Every one of us that are 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 for them.

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, Adobe Sign / 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.

The 7 Best Pieces of Business Advice I Was Ever Given

(note: an updated SaaStr Classic post)

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