5 Lessons learned as a First time Technology Manager

Jon Staples
3 min readApr 18, 2021

There are a lot of articles out there dedicated to the hard details of working in technology, but there are significantly fewer related to the soft skills of technology leadership and being an engineering manager at large.

I’ve enjoyed success as a technical expert, enough to find myself a leadership position running a software engineering team, but very little in my formal education or my work experience actually prepared me for the complex multivariate system that is human leadership at a technology company.

Here are a few tidbits that I’ve learned so far.

You will have to talk to customers

My particular set of personality traits give me a leg up as an Engineering Manager. I’m irreverent, willing to speak truth to authority, quick with a joke, and when it comes to technology - I know what I’m doing. With the typical motley crew of software engineering folk, these traits seem to have served me well. I enjoy collaborating and debating with software engineers, talking about nerdy things, and basically enjoying the generally odd group of people that tend to get into writing software.

I have; however, had to realize the hard way that your customers probably aren’t Software Engineers and that same irreverent jocularity may not be the right approach for engaging with every customer. The happy ones get into it, the others… not so much.

My advice, hire a good product manager who you can work with that can help keep you in line.

You will spend a lot of time (not) writing code

Be it technical specifications, customer facing documentation, internal processes/procedures, security policies, training materials, project scoping, etc. etc. you will spend more time writing documents and less time writing code. Embrace it, think of it as meta-programming or a high level abstraction.

You will spend a lot of time recruiting

This is one of the big adjustments for me. Being a Software Engineer is an enviable position because the economic principles of supply and demand weigh in your favor. As technical lead or manager however you end up on the opposite end of the spectrum. Software Engineers are scarce, high quality engineers more so, and high quality engineers you can afford to pay market salaries for… yikes.

My advice — establish a working relationship with a recruiter that gets you and your needs (internal or external).

You will spend a lot of time on relationships

Customers, co-workers, direct reports, bosses — you will need to build trust with, deliver feedback to, and generally learn to approximate healthy adult relationships with the people you engage with in your work life — like it or not. There is nothing about this that is specific to technology. It is just the basic human element of work and business. You will still dig in, headphones on, and crush some brilliant abstraction or automation, but to succeed as a leader you’ll have to disengage “beast-mode” and engage with other human creatures — probably pretty regularly.

My advice — coffee breaks, regular checkins, and try to make room for the things that aren’t just all about work. People have lives, families, interests, and things that go beyond the next sprint or Q2 financial goals.

You will try to fix things you can’t

There’s nothing about this particular lesson that is specific to technology, I’ve observed the same phenomenon in several people who have found themselves in first time leadership/management positions.

The core problem here is that when you move into your first time leadership role, you inherit everything that came with it. The bad practices, the sloppy behavior, the absence of process, and importantly — the direct reports who are just a bad fit for the job. At first, it may not be obvious who these people are, and often enough you may end up surprised by those who end up succeeding and those that don’t.

However, it is not uncommon to suddenly find yourself managing someone, potentially a former colleague, who just isn’t cut out for the job.

Some things look out for:

  • They require an inordinate amount of your emotional energy and you often have to go back and fix their work.
  • They say the thing you want to hear, but end up doing the opposite.
  • You don’t trust them to get work done.

And the big one:

  • They don’t seem to learn or improve even when others are.

My advice here - Take a step back and give yourself a break. It’s really easy to be insecure about your abilities as a first time manager and throw yourself head on at a problem. Sometimes though there isn’t a fix, it’s just a bad fit. Accept it — move on.

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Jon Staples

Software Engineering- Recovering Engineering Head, Recovering Neurogeneticist, Oenophile, Tech Entrepreneur?