• Karla Robertson

The Emerging Executive Skill: Knowing the Questions to Ask and Having the Confidence to Ask Them


Having the wisdom and confidence to know when to press pause to assess, ask questions and confirm you are on the right path will pay dividends in the long run.

There’s a saying among carpenters: “Measure twice, cut once.” It’s a way of making sure you’re going to end up with the right end product. It allows you to make adjustments before moving past a point of no return, especially when failure is not an option. It is a way of not burning up resources, time and money because you didn’t press pause and step back before making a cut that you can’t uncut.


Asking questions is like measuring twice.

There is nothing like a well-placed, spot-on question that dares to challenge current ideology, foundational beliefs and assumptions upon which decisions have been and are still being made. At a time when the velocity of change and innovation driven by ever-improving technology and global connectedness is moving at lightening speed, it is the executive with the skill, confidence and wisdom to know when to press pause and ask questions before taking action that is in demand.


I recall a C-Suite client of mine who was very frustrated with the lack of time and resources to get certain projects done due to his team having to deal with one disaster after another. He said it was amazing how they threw themselves on the multiple “grenades” that were tossed into their path - he was proud of them, as he should be. Still, he felt they were low on capacity due to all the distractions and was trying to find a way to get more resources. So, I asked, “Why do you have so many grenades to deal with?” "Good question.", he said. We discussed further. Follow up question: “If you didn’t have so many grenades that sucked up your resources, what would you and your team be able to do that you aren’t doing now?” It went from there to a deeper dive which resulted in a shift in his focus.


Sometimes it feels inconvenient to ask questions. In this “just get it done” world, we blow past the questions that would really ensure we were focused on creating the right things and solving the right problems. Sometimes it takes someone to press pause and ask something like: Why do we do this? People want results NOW! So, there is a need for speed and a close-to-zero tolerance for mistakes, missed deadlines or pushback. This is an alchemy for perpetuating disasters, missteps, wasted money, missed objectives, time and resources. Now sometimes, when “the bullets are flying” there isn’t time to ask questions. You need to move! Most of the time, however, that is not the case. A strong leader will have built the internal fortitude to know when it pays to press pause, and start asking the right questions, inconvenient as they may be. A confident executive will be able to stand behind that move. The dividends you get from building this skill will astound you. It will also signal that you expect your team to do the same.


How do you plant the seed to grow this in your people?

From a culture perspective, it begs the question why we seem to value the person who always has the answers and not the person who asks questions. For me, in the US, I would say it has roots in our early education methodology. How many of you remember in grade school being encouraged and rated on how many times your hand was in the air begging to be selected to answer a question the teacher asked. And if your hand was always up first, wow, you got a great note from the teacher that went home to your parents. If you didn’t have answers but had questions, or were quiet thinking and processing, well, that wasn’t what they were looking for and you were seen as “not getting it” or “not confident” or “not participating”.

Does this sound familiar? Do you see this playing out in your team or company culture? Do you say you want feedback and for people to speak up and then when they do, are they shut down in all the subtle and not-so-subtle ways we do that? What are you teaching people to do and to be in your organization?


Start seeing the big picture when things are moving fast and learn how to press pause to ask key questions. As much as you value team members who come up with effective solutions, also value those in your team who are willing to ask effective and inconvenient questions. Because I can tell you what’s really inconvenient…a failed initiative, a lost job, a promotion unattained, lost resources because you don’t.


Measure twice, cut once.

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