Becoming a Leader in Tech

I had several conversations at re:Invent that have got me thinking since I returned. No names or details will be given about those whom I spoke with, but I have been processing the how and why of one’s career arc. How does one go from individual contributor to say Director level or even one day become a CTO? Breaking down the trajectory I’ve come away with a couple of types of leaders. In this article how to become a leader in tech.


For those who know me know that in my current role, I’m a CTO for a software company. I didn’t magically one day ascend to this level and quite honestly didn’t even aspire all those years back to make it this high.

My journey if plotted on a graph looks something like this. Some up periods and some plateaus. Those aren’t title changes, but changes in my experience and growth. I don’t like to measure my career in titles but rather in personal development.

Becoming a Leader graph

None of that is to say that I don’t enjoy, appreciate and cherish the time I get to spend up here, but it wasn’t my intended goal.

Throughout my life and career, I’ve always enjoyed solving problems and helping people. Those two things have been constant. Fast forward many years later and here I am writing technical and leadership content here on the internet. I’ve chronicled some of my adventures and lessons along the way which has allowed me to meet, talk with and learn from some amazing people.

It’s in those adventures that I’ve been asked more than once, “How do get to the next level in my career?”. Such a broad topic and one that usually takes more time perhaps than the asker intends. But it’s a topic I love to chat about.

As I mentioned above, after re:Invent I began to think more about it and I wanted to put some encouragement and more of a generic answer out for those wondering how to become a leader in tech.

Start with the why

My father used to tell me as a child.

Benjamen, if you don’t enjoy the journey, you won’t enjoy the destination. -Sammy Pyle

That has stuck with me throughout the years because he was correct. So many things in life don’t come quickly so you had better enjoy the work. The reason being, if you don’t enjoy the work, you’ll be jaded or upset by the time you get to the top and well, the top just won’t feel so good.

I always ask people, “Why do you want to reach that ‘title’ that you are after?”. And be honest with yourself. If you truly just want the title, then I’d challenge you to dig a step further and see what it is about the title that will satisfy you. Money? Influence? Respect? Then I’d secondarily challenge you that all of those things can be achieved without the headache of a higher level position.

Nailing down your why is step one on your journey to becoming a leader in tech.

My evaluation of the next steps

When I was a young leader, I was fascinated by all the things that young leaders often are obsessed with. Access to certain meetings or lunches. A little bit more money that was tossed my way. I had this perception that being a leader was about “counts” and “stats”. How big the department was. How much budget I was responsible for? All of those superfluous things that a 20-something might be thinking leadership means.

Now, if you become a leader and none of this resonates with you, fantastic! I’m glad you skipped this phase. I’m torn as to whether I wished I had. On one hand, it helped shape me. On the other hand, I feel bad for those who had to endure Leadership Benjamen 1.0.

Looking back on my younger self, I tend to tell people now what I would have told younger Benjamen if I could go back.

You need to understand who you are. What I mean by that is this. What are your strengths, weaknesses, and non-negotiables and what are the core values that you hold dear and true? Let’s dive a little deeper into that.

Leadership has two sides

Leadership is nothing more than navigating problems and situations in a relationship where one side is responsible for vision and support while the other strives to execute that vision with full transparency.

Learning yourself

Let me first preface this part with, I’m not a trained psychologist or anything closely related to that. However, even without that expertise, you should start doing some self-exploration. Ask for feedback from those around you. That 360-degree view of yourself is invaluable. The types of things I would be seeking are this:

  • Do I listen more than I speak?
  • Where do I draw my energy from?
    • Being around people
    • Cranking out some code
  • When solving problems, do I go step by step or do I like to work backwards from the outcome?
  • How am I under pressure?
  • Am I a delegator or someone who holds onto details?
  • Do I guide people towards answers or do I push for my outcome?
  • How often do I say thank you?
  • Do people trust me with important details?
  • Do I show vulnerability?

This is just a start. In the absence of fancy tooling, I’d encourage you just to ask those around you some of those questions in addition to asking them of yourself. You should start to get a feel for how you are perceived. And remember, perception is 9/10th of the truth.

Quick aside. There are no “wrong types of people” to be a leader. If you truly desire to be a leader in tech, the most important thing I think you can know is this. What are your constraints? Those things you struggle personally with. And do those things present a barrier to building relationships? Because at the end of the day, being a leader means building relationships with those you are responsible for. So keep all that in mind.

Core values

Young Benjamen thought this part of the process was useless. Why do I need to sit down and think about what I value and what I’m willing to do and not willing to do? Simple.

Once you know what you hold dear, you have a position to make decisions from. If you value empathy, then why would you force someone to do something you aren’t willing to do? Value authenticity but you show two versions of yourself. One when things are good and one when the going gets tough. How are those congruent? I like to think of core values as an accountability checkpoint and filter for decisions I make and interactions I have. Here’s a nice article that outlines a process to help discover yours and underscores their importance.

I went through this exercise a while back and here’s what I ended up with.

