If I knew then… In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

The Mistake:

Pushing the email button instead of mulling it over for 48 hours.

I think while we’re young we might have a tendency to immediately want to give a response or have a comeback in a given situation. I recall a time when I was a young broker starting out in the business. I was then working at the Codina Group. I was working on a transaction that was very challenging, and it became a sort of internal conflict.

I remember drafting emails. This was in the early 90s so we were already communicating with emails, but the practice was still fairly new and I drafted this really passionate email about my thoughts on the situation. I pushed the button instead of mulling it over for 48 hours, going for a walk and thinking about it. I remember so clearly that my boss at the time, who today is a good friend and mentor, called me into his office and we sat down. We had a nice chat, and he looked at me and said, “Don’t push that button so quickly.” Sometimes it’s best to write that email, save it, go for a walk, sleep on it, come back, read it,read it again, read it again, and don’t even send it again. Sometimes the email you thought was appropriate was not the right approach.

The Lesson:

Email is tricky because you can never really tell a person’s tone through their writing.

Even today, I’ll receive an email that’s meant to be very efficient, but when you read it, you wonder if its author was in a bad mood when they sent it.

For me, it really is about learning to be less reactive and more thoughtful in my approach to challenging circumstances. So often you can resolve circumstances by having a face-to-face conversation, working out the issues, and settling it by getting everyone adjusted and creating real perspective around it.

That’s the moment to come back calmly to address an issue – when things have simmered down a little bit. That experience stayed with me all these years because I feel like in our business we’re juggling a lot of things. We have multiple transactions, multiple clients, and sometimes in this day and age of instant gratification, people want to send that email out and be efficient.

What I always remind my team and myself is: Listen intently, really process and have a conversation instead of sending an email whenever possible. Take it seriously. It’s a serious business and that’s how we need to communicate.