“Well, look, thanks for this. I’m glad we were able to get together. Thanks for reaching out.”

He pushed back from the table and looked for me to do the same. Instead, I extended the conversation another verse.

“Absolutely. Thanks for meeting with me. And, before we go, I just want to point out that we have considerable experience with transactions similar to yours. We have a streamlined underwriting process and use form legal documents which allow us to provide quick turn times. Also, we will always be competitive on pricing and can avoid being overbearing with covenant restrictions.”

“OK. Uh, that’s good to hear. Like I said, let’s stay in touch and maybe we can work together on something down the road.”

This time he rose from the table without waiting for me. It was time to go. We’d had a good meeting, right up until I’d made it awkward.

I wasn’t out of line. After all, our meeting had a business objective. But, the conversation had been light and had flowed with ease. We had several things in common and we’d both enjoyed the conversation. We had made a connection and I should have left it at that.

But, I didn’t. At the end, when the time for discussing business had passed, I forced a closing statement of all the points I’d failed to make in the hour we’d been there. It wasn’t wrong, it was just out of place and it caused the meeting to conclude on a low note.

In the parking lot, after we exchanged good-byes and parted ways, I sat in my car and stewed. I’d done this before. But, as I reflected on the meeting, I swore I’d never do it again.

There are times to deliver a message. Anyone at a business meeting knows that. We all understand the drill. However, we award style points for how smoothly a message is crafted into a conversation. We all try to abide by the unspoken rule of “Don’t make this awkward”. 

Sometimes the only thing worse than missing your chance is trying to force it once the moment has passed. Attempting a kiss after the lights have come on. Telling an ill-timed joke. It doesn’t work and we all know that from experience. The same thing applies to business, and it was exactly what I’d just done.

If you have a message that’s important enough to deliver, work it in early. Have a plan. Know what you’d like to say and think about how you’d like to say it. It doesn’t need to be your opening line, but don’t procrastinate in the safety of small talk for too long either. Chit-chat has its place, but then, get to the point and say what you came to say. You’ll be glad you did.