Questions Eliminate Our Flawed Assumptions – Conversation Principle #5

Assumptions don’t only create misunderstandings; they create consequences. 

Assumptions are my kryptonite. Most of the time, I think quickly. I can pull together disparate pieces of information, discover something new, and come to a conclusion or reveal a new and exciting idea. 

While this has allowed me to create a good life for myself, establish strong relationships and build two businesses, it has also put me in awkward situations, created chaos and resulted in some heartache. 

In other words, this same mind that spots patterns quickly can also connect dots that were never meant to be connected. 

So when our 2026 Real-Time Business Conversation Index revealed that 98% of business leaders know that real-time conversations are critical to their success, yet only 11% feel they are doing them effectively, I knew that assumptions were part of the problem. 

How do we avoid making assumptions?

Well, I don’t have an easy or perfect solution. What I do know to be true is that assumptions are eliminated when we ask more questions. 

Think about how your conversations progress. You’ve listened carefully to a prospect, client or consultant. You’ve taken notes. And you’ve certainly asked questions, perhaps the same questions you always ask as part of your discovery process. Yet it’s possible you’ve missed something, possible you’ve made an assumption. 

A Story About the Cost of Assumptions

I’m reminded of a project I did years ago for a hotel chain. They hired me to spend three days training six new Canadians for receptionist and concierge positions. In my initial meeting with management, I mentioned the possibility that accents could be a challenge. 

The First Assumption

The immediate response from the most senior person in the room was, “That’s not a problem.” This was the first assumption. 

The three days I spent with these six lovely people were amazing. They worked so hard. As a group, we recognized that accents were an issue, and I created several exercises to support them in speaking slower, enunciating and focusing on common phrases and words. 

The Second Assumption

In addition, I went back to management and requested that each person be allowed to participate in a call on the second day of our training. This included recording these calls so we could review them together and use them as a learning tool on our final day. 

I made this request a few times. I knew that if my students could hear themselves on the phone, they’d be much better informed and empowered to speak clearly. However, the senior executive believed this to be unnecessary. Enter the second assumption, built from the first.  

A month later, I followed up with the senior executive to see how my “graduates” were doing. We’d become quite close in those three days, and I was looking forward to hearing about their success. Instead, he acknowledged that he should have listened to me. Accents were an issue, and all six individuals were let go on the first day. Thinking about and sharing this, I still feel shattered. 

Assumptions impact more than one conversation, one project, one client or one sale. Each one has multiple consequences. So what can we do? 

The One Question That Changes Everything

The answer is both simple and hard. When you’ve listened intently and you believe you’ve uncovered everything you need to know, ask one more question. Stay curious rather than reaching a conclusion. 

The Mindset Shift

Replace your assumptions with your next question.

What I’ve learned as I’ve battled with my own assumptions is that it’s okay to ask for another conversation. For example, I can have a great conversation with a client about a new project and realize an hour or a day later that my conclusion is faulty. I no longer let my pride get in my way. I contact the client and let them know I need to ask a few more questions. 

My younger self would have been embarrassed, would have thought it unprofessional. It turns out clients and prospects are always pleased when I own up and show up. 

Try This This Week

Pay attention to the moments when you think:

• I know what they mean.
• I know why they did that.
• I know what they’re going to say.

Pause.

Ask another question instead of concluding. Examples include: “Tell me more about …” or “Help me understand ….” or “What else can you tell me about …”.

Every aspect of creating effective conversations relies on practice. Eliminating assumptions is an essential part of that practice.