Lessons From the Trenches

My name is Erica. I most recently was the Chief product officer at hired. I've been in the tech industry for a long time. Done lots of different roles. I've been in engineering management roles for over 20 years at various levels. I've run engineers, designers, product BD, every function you can think of.

When I grew up as an engineering manager was mostly speakers today. If we sort of learned from the school of hard knocks right there, wasn't a calibrate there. Wasn't a Play-Doh. So what I'm here to talk to you about today is some of the lessons I learned from my experiences and from those around me.

And I, when I share those with you in a story the characters in the story are fictional, but the stories are real. The names are made up, but the people are real. These things actually happen. So let's get started. So the story begins when I had joined this new company, a 15 person startup five person engineering team, and I was brought in to lead and grow the engineering.

As is typically true for me when I joined a new organization or an engineer is new into my organization. I tried to get to know them, to connect with them as quasi mentioned earlier. So my first, first week there, I set the stage. I tell the team that I'm going to try to get to know you better. And one of those engineers on my team, his name was Jared.

I skate on my preferred mechanism of getting to know somebody is actually out of the office because I like to get away from formality of the office. I feel like it, they bring it, it's more open when you're out in the open walking or just away from the office. The second reason why I like to be away from the office is I liked walking and doing these walk and talks on my one-on-ones actually helps me get to my 10,000.

So I reach out to Jared and I say, Hey, do you like walking lucky for me? He does. So we go on our first walk and talk. So like a good manager, I forced set the stage by telling him what this was going to be about. Dip was not going to be about work. It was going to be about us getting to know each other then Set an example by walking him through my background, through my various pitstops for my work history and why I made those decisions and why ultimately, why I was at this company, sort of like giving myself a pat on the back, thinking well done.

I've sort of set the stage for him to emulate. So then having done that, I look at him and I'm like, Hey Jarrett. So what about you? Tell me about you. And Jared looks at me and he says, how much I'm a front end engineer here. Nothing nada, zilch like shit. What do I do? All right. So now, okay. What about that company I saw on your LinkedIn profile, you were a company ABC prior to this.

What did you do there? Front end engineer. Okay. He's going to be a hard nut to crack. So tried lots of different questions, product. Couldn't get anywhere in back to the office happened sometimes, right? As we heard today, most of us are introverts 98.7% of us that are introvert. So I'm like, all right, let's figure it out strategy.

So on my drive home that day I'm trying to come up with alternate strategies of how I'm going to try to get to know Jared, but in our next walk and talk, I start the conversation by saying. Hey, I like gardening and I like pottery. What about you?

I just go, oh, sometimes I play video games. There was something he plays video games, but sucks for me. I know nothing about video games. What do I do now? But I'm like, okay, there is it opening? Let me walk through this door, see how far I can take it. So what kind of video games, which ones do you like?

Which ones do you not like? What do you think of Zynga? What do you think of the culture at Zynga? What do you think of EA? And through the course of that interrogation, I at least learned something about it. I learn what he likes. What kinds of engineering cultures he likes, what kinds of companies he likes.

So I'm kind of happy. I'm feeling good about it. So many such conversations later, many such coffees later, I basically come up with a varying degrees of stress, different strategies, and I keep them in my back pocket. So whenever I hit a wall, I can then try and alternate strategy to get to know him better.

Why am I doing okay? Because I really truly want to try to understand him. I truly want to understand what motivates him, what drives him, what he's passionate about, why he's here at this company and what he wants to accomplish at this pit stop that he's had while we're going through this process. We have a hackathon.

Super exciting hackathons are like the best days of the office for me. So usually during hackathons, I don't take on a project of my own. I just walk around the engineering part. I try to help engineers develop their ideas, brainstorm with them, whatnot. So I'm walking out the engineering pod and I come upon Jared's desk and I'm like, Hey, do you want to talk about your project?

No, I can help you. I'm good. Like, okay. He's being cagey, but fine. Doesn't matter happens. The day goes swimmingly. It's an exciting day. Hackathon ends and comes time for judging. I get selected as one of the judges. I don't like to be a judge, but fine. I'll do it new to the company and all. Now I'm a judge.

As luck would have it. Jared is up there presenting I'm sitting in the audience. I'm also a judge and somebody behind me whisper something to me, very brief conversation in skews, very innocuous, nothing happens. Jared continues to present and nothing really. So the judging end winners are announced. We celebrate everybody's effort.

