Dear Manager (Reflections on Leadership from 30+ Years in Tech) (#1)

With over 30 years in the software and technology industry — yep, I’m officially old — I’ve encountered all sorts of work situations. While most have been positive, some have been challenging. And often, the root of these issues wasn’t about software implementation but rather the way interactions unfolded between teams, particularly between managers and their subordinates.

I appreciate how professional groups foster positivity and encouragement in the professional world — we’re all here to do our best, right? But let’s be real: conflicts happen, and mistakes are made — by all of us, me included.

In this series (which could be two parts, three, or who knows, a hundred), I’ll be addressing some of the common issues I’ve observed in management. My goal isn’t to label anyone as a “good” or “bad” manager. Instead, I want to encourage reflection on certain practices we might adopt, often unknowingly, that don’t always serve our teams, ourselves, or our organizations in the best way.

This is based on my personal experience — both as a manager and being managed — and is intended to spark conversations about how we can all improve. If even one person finds this helpful and reflective, I’ll consider this series a success.

Let me know your thoughts!

Disclaimer: Expect some humor, intentional or not.

So, What Is a Good Manager Anyway?

A ton has been written about what makes a good manager. If you’re interested in a deeper dive, I recommend Andrew Lee’s excellent article, The Difference Between Good and Bad Management. In it, he highlights essential qualities such as:

• Being a good motivator
• Assertiveness
• Setting clear expectations
• Accountability
• Strong communication
• Trustworthiness and transparency
• Delegation skills
• Productivity
• Appreciation of others

These are all qualities we strive for in management. But as Lee points out,

“It’s not that a manager’s lifelong ambition is to be a bad one. But the promotion to authority and the increased workload can alter a manager’s personality.”

Managing is Aspirational

Now, I want you to think about this honestly: have you ever met a manager who ticks every one of these boxes? Or are you that manager? If so, you’re one of the lucky ones. Personally, I’ve never met that “perfect” manager, and I certainly haven’t been one myself.

Sure, I’ve encountered my fair share of self-serving management styles. But I’ve also been fortunate to work with people who embodied many of these attributes and helped me become a less terrible manager in the process.

The truth is these attributes are aspirational. They’re goals we strive for, but they can be elusive. Why? Because developing them depends not only on individual qualities but also on experience, preparation, corporate culture, and other factors.

And so…

For some, management comes more naturally than for others. But like most things, it’s a skill that can be learned, taught, and most importantly, improved. Managing requires constant relearning, readjusting, and staying mindful of the responsibility we carry — both to others and to ourselves.

I hope these reflections encourage some self-awareness and spark thought about the things we might take for granted in our roles.

Stay tuned for the next installment in this series!