Transitioning from Engineer to Leadership (Plus Interview Tips)

“I suddenly went from being a competent middle of the road engineer to Director of Engineering.” – Jeff Nettleton

If there is one characteristic common across all engineers, it’s their love of learning. From testing new technologies to practicing with new programming languages and frameworks, engineers spend ample time learning how to further progress their technical skillsets.

But how much do they learn how to manage people?

We spoke with Jeff Nettleton, former Director of Engineering at Aledade and Staff Software Engineer at Color, about his journey to engineering leader and the different responsibilities that engineers face after being promoted to a managerial position. As an engineer who had the responsibility of leading a team suddenly thrust upon him, Jeff offers helpful advice for software engineers hoping to smoothly transition into a management role.

In this interview, we cover:

  • How to make a more seamless transition into a leadership role
  • Questions that an engineer should ask in the interview process for a lead position at a startup
  • Helpful outlets for engineers looking to learn new skills


The conversation below has been edited for length and content.


What are some things that could have helped you make a more seamless transition into a leadership role?

Aledade was the first opportunity where I really needed to grow as an engineer. As one of the first employees there, I suddenly went from being a competent middle of the road engineer to Director of Engineering and I had to quickly learn how to make the really important decisions and live with those decisions. I definitely stumbled at times doing that. One of the biggest moments for me was the first time I had to fire someone; this really brought home the gravity of the responsibility of being an engineering manager.

That’s why I think leadership training is very important. It’s hard to know whether or not you’ll be a good manager or if you’ll even enjoy management before you try it. However, it is important that some element of training is offered – whether that be a third-party class or shadowing program within your own company.

Moreover, the most important aspect to consider about engineering management is that the individual contributor components largely take a back seat. A lot of people assume that management will be very similar to their current roles but with additional one-on-one meetings every week. However, your priority is ultimately making sure that your team is executing on the tasks that the company needs you to execute on.

Therefore, the best advice to put you into the right headspace is to go into it with an open mind and think about all the best managers that you have worked with in your career. You also need to accept that coding needs to take a back seat to your management duties. Once you have acclimated to the role and accurately estimated your capacity, you may be able to get back into individual coding contributions if time allows.


Are there any questions that an engineer should ask in the interview process for a lead position at a startup?

The most important questions for someone interviewing and interested in a management position are:

  • What is the path that current managers at the company have taken? Are the current team leads internal hires that started out as individual contributors or not? If the answer to that is yes, they were promoted internally.
  • Were they given any sort of resources to help them become a manager? It’s a sign of a healthy company when management is given what they need to succeed.
  • What is the management style within the company? Some places do one-on-one meetings only when you need them. I recommend seeking companies that do one-on-ones every week.
  • What is the current vibe within the company? It’s difficult to get people to say anything negative about their company. One way I like to phrase it when I’m interviewing is, “What do you like most about your role? And what do you like least about your role?” You can often get some honesty particularly around how the management team influences the software development life cycle (Check out these tips on how a healthy team manages their SDLC). For instance, if the response to what they don’t like about the company is, “Oh, the deadlines are really tight,” or, “None of the JIRA stories are ever fleshed out and they don’t change the estimates when it becomes clear there’s more work to do,” you can read between the lines and get a sense that the culture at the company is to push really hard and work more than 40 hours a week. Being attuned to what people aren’t saying when they respond to your questions is a tough skill to master, but I always recommend interviewing even when you’re not necessarily looking to leave your current role because it can teach you about aspects of your company that you’re not aware of, surprise you with new opportunities, or just show you that you really like your current job and want to stay there.

Need more inspiration about what questions to ask? Here’s what every technologist should ask before joining a startup.

 What outlets are helpful for engineers looking to learn new skills?

An often-undervalued resource is the free option of contributing to open-source projects. Almost every engineer uses open-source tools, so going in and fixing a few bugs that people have reported will give you a good understanding of the technologies that startups use.

Alternatively, starting your own project can be a great form of education as well as help you expel some of the creative energy that you might not be able to let out every week at work.

Author: Jonas Fryer

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