Communications Strategy

The Secret to Asking Good Questions

By Starr Million Baker


“It is not the answer that enlightens, but the question.”
– Eugene Jonesco

When thinking of the skills that could take you from being a good communicator to a great one, “asking good questions” might not be the first thing on your list. After all, you probably think you know how to ask questions – it comes second nature. But getting all of the information you need to run a successful marketing communications program is no small feat. You have to know how to ask the right people the right questions at the right time.

Often the communications team isn’t directly involved in company operations like customer service, product development, or even sales. And some teams may be wary of sharing information with those outside their department. Have you ever needed to get specific details about a new product from your head developer? Or tried to get “why the customer chose us” out of the sales team for that case study you need to publish?

Getting your foot in the door by asking good questions will help you break down silos and better plan, execute, and measure your marketing communications initiatives.

Here are five lessons to help you go from question-asker to question master.

1. The meat of the answer lies in the follow-up

When digging for information, it’s likely not going to be a one-and-done situation. Ask open-ended questions and let the conversation flow. Listen to the answers and ask follow-up questions that will encourage the person to dive even deeper with their response:

Tell me more about why customer X chose our security product.

Oh, so user error was a major problem then? What other issues drove purchase decisions?

Open questions and follow-up that keep the conversation going allow you to learn more about the topic at hand. These types of questions also have the added benefit of helping you build rapport with the person being questioned; they will recognize that you’re listening to them and taking what they have to say seriously.

2. Purposeful pessimism can result in a positive outcome

If you suspect the answer to a question you want to ask will be negative – for instance, that report you need isn’t going to be done on time – frame your question in a negative way:

That’s not going to be done on time, is it?

This is especially useful if you’re working with someone who is hesitant to reveal too much. Research has found that people are less likely to lie if a question is framed negatively. Your assumption eliminates any wiggle room to lie by omission and gives the other person permission to be truthful.

3. In competitive scenarios, closed questions are your best bet

Before jumping into a conversation or line of questioning, size up the room to assess whether an interaction is going to be competitive or cooperative.

A competitive interaction is when at least one person has an agenda: managing the budget, looking to find fault, attempting to ditch responsibility. A cooperative interaction is when all participants want to hear what is on the other person’s mind.

Closed questions are most effective in competitive (negative) situations so as to not let the competitive person’s agenda run the show. For example:

Is this proposal in line with your budget? vs. What do you think about this proposal?

Be direct and use yes or no questions as much as possible in competitive conversations.

4. Cut straight to the tough questions in difficult conversations

In difficult conversations, your instinct may be to start on a lighter note and then get to the hard part. But research shows the person being asked will respond with more information if you just begin with the hard questions.

Alternatively, if your goal of the interaction is to make friends or get on someone’s good side, start on the lighter end.

5. When all else fails, be the reporter

Journalists are the rock stars asking good questions. They train for it in school and hone the skill over their entire career. To glean new strategies for yourself, try watching the rock stars in action. Broadcast journalists, in particular, know how to use question strategies to make their subjects feel at ease, to get them riled up, or even to share information they had no intention of ever saying out loud when they walked into the studio.

Following a journalist’s lead also helps you to be thorough in your data collection. The five W’s and the H (who, what, why, when, where, and how) still work.

Don’t Underestimate the Power of a Question

Professionals are often wary of asking questions. In some businesses, they’re perceived as a sign of weakness; in others, those who hold the answer don’t possess the patience for question-asking. But questioning has been found to encourage learning and idea exchange, build rapport and trust, fuel innovation, and improve performance. Perhaps most importantly for business leaders, questions can proactively uncover unforeseen obstacles.

In the marketing communications field, curiosity – and thus, questioning – is the bedrock of our existence. Start putting these lessons into practice at work by rephrasing, reframing, and reprioritizing the types of questions you ask. Soon, asking good questions could be your most powerful skill.

“If I had an hour to solve a problem and my life depended on it, I would use the first 55 minutes to determine the proper questions to ask.”
– Albert Einstein