Tom Rose | Crain's Boston

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

Tom Rose


Along with his MIT classmate Miro Kazakoff, Tom Rose started test-prep company Testive in 2011 when he realized his high-priced tutoring service could be partially automated, making it better and cheaper for students. The company now has offices in Boston and Durham, N.C.

The Mistake:

I was hired to lead a really large volunteer organization of students to build the house of the future, which was an awesome opportunity—a great gig. But it had the interesting challenge of me being the only paid staff person in a really large volunteer organization. And also me being given a leadership role with lots of responsibility but little guidance. And because I didn't have a lot of experience with leadership, I quickly made the mistake of thinking, "I'm supposed to know how to do this. I need to prove to people that I'm good at doing it and I don't need any help to figure it out."

So I made a million little mistakes that you pick up working in professional jobs. Little things, like when I would send e-mails I would fail to copy the right people. Or I'm working on a project for the structural system for the house, and I tell the student team working on it to make some changes, but I forget to copy a faculty member who's the structural engineer on the project.

I'm also making all kinds of mistakes with incentives and volunteer recruitment. Like when you have a faculty member donating time, you want to make sure that you're really gracious about that and that you're deferring to their judgment all the time. It's not my place to even be telling the team to make a change. What I'm supposed to be doing is discovering that maybe something should be happening and then connecting students to the faculty and having them think through it.

Another classic early leadership mistake is micro-managing people. I was working with a large group of volunteers and it wouldn't be uncommon for me to bring in a team for a meeting, work out what I thought the next steps are on their project and then assign those steps to them. That's opposed to letting them figure it out. That management style is appropriate in emergency situations and really tactical operations, like if you're teaching a group of people how to put together a book shelf. But it's totally inappropriate for anything creative and for a group of volunteers. They want to add value by doing creative thinking. They don't need me help them figure out the next steps. So I was completely un-calibrated for leading creative people.

When you're starting out, it's OK to not know what you're doing. 

The Lesson:

I think the biggest source of all these little mistakes was failing to get good feedback. When you get your first job, everybody is bad at business communication. That's fine, but the way that you fix it is by getting lots of good feedback from some mentor or teacher or coach. And those little pieces of feedback, they help of course correct you over to being good at doing your job.

I was surrounded by great mentors, but my mistake was not being open to their feedback. I was turning people away. Now looking back on it I realize how many opportunities I had to get feedback that I was missing and I didn't even realize it.

Like that professor saying, “Hey you didn't copy me on that email—just do so in the future.” And my response to that would probably have been something like, “Oh yeah, of course, I'm sorry, I just forgot.” But that's not true. I didn't forget—I didn't understand the framework that I was supposed to apply in that situation. My mind wasn't even open to the idea that I was missing something.

When you're starting out, it's OK to not know what you're doing. You're supposed to not know what you're doing, and you're supposed to be asking people for lots of feedback, and you're supposed to be ignorant of lots of trivial things. Ask for lots of advice, especially about things that you think you know.

Now, I incorporate retrospectives in everything I do, and it’s a major part of life at Testive, where I currently work. I now know that it’s OK to make mistakes because they are inevitable. Learning from mistakes and not repeating them is what matters, and the only way to learn from mistakes is through feedback.

Follow Tom Rose on Twitter at @TheRealTomRose.

Photo courtesy of Testive. 

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