(Originally published on SaaStr — more on that here.)
Every one of us that is hyper-driven wants to grow our careers faster. We’re impatient. We want to learn, grow, manage more, earlier.
Let me share my best hack. My uber-learning:
- Find the best boss you can; and
- Take on every initiative, project, task and endeavor you possibly can from (and for) her.
The best career accelerator I ever got was working for a few great bosses. And doing the things they pushed me to do that I didn’t really want to do.
I had one great boss that pushed me to manage an HR team. The last thing I wanted to do was manage HR, something I knew very little about. But … he knew I had very little management experience, and this would accelerate my skills here.
At first, I declined. I said it wasn’t interested in HR. He said he understood. Then, I woke up the next morning, said I was wrong, and took over the department. He was right. Managing a team of 6, with their goals, issues, dramas and needs … in a functional area I did not understand … pushed me in new ways. I may not be a great manager, but I think I am a reasonably effective boss, and I learned this from managing this crew.
Without this, i could never have founded 2 successful startups. Period.
I had another great boss that pushed me to get on the road much, much more often. To stop waiting for customers to come to me. While I thought I understood “big deal”-type of sales and business development, I didn’t enjoy outbound sales and hunting < $500k-$1m deals.
In fact, I didn’t enjoy it at all. My boss pushed me. He said: You Have to Get on the Road. You have to go meet all those prospects, all those customers. All of them. Until you can’t literally take it anymore.
He said I had to completely get out of my comfort zone of a barbell combination of occasional huge deals + inbound sales, and work the large space in the middle.
He was right.
If I hadn’t done this, my second startup, EchoSign, would have gone bankrupt.
Great Bosses. That Push You to Do Things You Don’t Want to Do, That They Know Will Make You Better.
They’re usually right.