How to Get Your Boss's Boss to Understand

In the early days, I said AI was just Wikipedia on steroids. For general background, that is still true. What has changed is how far AI now goes beyond it.

The problem is that most senior leaders won’t stop a presentation to ask what an acronym means because nobody wants to appear uninformed in front of peers. Instead, they lose the message. One unfamiliar acronym may be tolerable, but no more than three.

Repeat the ask at the end with a short statement such as “To summarize, we are requesting approval of the design contract.” Without it, the discussion can drift into more questions or a polite request to come back next month.

In many ways, whether we insist on a formal approach reflects how much a technical professional values hard skills versus soft skills. A failed weld leaves wreckage. A failed presentation leaves nothing to investigate, so we treat the skill as optional.

Early disclosure is also an ethical choice. Withholding a known problem, even for a few weeks, erodes the trust that every future recommendation depends on.

Effective communication is the one thing that makes your life better, more fulfilling, and more rewarding. That is equally true in life and your career.

Test each example before the presentation. Ask whether it explains the problem or simply makes the presentation more interesting. Replace it if it only does the second. One well-chosen example is worth more than several clever ones.

Lecturing is not generosity. It works against the board's process and against your standing as its trusted advisor. Answer the question, stop talking, and let the next question tell you what the board actually wants to hear.

Executives and boards ask questions to test judgment, not to audit method. Give them the direct answer first. If nuance is required, say so in one sentence and offer to follow up. Their question is a request, not an invitation to perform the whole analysis on their time.

Boards and senior executives rarely say no directly. They ask a narrower question than the one you expected. They move to the next agenda item without a follow-up. They thank you for the presentation without committing to the recommendation. None of that is an oversight.

Our goal is to remain credible, transparent, and professionally grounded.

You may intend your feedback to be constructive. Most people on the receiving end still hear negativity, whether it’s about their work, the facts, or their behavior.