Ask the hard questions

Do you know that moment which happens at almost every meeting or conference call, when a participant refers to a concept that you don’t quite understand?  That moment happens to me often, and has throughout my career.

“The marketing funnel is part of the sales process.”

“We can just flurbuzz the bazznod.”

“We have plenty of runway.”

That is the moment when you can ask the hard question.

“Why is that connected?”

“What does that mean?”

“I’m sorry, I don’t understand.  Could you repeat that?  How do you define runway?”

Asking these questions is important.  Otherwise you and the other parties will be talking past each other, which will only lead to pain down the line when the misunderstanding is crystallized in people, process or code.

I’ve been asking these kinds of questions my entire career.  When I worked at a web consulting company in the early 2000s, there were often company wide conference calls discussing our precarious financial state.  I got a reputation as “the question guy” because I wasn’t afraid of asking the awkward question, even of the CEO in front of the entire company.  I was interested in hearing as real of an answer (as they could share).

If you’re interested in asking hard questions, here are some tips:

• Pay attention beforehand.  If you are asking a question about something that was just mentioned, or that you should have known, you won’t have credibility.
• Don’t worry about looking dumb (except if you weren’t paying attention, see above).  If it is a fuzzy concept, chances are others in the room are wondering what it is.  Besides, the goal is to increase your knowledge.  Check your ego.
• Ask the question from a place of humility and make it about you.  Maybe you just really don’t understand.  I always like the phrase: “I’m sorry, I don’t understand what you just said.”
• Approach with positive intention.  Don’t ask gotcha questions or try to prove you are smarter than the speaker.
• If the answer is a bit fluffy or you don’t understand it, ask a second time.  “Thanks, but I’m afraid I still don’t get it.  Could you explain it to me again?”
• If the speaker doesn’t answer or hedges again, offer to take it offline.  Depending on who is in the meeting, you don’t want to waste everyone’s time.  But then make sure you follow up.
• Recognize if the topic is sensitive (financial matters) you may not get a clear answer.  At that point, getting the speaker to define terms but perhaps omit numbers is a win.

Again, the goal here is not to ‘get’ the speaker, it’s to help get everyone on the same page.  Asking tough questions to pin down some of the nebulous concepts we work with every day can help everyone make better decisions.