Tony Tjan (Cue Bal) in “The Corner Office”

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 Tony Tjan, chief executive of Cue Ball, a venture capital firm based in Boston. He suggests waiting 24 seconds, 24 minutes, then 24 hours before criticizing a new idea.

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

Photo credit: Earl Wilson/The New York Times

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Bryant: Do you remember the first time you were somebody’s boss?

Tjan: The first time was when I was probably about 16 or 17. We lived in Newfoundland, and I was a distribution representative for a multilevel marketing company. I had to recruit other distributors and train them, and it was my first experience trying to understand how to motivate people.

But I learned some of my most important lessons when I founded an Internet advisory firm called Zefer. I was 25 and going into Harvard Business School. I certainly wasn’t as self-aware at that time — being really honest about my strengths and weaknesses — as hopefully I am now. I think early on in many people’s careers, you have a tendency to want to show off your good side, and vulnerability and degrees of humility are not viewed as desirable traits. It probably made me a more intimidating, more inaccessible person. I was also less direct than I am now.

Bryant: And what was the biggest lesson from that experience?

Tjan: The seminal inflection point for me was being at the highest of highs and then going right through the nuclear winter of the dot-com bust. We had a business that had grown from nothing to over $100 million in about five years, with about 900 employees. We had filed to go public, and I could probably tell you the second of the beginning of the dot-com crash, actually on the day we were to go public, April 14, 2000. We then had layoffs and a significant restructuring. It’s hard to even describe that period, but we eventually came out of it.

The lesson from that was that self-awareness trumps all. You need to know what your superhero strength is, but you really learn at tougher times what your and others’ weaknesses are. The biggest shift for me was that I realized how important intrinsic rewards are — like the value of a meaningful role — over extrinsic rewards.

Bryant: You must do a lot of mentoring. Any advice?

Tjan: One of my partners, Mats Lederhausen, has developed a good framework for mentoring. It was inspired by Deepak Chopra, but Mats has evolved it over the years. There are five questions to pose to someone you’re trying to be a mentor to: What is it that you really want to be and do? What are you doing really well that is helping you get there? What are you not doing well that is preventing you from getting there? What will you do differently tomorrow to meet those challenges? How can I help, and where do you need the most help?

The sequence is important. You have to understand the larger purpose; understand the person’s self-awareness around their strengths; understand external or intrinsic blocks to doing that; and understand the person’s plan and motivation to change before you just assume you can help. It’s just as important, for clarity and to reinforce self-awareness, to have the person play back to you after the meeting in an e-mail what they heard and said.

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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 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.

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