Ask Questions That Require Thinking

We are trained to ask questions. But our orientation is to ask questions that demand answers. As a result, conversations often resemble a ping pong game. The server starts with a question, then the response, back and forth. Then the other person serves, asks a question, expects a response, back and forth.

A lot of information is exchanged, but the exchange of information doesn’t mean that we are connecting and having collaborative conversations. And if all we are doing is sharing information, there are too many opportunities for others to get that information through other sources. As a result the value and importance of the interaction plummets.

If we seek to engage others–perhaps our people, our peers, or our customers. If we want to create something new with them, we need to start asking questions that require thinking.

What do I mean by asking questions that require thinking?

These questions go beyond a factual answer. They require some level of reflection, analysis. They may require imagination or creativity. What we want to do is go beyond what they know, but get them to think of what they may not know–that may be important. Or to help them discover something new. Or to help them imagine alternative futures or courses of action.

• We might ask them about something that causes them to reflect on something they have done, “What did you learn from this?”
• We could ask questions that cause them to dive more deeply into something that’s happening, “What might be causing this?”
• We could get them to explore new possibilities. “Are there other ways you might approach this that could be more effective?”
• We might help them consider shifting their perspective. “If you put yourself in the other person’s shoes, what would this look like?”
• Our questions might cause them to ask a question, “What are you seeing? Do you have a different experience?”

What happens when we make this shift? We move beyond just surface issues. As a result, it drives deeper thinking and engagement. It makes the conversational more valuable to each person. It enables us to explore the real issues that underlie the information exchange. We each learn more as a result of this deeper thinking.

The process of doing this shifts our relationships tremendously. It moves beyond a transactional relationship to a more meaningful connection. It enables us to build greater levels of trust with each other.

These conversations provide the starting point for moving forward. The ping pong match of exchanging information rarely provokes people to think about change and moving forward. They open both parties into thinking, “Where can we go with this, what are potential next steps?”

Why do so many of us struggle with moving to these types of conversations?

Part of it is an efficiency bias. We have our own goals and objectives, we are driven to achieve them as quickly as possible. We get impatient with anything/anyone that seems to slow us down. Ironically, when we are focused on the efficiency of the conversation, we overlook the outcome we hope to achieve. Shifting the conversation actually produces better engagement and outcomes–more efficiently than our efficient ping pong matches.

And the outcome we seek to achieve must be aligned with the outcome the person we are engaging seeks to achieve.

We tend to be control freaks. We want the conversation to go in the direction we intended. We want to achieve our goals. Now you can imagine two people talking to each other, each wanting to be in control. Questions that require someone to think may mean the conversation goes in unexpected directions. We have to be comfortable with this, at the same time being mindful of the outcome we and the person we are engaging seek to achieve in the conversation.

Sometimes these conversations may have pauses, there may be silences. Often we are uncomfortable with that silence, feeling the urgency to fill it. But questions that require thinking will create those high impact moments of silence. In doing this, we drive deeper levels of conversation and engagement.

Many organizations have a culture of rewarding answers. People who have the answers are viewed as more competent than those that don’t. Even when those answers may not be the best. What they miss, is the quality of answers developed in these collaborative conversations is likely to be much better than the knee jerk responses they get.

Finally, many of us don’t know how do have these conversations. They require training, practice, experimentation. Conversational intelligence will analyze the conversation, but cannot help with understanding the meaning and impact of these conversations. Beyond training, leaders need to role model what these conversations look like in every conversation they have.

How do we put this in practice?

Leaders with their people. Instead of focusing on just the facts and status report, ask questions like, “What have you learned in the process? What might you do differently? What are the most impactful things we might be doing next? Where do we need to go and how might we get there?”

With your peers. Go beyond status reports thinking, “Are we overlooking something? Do we need to change our approach? Are we still aligned with our goals? What do we need to focus on next?” Also, shifting perspectives, “If you were in my shoes, how would you approach this?”

With our customers, we need to move beyond what is known and our verbal ping pong. We have to start looking at impact, “How is this impacting you and your team’s abilities to achieve your goals?” Or open the conversation with, “If you had a blank sheet of paper, how might you redesign what you are currently doing?” Or sharing insights asking them, “Are you seeing these things? How are you dealing with them?” Or on change, “What happens if you do nothing? What worries you most about the change?”

We even need to reframe our interactions with LLMs. Rather than going to them to give the answers, we need to use LLMs as our debate partners, “Identify the 10 flaws in my thinking? What 5 things have I missed? Is there a more impactful way of doing this?”

Some of you may be thinking, “Dave, that’s all great in theory, but we need action! This stuff just slows us down!”

We could go in endless circles of information exchange, but those don’t mean we are making progress. They just mean we are sharing information.

The reality is that conversations that demand we think achieve better outcomes more efficiently. They shorten the overall process by creating alignment, deeper understanding of the underlying issues, and agreement on how to best move forward. In the process, the impact is greater because they deepen the trust and connection between people.

In a world drowning in information, the only way we make progress is by thinking more deeply and collaboratively.

Afterword:  The title of this article was inspired in listening to an outstanding podcast between Guy Kawasaki and Alison Wood Brooks:  Be sure to listen to it here.

Afterword:  This is a long but outstanding AI discussion of this post.  I really like the way the dive into the ideas and explore them in the conversation.  It’s worth the time to listen to it.  Enjoy!