Intelligent questions: The strategic importance

Intelligent Questions

Here’s a fun game that would be essentially impossible to play. Go into the office of an executive and say “I have a little proposal here about intelligent questions.” The dude will jab a pen in your neck, superkick you onto his velvet couch and scream, “I don’t need intelligent questions, I need fucking answers!” This is because we live in an achievement-driven culture. That’s very good in one way — we’ve essentially created the world’s greatest capitalism — but very bad in some others, including the deification of gasbag workaholics. In the process of all this happening, we’ve kind of lost sight of the importance of questions — and especially intelligent questions. I say “we” but I ain’t talking about myself, fool. I write about questions all the time. To wit:

If you respect the concept of Instagram — some of us do, right? — well, the founding of Instagram came about because of intelligent questions. Now they have 500 million active users. Facebook bought them. And their founders are richer than you. It all came from legitimately intelligent questions, not bellowing about solutions. I think this is what we often miss in a business context. Let’s dive a bit deeper.

Intelligent questions and crowdsourcing

Here’s a cool article on Fast Company called “Are You Crowdsourcing Or Wasting Your Time?” I thought that headline was interesting. It kills me — slowly, and softly — on Facebook when some wanker I went to high school with posts: “OK, Greece recommendations. Go!” I always want to post: “Their economy is a fucking train wreck. Buy everything you can airlift out.” I’m a terrible human being, you know?

But crowdsourcing is applicable in a business context too. The whole ethos of meetings, which usually suck donkey, is rooted in crowdsourcing or brainstorming. Brainstorming has been debunked by human science and psychology for decades now, but many managers believe it’s still the way to get the next billion-dollar idea. Usually, it’s a waste of time where a bunch of people fart around staring at each other and repeating what the last person said. Anyway.

Here’s a good quote from that article:

Make sure that the questions you ask are quality ones. “The leadership skill that we’re seeing a significant drop in is the skill of asking well-defined questions,” says productivity coach Jason Womack.

I don’t know exactly what the hell a “productivity coach” is, but let’s gloss that over for a second. The quote is money. The skill we’re seeing a significant drop in? Intelligent questions. And that’s straight-up assassinating business models all over.

Why are intelligent questions important?

Easy answers:

  • They move conversations forward
  • Help people to see blind spots or pain points
  • Provide for context or understanding around projects
  • Managers can figure out what their employees and customers want

I think we all realize this, but we don’t often actually act on it. But why?

What’s so hard about intelligent questions?

Look, we assign a lot of nice pie in the sky words to work. Strategy. Compassion. Thought leaders. Response. Critical thinking.

In reality, most enterprise-level (and midsize) company work is heads-down deliverables slop. “This project is urgent,” a manager snarls. “Get it done now.” So you work on that. 17 minutes later, your boss emerges from a meeting with her boss. “Stop,” she screeches. “Now this other thing is urgent.” This is work to most people. It’s really, really hard to deny that. The best synonym I can give you for most jobs is “massive priority vacuum.”

EMail has made this really bad. At this point, email is a giant cover your ass move. That’s all it really is. But because it comes in hot and fast, people think they need to respond steamy and quick. This leads to a lot of “reaction,” as opposed to “response.” In short, everything kinda becomes hair-trigger, sense of urgency garbage. Priorities die in the flood.


When you combine that mindset with achievement-driven culture, then toss in a side of “I want a fat bonus this year,” you see where intelligent questions probably aren’t the norm? Right. (Oh hey — also add in the fact that a lot of people are, admittedly, stupid and lazy.)

So how do we ask more intelligent questions?

In a work context, I’d start here: less accusatory and more empowering. We all know a lot of the other tricks — start with why, etc. — and let’s also realize that questions at work aren’t necessarily a bad thing. Intelligent questions don’t mean “Oh God, this guy is clueless.” Rather, they mean “This guy is looking for additional context to over-deliver on his project.” Many managers assume the former, when they should actually assume the latter.

You see this no more bluntly than in the hiring process. The hiring process is rooted in questions — that’s what interviews are, basically. Intelligent questions? Not so much. The 10 most common interview questions are a giant slop fest of cliches, ultimately leading to generic interview processes (“Walk me through your resume, Marc”) that lead to horrible hiring decisions. It’s all a giant circle of meaninglessness — and you know where it begins? Because we don’t ask intelligent questions.

So, what would be an example of an intelligent question in an interview?

Here’s an idea. We’re all chasing this era of Big Data right now, OK? So what if you said this to a candidate:

“Hey. Tell me about an issue you had in the past. How did you solve the issue — and what were you tracking and measuring to know you solved it?”

That’s in the subset of intelligent questions, as opposed to “What type of culture do you like, John?” (The answer there, BTW: “One where my boss isn’t a fucking jackass.”)

Intelligent questions as a strategic advantage … how?

If you’re asking intelligent questions and your competitor is just running around like a donkey with reaction-reaction-reaction, eventually you’re going to win out and he’s going to fade out. It’s that simple. You’ll offer better products and services because you used focused, intelligent questions — and corresponding problem-solving and solutions — to get there. It’s not rocket science.

What else would you add on intelligent questions, especially in a work context?

Ted Bauer


  1. I am being becoming increasing inclined to the view that “measuring and tracking data” may itself be a problem. For many staff these days the only question of any real importance to themselves is whether or not they meet the “Key Performance Indicators” for the month. If KPI’s are not met their jobs are at risk and the most important thing to an employee is keeping his salary coming.

    In such an environment relevance is assessed by impact on meeting the KPI’s.

    Too bad if the KPI’s are inappopriate.

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