How Conversations Can Connect People with Data
- Charlotte, North Carolina, November 2025
Through the conference room window, I saw two executives staring silently at each other from opposite sides of the table. I paused to gather my thoughts and think through the conversation before entering the room.
My client was installing a new ERP system after a recent merger. They asked me to help resolve a data access issue. One exec (the CIO) wouldn’t give the other team access to the data; he knew they weren’t prepared to keep it secure. The other was frustrated because his team was responsible for operating the new system. This was “a meeting about data security,” but I realized it was really a conversation about authority.
Who owned the data?
Communication breaks down all the time in the corporate world, and people often blame it on the data. Technical knowledge alone won’t be enough; you also need to understand how people in your company think. Then you can use your data expertise to help them work together.
The Matching Principle
In his bestselling book Supercommunicators, Charles Duhigg says that the most important goal of any conversation is to connect. The right conversation, at the right moment, can change everything, and we can learn to connect in more meaningful ways if we understand how conversations work.
A connecting conversation should answer three key questions:
What’s this conversation really about?
- How do we feel about it?
- Who are we?
Duhigg says, “The importance of this insight— that communication comes from connection and alignment— is so fundamental that it has become known as the matching principle: Effective communication requires recognizing what kind of conversation is occurring, and then matching each other.”
It’s tempting to skip past these questions, thinking every conversation is only about your data. However, the most effective data leaders pause before speaking and ask themselves, “What can I do to help the people around me connect and align with one another?”
Matching With Data
Conversations between IT people and business decision-makers often end in a trainwreck, especially when they’re talking about data. Their PowerPoint presentations illustrate this fact really well.
I recently helped a data leader avoid a train wreck by condensing his 14-point technical presentation down to three bullet points. The first bullet stated the business problem, and the second two summarized the technical changes. Without those adjustments, he would have forced business leaders to spend the entire meeting decoding his list, then debating whether the tasks would make any difference in their ability to make better, faster decisions.
Duhigg’s matchmaking principle can help everyone avoid communication trainwrecks. Three types of questions lead to a “matching” or connecting conversation:
- Practical decision-making questions. Asking, “What is this conversation about?” forces you to think backward. It should cause you to ask yourself what business problem the person you’re talking with is thinking about. How will my solution help them make better decisions? Even if you need to change their perception of the problem, you still need to put yourself in their shoes. Just describing what you’re going to do isn’t enough.
- Emotional questions. Asking “How do people feel about the conversation?” forces you to become a better listener. An executive told me recently that, if we couldn’t find a way to solve his analysts’ frustrations with their data, he felt that he might need to quit his job. That’s how passionate he was about their pain points. He thought it was his fault.
- Identity questions. Finally, everyone involved should ask themselves, “Who are we?” Executives, in particular, need to listen to this question. You might have the most authority, but you don’t have the most knowledge of the data or how to make the connection to decisions. Asking this question will help you listen to the data team and work together on equal footing.
Connecting Conversations
When I finally entered the room, I purposely sat at the head of the table between those two leaders.
“How can they do their job without data?” I asked the CIO. “Do you have a plan to protect the data?” I asked the other exec. Both thoughtfully told me they hadn’t looked at the issues from the other person’s perspective.
Access was granted, a truce was declared, and a small measure of trust was built.
No other part of an IT team crosses the divide between technical solutions and executive conversations like a data team. That’s a huge gap that few data leaders can navigate without help. If you find yourself staring at this divide, then don’t forget this simple truth: better, faster decisions don’t result from data insights.
Connecting data to decisions starts with connecting conversations.
To help remind you of these concepts, I’m now adding a hit 80s song to theFrictionless Data Spotify playlist each week. This week, enjoy Voices Carry by ‘Til Tuesday.