My first real experience in sales wasn’t quite Boiler Room or The Wolf of Wall Street, but I did join a high-performing, high-pressure team that expected me to perform—pretty much from the off. The hierarchy of top performers was clear, and I was at the bottom. Several of my team members had been top quarterly and yearly sales people, and it was obvious I wouldn’t be part of the team until I proved I belonged. 

Outside of my team, the question from other sales people was always “How’s your quarter going?” Meaning: how much revenue have you brought in? It was a challenge more than a question.

In those early days, I kept my head down and worked hard. Not just to succeed, but to belong. 

When I was still pretty new in the job, it was normal for me to be the last person in the office, working late and updating lead lists. My team had a manual way of saving important lists in our CRM, with no back up as everyone knew to make a copy before doing anything with the list. But one day I forgot, moved the list without copying, and then edited it for my work. Then I went home. 

The next morning, my boss noticed straight away. The whole team was there, looking at each other and ready to pounce on the guilty party. I immediately realized my mistake—but I couldn’t speak up. The job was too important, and I knew that my mistake was too big to ignore. I probably wouldn’t be fired immediately, but the team would lose the tiny amount of trust and credibility I had been building with them. I knew what the right thing to do was, but I just couldn’t do it. (Incidentally, if any of my old teammates are reading this… sorry, it was totally me.)

Don’t look at me, it was like that when I got here…

The incident eventually blew over, and not long after that I made my first deal. I belonged. 

My mistake, and my inability to speak up, stuck with me for a long time. In fact, I’ve never told the story until now. It’s really not like me to not own a mistake, and I’ve made plenty in my life. So why was that time different?

It wasn’t until years later that I got the answer—my team, and the wider business, lacked Psychological Safety. I was desperate to be accepted in my new team, and the stakes felt too big for me to speak up.