The Art of Technical Leadership — Complete Resource Guide for Technologists Considering Management Part 1

Originally shared on LinkedIn

You might be where I was a few months ago.

Wrestling this nagging thought — “Should I or should I not?”

Deciding if management is a fit for you is not always a straightforward decision. For technical individual contributors, it can be even more daunting.

If you managed to take the leap, as I did, you will likely find this post helpful to orient yourself. I have the advantage of the beginner’s mindset which provides a unique vantage point.

Breaking It Down

I broke the content down to some core areas I am fast learning is key for any good technical manager (new or seasoned).

  • Leadership
  • Strategy and Execution
  • Product Development and Innovation
  • Delivery Management and Supportability
  • Organization
  • Culture and Team Composition
  • Resource Management
  • Purpose and Meaning

I wrote this with engineers or technical individual contributors in mind. But, if you don’t fit that bill, there is also something here for you.

I walk through some great resources I have come across over the years. Would love to hear your feedback.

I decided to break this down into more than one post. The first will be covering the first four bullet points with the others covered in a later post.

On Leadership

Becoming a Technical Leader — Gerald Weinberg

There’s no other book on this list that is as comprehensive as this one on the topic of technical leadership. The title says it all. Gerald knows what he’s talking about having spent years in the technical domain. This is a book written by a real practitioner not a journalist or management professor.

His key ideas center around three things he argues a technical leader needs to be able to do

  • Motivate
  • Organize
  • Innovate/Ideate

A good manager has two of the three down. Excelling at all three makes you a gem.


Any leader must be able to influence.

According to John Maxwell, If you think you’re leading, but no one is following, then you’re only taking a walk”.

Gerald lays it out that the first obstacle to motivating is the inability to see yourself as others see you. Part of motivating is realizing the human reality behind work.

Robert Sutton author of Good Boss, Bad Boss emphasizes a similar point.

The most effective bosses devote enormous effort to understanding how their moods, quirks, skills, and actions affect their followers’ performance and humanity” — Robert Sutton

How would you answer the question: “What does it feel like to work for me?”


A great leader understands what it takes to get resources for their innovators. She also fosters an environment in which everyone feels empowered.

Everyone understands the problem, manages the flow of ideas, makes decisions and implements those decisions. Organizing well means less drama. Sometimes it is not about solving problems but avoiding them.

Management involves some administrative tasks (even though organizing goes way beyond this). Not fun for most, but if you ignore these you can put all your good work at risk. Your credibility might also be on the line.


A good technical leader understands that most “new” ideas are copies of old ideas from other contexts.

A good problem-solving leader explores other contexts for good ideas to use. You shouldn’t be providing solutions until you have confirmed that you understand the problem.

You must be able to say, with reasonable certainty, “ I understand,” before you can say any one of the following things: “ I agree,” “ I disagree,” or, “ I suspend judgment.” — Mortimer J. Adler (How to Read a Book)

This is key to innovation as a problem-solving leader. There are three traits you should exemplify in this capacity

  • No interest in re-doing what has been done well by someone else or yourself
  • Spend more time perfecting ideas than proposing them
  • Take time to listen to others when they explain their ideas

This is an older book published in the mid-eighties. Compared to some other books on this list it might feel a little dated to read. Nonetheless, it is packed with wisdom.

“Becoming a technical leader is not something that happens to you, but something that you do.” — Vít Kotačka

Quotes from other great reads

“Decision making brings together many of the finest traits of contrarian leadership — thinking gray, thinking free, artful listening, delegating authority while retaining ultimate responsibility, artful procrastination, ignoring sunk costs, taking luck into account, and listening to one’s inner voice. Weaving these traits together is an art itself. When it is done well, the result is a thing of beauty and a powerful tool for effective leadership.” — Steven Sample ( The Contrarian’s Guide to Leadership)
“People who are treated as followers treat others as followers when it’s their turn to lead.”
“One of the things that limits our learning is our belief that we already know something.”
“When an organization does worse immediately after the departure of a leader, what does this say about that person’s leadership?”
“Those who take orders usually run at half speed, underutilizing their imagination and initiative. — David Marquet ( Turn that Ship Around)

On Strategy and Execution

The Art of Action — Stephen Bungay

This one of two books that top my list of recommendations. The word Strategy is a common phrase in most organizations. But, what is not common is knowledge of why most fail with execution. Stephen Bungay tackles this head-on in this book.

He draws his inspiration from two military leaders from the era of the Prussian armies — Helmuth von Moltke and Carl von Clausewitz.

