/ Josh Dover / blog

My First Six Months as an Engineering Lead

March 19, 2018 • 7 minute read

It’s a transition that’s been rehashed by many before me: going from developer to manager. I’ve been making this transition over the last six months at Cratejoy and thought I’d share what I’ve learned so far.

For context, Cratejoy is a relatively small startup with about a dozen engineers. Before myself, there had only been two other engineering managers (our CTO and my boss). You could definitely say my “training” was ad hoc. I like to think of it as organic. This post summarizes what I’ve learned so far.

What does a manager do anyway?

At the beginning, I knew that I wanted to learn how to lead groups of people towards a bigger goal. I see it as one of the most useful and necessary tools to accomplish anything difficult. But what I didn’t know, is what the hell this managing thing actually was.

While I’m sure there’s much more to be explored, I’ve focused the first few months on a few key areas: - Guidance - Selling ideas - Team building (no, not that kind)

Sound simple, right? If. Only. As we look into each one of these, you’ll notice there’s quite a bit nuance, and while they definitely have some common traits, each one has distinct skills to be learned.


I put guidance first for a reason. With a prime directive of “maximize the output of your team,” I’ve found guidance to be the most effective tool.

This is how I help my team get better at their jobs. It doesn’t mean I know how to do it better than they do. In fact, I want to be hiring people who know more than me (more on that later). I’m here to provide an external perspective, challenge their thinking, and praise them when things go well.

Giving guidance and praise takes a lot of conscious effort for me. While I’m comfortable delivering the feedback that needs to be said, it’s not my default response. I have to constantly remind myself to make sure my team knows what they’re doing well and what they need to work on.


For me, guidance starts with building personal relationships with my reports. This relationship is an absolute prerequisite to being effective. Without knowing my team members, their desires, goals, and fears, I simply can’t be genuine or calibrated when I say “I’m telling you this because I care.”

I’ve found that showing that you care first puts much more weight behind these words later. I strive to show that I care by getting to know them, understanding why they’re at the company, and asking them to challenge my decisions and methods. Making each person feel heard buys me points in the future when things get tough. Knowing each person helps me tailor my communication methods and rhythm to each individual.

One mistake I’ve made in this area: assuming that a well-established relationship is going to stay that way. It’s too easy to get lost in the details and pressure of the functional work, but I simply can’t neglect these relationships. They need consistent attention. Kim Scott does a great job of summarizing this: taking care of your people is your job. It’s not some sideshow to the work. As a manager, it is the work.


As I build up a real, personal relationship, delivering both guidance and praise always become much easier. Guidance comes from a place of caring and praise sounds more genuine. I simply haven’t found a better way to make this an easier process and I’m skeptical there’s any quick hacks here.

Once I do have this relationship, I leverage it. I remind the person that I’m delivering this guidance because I’m there to help them, not belittle them. It comes across as genuine because it’s true. (Sidebar: if it’s not true, this may not be the job for you).

Selling ideas

To my team, I represent the leadership above me. Part of my job as a manager is to keep the ship rowing in one direction. I have to everyone on the same page and address concerns.

Selling to your team

Nine times out of ten, this is a relatively easy task. Explain the problem the company is experiencing, explain the solution. I’ve found that most people that work at startups are inherently optimisitic and will accept leadership is doing the right thing.

Other times, some decisions may rub some people the wrong way. Firing customers is a common one. It doesn’t feel good, even when it is the right decision. With these trickier decisions, I spend time massaging the message with the doubters and really hear them out. Then I’ll use what they tell me to help better communicate next time. I make sure to be paying attention to where their concerns are coming from, not just the words they’re saying. This can be an opportunity to gauge where their trust level with leadership is. Getting ahead of broken trust can save you from huge headaches later down the road.

Selling to your boss

Selling ideas also goes the other direction. This role also involves being an advocate for your team! Every time I’ve created change in the larger organization I’ve earned big kudos from my reports too. Defending their time, removing roadblocks, and getting funding for a new perk are all potentially good ways to throw your weight around here.

The most direct way you’ll sell for each of your reports is in performance reviews. Every company is a little bit different here, but most promotion decisions involve some form of recommendation from a manager. I fight for my reports when they deserve it. They may never see it, but that’s ok. Fighting (and winning) for your people eliminates those awkward “gotta wait until next cycle” discussions. They feel this.

Team building

We all want to assemble a rock star crew. There’s a ton of advice on the Internet about hiring and match-making, so I’ll keep this section short.

Hire for initiative

There’s a baseline of knowledge and skill I need on my team. There’s no getting around that. However, in my experience, the person’s chances of success on my team depend more initiative and drive than knowledge and skills.

Intuitively, this can be a hard decision to make. Hiring decisions at startups are almost always made when there’s an urgent need. Investing in good people who may lack the immediate skill needs sounds expensive and time consuming. I remind myself that these first hires are going to shape the culture for years to come, and that culture is much hard to change later. I try not to let that urgency cloud my judgement.

Never compromise

Not much else to say here. I don’t say “yes” to someone I don’t believe in. When I don’t believe in them, it’s real hard to persevere when things get tough.

There is a pitfall here: listening to my gut without analyzing why I’m hesitant. This is trap for biases to pollute my decisions. Next thing I know, I could turn around and my whole team looks just like me. Uh oh. I do my best to figure why I’m not hyped about a candidate. I have make sure it’s truly because they won’t be successful here, not because they’re not like me.

Identify talents

After I’ve worked with someone for some time, I begin notice there’s particular tasks and practices they care about more than others. I use this knowledge to my advantage.

Matching my reports’ skills to the work they do makes the product better and gives them a sense of ownership of their projects.

Areas of improvement

In these first sixth months, I know I’m just barely scratching the surface of what this management thing is all about. In addition to growing these talents, here’s my short-term laundry list of skills to be building and learning next: - Learning the benefits and tactics of building a team of diverse perspectives - Doubling down on coaching and not letting feedback go unsaid - Identifing and begin grooming future leaders on my team

Comments or questions? Drop me an email!