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Art of Leading

The Art of Being a CEO: Don’t Be Too Generous with “Good Job” Compliments

February 15, 2018

After interviewing more than 500 CEOs for the “Corner Office” series I started in The New York Times, I’m launching a number of new interview series around leadership in my new role at Merryck & Co., a senior leadership development and executive mentoring firm. In “The Art of Being a CEO,” I’ll be focusing on key lessons that leaders have learned about the nuances of the role.

Here’s the conversation I had (edited for space) with Austin McChord, the CEO of Datto, a data-protection company.

Q. You founded Datto a decade ago, and have had to scale yourself as a leader to stay a step ahead of the company’s growth. If you were to write a memo to your younger self based on what you’ve learned, what would it say?

A. Your job goes through a complete metamorphosis into different things. When you’re starting out, you want to do everything yourself or be super-involved in a particular project or have a really strong opinion that the entire world needs to look this particular way. The reality is that you have to change those views and be willing to not be so cut and dried.

Q. A big part of it is letting go – setting direction and standards but then letting others do the work. How did you think about that?

A. There are certainly values and standards that you want to retain. But in terms of the process of how you get there, you’ve got to be open to changing that all the time. It’s this tough balance because you have to hold these really high standards and you’ve got to push people, but on the other hand you’ve got to be humble enough to accept your imperfections and that you may not be the expert that you thought you once were.

Another way to think about letting go might be that perfection is unattainable, and instead you just constantly keep seeking that better way all the time, and that applies to almost everything. If you pick any part of your process, any part of who you are, any part of where you’re going or what you build, and you say, “Nah, this doesn’t need to get better,” then you’re sowing the seeds of your downfall.

Q. And you make that explicit with your employees?

A. Yes. Somebody might get two or three “good job” compliments a year. Focusing on what we’re not good at, and how to improve it, is pretty much what we do all day.

Q. But do you find people want more positive feedback? In this era of social media, a lot of people measure things by the number of “likes.”

A. As long as the feedback you provide is actionable, people will find it to be valuable. And as long as they believe that it is coming from a good place – “Hey, here’s how we could do this a little bit better next time” — that goes over well. Over time, you find that people actually want that more than just, “Great job, everything was perfect.”

Telling somebody they did a great job and everything is perfect is not actionable. There’s nothing you can do. It’s almost unhelpful. That level of honesty can be refreshing compared to a world where everything is likes and smiles and whatever sort of social media gloss that people try to put on their lives.

Q. In what ways do you want to be a better leader two years from now?

A. Being a better communicator. It’s something that does not come naturally, but instead it has been the skill that I’ve worked at more and more because it’s just become a bigger necessity as the company grows. How do I deliver a message to all those people that gets them fired up about working at the company? You have to be able to distill and deliver a message that can be repeated and will carry value through all of the layers of the company.

Q. And as the company gets bigger, there’s also more interest in trying to understand what makes you tick.

A. Absolutely. You just have to show a little vulnerability and be human and tell stories about the history of the business. I tend to be relatively self-deprecating, and admitting your faults is something that catches people off-guard.

At our last town hall event, I did a whole bunch of silly accents onstage, which is pretty embarrassing, but at least it shows people that I’m human.

Q. And where did the whole silly accents thing start?

A. It goes back to when I started the company, and people would call in for tech support. I didn’t want them to know that there was only one person who worked there, and so I would make up different accents and answer the phone. Early on, I created this fake employee called Peter Hedge, who had a ridiculously bad Michael Caine-esque British accent.

Q. How do you create a culture of accountability?

A. We use a pretty blunt term around here of the “single, wring-able neck” to get things done. We find that in big groups, accountability kind of dies. So it’s about making sure that there’s one person who is willing to step up and say, “I am responsible for this and I will get this over the finish line,” and then doing everything we can to support that person. Making clear who’s responsible for what is the biggest challenge, much more than people not getting done what they say they’re going to do.

Q. If a business school reached out to you and asked you to teach a class on any subject, what would you teach?

A. It would be around the value of inexperience. Sometimes not knowing how a problem is typically solved or not knowing potentially how difficult a problem might be can be an enormous asset. And when you approach things for the first time and are unbiased, you can achieve results that sit outside the standard deviation of the norm. And that can be really valuable in business.

Q. When you mentor people, what do you find yourself typically telling them?

A. Almost 100 percent of the time, it’s giving people a new context to look at a decision or a choice that they’re about to make or have made. As a company, we hire really great, talented, capable, smart people, and really great, talented, capable, smart people make the right choices almost all the time. And when they don’t, it’s almost always because they don’t have the right context or the right point of view.

In the book, “The Hitchhiker’s Guide to the Galaxy,” there’s this guy with a magical point-of-view gun that you can shoot somebody with and then that person will see your point of view. If you can, in some way, impart a new point of view to someone or give them a different lens to look at the same information, that tends to be the biggest thing that helps people grow and see different answers.

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