Asking the Right Questions

Andrea Belk Olson
4 min readFeb 26, 2024

We ask questions all the time. At work, at home, amongst friends. Often, we ask questions that we already know the answer to, and other times, we ask questions that validate our existing perceptions. But in business, when we’re trying to find answers to complex, layered, multi-faceted problems, we need excellent questions to get the answers and insights we need to make the best decision possible. But we’re usually pretty bad at it.

For example, I sat in on a discussion between a CEO and the VP of Sales at a large product company. Sales were flat to plan. The CEO wanted to know why sales were flat and wanted to know how they would reach their 10% revenue growth goal that year. The CEO began with the usual questions — “Why are sales flat?” and “What will it take to reach our growth goal?”. Obviously, the VP of Sales had the following responses, “We had two territories that missed their targets, and two others that surpassed their goals, making sales flat. But we will reach our growth goal by working more closely with the two lagging territories and get them back to the right trajectory.”

This conversation, while appeasing the CEO and making the VP of Sales feel like there was a clear “plan” in place, there is no plan. This is because the right questions weren’t asked. What insight does either party have as to the why? What is the CEO learning that will help them make better decisions going forward?

No one is really steering the ship, just riding the waves that already exist. More often than not in this scenario, the high-performing territories will continue to grow, making up the difference of the laggards, and the 10% growth goal will be met. The weak territories will be reshuffled, or those folks will be replaced with a fresh new set of sales personnel. The issue with this is that there’s no transparency to the actual problem. The right questions weren’t asked.

Take a different example — say you want to develop a new offering to increase revenue. Do you go and ask customers, “What do you want and need that we don’t offer?” and then simply go and do those things? Do you just pick the things that were within your budget to implement? What happens when revenue doesn’t meet expectations? Because you only asked a surface question and then went directly to implementation, there’s no insight as to why it didn’t work. There’s no insight on what to change, do differently, or eliminate, because you didn’t ask the right questions.

Furthermore, not asking the right questions gives you the same answers your competitors are getting. You need to ask deeper, smarter, better questions than the competition to get new and unique insights that drive differentiation, revenue growth, and organizational insight. Asking the same questions as everyone else will get you the same answers as everyone else.

To ask the right questions, you need to first identify what you’re trying to understand. This means in both of our examples, what is the real question you have that you want answered? For our CEO and VP of Sales, it’s not “Why are sales flat” but “What issues are impacting the success of our sales team?” For our new offering, the question for customers isn’t “What do you need that we don’t offer” but “What problems do you have that aren’t getting addressed?” The difference is exploratory — opening the door for more opportunities for different insights and perspectives.

You want to ask questions that generate further, deeper clarifying questions. You want to ask questions that help you gain new perspectives you hadn’t considered before. You want to ask questions that help you gain insights you can take direct action on and make a clear, measurable business decision.

Think about a 4-year-old, who asks relentless questions. They always dig into the “why”. There’s nothing wrong with finding out the why behind things. Utilize curiosity and drive for deeper understanding to create a questioning dialogue. This will help you not only ask the right questions and gain better information for decision-making but also set an example for your team on how to ask the right questions themselves.

About the Author

Andrea’s 25-year, field-tested background provides practical, behavioral science approaches to creating differentiated, human-focused organizations. A 4x ADDY award-winner, TEDx presenter, and 3x book author — she began her career at a tech start-up. She led the strategic sales, marketing, and customer engagement efforts at two global industrial manufacturers. She now leads a change agency dedicated to helping organizations differentiate their brands using behavioral science.

In addition to writing and consulting, Andrea speaks to leaders and industry organizations worldwide. Please contact Andrea to access information on her book, keynoting, research, or consulting. More information is also available at or

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Andrea Belk Olson

Behavioral Scientist. Customer-Centricity Expert. Prolific Author. Compelling Speaker. More at