Better decision-making with better questions

Satyajit Rout
2 min readMay 5, 2022

This is what Shopify CEO Tobi Lutke has to say: “Your skill in decision-making is directly proportional to your quality of information acquisition.”

Your decision quality cannot beat your information quality. Quality information is hard to get. You can’t always be running experiments. You gotta ask good questions. But not many recognize its worth. A high question-quotient is uncommon, if not rare.

Take these common scenarios.

#1: 𝐘𝐨𝐮’𝐫𝐞 𝐢𝐧 𝐚 𝐩𝐨𝐬𝐢𝐭𝐢𝐨𝐧 𝐭𝐨 𝐢𝐧𝐟𝐥𝐮𝐞𝐧𝐜𝐞 𝐛𝐮𝐭 𝐲𝐨𝐮 𝐝𝐨𝐧’𝐭 𝐡𝐚𝐯𝐞 𝐚𝐮𝐭𝐡𝐨𝐫𝐢𝐭𝐲
You’re in a meeting with heads of business units exploring a diversification strategy. Everyone is more experienced than you. It has taken weeks to set this one up, but now the discussion seems to be converging a little too quickly. You want to challenge the group’s assumptions. But you’re in a room of people who seem to know what they’re doing. So you clam up.

#2: 𝐘𝐨𝐮’𝐫𝐞 𝐢𝐧 𝐚 𝐩𝐨𝐬𝐢𝐭𝐢𝐨𝐧 𝐨𝐟 𝐚𝐮𝐭𝐡𝐨𝐫𝐢𝐭𝐲 𝐛𝐮𝐭 𝐲𝐨𝐮 𝐝𝐨𝐧’𝐭 𝐰𝐚𝐧𝐭 𝐭𝐨 𝐢𝐧𝐟𝐥𝐮𝐞𝐧𝐜𝐞
You’re the boss. You want unfiltered information to decide on a critical project. You quickly and clearly set the context for the core group and ask them leading questions: Should we go ahead or not? Do you think you’ll be able to give this bandwidth? Soon enough, you’ve the answers you’re looking for.

#3: 𝐘𝐨𝐮’𝐫𝐞 𝐜𝐨𝐧𝐬𝐮𝐥𝐭𝐢𝐧𝐠 𝐚 𝐬𝐩𝐞𝐜𝐢𝐚𝐥𝐢𝐬𝐭 𝐢𝐧𝐝𝐮𝐬𝐭𝐫𝐲 𝐞𝐱𝐩𝐞𝐫𝐭 𝐟𝐨𝐫 𝐫𝐞𝐥𝐢𝐚𝐛𝐥𝐞 𝐢𝐧𝐟𝐨𝐫𝐦𝐚𝐭𝐢𝐨𝐧
You’re paying by the hour for this expert. You’re hoping you’ll come out with clear direction. So you ask predictive questions that leave no room for ambiguity: Do you think we can win in this space? Is this a market trend that’s going to last? The hour’s done and you think you’ve got your money’s worth.

Whether you zipped up or leaned in or asked an expert to crystal-gaze, you probably could’ve gotten more out by asking better questions.
Here’s one thing you could’ve asked in each of the scenarios to unlock the right information:

✔When you want to explore disconfirming views without looking like a dissenter: “𝘞𝘩𝘢𝘵 𝘸𝘰𝘶𝘭𝘥 𝘩𝘢𝘷𝘦 𝘵𝘰 𝘣𝘦 𝘵𝘳𝘶𝘦 𝘧𝘰𝘳 𝘦𝘢𝘤𝘩 𝘰𝘱𝘵𝘪𝘰𝘯 𝘵𝘰 𝘣𝘦 𝘵𝘩𝘦 𝘳𝘪𝘨𝘩𝘵 𝘰𝘯𝘦?”

✔When you want to avoid groupthink around your views: “𝘐𝘮𝘢𝘨𝘪𝘯𝘦 𝘢 𝘧𝘶𝘵𝘶𝘳𝘦 𝘸𝘩𝘦𝘳𝘦 𝘸𝘦’𝘷𝘦 𝘮𝘢𝘥𝘦 𝘵𝘩𝘪𝘴 𝘥𝘦𝘤𝘪𝘴𝘪𝘰𝘯 𝘢𝘯𝘥 𝘪𝘵 𝘩𝘢𝘴 𝘣𝘢𝘤𝘬𝘧𝘪𝘳𝘦𝘥. 𝘞𝘳𝘪𝘵𝘦 𝘥𝘰𝘸𝘯 𝘸𝘩𝘢𝘵 𝘺𝘰𝘶 𝘵𝘩𝘪𝘯𝘬 𝘸𝘦𝘯𝘵 𝘸𝘳𝘰𝘯𝘨.”

✔When you want to tease out reliable information from a specialist: “𝘞𝘩𝘢𝘵 𝘴𝘩𝘰𝘶𝘭𝘥 𝘐 𝘣𝘦 𝘭𝘰𝘰𝘬𝘪𝘯𝘨 𝘧𝘰𝘳 𝘪𝘯 𝘢 𝘤𝘢𝘴𝘦 𝘭𝘪𝘬𝘦 𝘵𝘩𝘪𝘴?”

What’s your favorite question to ask to unlock insight?

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Satyajit Rout

I write about decision-making, mental models, and better thinking and things in between