Orland Yee is the first to admit he works too much. “I think on time management I’m the worst person to give advice,” he says. “I tell all my people not to do what I do.” That said, he has a lot of wisdom to impart about climbing the corporate ladder. After 12 years as a consultant at Microsoft, Yee went on to the executive level at several companies, stepping into the CEO role for the last decade at his own company, Softbase Inc.
For Yee, there is no unsurmountable obstacle. Proteges sing his praises because every time they come to him with an impossible problem, he’s able to outline an approach to take — he’ll often offer a book to read on the subject too.
Yee has long been a fan of mentorship and says he’s had many mentors himself. “But they were all technical mentors,” he says. Whereas these days, his proteges come to him with organizational dynamics issues. They’re working through how to change the way they are seen by colleagues and superiors.
We asked Yee about executive visibility, overcoming perception problems, and the qualities needed to make it to the C-suite.
Did you have any influential mentors who shaped your approach?
My father, I would say, has been the most instrumental influence in my life, because he gave me an appreciation for work. He taught me to work hard. We owned a family business, so we came in at 9 a.m. every day and we left at midnight. Even in the summertime, when I was off school, I was there at 9 a.m. We had very long days, doing lots of hard work, and I just got into that rhythm. That is how I still work. Today I start at 9 a.m. and end at midnight — not all the time. But a lot. Yesterday I started at 7 a.m., I was in back-to-back meetings, I skipped lunch, and then I left the office at 8 p.m., got some dinner with my family, and then started working again at 10:30 p.m. and ran meetings until almost 3 a.m. So I’m not saying that’s my everyday, but right now with the state of development that we are in and that’s probably what 50% of my days are like. My father wasn’t a technical person, he wasn’t formally educated, but he taught me how to work.
Tell me a little about the partnerships you’ve had through Everwise.
I have had fantastic people. In fact, I just started with a new protege yesterday. She’s a vice president at a marketing company in New York. And what I always start my protege’s with is: What do you think is your biggest problem right now? I drop the textbook stuff and try to really drill into what is the the pain point for you? For me it’s about the individual, it’s whatever they need to get them to that next level. They often don’t know what they need, so I asked very dumb questions about where they are in their career and what they want to do. I try to really focus in on how I can help each individual. If you want to take an executive management class, you should, but this isn’t that.
Were there any challenges that all or most of your proteges shared?
All of them wanted to advance. Most of them were in the position to do so — in fact, only one was not in a position to do that at the time.
How did you know he wasn’t ready to advance?
If you read between the lines, he was asking me: How you cheat your way into it? And I basically told him: You’ll have to ask someone else. I don’t know how to cheat your way into it, I know how to work your way into it. But that’s just one example; A lot of the time something you’ll notice is that they have a very narrow focus. And as an executive, you have to have a broad focus. It’s kind of like having zooming binoculars. You can focus on one tree in the forest, but you can zoom out and have a wide field of vision. And some people I talk to just don’t have that.
One of your previous proteges mentioned that you were particularly good at helping with executive visibility. What did you tell him?
When it comes to executive visibility, one of the first things to do is to figure out the org chart. And I don’t mean the org chart that the company prints. That’s not the org chart I’m talking about. I’m talking about the org chart of how people are really connected. Who is friends with whom? Who works for who? Who has a vested interest in something that this other person might be interested in? So the political org chart, if I had to put a name to it. That is what you have to figure out in order to get to Director, VP, or C-level.
Another protege mentioned that you helped her leave her comfort zone. How did you manage that?
When we started, she said, “I have developers who don’t listen to me, I have an architect who is arrogant, but I don’t know what I can do about it.” And I said, “Okay, you have to have responsibility for a project, and if you don’t have that, then you cannot effect change. So, knowing that, what are your levers?” And that’s what we worked on. The first thing she needed to do was to get more responsibility, but how do you get that? How do you make people feel comfortable with giving you that responsibility? For her it was an amalgam of laying out the org chart for the project, establishing the roles and responsibilities. She relayed to me, “This developer already has a manager. What can I do about that?” I said, “What you need to do is on this particular issue is adopt matrix management.” And matrix management, if you don’t know what it is, it’s very hard to explain. I gave her a bunch of resources and things to read about implementations of matrix management. I pushed her to do things she didn’t think were in her scope or responsibility.
Has your approach to mentorship changed as you’ve gained experience?
Oh, absolutely. I’m more analytical and methodical in my approach now than when I started. Now I am tracking progress and writing notes to myself and giving them homework. When I first started this I would just talk to them, and I found that it was effective, but not as effective as it can be.
Do you have any advice on time management?
Yes. Don’t do what I do. I’m a very productive person and I change what I’m doing (and what the people under my charge are doing) depending on the circumstances. I have very little down time, but I’m just not the kind of person to schedule one meeting and then go lie on the beach. That’s just not me.