mentioned some of them but are there any other, I dunno, tools, websites, apps, or something that you find useful in your job?

[35:18] Anjuan: Again, going back to what I said my key app is by his Google calendar. That’s the key app. Other apps that I really like, we like almost every software company. We use JIRA for work management. So I use the JIRA app both on my phone, the Mac app I used that. Slack again, like a lot of other companies, that’s our tool to talk to each other, stay in touch. So that’s critical. I’m using Duolingo to learn Spanish, which is not a work app, but it’s something that I’m doing for self-development. And so I have, I think an 89-day streak right now of like every day doing Spanish lessons. So that’s more of a personal thing, but I really liked that.

And I will say that the other app. It’s probably one more besides Slack. And this is going to sound weird, but the camera app on my phone is indispensable because I have a wife and three children. My wife and I are celebrating 20 years of marriage next in March next month, this March, and my kids are 16, 15. And in 14. And so I take lots of pictures of my family as we do things.

And so that’s an irreplaceable app. So one of the biggest things I look for in a new phone is how good is the camera. And that’s why I almost always buy Google pixel phones. Though the iPhones have caught up.

[36:35] Vidal: Nice. Congratulations, 20 years.

And that’s great. Like you say pictures. I have kids too, and yeah, I take lots of pictures of them, so that’s awesome. If you could recommend one book to managers, what would it be and why?

If you could recommend one book to managers, what would it be and why?

[36:48] Anjuan: There’s so many that I could pick. So I’m I saw this question earlier, before we started, I would say Resilient Management by Laura Hogan. I mentioned Laura earlier. I think that it’s a very easy read. It’s not a long book, but Laura’s book does a great job of really getting to what I think is another part of what makes a good manager and that’s resilience. So I would say Laura Hogan’s book, Resilient Management.

If I could stick in like maybe one or two more, I know you said one Managing Humans is another one, I would say The Manager’s Path and Grit by Angela Duckworth are a few other kinds of bonus ones. But I would say that Laura’s book is such a snackable book. They can get through it quickly, but so much amazing information that is inside of it.

[37:41] Vidal: Okay, awesome. Yeah, those are all really good books. Thanks.

What is your approach to developing & coaching members of your team?

Vidal: So I know we’ve been talking about, being a coach. What is your approach to like how you develop and coach up the members of your team?

[37:53] Anjuan: Yeah. I think that one is understanding that mentoring and coaching are different. Mentoring in general is helping someone in a certain domain get better. And so typically, if you’re mentoring someone on how to be a better front-end developer, right? You get a front-end developer who has more experience, you hook them up, and then the more experienced person upgrades, the skill set of the less experienced one.

Coaching goes beyond mentoring because coaching is helping an individual understand their goals. And then finally, in many ways inside of them how to achieve those goals and a big part of coaching is one being curious, but two understanding what are those really catalytic questions?

That can be really powerful. And what’s a catalytic question like that? That’s the kind of question that people, you know that when you ask them that they say, oh, wow, that’s a great question. I was quoted through one of my one-on-one documents because some of the things that I ask are oh, so like for example I started having what are called stay conversations about three months ago, and that’s the kind of conversation you have to be like, it’s the opposite of a let me back up.

So let’s take for example an exit interview. Yeah, exactly. Yeah. That’s the canonical definition. So it does not say it’s not your legalist talk, but it’s, let’s talk because I don’t want you to leave. Basically. So you understand the concept. And so basically all of my players, all my directs I asked them if you had the opportunity to do something at an amazing company that was offering you way more money you ever thought that you would earn and doing work that you would love, what would convince you to stay at help scout? That was the question. And so what I was probing for is one okay, what are the things that this person really values and.

A lot of the answers were what we talked about earlier. They were kind of dissatisfaction answers and satisfaction, right? So this satisfaction, reducing answers and satisfaction increasing answers. And I learn that, but also learn about what is it about help scout that this person really values.

And then by understanding that. I got a picture of all my directs. Cause they all gave different answers. Some were similar, but a lot of them were different. And then that helped me to understand what did I need to do to make sure that the things that were really satisfying, I put protection around those things and the things that were dissatisfying.

I tried to improve in some way. So that was as a coach, that was something that I did. That question and other inputs that I gathered led me to do something that was very difficult in that one of my engineers on my team, who I had been on my team since I started if we’re talking like a multi-year relationship, I decided that he should go to another team that would be more aligned with like his deep interests.

person in black pants and black shoes sitting on brown wooden chair

Photo by cottonbro on Pexels.com

Like he was okay on my team. What I mean by, okay. He was a fantastic engineer, but he had an okay sense of things are okay here. I kinda like when I’m doing it’s just okay. But I felt he will be thrilled by going to this other team. And so those stay interview questions reinforce that.

And I began to go through the process of transferring him from my team to this other team. And that transfer was effective January one of this year. And just even in the short few weeks that I’ve been able to get feedback, he is so much happier on that team. That’s coaching. Sometimes coaching means that I don’t hoard engineers to keep them on my team and be selfish. But I liberate engineers to go to where they are most aligned with not only their skill set but also their interests. Now I can’t do that every single time. And sometimes I think to wait for that to happen, but that coaching exercise caused me to lose quote unquote an engineer.

