Talking to executives
How to be relevant and communicate effectively as a Software Engineer IC.
It was my first office job. I was pitching my team’s roadmap at an internal sales conference with my product manager. After the first round, I was surprised by feedback I got from an executive. “You’re talking too technical. No one is here for that,” she said. I was confused — I only explained our product thinking and I was careful to avoid any jargon. What I realized after another round of pitching was that I needed to completely invert the story I was telling to be from the point of view of the sales teams and executives, not my team’s. This was the first lesson I learned.
Whether you want an executive to make a bet on your proposal, build your credibility, or form a strong working relationship, you will need to develop the skill of talking to executives. This is not the same as talking to peers or your manager. Executives care about different things, have less overlapping context, and have less time. This is a critical and underrated skill to develop in order to have more impact.
Talking to executives well means you reframe your storytelling, recognize that they are across different context to you, and use their time well.
Tell the story from their point of view
Some think that all you need to do is avoid jargon, like I once did. But in fact, you need to completely invert the story, and tell it from the perspective of the executive.
Avoid jargon, and introducing new concepts. The quickest way to lose someone’s attention is to use opaque language. Everyone knows this one, but I need to really drive it home, because plenty of engineers still use too many “new” concepts. Think about what your executive already knows about, and try to use those concepts, even if you need to zoom out a bit.
Learn what your executive cares about. What do they worry about, and what are they excited about? Properly understanding this will allow you to go beyond just substituting jargon with normal language, and will help you craft a compelling story that matters to them.
Don’t only talk high-level. This is also a trap. Avoid coming off as hand-waving. You need to be able to connect the details to the outcomes to be credible. Weave the important and relevant details into a coherent argument, but again you need to be careful to ensure you are framing it from their perspective.
Don’t forget about the context gap
While every IC knows that they have context that their executive doesn’t, few recognize that the executive has context they don’t. This can lead to unnecessary misalignment. Plenty of IC’s disagree with the decisions of executives and just say “this decision makes no sense to me, it’s wrong.” However, they have probably thought through that decision more than you, and there are almost always additional factors you are not aware of.
Ask curious questions. Try to uncover your own unknowns. The right way to frame a disagreement is not that they are wrong, but by default you are missing something.
Don’t disagree without adding value. If you still disagree don’t just tell them they’re wrong. Tell your executive something they don’t already know — which is rare. Otherwise, if your disagreement is based on an an unexplainable hunch, it might be worth keeping that to yourself.
Require less effort
Executives are busy people, and the opportunity cost of using their time is high. Put in more effort yourself, to reduce how much effort you are requiring from them.
Go to them with a recommendation. If you do this and get it right, your executive will just need to sense-check your proposal and sign off on it. This can save them loads of time and free up their attention for other problems on their plate.
Show your working. If you only go to an executive with a recommendation, they will need to do the analysis themselves. Support your recommendation with a clear and concise argument.
Prepare well for meetings. This is especially important for 1:1’s. It can be quite jarring for an executive to show up for a 1:1 with an IC, but needing to spend the whole time searching for things to talk about. Instead, prepare with a list of clear issues to work through together. Prepare thoroughly for presentations in order to build credibility.
Get better at it with practice
I was fortunate that at the last 50-person startup I worked at, I had no formal reporting lines. In effect, I reported to the CTO, CEO and COO for different projects. I was able to learn each of their languages, what they worry about, and what they are excited about. I had a weekly 1:1 with the CEO which was an especially strong forcing function for me to figure out how to explain the decisions I was making in a framing understandable to the CEO and stay relevant.
But how can you develop your skills without this training ground? Chat regularly with cross-functional colleagues. If you’re an engineer, pitch the work you’re doing and the decisions your making to someone from support/sales/customer success.
Conclusion
Don’t chat with executives the way you would chat with a peer or your manager. Learn what they care about, and tell the story in terms of that. Bring humility to disagreements and make them constructive. Use their time effectively by requiring less effort. Mastering this skill is an investment in your professional growth that will open the door to more opportunities and impact.