The Art of Technical Leadership — Resource Guide for Technologists Considering Management Part 2

It’s 5AM.

You just realized that you forgot to charge your phone overnight.

That doesn’t keep your phone from buzzing as you reach to find it in the dim light. You definitely don’t want to wake your significant other. It’s been a little stressful for everyone at home as you have adjusted to being a first-time manager.

You notice the chatter back and forth on the work messaging group. It is due to issues on the front end. So, you breathe a sigh of relief.

“Thank God! It’s not one of my applications”, you mutter under your breath.

Your responsibilities go beyond supporting a reliable system at scale. You also have to manage your people and motivate them while driving innovation, strategy, and execution. Not to mention the administrative tasks of approving timesheets.

Right. You still have to approve last week’s timesheets.

If would be nice if this all go a little smoother.

Some Background

If the story above resonates with you, then I had you in mind when I wrote the first part to this post. I have since realized that these lessons go beyond technologists or people with the title of manager.

Technical leadership does not need an official title, role or position. You know that by now.

You could be deliberating a decision on getting into management. Or, you are a first-time manager trying to figure out what it takes to succeed while avoiding pitfalls.

You also may be a seasoned manager contemplating what can set you apart as a great technical leader. Better still, you are an individual contributor interested in growing in technical leadership.

If any of that speaks to you, then there is something here for you.

Reviewing The Big Picture

These ideas have served me well since getting my first taste of technical management.

This follow-up to my first post continues a break down of areas I believe every Technical Leader (new or seasoned) needs to give attention.

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

I covered the first four points in the first post. I’ll be delving into the last four bullet points here.

I will be covering some great resources (books) I have come across over the years. There are so many to choose from. I would love to hear your feedback.

In fact, if you read this and the first post in one sitting I owe you a cup of Coffee. Hit me up on LinkedIn if you are in Cincinnati.

Let’s get to it.

On Organization

The One Thing — Gary Keller

We must never confuse activity with productivity.

There is great danger in thinking that being busy is a reflection of how much we are accomplishing. No need to ask the hamster on the wheel how far it has traveled.

Gary’s book was impactful for me because the lessons are applicable to all aspects of life. He drives home the need to focus on one thing.

Did you know that the word priorities didn’t exist until about a century ago? There was no plural for the word priority because it addressed one thing. So the concept of top 5 priorities would have been an oxymoron.

Until my one thing is done everything else is a distraction — Gary Keller

Questions like the below draw this much-needed clarity:

  • What’s the one thing I can do to achieve my diet goals?
  • What’s the one thing I can do to increase my net worth?
  • What’s the one thing I can do differently to manage my people better?
  • What’s the one thing I can do to move the project along?
  • What’s the one thing I can do differently to deliver higher quality results on time?

Can you feel that sense of clarity by how the questions are framed?

You can reframe this focusing question as: What is the one thing I can do so that by doing it everything else will be easier or unnecessary?

A poorly organized technical leader is building his castle on sinking sand. You need organization even if you have to delegate parts of it. You can get better organized if you focus on your One Thing.

As I said, this is a great book way beyond work. It makes for an enjoyable read as well.

Other great reads

  • Managing Oneself by Peter Drucker
  • The First 90 days: Proven Strategies For Getting Up to Speed Faster and Smarter by Michael D. Watkins

Culture and Team Composition

The Success Matrix — Gerry Langeler

I mentioned OKRs (Objectives and Key Results) in the first post. But you have to get the culture right to let it shine.

In Good to Great: Why Some Companies Make the Leap…and Others Don’t, Jim Collins makes it clear that you need to figure out who should be on the bus and the right seats for them.

The Success Matrix (another solid fictional book) is on the mark here.

The story starts off with the main character preparing for the final stage of an executive interview.

He reflects on several best-selling management books but didn’t find a fitting one to help prep for this final interview. So he resorts to reaching out to an old mentor who walks him through the Success Matrix.

The Success Matrix is a breakdown of the kind of people you might expect to see within an organization. It very well might also reflect the DNA of an organization as a whole. Three key elements make up the core of the Matrix.

Vision, Process, and Output.

Vision — Is a broadly understood sense of direction which encompasses competitive leadership over time. On a personal level, it is a deeply held conviction on where you want your life to go over time.

Process — These are structures, methods, and procedures to repeatedly produce timely high-quality products and services independent of changes in personnel. On a personal level, it is the means, methods, and techniques to achieve your vision and goals independent of temporary setbacks or distractions.

Output — Consists of profitable products and services produced with predictable regularity. On a personal level, it is tangible evidence that you’re achieving your life goals.

A mapping of the resulting matrix and the related personas breaks out into the following:

A Dreamer does well with vision but lacks a process and output to match that vision. You know that person you work with who has great ideas but has no clue how to make it happen and never does much with it.

A Brute lacks a process. They generate output even if it means hacking it. But, the solution is likely not scalable.

