Why tech experts so often struggle to become leaders — and what they can do about it - Technical.ly Philly

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May 15, 2019 1:58 pm

Why tech experts so often struggle to become leaders — and what they can do about it

Web development industry veteran Jim Keller offers advice about how to better transition from behind the screen to the head of the team.

Working with computers is like a fresh chess board.

(Photo by Flickr user Angie Garrett, used via a Creative Commons license)

This is a guest post by Jim Keller, a founding partner of web agency Eastern Standard.
There was a short essay published on the early internet — 1986, to be exact — called “Hacker Manifesto.” It’s a cringe-worthy screed that would be right at home on the “I’m 14 and this is deep” subreddit, but there’s a concept buried within it that has stuck with me over the years, even if my own teenage angst has faded.

Amidst its cyberpunk-inspired social commentary, the manifesto describes the objectivity of computers: They are impartial machines, free from bias, and carrying with them no particular agenda. “If it makes a mistake, it’s because I screwed up. Not because it doesn’t like me.”

Especially for socially awkward kids who gravitated toward computers at an early age, there’s something appealing about that type of objectivity. The machine doesn’t treat you differently based on your physical appearance or your social status. It doesn’t bring any prejudice or past experience to that table. It isn’t still upset because of something that happened yesterday. It’s a fresh chess board, a puzzle to be solved. Ordered. Predictable.

We spend hours alone evolving our problem-solving skills in that unbiased world where the right solution always exists if you press the right keys in the right order. We get very good at solving puzzles, and eventually join teams of other folks who have presumably mastered the same skills.

At some point, we’ve advanced to being put in charge of our fellow key-pressers. We’re spending less time working with the machine and more time working with the team. And this is where things start to unravel for us, at least from what I’ve observed in myself and others around me. As emergent leaders, we’re often seen as dismissive, contrary, and lacking empathy. We’re terrible at delegation. The technical solutions often seem so obvious to us that “it’s faster if I just do it myself.” We’re constantly putting out fires rather than spending our time building a fire-resistant team and implementing processes that serve as fire-suppression systems.

If this sounds familiar, you’re not alone, and you’re also not in checkmate. There’s a way to break through the leadership barrier, but it involves admitting to a fundamental truth: The practices you’ve used to become such a quick-witted technical problem-solver will very often fail you, and you need to introduce some entirely new, possibly very foreign skills into your repertoire in order to succeed.

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Applying a new problem-solving framework

Humans, unlike machines, do bring their individual biases, past experiences, and hopes for the future to the table. They have external complicating factors in their lives that might alter how they act, even on a day-to-day basis. Where the machine was ordered and predictable, people are constantly adapting and reacting to changing circumstances in their lives and in their work.

They also don’t all operate on the same instruction set: Each individual’s personality has been shaped by genes, upbringing, and life experiences. If you apply a rigid problem solving framework to management — one where you expect the same set of inputs to always produce the same results — you’re in for a very tough time.

When moving from technology practitioner to a leader, success is probably not a matter of tweaking a few of your old habits or adding a few new problem-solving tools to your belt. You need to deeply assess your own skills and personality and be willing to deconstruct everything you thought you knew about communication and problem-solving. It’s not just about learning “leadership”; you will almost certainly have to unlearn some deep-rooted habits and break through assumptions you have about how effectively you interact with people around you.

Taking a candid self-assessment

How well do you really communicate with other people? Most of us, in my experience, have learned frightfully bad habits when it comes to communication. We hold back where we should be candid, and we take a strong stance when we should be open-minded. Have you ever thought about communication as a skill you should develop, or do you think of it as an intrinsic personality trait? (Spoiler: It’s not.)

How empathetic are you, really? That word has been thrown around so much that it’s losing its meaning. Empathy is not just about being nice to people. Do you actually acknowledge other people’s perspectives, personal constraints, and long-term goals, and use that as a way to inform your behavior and decision-making? Or do you just broadly apply your own life experiences to your expectations for other people, then get confused when they act differently than you would?

How good are you at accepting criticism and feedback? Do you default to a defensive posture when people suggest that you have deficiencies, or do you accept constructive criticism as the gift that it is? When was the last time you changed your mind?

These are the kinds of questions you need to ask yourself, and you need to be honest about the answers.

Building yourself from the ground up

To bolster your leadership skillset, I strongly recommend seeking out books, podcasts, and articles about psychology, communication, relationship-building, and general self-help. Remember, you’re not just “adding” leadership skills: You need to develop a clear lens through which to view yourself, and the proper tools to motivate, inspire, and mentor others. Construction almost always starts with some amount of demolition.

Make sure to expose yourself to content that will help you question yourself at a more fundamental level. You want to break down assumptions you hold about yourself, your values and motivations, your communication style, and your decision-making practices. Some of my recommendations to these ends are below:

“How to Win Friends and Influence People” — Dale Carnegie

  • I feel like people often roll their eyes when I recommend this book, like it’s somehow just too old-school to be valuable. But I find myself referring back to it again and again, and it really helped to transform how I think about my communication practices.

“Predictably Irrational” — Dan Ariely

  • Another book I find myself referencing often, Predictably Irrational offers compelling insight into the decision-making patterns behind human behavior, highlighting how often we are wrong not only about the motivations of others, but even in predicting our own motivations behind decisions we make.

“Dare to Lead” — Brené Brown

  • This one was recently recommended to me by our director of projects (and digital PM extraordinaire), Abby Fretz. While, yes, it’s technically a “leadership” book, Brené’s approach to leadership through courage and vulnerability insists that emerging leaders inspect their own behavior and be honest about their own deficiencies. Brené and I also shared a similar perspective on the dangers of misconstruing skills (courage, communication) as inherent personality traits that you either have or don’t have.

Facing the new challenge

Finally, in addition to reading as much content as possible, expose yourself to situations that ask you to draw upon your emerging leadership qualities. If there’s an opportunity to lead a new initiative or to have a conversation with someone that you might otherwise put off, just dive in. Approach it as a necessary learning experience — you need a lot of those at this point. Remember: Your comfort zone is a tomb; stay away from it as much as possible.

People: Jim Keller
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