Adam Bryant conducts interviews of senior-level executives that appear in his “Corner Office” column each week in the SundayBusiness section of The New York Times. Here are a few insights provided during an interview of Tim Bucher, founder and C.E.O. of TastingRoom.com, a wine site, who has also held executive posts at Dell, Microsoft and Apple. He says he takes his team to weekly dinners, as it’s hard to discuss the big picture amid distractions at the office.X

To read the complete interview as well as Bryant’s interviews of other executives, please click here.

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Monday-Night Strategizing, With the Team

Bryant: Talk about your approach to management and leadership.

Bucher: Quite honestly, I think I’m a lousy manager. I think I’m a pretty good leader, and I didn’t realize that until about halfway through my career.

Bryant: Can you elaborate?

Bucher: There’s a saying I like: Management is about doing things right — dotting the I’s, crossing the T’s, giving reviews, doing all the H.R. stuff. But leadership is about doing the right thing. And it’s very different. There might be a situation with a team member, for example, that should be handled a certain way, according to H.R. But as a leader, you have to understand the broader context. You have to make a call, and in some ways it might be against company policy.

That’s why I also like smaller companies, because you can violate company policy a little easier than you can at large corporations to maybe help someone, maybe even giving them $1,000 to take care of some financial emergency. And when you do the right thing, you usually have an employee for life. They’re very motivated to work for you and work for the company, and I think the output is just tremendous compared to whatever the expense was.

Bryant: Can you give me another example of how you lead?

Bucher: I just hired a new senior vice president of marketing. I sat her down and I said, “You need to know I’m a terrible manager, but I will lead you, and we will do great things together.” That’s not a normal management style, but if you set that expectation with folks, it works. I told her, I will challenge you. I will challenge you beyond the breaking point. And it’s up to you to push back. But you need to understand I’m challenging you not to make your life miserable. I’m challenging you to make the impossible possible, which is what you do in start-ups.

Bryant: What do you consider some of the most important leadership lessons you’ve learned?

Bucher: I believe that start-up managers need to be a little different. I learned that one of the most important leadership things — again, for start-up life — is an expression that I tell my team every time we have an all-hands meeting: “Trust until trust is broken.” Because when you trust until trust is broken, you can move really fast. I will tell a new executive on the team when I hire them: “From Day 1, you have my complete trust. I trust you to run your part of the business the way you deem appropriate. And I’m going to support you in that, and you’re going to make decisions and I’m going to back you. I’m going to do that until trust is broken, and hopefully trust is never broken.”

You can move really fast as an organization with that philosophy, especially if you can get that philosophy throughout the whole organization. When you instill that from Day 1 in a company, it’s pretty powerful, because then everyone’s got everyone else’s back. Have there been times when trust has been broken? Yes. It does expose you a lot more. I’ve got a couple of knife wounds in my back to prove that.

Bryant: But parse a little more for me what you mean by “trust.” I mean, people take risks, they make mistakes. Does that mean they’ll lose your trust for that?

Bucher: So the other part of leadership, and my leadership style, is that you have to show the vision. You have to communicate the vision. You have to show the team where you’re going. Now, if the leader doesn’t do that, and they just trust until trust is broken, you’re going to have those situations, and it’s just mayhem. So the key is you have that in the background — you’ve got to pull the whole organization in the right direction. With that culture, people are going to do the right things operationally. In a start-up, everyone is pulling on the same oars. But the philosophy does not work as well in a large organization, where you have people working on their own tangents.

Bryant: At what point does it start breaking down as a new company grows?

Bucher: If you’re starting a company from the ground up, it’s probably at about 150 people. But there are a lot of variables. How quickly you grow is probably the most important variable, because if you’re growing too quickly, you cannot instill a culture where everyone plays together nicely. If you’re growing slowly, you can hold onto the culture longer, with more employees.

Bryant: You’ve worked at a lot of different companies. If you went into any company to get a feel for its culture, what would you look for as clues?

Bucher:  If you walk the hallways, and if you see people talking to one another in the hallways, and yelling over the cubicles, and going inside each other’s offices, that’s a good sign. There’s a certain buzz. But I’ve been acquired by some companies where I’d walk the hallways and it’s just like a mortuary. You’ve got to see the interaction going on between everybody in the company, not just between the executives. And not just in meetings. How are people working together? Are they really working together as a team? Obviously there’s a lot of e-mail and digital communication that occurs, and that’s all good. But there’s a much higher bandwidth when people sit and work together. We might sketch out something together, and we’re yelling at each other, and all that stuff. And that’s when you really can tell whether the culture is innovative, too.

I use weird metaphors about great ideas. I view them as volcanoes, and the lava is like all the people working together. And if you’re working on it, working on it, and you work on an idea and you refine that idea, eventually the best idea is going to blow off the top. I call it the idea volcano. And if you work together, the best idea is going to erupt.

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Adam Bryant, deputy national editor of The New York Times, oversees coverage of education issues, military affairs, law, and works with reporters in many of the Times‘ domestic bureaus. He also conducts interviews with CEOs and other leaders for Corner Office, a weekly feature in the SundayBusiness section and on nytimes.com that he started in March 2009. In his new book, The Corner Office: Indispensable and Unexpected Lessons from CEOs on How to Lead and Succeed, (Times Books), he analyzes the broader lessons that emerge from his interviews with more than 70 leaders. To read an excerpt, please click here. To contact him, please click here.