How To Ask More Powerful Questions

“I got this.”

This was my go-to line when I knew what I was doing and wanted to get my boss off my back. What I couldn’t see was how it highlighted a major mistake. I wasn’t evaluating the situation, I wasn’t asking questions. I assumed I knew all the answers, and I was usually wrong.

I didn’t realize the error in my ways until a major client rollout flopped and I had no one to blame but myself — my own stubborn belief that “I got this,” even though I clearly didn’t.

In a debrief with my boss, he said, “Aaron, when you say 'I got this' and have no concerns about a situation, that is when I get concerned.”

What he meant was that as soon as I stop asking compelling questions, I assume I know what’s going to work and stop evaluating potential outcomes and solutions. It’s a tendency they all have when they want to take the quick route. It’s what holds us back from being powerful leaders.

Why is asking powerful questions an essential leadership habit?

It provides leaders with a means to mitigate their confirmation biases and dive deep into the evaluation of a situation, a person or their team as a whole.

I had biases for how the rollout was going to play out. I’d done this before; I knew what was going to happen, so why should I look further into it? I wish I could say this was unique to me, but they all do this. Their brains are wired to jump to outcomes, to look for shortcuts.

Not sure if this relates to you? Watch this quick video to test yourself.

Daniel Kahneman, Nobel Prize-winning behavioral economist who was the first to highlight these biases, states, “Confirmation bias comes from when you have an interpretation, and you adopt it, and then, top down, you force everything to fit that interpretation.”

This bias can be disastrous for leaders; it can hinder their decision making ability and blindside them completely. Asking powerful questions is their way around it. It can help us avoid this common miscalculation.

What does a powerful question look like?

I’m going to share a definition of and the criteria for a powerful question, but I also want to be clear there is no script for asking a powerful question. Powerful questions evoke clarity, create greater possibility, reveal new learning and generate action. Here are a few ways to determine if a question is powerful or not.

A powerful question …

• Is open-ended: Ask what, when or how instead of asking a yes or no question.

• Comes from a beginner’s mindset: Start by telling yourself, “I don’t know the answer.”

• Is clear and succinct: Keep it simple, don’t use too many words.

• Is impactful: It’s important to remember that not every question in a conversation should be powerful. In a 30-minute conversation, aim for 2-3 powerful questions.

• Happens in the moment: Here is probably the most crucial point to remember about powerful questioning. You can’t plan it! Formulaic questions outlined before the conversation won’t work. You have to be in the moment.

There is no script for asking powerful questions. There is, however, an often-overlooked trait that will set you up to ask powerful questions in any situation.

What’s the trait?

Curiosity. Want to discover a master of curiosity? Find any 3-year old and watch them for an hour. They ask what, why and how to nearly everything they see in the world around them. They want to know more and do not limit themselves to the societal expectations of what’s right or wrong. They just ask.

As they get older, they are trained to lose their curiosity when it becomes clear it’s not acceptable to ask all the questions that come to mind. Instead, they go about their days having surface-level conversations, rarely digging more in-depth with a co-worker, client or even a friend.

The secret to asking more powerful questions is digging deeper. It’s triggering their 3-year old selves and reconnecting with their curiosity.

I found it hard to come up with a way to share this concept with you. I realized it’s so hard to explain because, as adults, there are very few situations where they are curious. Then I remembered riddles. They are a great way to bring the curiosity right back. Try this one out.

“What has a head, a tail, is brown and has no legs?”

As you are reading this, trying to figure out the answer, your mind is swirling with questions and possibilities.

What kind of animal has no legs?

Is it an animal?

What else could it be?

What sorts of things have tails?

The series of questions running through your head is your curiosity showing up. It’s the little kid inside of you wanting to understand, to know. Curiosity is the genuine desire to learn more -- to explore.

To be able to evaluate people, teams or situations with greater fidelity, go back to the curious part of you that wants to explore. Instead of restricting yourself, open yourself up and allow your mind to ask any question.

Allow yourself to ask the powerful questions. You already have them in you.

Sometimes it may take priming yourself with a riddle to get you there.

“What has a head, a tail, is brown and has no legs?”

A penny.

BIG QUESTIONS

Winter Garden tries to ban tough questions | Commentary

I’ve covered politics long enough to know some politicians hate tough questions.

But never before have I witnessed what we’re seeing in Winter Garden — where the city leaders are trying to stop citizens from even asking some questions in the first place, particularly when others are watching. Talk about snowflakes.

