Early in my career, I believed that deals were mostly about numbers. Price, timing, and structure seemed like the drivers of every outcome. Over time, that belief fell apart. Not because numbers stopped mattering, but because I started paying closer attention to the conversations happening around them.
Looking back, three conversations have reshaped how I approach deals. None of them happened in a conference room. None involved spreadsheets or formal presentations. Each one changed how I listen, how I ask questions, and how I decide when to move forward or step back.
A Leasing Office Conversation About Power
My first real lesson did not come from a senior executive or a mentor. It came from a resident standing in a leasing office.
I was early in my career, working on-site at an apartment community. A resident came in frustrated about an issue that, from my perspective at the time, felt minor. I was focused on policy. They were focused on how the situation made them feel.
At one point, the resident paused and said something to the effect of, “You are not hearing me.” You are just explaining the rules.
That moment stuck with me.
I realized that having authority in a situation does not mean you have understanding. The rules may be clear, but that does not make the outcome feel fair to the other person.
Later, when I started working on deals, I noticed the same dynamic. One party often has more leverage, more information, or more experience. It is easy to rely on that advantage. It is harder, yet more effective, to understand how the other side experiences the process.
That conversation at the leasing office taught me that people remember how decisions are handled, not just how they are justified.
A Pandemic-Era Call About Execution
The second conversation happened during the early months of the pandemic. Everything felt unstable. Assumptions that had held for years suddenly no longer applied.
I was on a call with a colleague discussing how to respond to the uncertainty. There were a lot of ideas being shared. Creative strategies. New initiatives. Plans that sounded smart in theory.
At some point, the conversation stalled. Someone finally said, ideas are not the problem. Execution is.
That line cut through the noise.
It forced a shift in how I thought about value. In uncertain environments, the best plan is not the cleverest. It is the one that can actually be carried out.
Since then, I have paid closer attention to whether a deal is executable, not just attractive. Who has to act? What decisions have to be made? What happens when conditions change?
That conversation changed how I evaluate risk. I stopped asking only whether a deal could work. I started asking whether the people involved could make it work.
A Quiet Comment About Timing
The third conversation was short and almost forgettable on the surface. It happened after a deal fell through.
I asked someone more experienced than me what went wrong. They paused and said, nothing was wrong. It was just the wrong timing.
At the time, that felt unsatisfying. I wanted a clearer explanation. A specific failure. Something to fix.
Over time, I understood what they meant.
Some deals are well-structured and fairly priced, but misaligned in timing. The owner is not ready. The market is not ready. The partnership is not ready.
Before that conversation, I treated timing as something to push through. Afterward, I began to respect it.
I learned that forcing timing often creates hidden costs. Strained relationships. Compromised terms. Future regret.
Now, when a deal stalls, I try to listen to what the pause is saying. Sometimes the best move is to wait. Sometimes it is to walk away without frustration.
How These Conversations Changed My Approach
These three moments reshaped how I think about deals in practical ways.
I listen more than I speak. I pay attention to who feels unheard. I look beyond the numbers to see whether execution is realistic. I treat timing as a variable, not an obstacle.
Most importantly, I stopped assuming that a deal failing meant something went wrong. Often, it means something important was revealed.
Deals are built on conversations long before documents are signed. The quality of those conversations determines the quality of the outcome.
What I Look For Now
When I approach a new deal, I pay attention to tone as much as content. Are people rushed? Are they defensive? Are they willing to slow down?
I notice whether questions are welcomed or avoided. Whether explanations are clear or vague. Whether decisions feel forced or deliberate.
These signals matter. They show up early, long before results do.
The conversations that shape outcomes are often quiet. They happen in passing. They happen when people are not trying to persuade.
Those are the ones that changed how I approach deals, and they continue to guide how I work today.