The Secrets Of Working With Bill Gates

What's it like working for a billionaire? Barry Moltz interviews Microsoft's former COO Bob Herbold for an inside look.
Getting Small Businesses Unstuck, Shafran Moltz Group
May 19, 2011

I recently got the opportunity to interview Bob Herbold, the former COO of Microsoft. During his 8 year tenure, he was able to  increase company profits by 700 percent and revenues by 400 percent. I wondered what the secret was to working with Bill Gates. Here is an excerpt from the interview.

Q: We have a lot of small business owners that are founders and eventually they hire a COO. Tell us what Bill Gates was like to work with?

A: Well, you know every organization has to look at the work that needs to be done and assign people to it. That's really what Bill was doing. In my case, the COO role was defined as managing the business aspects of the company. Bill wanted to spend most of his time on the product groups and he needed to. Steve Ballmer was the sales guy on a worldwide basis and Bill needed someone to manage things like finance, information technology, PR, marketing, human resources, and all these other functional areas. And so that's the job that I accepted and it was a lot of fun. I enjoyed it very much. It was a great bunch of people to work with.

Q: Tell us one of your favorite stories about working with Bill Gates?

A: Well I learned a lot of things at Procter & Gamble and I learned a lot of things at Microsoft but the one story sticks out in particular. When we would have business reviews or reviewing an important project and alike, Bill required that the first slide in the deck be the lowlights—not the highlights—the lowlights. In other words, what's not going well and you would tend to focus the whole meeting on the first slide which is the lowlights which is what you should be doing. I can't tell you, and I suspect you've experienced the same thing, how many meetings you go to where all they want to talk about is the highlights and the fact is you only have 10 percent of the time left at the end of the meeting and you're finally getting to the nub of the issue and you've wasted all that time.

Q: You have a new book out called What’s Holding You Back: 10 Bold Steps that Define Gutsy Leaders. Would you call Bill Gates a gutsy leader?

A: Very much so. If you think about the movement from a 16-bit operating system to a 32-bit operating system, I'll talk technology for a moment here, but the fact is it greatly increased the capability of a PC in 1995/96 when it was launched and became very, very successful. That's really what put Windows on the map was the strong performance of Windows 95, in my estimation. Anyway, a nervy decision because you’re taking the franchise and moving it to a different technology platform and you have to make it a success. Similar things happen in that industry all the time and a lot of companies miss those inflection points. Look at Nokia today. They, in fact, missed smartphones you can claim. That's why they're having such a difficult time. Look at IBM in the late 80s where they missed the PC business, so to speak. They marketed one but they really didn't put their feelings behind it. You get these trends that move fast in that particular industry and you better get a head of them.

You can listen to the entire interview here!