The Sisyphean Challenge of Senior Technology Leadership

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.

Flat illustration of man pushing a rock up a hill

This article was published on 11/6/2016 in VentureBeat.

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?

But is it true that if I spend too much time diving deep into technology I’ll lose my leadership ability? Does the mere act of writing code cause my leadership muscles to atrophy?

Not exactly. But as managers, we have a limited amount of time during the day (even if we work long hours), and if we’re spending the majority of our day diving deep into technology and actually building the product, then we’re spending less of our time performing our responsibilities as a leader, like hiring employees, retaining staff, improving processes, managing budgets, growing revenue and promoting innovation. If we insert ourselves into the development of the product, then the product will be our master, and our leadership responsibilities will take a back seat. Over time, this will diminish a manager’s ability to be an effective leader, as the role necessitates cultivating a professional network, understanding changing business needs and implementing long-lasting improvements, all of which require sustained effort.

This is why a strong senior technology manager will never be the best engineer in the company (outside of small, early stage start-ups). A great technology leader isn’t spending her day writing code, but is instead hiring talented engineers who are better than her. How could you ever be a better engineer than the rock stars you hire who are working hands-on with the technology every day? You can’t, not if you’re doing your job well.

Focusing on Leadership

So if a good senior technology manager needs to focus on leadership responsibilities, does he shift his focus away from technical details altogether, and simply embrace becoming the pointed-haired boss he was always destined to be?

No, that’s not an effective strategy either. The deeper your knowledge of technology is, the better a technology leader you will become. 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.

To illustrate this last point, take an emerging technology like machine learning (ML), for example. ML is unequivocally changing the way we build software. It is also a completely different approach to solving problems. But in order to capitalize on this paradigm shift, technology leaders need to be able think in terms of ML algorithms, and this requires a fairly detailed understanding of how it works. Even if you’ll never be a full-time data scientist, knowing how the most popular algorithms work and the problems they are best suited to solve gives you the ability to envision the future possibilities of ML. And if ML isn’t your thing, then pick your favorite emerging technology—the same deep-dive approach is required. When a technology is new, the devil is in the details, and getting your hands dirty will give you an understanding of the details that are crucial for success.

Resolving the Paradox

So how does a senior technology leader proceed? Too much focus on technology leads to weak strategic leadership. Too little focus on technology leads to weak technical leadership. It seems we’re damned if we do, and damned if we don’t.

For me, the solution to this paradox comes from an unlikely source—French philosophy. In the mid-20th century, the Existentialist philosophers also struggled with a perplexing paradox (albeit, a far more profound one). The Existentialists believed there was no true measure of right or wrong, and that there was no inherent purpose in life. However, this group of thinkers also lived through the moral atrocities of World War II, and understood that moral relativism was an unacceptable alternative. The challenge for the Existentialists, then, was to determine how we should live and make decisions when there was no true, singular moral compass or purpose. The question for them was: how do we take action in life, knowing there is no fundamental way to know if our actions are correct and moral?

Existentialist writer Albert Camus proposed a unique solution, looking as far back as ancient Greece to find an answer. In The Myth of Sisyphus, he argued that in order to resolve the seemingly intractable Existentialist dilemma, you needed to live your life under the illusion that a universal notion of right or wrong exists (that is Truth, with a capital “T”, exists), yet always recognize that this illusion is a fantasy. For Camus, the Greek mythological figure Sisyphus perfectly symbolized this approach. Sisyphus was a Greek king who was punished by Zeus for claiming he was cleverer then the gods. Sisyphus’s punishment was to endlessly push a giant boulder up a steep hill, only to have it roll back down after he reached the top. The next day, Sisyphus would push the boulder up the hill again, 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, however, we have to dust off our Existentialist angst and move forward again with rose-colored glasses, pretending Truth exists until the next moment of realization occurs.

Where Camus saw the myth of Sisyphus as an allegory for the human condition, I see it as a blueprint for tackling the paradox of senior technology leadership.

Strong technology leaders must cultivate deep technical knowledge. This means they must be constantly learning and improving their technical abilities in an attempt to master new technology, just as Sisyphus rolled the boulder up the hill every day in an attempt to put it to rest. However, once the technology manager feels he’s reached a summit of understanding, he looks around and realizes he’ll never be able to master the technology: there’s just too much to learn and his leadership responsibilities will always keep him from becoming a true master. Rather than giving up, however, the strong leader dusts off her technical angst, puts on her rose-colored glasses, and pushes forward in a futile attempt to master the technology again. This endless struggle of a failed mastery will never make the manager a better technologist than the engineers on her team, but it will absolutely help her become a better technology leader. This is the Sisyphean challenge of technology leadership.

Sounds sort of depressing though, right? Ceaseless toil. Never-ending disappointment. Constant repetition. Why would anyone sign up for such a horrible fate? And indeed, it would be a horrible fate if you lacked passion for technology and didn’t have an insatiable sense of curiosity. If learning doesn’t float your boat, your life as a technology manager will be dreary. Fortunately for most of us, we have earned our success in technology precisely because of our passion for technology. For the curious-minded, learning a new technology is more like bouncing a beach ball across a field than it is pushing a heavy boulder up a hill. We recognize that learning is a journey, not a destination, and we really enjoy the ride.

So what are some of the things we can do to help us learn new technology without being consumed by it, to the detriment of our leadership responsibilities? Below are some of methods that I’ve found effective during my career:

  • 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 Meet-Ups. Presenters usually show hands-on demos.
  • Weekend Project. Start a side project and build something cool with technology that you are interested in. Side projects are the technical learner’s secret weapon. They allow you to get hands-on with code and/or infrastructure at a pace that works for you. The best technologists I know all work on side projects to cultivate their skills.
  • Dive Deep. 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 and it will supercharge your technical knowledge. However, do this thoughtfully and with great caution. The time you can devote to the project will be limited, and if you can’t fulfill the responsibilities of the role, you’ll let your team down. Conversely, if you get completely sucked into the heads-down technical work, you’ll end up ignoring your leadership responsibilities. The key here is finding a small, bite-sized chunk to work on and being realistic about the time you can devote to the project. Also, when you’re acting as a project team member, try to 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. This is one of best aspects of being a manager!

Most importantly though, 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. Even if you spend the majority of your time as a senior leader attending management meetings, creating PowerPoint decks, and managing budget spreadsheets, there’s nothing stopping you from occasionally setting Excel aside and tinkering with technology. If you’re the CTO of a Fortune 500 company you’ll probably spend less time doing this than the VP of Engineering at a small start-up, but the adoption of a hacker’s mindset is a universal need that transcends company size. Just because you wear a suit every day, doesn’t mean you have to stop embracing your inner hoodie. 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.