What if the thing you’ve been told is your biggest weakness is actually your greatest advantage? I didn’t believe it either. Then I spent four days in a classroom at Columbia.
The course was called Quantitative Intuition, and it tackled the challenges of decision-making in a world of big data. There is so much information available to us, yet it has not led to better decisions.
I didn’t know what to expect.
I walked in as someone who had spent an entire career being told she asked too many questions and relied too much on instinct. I walked out as someone who learned that both of those things were strengths.
After a career of being told that I ask too many questions, you can imagine my surprise when we started discussing the most powerful tool of decision-making: asking questions.
Specifically, precision questioning. A technique that helps clarify priorities, define outcomes, and identify knowledge gaps.
One of my favorite sayings from the class: “The smartest person in the room asks questions. They do not have the answers.”
I’ve had the misfortune of having worked with some leaders who saw questions as weaknesses or fighting words. I couldn’t ask clarifying questions without being told that I should just know. How? Questioning the viability of any plan was seen as negative and unproductive.
But here it was seen as an essential skill.
And that was day one.
On day two, we discussed the backward approach, where the problem is formulated first.
Decisions usually follow a simple script. The course called out five steps: defining the problem, data discovery, data analysis, insights, and implementation. In that order.
But what if you start at the end? Begin with the desired outcome, figure out what analysis you would need and what data would feed it, and then, and only then, go collect it.
Almost like traveling forward in time. You start with the ultimate outcome and trace back through the possible branches of decisions that got you there. Choose a branch and start your process from that point.
I never thought of problems that way. After being introduced to the concept, I sat in the classroom thinking of all the time wasted looking for data that simply doesn’t matter.
All the reports that no one read. The emails no one opened because they answered questions that no one had asked.
We also talked about guesstimating. I thought guesstimating was a shortcut you used when you didn’t know anything. It’s actually a legitimate technique to operate with limited information.
Rough estimation and back-of-the-envelope calculations to approximate an answer. Not an end result, but a way to move forward when enough data is not available.
In a way, accounting is full of estimation. Non-accountants think that we are strict and that our numbers are set in stone. In reality, so much of our work is guesstimating.
Accruals are nothing but a guesstimate of how much the company earns and owes. There might be contracts, emails, and purchase orders, but at the end of the day, until that invoice or bill is received with a total amount and a due date, we are just guesstimating.
Financial statements are built on that concept. So it can’t be too wrong.
Then we got to biases. The one that hit me hardest was overconfidence. I didn’t think I had a problem with overconfidence… I was wrong.
We did one exercise that truly opened my eyes. We had 10 questions on a sheet of paper. The challenge was to provide ranges that would contain the answer to each question. For example, what is the length of the Nile River (*4,130 miles), and how many books are in the Old Testament (*39).
There was no limit on the ranges. I could have answered zero to infinity for every single question and gotten all 10 right. But I didn’t. Because I was sure I knew better.
A little humility about what I didn’t know would have produced a win.
On day three, we did a simulation.
Teams of five played characters who were climbing Mount Everest. The exercise lasted 90 minutes with five rounds of decisions. In each round, we were given a choice: advance to the next camp on our way to the peak, stay put, or go back. The group had a shared goal of reaching the mountaintop, and each participant had their own personal goals as well.
Some groups prioritized staying together instead of reaching the top. My team, where I played the leader, decided that it was better to split and allow at least some of us to attain our goals. Two team members, the environmentalist and the physician, were left together at an early campground. The remaining three players reached the summit.
Afterwards, I questioned if we made the right decision. We scored the most points, but did we win?
There were no right or wrong answers. Each team took the same information and used it in very different ways and achieved very different results. No different from real life.
And that was the lesson.
On our last day, classmates kept going back to the simulation, highlighting it as their favorite part of the class.
But for me, the best part wasn’t the simulation. It was learning alongside my classmates in real time, watching how the same ideas reached each of us differently.
I think about this class often. Not the frameworks or the vocabulary, though those stayed too. What stayed most was the permission it gave me. Permission to question, to estimate, to act without certainty, and to trust that doubt is not the enemy of good decisions.
It is the beginning of them.
Real Thoughts 