Brooke Brown

Why it pays to ask better questions

September 18, 2017

Your best business solutions and worst headaches stem from whether you are asking good questions.

The best questions — those that position your company for success — dig deep, aren’t always easy, and may elicit unexpected responses.

To that, I remind you of George Addair’s inspirational quote that you see everywhere these days: “Everything you want is on the other side of fear.”

You want clarity.

You want efficiency. You want growth. You want solutions. Well, then, ask the hard questions.

Here are a few strategies:

Start with the basics

Organizational leadership guru Simon Sinek states, “All organizations start with why, but only the great ones keep their why clear year after year.”

Questions that begin with “why” lead to clarity about motivations and are the root system from which actionable steps grow.  

“Who” and “how” questions help clarify roles and responsibilities and inform policies. Chain-of-command issues and problems with haphazard execution, for example, can be addressed with these types of questions.

“When” and “where” questions orient us to time and space. If you want to discover the source of a manufacturing delay or miscommunication about a vendor order, start there.

“What if” prompts can be just as revealing. When you see this problem unfolding, where do you go for a solution? Why there? What do you do next? These questions can reveal the decision-making processes your team members and customers are using.

Think Open-ended

Questions that only require a yes or no answer limit the amount of information and feedback available to you.

Open-ended questions encourage thoughtful analysis and may lead to an effective solution. “Can we meet on Friday?” will produce a yes or a no.

However, the question of “What time on Friday can we meet?” will produce a conversation about what will work if Friday does not.

Don’t assume

Assumptions persuade us to build a case out of few facts. Many workplace misunderstandings occur because of assumptions gone unchecked.

Consider first whether your questions are based on a bias or an unconfirmed belief. Do you think you know what the answer will be? Are your questions set up to avoid any opposition?

Then, seek out multiple perspectives and take them seriously.

Let go of your pride

Sometimes questions expose our blind spots.

Admitting that we are wrong, that we don’t have all the answers or that we need more guidance can bruise our egos a little bit.

Honor those who ask questions with respect and create an environment where asking questions is encouraged and celebrated. Vulnerability, after all, is the birthplace of innovation.

Listen to understand

Steven R. Covey, author of “The 7 Habits of Highly Effective People,” said, “Most people do not listen with the intent to understand; they listen with the intent to reply.”

Rather than taking a defensive posture, consider whether the respondent feels unheard, threatened or intimidated.

What matters most is that the people making a difference within your organization feel heard and valued. You do this by listening to and respecting positions that differ.

But all that starts by asking for their perspectives in the first place.

Feel free to share your thoughts — and your best questions — with me at