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11 Powerful Quarterly Questions Every Small Business CEO Must Ask to Ensure Progress and Avoid Stagnation

Nate Anglin
3 min readNov 9, 2021

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We all feel trapped at some point.

When we let our emotions control our logic, we get sucked into a cycle of complacency or paralysis by analysis. But the best habit you can create as a CEO is dedicated thinking time, an idea from the incredible book The Road Less Stupid.

I have a time block every Friday that I designate for thinking time. During this time, I ask a question and write an endless amount of answers or ideas to that question.

It gives me profound clarity.

But not all questions need to be done weekly; these are the quarterly questions you should ask as a CEO:

1. The Focus Question

“What is the biggest strategic objective that I’m working on that if I and my team fully rallied behind, would have the biggest positive impact on helping the company achieve it’s strategic goals?”

2. The Clarity Question

“What don’t I see?”

3. The Reasoning Question

“What’s the good business reason for doing this?”

4. The Leverage Question

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Nate Anglin
Nate Anglin

Written by Nate Anglin

Small Biz Investor, CEO, & helping others improve their performance, profit, & potential w/out sacrificing what’s most important. www.nateanglin.com/newsletter

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