Technology Leaders: Stop Explaining, Start Teaching

This was originally posted as a LinkedIn article.


Ronald Reagan famously said, “If you’re explaining, you’re losing.” And while he was talking about politicians getting bogged down in the minutia of policies rather than communicating in plain-spoken, intuitive ways, I think his advice is incredibly relevant to executive leaders in the business world today. Especially technology leaders.

It happens all the time. The technology leader (or consultant, in my case) is asked by the big boss to “explain” or “justify” an investment. “Why is this so expensive?” “Why is this so complicated?” “Why do we need an external partner to help?”

The questions as stated are traps, and all too often, we take the bait. We start rattling off data points and building in-the-weeds slides that walk through complex architectures, software comparisons, explanations of technical debt and mistakes of the past, security vulnerabilities, and on and on and on. We go down rabbit holes about GPT-3 vs. GPT-4 and point-to-point integrations vs. an integration layer and homegrown systems vs. SaaS applications. The result is at best a bored executive and at worst a frustrated one questioning the value and role of technology in the organization.

The issue isn’t that business-oriented executives are anti-technology or unwilling to listen. And, even though it’s commonly used as an excuse, it’s not because they’re “too busy.”

The problem is that we are framing these conversations the wrong way. We need to quit “explaining” and start “teaching.”

When I think about some of the most impactful mentors in my life, I think about some of my teachers. People like my high school calculus teacher Richard Eleazer, who changed my life by telling me he saw potential in me and challenging me to “put in the work” to do something with that potential. He didn't just explain things to me. He spent hours and hours after class helping me understand and internalize the concepts. Professors at UT like Prabhudev Konana and Robert Prentice who taught me not only new information and concepts but also new ways of problem-solving and thinking. And on-the-job teachers in my career like Paula Bookidis who taught me how to navigate tough conversations and Josh Rachner who taught me how to build SSIS data integration jobs (sorry, Josh – I don’t remember any of that anymore!).

None of those people left an imprint because they explained information to me. Rather, they approached our interactions as opportunities to teach, and I approached them as opportunities to learn.

Merriam-Webster defines the word “teach” in five ways:

  1. To cause to know something

  2. To guide the studies of

  3. To impart the knowledge of

  4. To instruct by precept, example, or experience

  5. To conduct instruction regularly in

And while the first definition sounds an awful lot like explaining, 2 through 5 go way beyond that and remind us that teaching is more multi-faceted and nuanced than explaining. Teaching – unlike explaining – asks us “guide the studies” and “impart the knowledge” and “instruct by precept, example, or experience” and “conduct instruction regularly in.”

And Reddit – perhaps not as distinguished a source as Merriam-Webster but nonetheless very helpful – sums it up even more clearly:

“Teaching is guiding someone's learning so they can figure it out on their own and learn to solve similar problems. Explaining is breaking down a singular issue without the intent to really explain why.”

How much more effective would our organizations be if we were helping each other learn and figure things out and apply our learnings to similar problems rather than simply regurgitating complex concepts and hoping for a lightbulb moment? What if our CEO was connecting the dots between business strategy and technology decisions? What if our CFO was seeing ROI on reducing technical debt and simplifying integration patterns? What if our COO or CMO or CHRO was evangelizing AI as an enabler of operational excellence rather than a shiny technology fad? This is the golden opportunity – to teach and empower our business leaders to be partners in technology transformation rather than simply consumers of technical minutia and cost models.

Here are five specific tactics I recommend:

  1. Identify what learning objectives are most valuable to your audience. Identify what’s critical for your audience to learn before you start teaching.

  2. Determine the best teaching modality. Is a PowerPoint “lecture” really the best medium for teaching this concept or would a demo or show-and-tell be more effective? Sometimes a lunch meeting with a colleague from another firm who has “been there and done that” may even be your best bet.

  3. Be clear on “why” this matters to your audience. How will it impact their day-to-day or the business at large? How can they use this knowledge to be better at their job? How does it affect employees and customers?

  4. Get their buy-in and commitment to learn. Teaching is a two-way street. You won’t have any success with a disengaged student, so have the conversation with your boss or peer or whomever you’re talking to about how and why you’re trying a new approach. I’m willing to bet they’ll be on board and ready to learn.

  5. Remember that different students learn in different ways. The very best teachers tailor their approaches to different learning styles. One size definitely does not fit all. Be ready to style flex and test out different communication approaches and teaching modalities for different audiences.

So, the next time someone asks you to “explain” a complex concept – whether it’s a technology project or an accounting practice or an approach to improving inventory planning and replenishment or a complicated engineering problem – put on your teacher hat!

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