We celebrate all of the projects. Jared doesn't know. We go out for drinks to celebrate. And Jared, isn't a really solid mood. I'm thinking sore loser. I try not to reach out to him. Like I don't have the time for this. That's a great day. I just celebrate with the rest of the team and the, these over the next couple of days, his audit who doesn't get any better, his demeanor doesn't get it.

And I noticed that he has that demeanor just with me, not with anybody else at the office. So I I'm completely baffled, I must have done something. I just don't know what so I, again, request him for a walk and talk lucky for me, he agrees. So we go on another walk though. And. Again, it's monosyllables cryptic and I'm thinking, oh my God, we've taken 20 steps back.

What happened here? So a lot of conversation later, a lot of walking later, it turns out that, you know, that little whispering thing that I had when he was presenting, he's hot. That in that conversation, he overheard me putting down his hack project and I'm like, dude, that just didn't happen. It didn't happen.

And he looks at me, he's like, of course I did. I heard it. I chart, I don't lie. I'm just denying. I'm becoming defensive. And I'm just denying because of just didn't happen. Then he goes on to say that, you know why I didn't share my project idea with you? Like why he's like, I didn't trust that you could keep it to yourself.

That heart. I looked at him and I'm like, you trust me, don't you. And he didn't, you even have to answer that the answer was staring me in the face. He didn't. So why not? I had worked really hard in establishing a relationship with him. That relationship was just a connection. It was not a relationship of mutual trust and respect.

Okay happens because with some people, trust is given with other stresses around and in his case, I clearly had to earn his trust. And I just hadn't been long enough at the company to earn his trust yet. So in a way it was really painful, but at least we had a problem. So the Ms. Problem-solver and me was very happy that at least I had a problem to solve.

Right. So on this walk and talk, we try to come up with strategies on how we can go about establishing that relationship of trust. First step towards that is communication. So we come up with a plan together, which was great. We come up with a plan where we say now from this day onwards, we are actually not going to have any digital committee.

No slack, no email, no text. I'm his manager. How do we communicate? We got chick to deliver. So the way we do that is through walks and talks. So he scheduled to twice a week walks and talks. And during which we're going to talk about. What we liked about each other over the last few days, what we, what, what rubbed us the wrong way and like offer clarification as needed.

And of course, any tactical stuff we had to talk about from a project delivery standpoint. And since there are realities of business, if we needed more time, we would just talk to each other to schedule additional time. First few of these extremely excrutiatingly painful. He was imagining things that didn't exist.

He was volleying all sorts of allegations, but he was hurting, I guess it was really hard not to get defensive. It was really hard not to justify, like do Nope, you're wrong. I had to really keep a calm, demeanor force myself to keep my eye on the prize, which was repairing this relationship. As I knew in my heart that I could repair.

And I'm happy to say three weeks later, six of these walks and talks later, he comes up to me and he says, nitty, I think we're good. We don't need these anymore. Yes. So Marlon story connect, right? Connect with your energy. Before you think about managing your engineers, connect with them at a human level, but just that connection is not.

In addition to that connection, you need to have that relationship of trust and respect. So maybe pause here for a second and talk about my management philosophy. So over the year, because you know, the engineering management is such a crazy multi-dimensional tool at any given point in time, you're wearing 20 different hats.

You're juggling 20 different things. Sometimes it's just hard to remember. Like if you become a project manager for a long time for like two months, and you just focusing on projects, you forget to focus on strategy. And I used to do that all the time. So to remind myself and to aid myself in remembering what a highly multidimensional role mine was, I had to come up with this philosophy of five piece.

So you have five PS. I'll walk you through those today. And these are the pieces that I remember. Two that I use as a rubric for myself in terms of onboarding offboarding in terms of onboarding, in terms of training my engineering manager for all sorts of things. So that this brings me, the story brings me to my first P, which is people.

When you get trained to become an engineering manager, you learn about how to do effective one-on-ones quasi gave an amazing talk about effective one on ones. And as three, A's a strategy you learn about onboarding people off boarding people, performance management, perhaps all of that. The thing I learned from the school of hard knocks.

In addition to all of that is keep your pulse on the organization. Once you have that human connection, once you have that relationship of trust and respect, you actually will be able to read your engineer's body language and figure out what their stress level is. And that truly is keeping a pulse on the organization as opposed to managing the organization.