Not surprising to see the military tie-in. A lot of business lingo draw inspiration from the military: company, command and control, HQ (Head Quarters), Strategy, Campaign etc

He attributes failure in execution to three factors:

  • Knowledge Gap (Difference between what should be known and what is actually known)
  • Alignment Gap (Difference between plans and actions actually taken)
  • Effects Gap (Difference between actions and the expected outcomes)

The key lesson from this book centers on closing these gaps using an approach described as directed opportunism. Below are some central ideas

  • Leaders should focus more on defining and communicating clearly the general intent and objectives while spending less time on detailed strategies
  • As you progress further down the ranks leave it to those below to decide on the actions to take. After getting a clear What and Why from leadership, teams should focus on how to align their actions with the intent.
  • These same group should have autonomy to adjust and adapt their actions to changing circumstances or situations while staying guided by the overall intent

If you are familiar with OKRs you might find it insightful how this framework lines up with that concept. You understand why OKRs work when executed as intended. More on this a little later.

This was the most tasking book to finish because of how rich in content it is. But, I assure you that reading half the book will give you enough to start making big changes.

Quotes from other great reads

“Leaders must get across the Why as well as the What. Their people need more than milestones for motivation. They are thirsting for meaning, to understand how their goals relate to the mission.”
“There are so many people working so hard and achieving so little.”
“Individuals want to drive their own success. They don’t want to wait till the end of the year to be graded. They want to know how they’re doing while they’re doing it, and also what they need to do differently.” — John Doerr ( Measure What Matters)

On Product Development and Innovation

Inspired — Marty Cagan

Any technical manager has a great opportunity to help drive innovation. Yet, it’s not enough to think up good ideas and do nothing about it. In this book, Marty lays out a great approach to enable building products customers will love.

He starts off by clarifying the risks you want to mitigate early during product development.

They include

  • Value
  • Usability
  • Feasibility
  • Business Viability

The approach to doing this accounts for two separate phases during product development: The discovery phase followed by the delivery phase. The former is where a lot of organizations fall short.

In reality, when you start out building a product you have a set of hypotheses. You need a quick and solid way to confirm these before getting too far. You are hoping to mitigate some of the above risks in this discovery phase.

Another key shift involves replacing roadmaps with product discovery. It’s a lot more worthwhile investing energy in the product discovery than trying to guess a roadmap. I’m sure you have seen many roadmaps that have failed to live up to their promise. So, why do we keep using them?

Organizations need to drive towards outcomes rather than output. If you are not sure which way your organization currently leans you can explore the 12 signs that you’re working in a feature factory. Don’t focus on output over the outcome.

One solid way to shift to an outcome-based mindset is to think embrace OKRs — I did come back to it!

The common knowledge is that OKRs started with Andy Grove at Intel. John Doerr, also from Intel, helped evangelize it seeing it make its way to Google and several other high-achieving companies. OKR stands for Objectives and Key results. It helps position you to measure what matters.

Check out Measure What Matters by John Doerr to go to school on this topic.

Few things are as satisfying as getting rave reviews from users of your product because you solved a pain point or increased delight. This book has some great ideas that can help you deliver on this aspiration.

Other great reads

  • The Innovator’s Cookbook: Essentials for Inventing What’s Next by Steven Johnson
  • Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days by Jake Knapp

On Delivery Management

The Phoenix Project — Gene Kim, Kevin Behr, and George Spafford

So, you have a great idea and you have learned to build it. How do you now deliver it at scale repeatedly?

For a fictional book, this is an amazing read for any technical leader. It walks through the story of a fictional company on the brink of collapse. The company discovers DevOps practices inspired by lean manufacturing principles. This gives them a way out.

There are many lessons, but the key takeaways center around ‘The Three Ways’ and ‘Four kinds of work’.

The three ways focus on the theme of

  • Emphasizing performance across the whole (value stream) and not only the parts
  • Building in feedback loops
  • Continuous learning

Each way has its purpose and expected outcome if done right. This three ways of DevOps summary does an amazing job of summarizing this topic. I’m not sure I could do a better job. Check it out.

The four kinds of work help you assess the value of what you are working on. A dangerous place to be is WIP (Work In Progress) land where there is only gnashing of teeth. You need a special lens to check where team time is being spent.

The kinds of work break down to

  • Business projects that link to business outcomes
  • Internal projects which help sustain a high rate of business project throughput
  • Operational changes which manage flux or fixes based on the first two types of work
  • Unplanned work which could eat you for lunch (avoid these at all cost)

How clear of a view do you have on where your resources are spending time? Unless it’s by design the last two bullets is where you want to spend the least of your time.

If you are brand new to DevOps, this is a great book to paint a clear picture. Otherwise, it provides a refresher on the chaos that could ensue in its absence.

This rounds up this piece. Look out for the next post covering the other areas I have learned are key to succeeding as a technical leader.

Please share, clap, and tweet if you enjoyed reading this. Also, leave comments on books or resources you have found valuable on your journey.