A Success, which is what you want, excels in all three areas — vision, process, and output.

It helps to evaluate your team or organization through this lens.

You want all Successes on your team. And, this starts with figuring out where the opportunity is for development.

The Success Matrix is a great tool for guiding that development as you find the right seats for your people. It also aids in pairing up folks on your team to manage team composition and maximize synergy.

Other great reads

  • Overcoming The 5 Dysfunctions of a Team by Patrick Lencioni
  • Powerful: Building a Culture of Freedom and Responsibility by Patty McCord
  • Tribal Leadership: Leveraging Natural Groups to Build a Thriving Organization by Dave Logan, Halee Fischer-Wright, and John King

Resource Management

The Coaching Habit — Michael Bungay Stanier

As a manager, you must guard and treat with care the limited time you spend with members of your team.

For most folks, this happens through a 1:1 meeting.

I have observed over the years that the best managers use this time to coach.

In this book, Michael drives home the importance of asking questions while coaching.

According to him a busy manager only needs seven good questions to radically lift their leadership game. He then goes on to lay out the seven essential questions all great managers ask their employees.

The first question is the one I have found the most useful.

It’s simple yet effective: “What’s on your mind?”

To no surprise it is the same prompt Facebook uses in its status section.

Your schedule might allow you 30mins or less and you don’t want to spend half of it on small talk. A friendly conversation on the weather or sports is great, but should not dominate a 1:1.

If this time is about members of your team then make it about them.

It’s also often dangerous for 1:1 time to focus on status updates. That is a small component of it, but don’t make it all about that. It needs to cut deeper to use this as a coaching time.

You’re trying to build a great team and you need to get a pulse on where things are to provide vital feedback both ways

Google carried out a study exploring what makes a manager great and being a good coach was number one.

Also, if you find you are doing most of the talking in your regular 1:1, you’re doing a poor job of coaching. Nothing beats using effective questions to guide your team to figure things out on their own.

Note, this is not from the book, but I have had moments when something comes up and my 30 mins shrink to 10 mins. Rather than skip the time as a whole I ask a different question.

The most effective question I have found given time for only one is: “What challenge in your world needs immediate attention?”.

Smart people ask questions because that’s how they learn. A great coach can’t do without this much less a manager.

Other great reads

The One Minute Manager by Kenneth H. Blanchard and Spencer Johnson

Good Boss, Bad Boss: How to Be the Best… and Learn from the Worst by Robert I. Sutton

Purpose and Meaning

How Will You Measure Your Life? — Clayton M. Christensen, James Allworth, and Karen Dillon

A friend once told me that growing up he could never say with certainty what his father was working on. Yet, he was clearly able to know when his father had a good boss or a bad boss.

As much as you might choose to avoid it, life affects work and vice versa.

If work has such a strong impact then life must be lived with meaning and purpose — both at work and outside of it.

Dan Pink, in his TED talk titled The Puzzle of Motivation, highlighted Purpose as one of the three components to creating a high-performance environment. The other two are Autonomy and Mastery.

Purpose: the yearning to do what we do in the service of something larger than ourselves — Dan Pink

You can’t help your team navigate working with a sense of meaning and purpose if don’t have a handle on it yourself.

So, how do you discover meaning and purpose at work and beyond?

One popular answer is to follow your passion. This might be true for a few but for most, this answer is misguided. I plan to explain why in a future post.

A more reasonable path requires two key things. Having a clear understanding of what you are good at as well staying connected with the ‘Why’ behind the ‘What’. Simon Sinek hits on the latter in his now famous TED Talk.

On a personal level, what you are good at can propel you to doing something impactful. This is fertile ground for discovering personal meaning and purpose.

You can also apply this to your team. You also want to help them connect to the ‘Why’ behind your organization or product.

Clay Christensen takes these ideas further in this book. He does this by drawing illustrations on some principles that helped specific companies to succeed. He then maps those lessons for personal application. All with the intent on getting you to evaluate how you will measure your life.

He recommends three steps towards seeking purpose and meaning:

Likeness — Involves figuring out who or what you would like to be like as a person, team or organization

Commitment — Allocating time, tools and resources along with a deep commitment to becoming who you want to be

Metrics — Having clear ways to measure your progress

Ray Dalio speaks a lot about pursuing meaningful work and meaningful relationships. This is the heart of it.

As a technical leader, you need to help your team navigate this, but it has to start with you.

Other Great Reads

Principles: Life and Work by Ray Dalio

How to Fail at Almost Everything and Still Win Big by Scott Adams

So Good They Can’t Ignore You by Cal Newport

Rounding Up

I didn’t do all these books justice so you might have to read some of these yourself. I also don’t share every opinion expressed by the respective authors. These books no doubt hold some nuggets you can benefit from.

Hopefully, you found at least one thing useful here to help you grow as a technical leader.

If you did, please share, like, and tweet. Do share what has been key to your success as a technical leader. Also, leave comments on books or resources you have found valuable on your journey.