All right. So going back to my story. So we're growing, we've grown from a five person organization, 5% engineering organization, 15% organization. So now is the time to start thinking about processes and or design and what have you. So from an org design standpoint, it's kind of clear. I think we have three natural teams based on expertise and functional areas, which has growth data and So I talked to my leads.

I propose these three. They agree. Totally makes sense. Completely. Non-controversial then we talk about process. I'm thinking everybody does. Yeah. Agile today. Like this is going to be a breeze. Ha was I wrong? Not so much. My growth person didn't want any process whatsoever because he wanted to be super agile.

The applications person. Wanted rigidity. You wanted all the sprint, rich worlds. You wanted it to biweekly sprint or two weeks spread for 90. I always get confused with that. And my data person just wanted combined. He's like, you know, there are so many interrupts. We get, I can't do a two week sprint. I don't like agile anyway.

I was like, okay. All right, take a deep breath. I've done agile before in my previous job, we successfully did it across all of these three seats. There was no issue makes my life so much simpler because there is so much cross-functional communication I have to do. I can, every, if everybody has the same cadence, I can communicate this.

We can schedule a company-wide demos. It's easier to communicate to the executive team, send company-wide emails that are, this is what we want to do. I dug my heels, the conversation been going on. Because they dug their heels too. It got it to the point where at the end of that conversation, my growth Lee looks at me and he says, daddy, you just don't understand what we do.

I was livid. I was fuming. I licked my wounds, went back in my car, driving back home and I'm thinking, you know what? I need to vent. As Ali said, own your emotions. I had to like do the, my feeling so same thing. So I called a fellow VP and that I know, and I was hoping she would like, I she'd let me vent.

She'd hear me hear me out. So I call her and I started, started venting. She's not in my corner. Aren't you listening to me? My life becomes so much simpler. What is the problem with agile? Through all my venting. Finally, she made me realize that I was wrong. And the reason I was wrong is because I was bringing a process and trying to force fit that into the organization.

But just like people are unique. Every organization is unique. Every team is unique. And if you do not customize the process and make it work for the organization, you're not going to be. So that brings me to my next piece, which is process. What you learn is you have to be the hard bringer of process. You have to be the stewards of processes within your company, but remember your company now is different from your company before and your company tomorrow is going to be different from the company from today.

So you always want to continually look at your processes, evolve them and customize them to the needs of your organization. All right. So did I not do that? Okay. Now let's get back to Jared. So we're six months in. Jared's doing great. We have a great working relationship. And Jared is older than are my top engineer.

He's always been great in terms of his deliveries and deadlines and communication and everything. And all of a sudden, I started to notice that Jared is now missing deadlines and the stories Mesa built sound very similar to the one. Cause he said quasi, quasi related audio. He starts to miss deadlines.

When I reach out to him, he replies back 48 hours later, which is so unlike him he also has bugs in his car. And these bugs are actually making their way into production, which is really bad. So the combination of these missed deadlines and bugs is actually now has exact level of visibility in my tiny startup.

So I'm really sweating it, it does an engineering manager. You, you are responsible for delivery. It's your responsibility to make sure stuff makes it into production and it's good quality, good high quality. The other thing I noticed is he's no longer making eye contact. So simple things like, Hey Jared, good morning, Jared.

Essentially like he's mumbling. So, okay. We go for a walk and talk and I'm anxious. I'm really anxious because we're not hitting our dates. So I put my project manager hat. And we're walking. And I first talked to him about his missed deadlines. Then I talked to him about the fact that he's not responding to me in a timely manner.

Then I talk about bugs and all, as the conversation goes on and on and on, he's getting even more anxious because I'm passing my anxious lists over to him. The guys was stressed to begin with and he's even more stressed. He always had a strong sense of ownership. So obviously he's feeling very bad because I'm making him feel really shitty.

And it gets to the point where he just quits, he quits right then and there on the spot as we're walking and the earth just moved. Like,

so then I walk in silence for the whole world. And during that one minute, my brain is like rapidly processing information and I realized something. I feel lies that I was wearing my project manager hat on. I should take that off and put my engineering manager hat back on because the engineering manager hat on allows me to be his guide, coach and mentor.

The thing that was bugging me the most was lack of eye contact. I don't even know why I don't even know why that is. And I haven't even broached that topic with him because I'm so obsessed about the dates. So I decide to just be straight with him and I'm like, Hey chair, we worked together for six months.

I know you're welcome. At this point what's going on. There seems to be something we on because the version of UIC in the office is not the version I've seen over the last six months. If you share with me as a friend, meaning I can help you maybe together, we can come up with strategies to figure out how you can get to a better place.

