A Study in Reverse: The Importance of Thinking Backwards

I grew up in Maine reading Sherlock Holmes. Stephen King had walked the same high school halls I did, though years before, and the woman who taught me English had once been his high school newspaper advisor. She liked to mention that. She never quite understood why I ignored King’s books and chose Conan Doyle instead. But, I wasn’t interested in horror. I was interested in thinking. Holmes solved the problem of how to know things. That felt more useful than a haunted car, a body on the train tracks, or a killer clown in the woods. Years later, I found myself using those same habits in boardrooms, strategy meetings, and even on the road touring with the biggest bands in the world.

There’s a case I use often, though it isn’t from the canon. It’s a thought experiment in Holmesian style. A banker is found unconscious in his locked office. The gas lamp is out. The windows are latched from the inside. His keys are still in his coat pocket. Nothing has been stolen. The only clues are an open ledger, a toppled chair, and the faint smell of laudanum. Scotland Yard assumes a failed robbery or a suicide attempt. Holmes refuses to speculate. He asks what would have to be true for someone to enter the room, drug the man, and leave without forcing a door or a window, and without taking a thing.

Perhaps there is a hidden passage. Perhaps the victim let the person in. Perhaps the door was locked afterward. Perhaps the drug was taken willingly.

Each of these is a testable condition.

Holmes finds tea leaves in the banker’s cup. The tea tin had been swapped recently. Traces of laudanum are found in the leaves. There had been no break-in. It was a meeting. The assailant was someone he trusted. They stayed for tea, laced the drink, and left while the victim slept. The door had been locked behind them with the assailant’s own key; a partner’s key.

No guessing. Just logic.

This is how strategy should work. Roger L. Martin (in 2017, named the world’s #1 management thinker by Thinkers50, a biannual ranking of the most influential global business thinkers Roger L. Martin, Inc.) urges leaders to replace premature judgment with curiosity by asking what would have to be true for a given possibility to succeed. The question moves the conversation away from opinion and toward structured inquiry. It surfaces assumptions and brings them into the open. Each condition can then be tested before a decision is made. Ogilvy UK ad legend Rory Sutherland (MAD//Masters by Rory Sutherland) has made a parallel case for years. His view is that marketing works best when it borrows from detective work rather than science, and often says that human behavior is too unpredictable to be modeled cleanly. It must be studied the way Holmes studied a crime scene: without assumptions, and with a willingness to be surprised.

In most marketing meetings, someone proposes an idea and the room begins to debate whether it is strong enough. People try to recall what worked in the past. They look for patterns. They look for proof in the past (more on outcome bias in articles to come). What they rarely do is ask what must be true. That single question changes the rhythm of the conversation. It slows things down just enough to expose what is being taken for granted. The assumption that the customer knows the brand. The assumption that the offer is different. The assumption that people will care. These are not truths. They are conditions. And once they are treated that way, they can be tested.

This way of thinking begins by treating beliefs as hypotheses. Nothing is sacred. Each element of the strategy is a question waiting to be asked. The idea that people want simplicity. The idea that price is the barrier. The idea that reach will solve the problem. Each of these can be made explicit, written down, and examined. Some will be right. Some will break. Truth in this model is always conditional. A good strategy is one where all the necessary conditions happen to hold. It’s not enough to have a good idea. The environment has to support it. The timing and context has to favor it. The customer has to believe it…. If any part of that chain fails, the whole structure falls.

This kind of thinking also turns your attention forward. The past provides data. But, that data is all from the past. There is no data about the future. Strategic reasoning works best when it imagines what must be true and then works backward to check whether that world can exist. The final habit this builds is elimination. Bad assumptions are crossed out. Flawed premises are dropped. What remains becomes the basis for what to do next. Holmes said that when you eliminate the impossible, whatever remains, however improbable, must be the truth. I imagine Martin and Sutherland would say that when you eliminate the unsupported, what remains is what you can begin to test. Sutherland would also probably remind you to stay curious all the way through.

Reverse thinking is not a trick. It is a refusal to coast on instinct. It is what allows teams to avoid expensive guesses. It is also what allows unexpected ideas to surface and stay alive long enough to prove themselves. Most importantly, it gives people a shared language for thinking together. Instead of arguing over what is better, they start asking what would have to be true. And once they do that, they start solving problems faster, and with less waste.

I read, and enjoyed, more Stephen King later in life. But Holmes taught me how to ask better questions. That has been useful since day one.