Microsoft’s CSO on Decision Making

Mike Howard, Chief Security Officer at Microsoft, told me one of his best decisions was becoming a police officer.  I listened carefully for his explanation because Mike spent 23 dynamic years with the Central Intelligence Agency and has been with Microsoft since 2002.


Mike explained, “I proved to myself that I could make decisions under pressure.” I knew instinctively what he meant. Leadership requires self-awareness and self-confidence born in the crucible of experience.


I asked Mike if he had suggestions for decision makers and he told me he has General Colin Powell’s approach on his white-board.

“Use the formula P=40 to 70, in which P stands for the probably of success and the numbers indicate the percentage of information acquired. Once the information is in the 40 to 70 range, go with your gut.”

It’s not unusual for leaders to hesitate on the decision-trigger while searching for that last bit of confirming information.

Gathering information

“One way to answer the need for information, Mike explained, is by encouraging constructive dissent.”  I thought how simple and useful.

I’ve been in group-think environments where constructive dissent is discouraged and irrelevant decisions flowed down like glistening fools gold.

I’m adding a second “information gathering tip” that came up later in our conversation. I asked Mike what he wished he had known when he was younger. He insightfully said, “It’s ok to say you don’t know. If you’re thinking you don’t want to look like an idiot, others are thinking the same thing. Don’t be afraid to ask.”

I asked if it’s ok to say, “Be dumb up front it’s easier,” I heard Mike smile and say, “That works.”

Pull the trigger

“Make decisions and have enough confidence to stand by them,” Mike Howard.


Part 2: The Leadership Secret – What it takes to become a leader.

What decision making tips help you pull the trigger on decisions?