But there was so much that he gained that if I had to do it over again, a thousand times I would do the exact same thing. But that’s what coaching does is deeply interrogate the reality of the people that you said that you’re coaching to understand what are their strengths, what are their weaknesses?

How can I help them maximize their strengths? Mitigate their weaknesses, but also what can I do to align them with something that like when they get out of bed each morning like they spring out of bed because they felt like I get to go to work today. That’s what a good coach does. And it’s a lot of intangibles, but I think that the results are amazing and that you get people, places that they previously would have thought were impossible.

[] Vidal: Wow. You’re really a great engineering coach. This is a fantastic answer given. I like how you sacrifice your own short-term productivity, right? To transfer someone to another team where they would be happier and to be better for them. I think that’s awesome. Okay.

And you’re asking these really good probing coaching questions. I think the standard views are very good. Like we do those at LinkedIn as well, and I think that’s very powerful, so there’s a lot of really powerful techniques you shared. This is awesome.

I got one more kind of question to ask and that is what does it take to be a great engineering leader?

What does it take to be a great engineering leader?

[] Anjuan: A great engineering leader operates across those three domains that I described, right? People process and technology. You have to understand the technology enough where you’re probably not writing code every day and night like you used to, but you can be curious.

You can ask probing questions about the code. You have enough experience with the technology to be able to know when engineers may not be fully diving deep enough in their answers that’s key. With process, right? You have to understand what makes a good process when it comes to software development.

When it comes to people management, when it comes to company management, you have to be cognizant enough to understand. What processes will work, what processes won’t, and even how a process that has been working when needs to be abandoned, what needs to be changed. I’ll give you a quick example there.

One change to our hiring process that I started at help scout. Now maybe three, four months ago is we were a fully remote company and we have a very great remote culture. I think the best that I’ve ever seen or heard about but when we’re hiring people, we have a great onboarding process.

But I felt that between when we extend the offer and when people walk in and then that first couple of weeks, like it’s daunting, right? Cause I’m working with people who I’ve never met in person, and I have to learn all these things. Basically started a dear new HelpScout engineer campaign. Now we have it automated where when you start at Help Scout, you get these like personally written letters from engineering coaches like myself say welcome to Help Scout.

Here is something that will be great for you to know. And then it’s scheduled where like we send one the first week they get one a week later. So these letters rolling. They’re like personally written handwritten letters from the engineering managers to this new joiner. And they tell us themselves.

Hey, we work promote, here’s some things that really think that I think will help you do that. Or Hey, you’re working across time zones. Here are a couple of hints for how to be good at that. And so this was a change to the process. That, again, I’ve gotten feedback from people who, when they were hired, I said, this is amazing.

I love this. So it’s being able to understand what do we need to do to make the processes better? So that’s the second thing. And then we talked about the people side, most of this interview, it’s being curious enough about people to want to dive deep into the universe that every person is and have fun exploring around.

But it’s also understanding that at the end of the day, every person and a company that works for a paycheck serves the company. And there are times when you have to have hard conversations when this person is no longer serving that company. And so that’s what I would say makes great engineering managers is operating across to people, process, and technology, and at a very high level.

[] Vidal: That’s great. I that concept, the letter thing you do that is very cool, never heard that. That’s very nice.

Where can we go to learn more about you?

Anjuan, you’ve been really generous with your time. You’ve shared some fantastic stuff. This is great. Where can people go to learn more about you if they want to connect with you afterward?

[] Anjuan: Absolutely. I’m so easy to find. I’m @anjuan on Twitter, Instagram. If my LinkedIn URL is linkedin.com/in/anjuan. And so I’m really easy to find. So if you. If you look for A N J U A N, you will find me whenever you send me a friend request on Facebook, and I’ll probably add you there. So happy to connect with anyone who reads or hears this let’s continue the conversation.

[47:08] Vidal: Thank you so much. This has been fantastic.

[47:11] Anjuan: Thank you. Thank you.

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Key Takeaways

  • …there are coaches in engineering. There are coaches in marketing, coaches in sales. Anyone who manages people is a coach. And the reason that we like the term coach is because that really better describes what we want to do with our people.
  • I think that as an engineering leader, I always frame engineering around the three typical categories: technology, people, and process.
  • The key takeaway from this article is people often assume that the opposite of satisfaction is dissatisfaction and the opposite of dissatisfaction is satisfaction. Meaning if I remove dissatisfaction from my life, then I’ll be satisfied. That’s not true. Actually, the opposite of satisfaction is no satisfaction. And the opposite of dissatisfaction is no dissatisfaction.
  • The other thing that I would say as a new manager that is critical is to find some way of achieving a team success milestone.
  • Get to know your team. One on ones for new managers are critical for managers to get to know their players
  • [re: Hiring] it’s not just, can you do the technical aspects of the job, but can you be someone who I can see working on my teams?
  • [With regards to time management] one of my rules is no white space.
  • I always go back to what is the impact on the people involved.
  • Coaching goes beyond mentoring because coaching is helping an individual understand their goals. And then finally, in many ways inside of them how to achieve those goals and a big part of coaching is one being curious, but two understanding what are those really catalytic questions?

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