The Sisyphean Challenge of Senior Technology Leadership

by Jake Bennett

Technology managers find themselves between a rock and a hard place, forced to choose between focusing on technical depth or leadership excellence. A potential solution comes from an unlikely source.

Sisyphus pushing a rock up a hill

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 hands-on technologists in the room want to determine if the manager understands what they do on a day-to-day basis. The non-technical people want to asses 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. On the one hand, technology managers must create and operate code and infrastructure, which requires detailed, technical knowledge. On the other hand, they must translate technical concepts into business strategy and manage a team, which requires communication and leadership skills.

The challenge for senior technology leaders is that we can’t do both perfectly. Therefore, the goal of the CTO and other senior technology leaders is to strike the right balance between technical depth and business leadership, based on the size and focus of the company. However, this is easier said that done.

Focusing on Technology Depth

As a technology leader, you can never be too technical. We rely on technology managers to make the right technical decisions and resolve technical problems quickly when they arise. The deeper their technical chops, the better they’ll be able perform these duties.

However, this mantra comes with a proviso. As a technology manager, you can never be too technical, provided however, that you spend sufficient time and focus on your leadership responsibilities, which are your first priority. And herein lies the paradox of senior technology leadership: to do your job well, you need to dive deep into the technology, but if you spend too much time diving deep into the technology, you’ll lose your ability to be an effective leader. So what’s a technology manager to do?