How to start working your way up

Remember, your progress is fueled by your why. I intend to share some guidance that I’ve found useful along the way. I’m writing this from my progression upwards, not from a position of understanding all the ways you can make it to your destination.

How can I help

Early on in my career, I was shaped by this idea of finding a way to add value as soon as possible. Adding value requires finding value gaps. Sure, you can go on a value gap exploration. Or, you can do what a leader does and ask questions about what’s working and not working. From there, you simply start filling gaps by getting to work and helping close them.

Remember above where I asked you to discover a little bit about yourself? That’s essential to understanding how you can best fill gaps as a leader. For me personally, I’ve learned that I’m good at two unique things:

  1. Breaking down the complex into simple terms and sequences
  2. Learning and understanding people’s strengths and weaknesses and then putting them in positions to succeed.

When I find gaps, I usually default back to these talents. I promise you this, YOU HAVE UNIQUE TALENTS. Your job as a leader is to find them and then deploy them to help others.

To become a leader in tech, I believe you need to first learn how you can help.

Letting go of the details

Jocko Willink talks a great deal about Decentralized Command. I subscribe very highly to this concept. I won’t repeat what he says but give you my take on what it means in tech.

If a team is constantly coming to me for answers then the following is true:

  1. They don’t own their outcomes which is bad
  2. They will move slower as I’m a bottleneck
  3. They won’t grow as developers, testers and leaders

I want teams that operate as their own free enterprises. Anytime that human nature and my ego get the best of me, I remind myself, that those closest to the information are best suited to make those decisions. On the flip side of that, it is my responsibility to step in from time to time and just ask some hard questions and give little nudges if I see things getting off track from the broader objective.

Innovation comes from the producer – not from the customer. -Edwards Demmings

Raising your hand

This part of what I tell people about how to become a leader in tech is sort of contra to how most of us work. All of us need help. And it’s much easier to get “pulled up” than to figure out how to “climb through” on your own. You will need some help along the way and your leader above you needs to know you want more. More responsibility, projects or challenges. Whatever that is you want more of, be willing to take any of it on. In this phase, get ready to get busy.

If you desire to move up, your leader needs to know they can count on you in the good tasks and the bad. And they need to know that you can handle some adversity when it supports the broader objectives.

Being willing to do the things that others won’t do will add credibility to your words that say “I want to move up”. For clarity though, I’m not asking you to work 80 hours a week or violate your core values above. What I’m saying is. Raise your hand, speak up and then back up those words with action that shows you are someone who can be counted on.

Building partnerships

The last piece of advice I give to those looking to become a leader in tech is to build partnerships with those in other departments. Unless you end up becoming a CEO, you’ll always have peers. And when you become a CEO, you have others you have to partner with, so technically you always need partners.

When I’m looking to pull someone up for a bigger role, I like to look at how well that person has worked with their peers and how well I think that person will do partnering with their new peers. I’ll repeat the thing I say a great deal.

Software is a team sport and the technology business is a human business. –

Tying it all together

Being helpful, raising your hand and building partnerships are some of my tips for how to become a leader in tech. I honestly though need to point you back to finding your why. I believe that this is the single most important piece of advice I can give you.

I personally never set out to become a CTO. Early on in my career, I thought climbing the ladder was important but I realized was this. The more I climbed the more empty and unsatisfied I felt. How can this be?

Well, results without purpose our often like Diet Soda. Tastes good at the time, but they are empty calories. I needed to find out who I was and what I valued. Solving problems with people is my why. And I don’t need to be a CTO to make that happen. I ended up becoming one because I followed my “yeses” and applied my craft.

Another key piece of advice my father gave me was

Find something you love to do and you’ll never work a day in your life. -Sammy Pyle

And I love the core of what I do. Additionally, I’m able to add some spice to that love by being able to share it all with those who follow along with my writing.

Wrapping up

Becoming a leader in tech is more than just a title. It’s about finding your why, learning who you are and then figuring out how to apply it. There will be points in time in your career that you are under-leveled and times you might be over-leveled but if you are fulfilling what you love, you won’t be “working”.

My closing words are. Don’t be discouraged in the journey. When you get down, lean on others. Reorient towards your why and stay focused on what matters most. Figure that out as soon as possible. Because once you do, your life and career will take on new energy.

Harry Burns realized this when he fell in love with Sally Albright. (it’s a movie, look it up)

When you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible. -Harry Burns

Thanks for reading and happy building!

Published by Benjamen Pyle

Benjamen is a genuine and resourceful technology creator with over 20 years of hands-on software development, team building and leadership experience. His passion is enabling technology teams to be their best by bridging modern technical design with outstanding business problem-solving. Recognized as an AWS Community leader in the areas of Event-Driven and Serverless Architecture, he brings multiple years of pragmatic experience designing and operating modern cloud-native and containerized solutions. When Benjamen doesn't have his head in the clouds, he's either playing golf with his wife and 2 boys or they are outside with their 12 paws.