Just that authentic conversation. The damn bro. And he went on to share with me. There was a lot of stuff going on with his personal life. He was in a terrible relationship. He had gotten into some debt. It was a great conversation. And in that conversation, he shared that with me, we were, should be able to problem solve together, not as personal life, but we were able to problem solve is how I could help him reduce stress from a work stand.

So the Mo the lesson learned here is yes, you are an engineering manager who is also responsible for delivery. You are also a part time and project manager, but you are always an EMT first. So remember that. So a year goes by now. Jared has Jared is doing really well at the company. He, I promoted him to be an engineering manager.

He now he's 30, 30 days in as an engineering manager. So I do a quick 360 degree feedback survey from the team to figure out how he's going, how he's. The feedback's mixed. I have expected that, but one of the remarkable things and his feedback is that I feel like the team doesn't have any sense of ownership.

It sounds familiar. As I dig in, nothing's surprising essentially this scenario repeats itself. Jared walks into a meeting they're discussing something. Jared knows the answer. The team doesn't know the answer because he basically built this code base. And Jared would walk in. He would get on the white board, blah, blah, blah, blah, blah, blah, blah.

Clear, clear. So, of course the team has become order-takers. All of us have gone through this. I get this like all the time when I first became an entry manager. So no wonder they don't have a sense of ownership. Okay. I can solve for this. What does a senior engineer is actually gives really great feedback.

So he says nitty, we seem to be refactoring a lot. We are about to put something into production and then we learn something else at the other team is doing. So we have to go refactor and read it. And then a week later, the same scenario repeats itself. Where's our strategy. Where's the company going?

Where's the product going? Jared's trying to do that because obviously he's a new engineering manager and he's trying to prove his technical word. He's trying to figure out how he can technically dissipate, but there's another way. Jared, isn't a unique position where he has a bird's eye view of the entire company, the entire product, all of the teams.

That's the value he can bring to his team so that they can be better connected with the business and with the strategy. So that's how we solve for that. That brings me to platform. You are no longer, the best technical mind on your team. You should not be, if you are, that's a mistake, but you can still prove your technical worth by guiding the technical product in the right direction.

By bringing that back. Okay. All right. So you maybe you'll figure it out by now. I'm a fairly opinionated person. I have opinions about everything. But in this case, I'm specifically talking about the product, right? So I've never been an order taker. Some of the PMs have found it very hard to work with me because I just want to be.

I just want to know. I just want to know why we're building what we're building and that's sort of the, the mindset that I've inculcated in my organizations. I want my engineers to be product opinionated. So usually I, if I understand why I think something, and if I've heard it directly from a customer or from a sales call or from user feedback, then I'm totally being.

So I've always encouraged him, even this organization that I built, I've encouraged all of them to participate very actively in all of these conversations. So my PM counterpart comes to me, we're doing our roadmap planning for the next quarter. And he said, Nitty, you know, I have a long list of 20 things and I'm like, yeah.

So he pretty mommy and I pretty much know I can maybe fit like five we're a small team. But instead of being that wall of no, the way I pursued this conversation is so it's a long list, but based on the strategy conversation we just had. I think the top five are the most important. Do you agree? And he says, yeah, I agree with that.

I'm like, great. Let's lock these in first and then see what we're left with. Right. So most of these are like very large t-shirt and t-shirt sizing as we're, as I'm snorting those. Yeah. Jared. And one of the engineers, they walk into the room and Jared looks at the list. And for the next few, he actually comes up with a really brilliant idea because he's heard this and seen this with them, with the customers.

And he's like, you know what? This is really what the customers were asking for. And if we take this shortcut, we can make this change. This t-shirt size from extra large, to a medium or a small. So great idea, great collaboration. We're able to fit those in. And the engineer has recently been in a customer call and Don engineer actually points out a feature that's not even listed in these 20.

And she comes up with a brilliant idea, which actually opens up a brand new market segment for us. If we were to just do this one MVP. So by the end of this conversation, we have actually what I thought we were only going to be able to fit five. 20 Mister 20 when I'm actually able to fit about 15 and then some that's the value of your team and you being product opinionated.

So when it comes to product, my advice to you is be product opinionated, go beyond technology and a roadmap and projects and focus on. The product that you and your teams are building because that's how you can make a greater impact to the business and to the company at large. So ladies and gentlemen, these are my five PS.

Thank you.