Think Like a Senior Executive and Ask More Questions

Do you know the difference between a “worker bee” and a senior executive? Have you ever wondered what it takes to move up in the world to those loftier roles? It’s pretty simple. You need to move from a world where you provide all the answers to a world where you ask all the questions.

I know there’s a cheeky clueless executive joke in there somewhere but I’m actually not joking around (which I know comes as a shock to you longtime readers).

As we enter organizations and rise through the ranks, we’re expected (and trained) to have the answers. We, after all, are the front line. We do the work. When someone more senior asks us for information, our job description is to provide it. And provide it we do. We become experts in our field. We know all the answers. We become that “go to” person Scott Eblin describes in this post.

And every day we kick butt. We know everything that’s asked of us. Heck, we get to a point where we’ve created everything around us. But one day we wake up wondering why we’re not getting promoted. We can’t figure out why we, the expert of all experts, isn’t rising to the executive ranks. After all, those guys are clueless. All they ever do is ask questions that we have to provide the answers to.

And that my friends is the key to the paradox of advancing to senior management. Questions.

Why Questions are Important

Along with an opposable thumb, we share one other trait with our hairy primate cousins – curiosity. We have an innate desire to understand “what happens if…” that begins in childhood. As we grow into adults, that natural curiosity dissipates and we’re expected to have those answers (school, anyone?).

Unfortunately, answers are all about what has already happened. By definition, arriving at an answer means we’ve understood some aspect of an inquiry. And yes, we now have new knowledge to share, act on, and impart to others.

But rooted in that new knowledge is that original question that led us to insight. Sure, sometimes it’s a dumb question that led to interesting answers but more often than not, the person asking the question has taken a step back from the day to day answers. They’ve tried to make connections, see trends, or predict the future and that’s what their question is about. They’ve looked in crannies others have ignored and they’ve shone the light of knowledge upon dark and overlooked recesses. That’s how they’re finding those new insights.

Now think about the smartest senior executives you work with. Ask yourself the balance between the number of questions they ask versus the answers they have. I’ll bet you’ll find the smarter ones ask really good questions. The weaker executives tend toward offering all the answers. The latter dynamic in its extreme can make them seem like autocratic dictatorial micromanaging know-it-alls who don’t let their team have any space to grow (a dynamic I’ve berated before in this post – I suggest you read it so you don’t become a detail-oriented control freak yourself).

What’s so cool about working with inquisitive execs like this is they open our eyes to new connections and possibilities. Even better is they’re not pompous asses – they’re not afraid to admit they don’t know the answers. In that admission is an incredible statement of confidence in their abilities. They view not knowing something (but knowing what they don’t know) as an asset versus the massive insecurity other execs demonstrate by thinking they have to know everything.

Hmmm… seems like the better execs and leaders out there tend to ask more insightful questions, have more comfort in not knowing things, and are willing to step back and let their teams kick butt in the pursuit of the answer. I’ll bet you’re thinking “Gee… maybe I want to be like them…”

How to Ask the Right Questions

Now look at your ratio of question to answers. If you spend 100% of your time providing answers, clearly you’re not stepping back and asking questions. But not every question is a good one. I hate the phrase “there are no stupid questions” because, actually, there are a LOT of stupid questions – we just don’t want to make the stupid people feel stupid for asking them.

You have to ask GOOD questions. So how do you do that? Step away from the need to answer it yourself. Step back from the knowledge you have and look across domains to find connections. Ask what things will look like in a year. 5 years. 10 years. Ask what happens if something new or unthinkable happens. What will the result be? And if that’s the result, what will happen next? Look deliberately for connections, trends, or predictions. Shameless plug for my business: if you’re interested in building your question-asking toolkit and you too want to be more insightful, I encourage you to learn about our course called thoughtLEADERSHIP: Thinking Beyond Business as Usual. It’s fun and awesome. Even better, it will help you become a much better question-asker.

Try floating these questions in a safe environment (a team meeting, with a peer, etc. – not with the Board of Directors, the CEO, etc.). Preface the question with “I don’t know the answer to this but I think this is something important we should look into.” By doing so, you’re signaling you’re not the answer person on this one. You’re inviting others to provide input. The more often you do this, the more folks will expect this behavior from you.

Now to pull this off successfully, you can’t then run off and come up with the answer yourself. Have others help you (or better yet, have them come back to you with answers). By moving out of the answer guy realm and into the question guy realm, you’re freeing up even more time to generate insightful questions, look at macro trends, and make future predictions. Before you know it, you’ll be the person asking all the great questions that your team will be eager to run off and answer.

Your task: go ask one really good question today. Resist the urge to answer it yourself. See what happens.

– Mike Figliuolo at thoughtLEADERS, LLC

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Photo: ??? by Charles Chan