5: When you know what you want, make it clear

You may not know exactly how you want to progress in your career right off the bat. That’s fine. Actually, you shouldn’t know. You should take the first six months to a year to master your current role. During this time, you should be observing the people and the different roles around you.

When you do know what you’d like your next step to be — whether it’s people management, moving into product, or increasing your responsibilities as an Account Manager — make it very clear to your boss. Why? Because it’s your boss’ job to help you progress in your career. Any good manager will want to have a “plan” for each of their direct reports and help guide them in that direction. But managers are not mind readers! When you know what you want, tell them.

I think we shy away from having this honest conversation because we don’t want our bosses to think we aren’t interested in our current roles. But it’s not like you’re asking to change jobs right away — you’re just making it clear where you want to be in six months or a year or two years. By making this clear early on, your boss can start to give you additional responsibilities to help you prepare and keep an eye out for opportunities within the company as they arise.

Again, you shouldn’t feel bad about making this clear with your boss. If you’re killing it in your current role, your boss will want to help. And remember, if you succeed, they’re succeeding as a manager.

When I helped start the Sales team, I made the mistake of not making things clear with my boss. I knew I wanted to start managing people as we grew the team, but the two of us never had that conversation. I just assumed it would work out that way. It didn’t and I have no one to blame but myself. If I wanted to be a people manager, I should have made that clear months earlier.

Later, when I helped start the Account Management team, expectations were clear from the beginning. In fact, it was the first conversation I had with my boss. Nothing was guaranteed in that meeting, but my boss knew right from the start that I wanted to eventually become a people manager. He told me that if I worked hard and executed, we would grow the team and good things would follow. And that’s exactly what happened. We worked extremely hard and executed and by the time I left Square, I was managing the entire Account Management team.

I understand that deciding on your exact path can be difficult. It’s almost like asking someone to pick a passion when they’re not really sure what they’re passionate about. I don’t have a great answer as to how you can hone in on your path. I always just watched those around me and followed the people I respected the most and thought were the most interesting. I also just listened to my heart — as vague and cheesy as that sounds.

All I really know is that once you decide on what it is you want, make it clear to your boss so that the two of you can start executing against it. Otherwise, you will wallow with no direction and wonder why/how those around you are progressing in their careers when you are not.