As the Sentinel recently reported, Winter Garden Mayor John Rees and his fellow commissioners approved new rules for “public input and decorum at public meetings.”

Winter Garden’s new restrictions on journalists are unconstitutional, First Amendment experts say

One rule tells citizen speakers they shouldn’t address any individual commissioner. So if you’re really miffed at something one of your elected officials did, you’d better blame them all … so that no individual politician’s feelings will be hurt.

Another tells citizens that “No question shall be asked by a speaker of a City Commissioner except through the Presiding Officer.”

These are politicians literally telling you not to question their authority.

Heaven forfend you say something outrageous like: “Commissioner So-and-So, do you really think this sign ordinance is fair?” How anti-decorum of you.

Listen, politicians are under absolutely no obligation to answer any question. They can ignore it, run away with their tails tucked between their legs, respond calmly or with fiery force.

But in what authoritarian, anti-democratic universe do you think it is OK to tell citizens they can’t even ask a question in the first place? In Winter Garden apparently.

If that wasn’t enough, the city passed additional “RULES OF CONDUCT FOR THE MEDIA.” (That’s the city’s angry ALL-CAPS, not mine.) One says journalists — who can’t ask unauthorized questions during a meeting, mind you — also can’t follow any elected official after the meeting “to request interviews, to obtain comments or to respond to questions.” Quite the Bravehearts.

As you may have surmised, it’s actually a member of “THE MEDIA” who seems to have city officials worked into a lather.

They don’t like the questions from Winter Garden resident Norine Dworkin, a local news blogger who sometimes queries city officials during the public-comment period of city meetings and says she was informed the city’s police department was investigating her for doing so.

“Politicians are never obligated to answer a question,” Dworkin told residents in a statement she posted on YouTube. “But journalists must always be permitted to ask without interference.”

She’s absolutely right.

Listen, does Dworkin report the way I do? Nope. I can’t imagine ever standing up in a city meeting to make a statement or ask a question. I’m more old-school and ink-stained.

But it doesn’t matter what I do or think. It also doesn’t matter if Dworkin is a journalist, a plumber or a professional pickleball player. Government shouldn’t try to stop citizens from speaking freely just because that speech might make them uncomfortable.

Winter Garden officials don’t seem to consider their stance anti-journalist or anti-free speech as much as they do anti-Dworkin. They find her particularly annoying. So they’re quite OK trying to shut her down.

That doesn’t make it any better. For starters, politicians don’t get to choose which journalists cover them any more than burglars get to decide which cops patrol their neighborhoods.

Also, some hyper-local websites only have one journalist. So, claiming you’ll accept questions from any journalist at one of those hyper-local sites — except the only one who works there — is like saying you’ll eat any product Ben & Jerry’s makes, as long as it’s not ice cream.

Plus, free speech is for everyone — even those they dislike. This is a concept many people struggle with. But it doesn’t matter if the person who wants to speak is a nun or a Nazi, a Pulitzer Prize winner or a Ku Klux Klansman. In this country, they are all allowed to stand up and speak — and, yes, to make people uncomfortable.

Politicians get into trouble when they make sweeping policies trying to target individuals — as Winter Garden has done before.

Back in 2014, Rees tried to force citizens to stand for the Pledge of Allegiance — even going so far as to ask the police chief to oust one citizen who refused to do so.

Today’s special meeting in Winter Garden may start without an invocation or the Pledge of Allegiance

Now, I’ve always stood for the pledge, hand over heart. So do most people. But government doesn’t have the right to use police powers to make everyone else do the same. In fact, the very “liberty” they honor in that pledge protects that right to make personal choices.

After a bunch of ugly publicity, the mayor and city backed away from their mandated-pledge-stand provision. I’m guessing and hoping city officials will do the same again on this issue.

City attorney Kurt Ardaman said Wednesday that the city was listening to concerns and considering “proposed revisions” from the First Amendment Foundation of Florida.

They sure should. Because, while politicians are free to ignore the people they swore to serve, they aren’t free to muzzle them.

In happier news, I am working on this year’s list of “10 People who Make Orlando a Better Place to Live” — and I’d love your suggestions.

If you know someone who doesn’t normally make headlines and yet works tirelessly to improve Central Florida better — an educator, nonprofit leader, entrepreneur, philanthropist or anything else — let me know. Just send me a short email telling me who they are and why you think they’re worthy.

smaxwell@orlandosentinel.com