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Comment: The Biggest Decision in your Technology Career

R. Michael Anderson


Technology Leadership

Leadership tutor and former software entrepreneur, R. Michael Anderson, discusses the skills technologists must learn and hone if they are to become great tech leaders.

There are a few decisions you’ll look back on and realise that they had a massive effect on the rest of your life.

Career decisions often fall into this category because having a job you like or don’t like dictates so much. Think about times you hated your job; it doesn’t just affect you when you’re at work, it saps your energy and sucks the soul right out of you. Often your family relationships suffer, and even your health.

You also can back yourself into a career dead-end. After having a few promotions and climbing the corporate ladder, you get stuck and there’s no more upward mobility. Your salary and responsibilities are capped out, and the thought of backtracking and starting again fills you with dread.

On the other hand, when you have a job you love; one that you’re engaged in, making a difference, learning and growing, and really contributing; it makes all of life a whole lot better. Your relationships, mood, and even your health seem to bounce right along.

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As someone who has had a wide range of jobs, from ones that I hated every second of, to ones that woke me up with excitement every day, I know the difference this can make.

In tech specifically, it’s important to know the routes you can take in your career because if you don’t choose, the decision will be made for you – and it may not be what you’re looking for.

Because I started my career assembling workstations and fixing bugs in code, climbed the corporate ladder, and later founded, scaled and sold three software companies, I have a pretty good view of technology careers from end to end.

Starting out

Like myself, most of us in the tech industry start out with roles such as coders, programmers, analysts, IT technicians or testers. We typically spend a couple of years in these positions honing our craft.

In these highly technical positions, analytical skills are the key to success. The ability to pick up, learn and master new technologies is crucial. Working hard and persistence in solving complex technological issues is what pushes us ahead during this stage in our career. Strong interpersonal skills are often seen as a bonus.

A Fork in the Road

After a few years of service and positive work, you come to the all-important decision that will affect the rest of your life; you can continue on the technical road or transition into management and leadership. It is an important choice because it determines what you are going to do for literally the rest of your life. It also determines what it’s going to take in order for you to continue to be successful.

Becoming a Technical Expert

If you’re one of the best in your field and want to stay with the technology, you can develop into a technical expert. You’ll continue to use those same analytical, problem solving and development skills. There are relatively few positions available to technical experts, for example, senior programmer, product specialist, chief technology officer, and vice president of technology. These positions tend to be highly competitive.

Becoming a Manager

If you enjoy business and not just technology, and want to expand past just the technology, the other career path is to become a manager. The good news is that there is plenty of room for advancement in this route. As you improve, your responsibilities will expand, and you will become responsible for larger and larger teams. Your technical knowledge, while still important, won’t be what determines your ultimate success in this role. You’ll be forced to evolve and develop a whole new set of skills and disciplines.

Transitioning into a Leadership Role

If you’re anything like me, the transition into management can be bumpy. When I first started leading teams I had a number of misconceptions about what makes a good manager: I thought my job as a leader was to simply divvy up tasks, and I became frustrated when my team didn’t accomplish them as quickly as I thought they should. I was not good at communications, I was arrogant, and I thought everyone should automatically respect me.

I was certainly not getting the best out of my team. It was very stressful for everyone involved. I knew that I was struggling, which made me feel insecure. This, of course, made my leadership even worse.

I had to face it: I was a horrible leader.

It was at this point that I self-assessed and realised my analytical skills were of little help in my new leadership role. Simply being able to outwork the problem, as I had before, didn’t work in leadership. It took a long time for me to see what being a good leader meant.

Being a leader is all about having a vision and being able to demonstrate that to your team. It requires communication and collaboration. You also need to facilitate communication between team members and make sure they’re able to get along. It is important to identify everyone’s strengths and weaknesses. All your team members are individuals, and they’re strengths and weakness are probably (hopefully!) not the same as your own. As a leader, you need to be able to motivate and inspire your entire team and earn their respect. You must develop positive strategies to coach them when they must improve their performance. Ultimately, leadership is about being able to get the best out of people.

I realised that I had to learn how to be a good leader. Before, I thought it just sort of happened. That’s absolutely not true – just like coding, project management and finance are learned disciplines, so is leadership.

Make the choice to Learn Leadership

Once I made the choice to be a ‘professional leader’ I set out a learning plan. I took courses, read books, got coaches and mentors, and sunk myself into it. I took many years to hone these skills, and it paid off. My companies made the Inc. 5000 list, we were voted the #1 Best Place to Work, and I won Social Entrepreneur of the Year.

That was on the outside. On the inside, I was finally having fun. I was seeing myself and others grow. We were providing excellent service to our customers. And we were giving back to the community.

And now I dedicate myself to teaching this same transformation to others. Nobody is born as a natural leader. I have worked with thousands of technology leaders all over the world, and they all needed hard work and practice. You can learn how to communicate effectively. You can learn to hold people accountable. As you become more comfortable with yourself, you can even learn how to be inspiring.

To become a manager or business owner, you will need to develop this skill set. Once you start down this path, learning leadership will be the one thing that will determine your long-term success and impact. Give yourself and your team the tools to transform into leaders who can drive your company towards growth, success and profits. It is the best investment you will ever make in your life.

  • Want to find out more? At the DIGIT Leader 2019 summit on the 30th of May, 2019, Michael will be teaching a breakout Masterclass called ‘5 Steps to becoming an Inspiring, Influential, Highly Effective Technology Leader’ – learn the proven system that shows you how to transform yourself and your career.
  • Join us at the conference and attend his session. R. Michael Anderson is a former Inc. 5000 software entrepreneur from California who now teaches technology executives around the world how to get the most out of their leadership careers. Companies who call Michael to level-up their leaders include Microsoft, Uber, PWC, and Stanford University. Learn more at

R. Michael Anderson

R. Michael Anderson

Leadership author, speaker and trainer

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