Tim Casasola — Tim Casasola

“I love being told things I already know,” said no one ever.

Think about this scenario: You and your colleagues are tasked with a major project. You all are stressed out because of the pressure you all are receiving from your managers.

One day, as you’re working on the project with your team, a colleague (who isn’t your manager) tells you to “Make sure you check with Alex about how the header image looks to her.”

You’ve ran images by Alex on tons of past projects and respond with, “I know, I’ve Slacked a draft to Alex in the #design channel.”

Your colleague responds with, “Send her more than one image so she can have options to choose from.”

You respond politely with, “I know.”

More often than not, this advice giver has good intentions. They aren’t trying to control you, and just want to make sure you’re doing a good job on your part of the project. They genuinely care about your success and quality of the project when it’s finished.

Now you, the receiver, might be a little annoyed since:

That colleague isn’t your manager.
You know the drill (you always send images to Alex for feedback).
You already did the suggestion and there is evidence of it on a transparent communication channel.

We live in a culture of more telling and less asking, and we see this in our everyday conversations. This fact was once very apparent to me when I met up with someone who reached out to me for coffee. At the end of our hang out, they said, “This was great–I’ve learned a lot from our conversation.” The catch? They had talked about themselves the entire time.

Of course, there is real value in telling others what we know, especially at work. Great leaders must share knowledge with their teams in order for the team to best work together. Yet, as our complex world increases the need for collaboration, leaders can be the catalyst of enhancing collaboration in their organization simply by telling less and asking more.

Asking Questions Through Humble Inquiry

While it’s important for leaders to ask more questions, it’s equally important to know how to ask questions. We can find insight on what makes for a good question through Edgar Schein’s concept, Humble Inquiry.

“Humble inquiry is the skill and the art of drawing someone out, of asking questions to which you do not already know the answer, of building a relationship based on the curiosity and interest in the other person.”— Edgar Schein, Humble Inquiry

Telling implies that the other person does not know what you are telling them, and that they ought to know it. Asking questions temporarily empowers the other person in the conversation.

Good questions result in building trust, because it makes the asker vulnerable in the moment. They come from a genuine interest in the other person or in the discussion topic. In other words, you must truly want to know the answer to ask a good question. As Clay Christensen puts it,

“Questions are places in your mind where answers fit. If you haven’t asked the question, the answer has nowhere to go. It hits your mind and bounces right off. You have to ask the question — you have to want to know — in order to open up the space for the answer to fit.”

Most leaders say they have an open door policy and are open to being asked questions, but therein lies the problem: you’re telling your employees to ask you questions instead of asking questions yourself.

If you’re in a leadership position, your direct reports will consciously or unconsciously look to you as an example of how to behave and act (whether you like it or not). So if you’re asking a lot of questions, your reports will feel comfortable asking more questions, too.

Here are seven of my favorite questions that great leaders ask:

“What challenges are you facing in your work? How can I help?” This is better than asking “Why isn’t your project done yet?” Asking this can lead to them asking you for advice and thus, the advice will be requested, not unsolicited. Here you’re offering support and empathy — you want to understand what they need.
“How do you feel about that? What’s your emotional reaction to that?” It’s the classic therapy question “How does that make you feel?” This question is open-ended compared to “Did that make you feel angry/upset/etc.?” It gives the space for the answerer to own their emotional reaction, instead of gently forcing them to agree with how you thought they reacted.
“What shall we do from here? What do you think we should do next?” It’s tempting to offer “Why don’t we do this?” as a ninja suggestion disguised as a question. However, this is great to ask after someone brings you an issue, concern, or problem. It’s opinion-free and non-judgmental.
“What would you add to my thought/suggestion?” Asking this is the “Yes, and…” version of collaborative problem solving. It’s humbly acknowledging that your suggestion might be incomplete, and the listener may have more to say, which would make the suggestion even more valuable.
“From what I suggested, what doesn’t ring true to you? What would you disagree with?” These are great to ask after providing suggestions or feedback. It lets your listener know that you are open to healthy disagreement.
“What have we learned? How should we work together to make sure this goes more smoothly next time?” This works well when you want to know what didn’t go well in a project. It frames the work as a learning opportunity. You’re letting them know you’re their teammate and want to work with them to make future projects even more successful.
“What about your project made it successful? What should we continue doing?” It’s easy to point out everything that went wrong and forget to point out the parts of the project that went right. If a project went exceptionally well, understand why!

We ask questions all of the time — at work, networking events, dinner parties, dates, with our spouses, with our friends — it’s hard to think of scenarios when we aren’t. This is why humble inquiry is so powerful. It’s simple, practical, and can be used at anytime.

Asking the right questions is what builds relationships, solves problems, and moves things forward. By asking more great questions, and creating a culture around asking, teams can truly collaborate in a complex world.

Now, what would you add?