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Questions, Decisions and Leadership

I was consulting for a large company. The project was to tie the company’s data and analytics to their decision-making in a particular area. They had tried to do it several times before but hadn’t been able to make it work. They were desperate to get it right, so I had the freedom to take a different approach.

Step one was simple: Talk to the top 40 leaders in the company and have them tell me their questions.

I asked the leaders to ignore their current data. I asked them to forget what they knew about their market. I asked them to look ahead and tell me their most important questions about their area of responsibility and the future of their company.

For some leaders, the questions came easy. They gave me lots and lots of questions. For others, it was hard. It was hard for them to think about what they wanted to know. It was hard for them to put it in question form.

I saved the CEO for last. When I met with him, he had a ton of questions. And they were great questions. I wrote them down. Then, he asked who in the company had asked similar questions. And who hadn’t asked many questions.

When it was time for the CEO to retire, the choice to replace him came down to two people, a man and woman. I had taken both through the question-asking sessions. Plus, I’d worked with each of them separately.

The woman was one of the leaders who asked a lot of good questions. She saw the gaps in her knowledge and figured out what she needed to know. She knew how to phrase questions in a way that got good answers. She asked good questions.

The man didn’t ask a lot of questions. He expected you to come to him with what he needed to know. When he asked a question, they were hard to answer. It wasn’t clear what he wanted to know. He was a good guy, but he didn’t ask good questions.

The woman, not the man, became CEO.

“’In the early 2000s,’ Famous CEO said, ‘Jobs was splitting his time between Apple and Pixar. He would spend most days at Apple, but then he would parachute into Pixar. He would have to figure out where his attention was needed really fast, so he would arrange sessions with all the different teams—the Cars team, the technology team, whatever—so there were a dozen or so people in each one. Then he would point to one person in each session and say:

‘Tell me what’s not working at Pixar.’

Famous CEO continued: ‘That person might offer something like, ‘The design team isn’t open to new technology we’re building.’ Jobs would ask others if they agreed. He would then choose someone else and say:

‘Tell me what’s working at Pixar.’

According to Famous CEO, Jobs would alternate between the two questions until he felt like he had a handle on what was going on.”

In A Spy’s Guide To Thinking, we use a simple model that puts data collection, analysis, decision-making and action together. It looks like this:

The decision-maker starts the process. He or she looks ahead to the actions they will take. To the options they have. To the decision they’ll make.

To make the right decision, they ask questions. The process works best when they ask good questions.

There’s a ton of data in this world, secret and otherwise. A lot of data is now digitized and stored, but some of the most important data still resides in people. To pull data from people to generate the insights that lead to a good decision, decision-makers must ask the right questions.

When leaders don’t ask good questions, there’s a lot of wasted time and effort. There’s a disconnect between data collection, analysis and decision-makers. Which means the decision isn't informed. Which means the right action won't be taken. Which means the business suffers.

Good leaders learn to look ahead, figure out the decision to be made and ask the right questions.

Good leadership doesn’t happen without good questions.


We put the first two books of the Spy's Guide series into a single paperback because people were asking for it.

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