Ask Better Questions

Business Leaders Should Be Asking More Questions: A Guide to Curiosity

  • Asking bold business questions that dig below the surface can be scary. But it’s a vital part of being a great leader.
    But before you even start asking questions, you have to learn how to listen carefully and embrace some much-needed silence.
  • It’s worth it to be vulnerable when it comes to the important work of getting people’s input that could lead to more innovative and thoughtful business
  • Asking good questions is a characteristic that is often overlooked when thinking about the most important skills to implement in your business strategy. However, the art of asking questions is vital to developing business relationships and growing as an impactful leader.

Dale Carnegie, the well-known self-improvement and leadership trainer, advised people about the importance of asking questions and listening to the responses in his seminal 1936 book, “How to Win Friends and Influence People.” Almost a century later, Carnegie’s advice still rings true.

Asking questions is one of the best ways to foster a business environment where people feel like they’re able to contribute, and that kind of communication will lead to really great, creative strategies and outcomes.

Sometimes formulating the right questions can be difficult. But just remember: at the core, being inquisitive comes naturally to humans, even if it takes some time to figure out exactly what to ask.

“I think questioning is a basic element of human nature,” Mickey Desai, the founder of consulting group Nonprofit Snapshot, says on an episode of The BOLD Business Podcast.

“I don’t think you need skills to ask questions,” he says. “I think you may need skills to figure out how to properly articulate a question and to wrap the right vocabulary around the question –– and, of course, to listen. But the actual questioning itself is innate.”

We’re here to help you hone those questioning skills and figure out how you can ask business questions that will help your company be more creative, innovate and grow.

Mickey, along with Max Irzhak of the National Society of Leadership and Success and Elizabeth Bachman of Strategic Speaking for Results, joined the BOLD Business Podcast to talk about why we need to ask questions, and how to ask good ones.

Max Irzhak - p261

Why Do We Need to Ask Questions?

With our fast-paced work environment, leaders can be afraid to take up time by asking questions, worried that they’ll be slowing down productivity. But that time spent asking questions will really help with productivity and functioning down the road.

Questions are a key part of productive and creative conversations that lead to innovation. By asking questions, you’re getting other people’s perspectives and paying attention to what actually works — not just what you think works. But asking questions is a vulnerable thing to do: when you ask a question, you’re admitting you don’t have all the answers. With the constant rotation of meetings and chatter that we’re used to, we aren’t given enough space to be vulnerable.

The Art of Asking Questions

In our conversation with prominent business leaders who are adept at asking great questions and fostering curiosity in their work, a few important themes came up, and they’re worth keeping in mind.

1. Challenge what you ‘know’

You might think you know your business and its possibilities better than anyone else. But what if you could gain a lot from getting other people’s input? (Hint: you can!)

Max references a conversation with Headspace CEO CeCe Morken. CeCe would rather hire someone who is a “learn it all” than a “know it all.”

That insight inspired Max, who says that it’s really important to be able to soak up new information, which you can’t do if you’re pretending you know everything.

And let’s face it, nobody knows everything.

Challenging what you know requires seeking advice from a diverse group of people. Getting many different perspectives allows you to come up with more creative, intriguing ideas.

Elizabeth’s work revolves around training female executives to become great public speakers and powerful leaders. She says that she sees this problem come up in many “masculine” workplaces, where people are more single-focused, and less likely to want to listen to their female counterparts.

“Multi-focus people are going to notice things that the single-focus people are blind to,” she says. Elizabeth’s goal is to help empower women to speak up and offer their great perspectives, which she says are often shut down in more male-dominated settings. By making it a priority to ask questions and enthusiastically seek out diverse viewpoints, business leaders can encourage this empowerment instead of shooting down someone’s excitement.

2. Do some inner work: learn how to listen carefully and embrace silence

Have you ever had a conversation with someone who you can tell isn’t really listening to what you’re saying and is just waiting for their own turn to talk? Be honest: have you ever been that person? You’re not alone, but as Max points out, if you’re having a conversation where “you’re not actively listening, and you’re only waiting for your chance to talk, that conversation is going to suck.”

So, before you can begin to ask great questions, you need to learn how to listen –– really listen –– to the answers. This means re-thinking some of your current priorities that might be more oriented around getting things done quickly instead of doing things well.

Mickey calls this “getting used to your own quiet,” and he says it’s necessary in order to start having really productive conversations built on really listening.

“If you’re going to be a good listener to someone else, then you have to filter out your own noise in order to get there,” Mickey says.

Mickey Desai - p261

It can be really hard to filter out our own noise: we aren’t used to sitting in the silence without attempting to fill it with TV or another form of media. But if you learn to sit in that initial discomfort, you’ll find that you gain a lot from it down the line.

3. Embrace your curiosity

Like silence, curiosity isn’t always valued in our hectic culture. When we move from meeting to meeting without a minute to take a break and think, is that really an environment where we can think with genuine curiosity and encourage our colleagues to do the same?

Sadly, there are a lot of aspects of our society that don’t set us up to be curious thinkers, to allow ourselves the opportunity to ask questions and make mistakes.

Max says that as professionals move up in their careers, they might feel a bit stuck: like they don’t feel they have the license to ask the kinds of questions they could ask earlier when they were interns and young professionals straight out of college who felt like they were able to make more mistakes.

At the core, it could be because of how expectations change over our career trajectories. “Unfortunately, I think that dies a little bit because people are no longer expected to ask questions; they’re expected to give answers,” Max says.

Max also points out that our education system teaches kids they could be punished if they aren’t immediately correct, which is a good way to eliminate curiosity: one of the most important elements that can help you and your business grow.

Remember: you don’t have to have all the answers. Accepting that no individual can ever be expected to have all the answers is the first step to allowing for a more creative environment.

4. When asking questions, have a goal in mind

Now that we’re on the path to asking better business questions, we don’t just want to be asking questions for the sake of it with no other goal. You don’t want to ask shallow questions: it’s necessary to dig deep to get the answers that will really be beneficial.

Elizabeth says it’s important to consider what you need to know before you start asking questions –– and that you might have to dig deep.

“Figure out what it is you need to find out, then reverse the language and turn that into a question,” she says. “The key is to go below the surface. And that’s always the hard part because it’s really easy to have standard answers to questions.”

When you don’t have objectives in mind, it’s common to be aimless in your work. For example, a workplace with a strong “meeting culture” can succumb to disorganization, especially when you start having meetings with no agenda because you’re too busy to have done any meaningful preparation (probably because of another meeting!).

You don’t want to ask questions just for the sake of asking questions. Taking the time to think about what questions you really want to ask and what you want to get out of asking those questions is vital for accomplishing your goals.

5. Be open to vulnerability

All of the above steps are contingent on opening yourself up to vulnerability: seeking other people’s input or asking them for help means acknowledging where your own expertise falls short. This can be a really hard thing to do.

But keep in mind that you will get better at it as you keep practicing, and you’ll gain a lot from admitting that you are fallible in the form of asking questions. Nobody has all the answers. Remember, this isn’t just for you, but for everyone around you, too: asking questions is how you become an excellent leader, and your colleagues will be grateful for the space to contribute their thoughts.

“I think that we can work from the top-down as a leader allowing people to be themselves and truly bring themselves to work every single day,“ Max says. “If you allow people to be themselves and to bring their beliefs, their processes, their free-thinking to the job and to the position, you’re going to get remarkable answers and remarkable results.”

Want to learn more about good leadership? See what else Mickey, Max and Elizabeth had to say on the topic in our podcast episode, “How to Ask Better Business Questions.” Don’t forget to subscribe to The BOLD Business Podcast for more insights on leadership and success.

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