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A workplace dynamic I’ve always found fascinating is the instinctual need for people to size up the technical depth of a technology leader upon first introduction. The technologists in the room want to determine if the manager understands what they do on a daily basis. The non-technical people want to judge if she’ll be able to communicate clearly, or if she speaks in technical gibberish.

This social dynamic is a natural side effect of the dual nature of the senior technology leadership role. Technology managers must create and operate code and infrastructure, which requires detailed, technical knowledge, while also translating technical concepts into business strategy and managing a team, which requires communication and leadership skills.

Technology depth vs. leadership excellence

As a technology manager, you can never be too technical. A deep, hands-on understanding of technology gives you superpowers because:

  • Your decisions will be better informed.
  • You’ll be more effective during an outage.
  • You’ll need to defer to subordinates for technical answers less frequently.
  • You’ll earn greater respect from your team, who will appreciate your passion for technology, even though they know they are better engineers than you.
  • You’ll have a greater appreciation for the amazing technical feats your employees perform, which often occur at a very detailed level.
  • You’ll have a better understanding of the nuances of emerging technology, which will allow you to make better bets on where to invest, and where not to.

But, that said, a good manager has to put their leadership responsibilities first. If you spend too much time diving deep and actually building the product, then you’re spending less time performing your responsibilities as a leader, which include cultivating a professional network, understanding changing business needs, and implementing long-lasting improvements.

So what’s a technology manager to do? Shift their focus away from technical details altogether and simply embrace becoming the pointed-haired boss they were always destined to be?

Resolving the paradox

For me, the solution to this paradox comes from an unlikely source — Greek mythology. In The Myth of Sisyphus, Existentialist writer Albert Camus argued that you need to live your life under the illusion that a universal notion of right or wrong exists. Sisyphus was a Greek king who was punished with endlessly pushing a giant boulder up a steep hill, only to have it roll back down after he reached the top, repeating this cycle for eternity. For Camus, the myth of Sisyphus illustrated the human dilemma: We must move forward in life, working under the illusion that a universal Truth exists, only to be smacked in the face every so often by remembering that our notion of Truth is a lie. Rather than roll over when this realization happens, we must move forward.

I see Camus’ argument as a blueprint for tackling the paradox of technology leadership. As leaders, we must relentlessly strive to learn new technologies, knowing deep down that we’ll never be able to master them. Fortunately, for the curious-minded, endlessly learning new technology is more like bouncing a beach ball across a field than pushing a heavy boulder up a hill.

So how can we help ourselves learn new technology without being consumed by it, to the detriment of our leadership responsibilities?

Below are some of methods I’ve found effective:

  • Read books. Read blog posts. Read white papers. Constant reading is key.
  • Listen to podcasts during your commute or when you go for a run.
  • Take an online class. Coursera and Udemy have some great online courses.
  • Attend technology meetups. Presenters usually show hands-on demos.
  • Start a side project and build something cool. The best technologists I know all work on side projects to cultivate their skills.
  • Occasionally, consider filling a role on a project that has hands-on technical responsibilities. This is a great way to see firsthand how the team operates at a micro-level. However, do this thoughtfully and with great caution. Be realistic about the time you can devote to the project. And, when you’re acting as a project team member, behave like a peer, not a boss.
  • Attend code reviews and technical show-and-tell demonstrations presented by your team. Anytime you have a chance to learn from your engineers, you should jump on the opportunity.

Cultivate a hacker’s mindset

Most importantly, technology leaders should always cultivate a hacker’s mindset. Hacking is the tangible manifestation of technical curiosity. A good hacker is always experimenting, exploring new technologies, and getting her hands dirty. Granted, you may never be the best engineer in the company, but you’ll certainly be on your way to becoming one of its best leaders.

Jake Bennett is CTO at POP, a Seattle-based creative technology agency that has worked with such companies as Starbucks, Pokémon, Target, Microsoft, and Major League Soccer. Follow him on Twitter: @jakebenn.

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