Chapter 8. Communicating with Executives

Travis Kimmel

Early in my career as an engineering manager, I would become frustrated when upper management seemingly brushed off challenges in engineering or asked me questions that seemed irrelevant. My perception was that the nontechnical side of the business was out of touch or even at odds against technical initiatives—to the detriment of the business as I saw it.

In hindsight this all makes a bit more sense. As organizations grow, an inevitable amount of complexity is introduced. The sheer variety of projects, people, and responsibilities on the minds of those at the top can be overwhelming.

In my tenure as CEO, I’ve learned how to navigate a constant stream of demands competing for my attention, where it is not possible to unpack complex topics in real time. I now recognize the problem was probably twofold. First, senior leaders faced raw, demanding items and were often fighting fires where mine wasn’t the priority. Second, I probably didn’t communicate in a way that got their attention.

Here are a few tips for communicating with and presenting to executives that have held true for me in the years since joining the ranks of management:

The granularity of your conversations should scale to match your company size
On the smallest teams, you might spend time talking about specific tasks. A bit larger, and you’re talking about sprints ...

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