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Hi {{first_name}},
Brad Jacobs has started and scaled eight companies worth over a billion dollars, and one of his core management tools is two questions you can ask tomorrow for free.
When he takes over or visits a business, he sits with people at every level and asks: what’s your best idea for improving the business? And then: what’s the stupidest thing we’re doing as a company?
The questions look symmetrical. They’re not.
The first one, the best idea, is a search for upside. It works because the people closest to the work have been quietly compounding observations for years: the customer request that keeps coming up, the pricing anomaly, the bottleneck everyone routes around. Most companies have a suggestion box that nobody believes in. A senior person asking directly, face to face, and writing the answer down is a different instrument entirely.
The second question is the sharper blade. Every organization accumulates things that everyone privately knows are dumb. The weekly report nobody reads. The approval chain that exists because of one mistake in 2019. The product line kept alive out of sentiment. The frontline can name these instantly, with precision, because they live inside them daily. What they lack is not knowledge. It’s permission. “What’s the stupidest thing we’re doing” is a permission slip, issued from the top, to say the quiet part on the record.
Three conditions make it work, and skipping any of them turns the exercise into theater. Ask at every level, because the view from the shop floor and the view from the boardroom disagree in exactly the places that matter. Make honesty safe, which means the first brave answer gets a thank-you in public, never a defense of the status quo. And act visibly on something you heard, quickly, because people extend honesty as credit and it has to be repaid at least once before they’ll extend it again.
I’ve been using both questions in the businesses we operate, and here’s the pattern that strikes me: the answers rarely surprise the person giving them. They’ve known for months or years. The answers regularly surprise me. That gap, between what the organization knows and what its leadership hears, is where an enormous amount of value sits. The questions don’t create the knowledge. They just move it across the gap.
If you run a company, the exercise for this month: ask both questions of five people at different levels. Write every answer down. My prediction is the stupidest-thing list alone pays for the time before you finish asking.
Talk soon,
Matt
P.S. When I’m not writing this, I’m buying and operating founder-led businesses for the long term at Eidolon Capital. If you’re a founder thinking about your next chapter, or you advise one who is, just hit reply. I read every note.