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Bob, the chief executive officer of a small startup, was talking with Mary, his chief technology officer.

“I’m struggling to justify my plan for next year,” Bob said to Mary. “I know what I want to do. But, I don’t know how to explain why I want to do that. Every explanation is some variant of, ‘Well, it’s what feels right.’”

“I struggle with explaining plans too, sometimes,” Mary empathized. “Would you like a suggestion that might help?”

“Yes, please.”

“Anytime I’m unsure whether my plan makes sense, I ask three questions.”

Question 1: What is your plan?

“The first question is: What is my plan?”

“What is your plan?” Bob asked. “Isn’t that the reason you’re asking these questions? Because you have a plan you’re uncertain about?”

“Well, I always think I have a plan. I’ve learned, however, that sometimes I only have an idea for a plan. Something I imagine might be a plan. When I ask myself, ‘What is my plan?’ I imagine describing it to you, the board of directors, my team, my family, whomever. More times than I’d care to admit, I discover I don’t really have a plan.”

“So, asking ‘What is my plan?’ points out one reason you may be uncertain about it.”

“Yes. It also highlights another reason for my uncertainty: while I may understand my plan, I may not yet know how to explain it to anyone else.”

“You’re actually asking two questions, then.”

“Yep. A plethora of questions, in fact. But, I can’t remember so many questions. So, I remember just this one.”

“That makes sense. I imagine that asking that one question triggers all the other questions?”

“Yes, generally. And, if it doesn’t, my second question often does.”

Question 2: How do you feel about your plan?

“That second question is: How do I feel about my plan?”

“How do you feel about your plan? What do your feelings have to do with anything? Your feelings won’t change whether your plan works or not.”

“Maybe not. That’s not why I ask this question, though. My feelings about my plan often help me identify data I may be missing.”

“Like, if you’re feeling sad about your plan, it’s not good enough?” Bob proposed doubtfully.

“Yes, exactly.”

“More examples, please?”

“Sure. If I’m happy about my plan, I know it is good enough. If I’m reticent to share my plan, I know it needs more work. If I’m absolutely loath to tell my plan to anyone, I know something about it is way off.”

“Oh, OK. I get it now. My feelings must mean different things than your feelings do, though. I’m more loath to share an idea with people the more certain I am my idea is right.”

“I’m sure at least some of your emotions do mean different things for you than the same emotion would mean for me,” Mary agreed. “I’ve yet to meet anyone with exactly the same emotions in exactly the same circumstances as anyone else.”

Question 3: What else might you do?

“Which brings us to my third question: What else might I do?”

“What else might you do? If you can clearly describe your plan, and you’re not feeling anything amiss about it, what’s left to do?”

“This is my reminder to consider other options.”

“Again, if you have a good plan, why consider others?”

“If I’ve only considered one option, I haven’t considered options. If I’ve considered only two options, I’ve given myself a quandary, not options. If I’ve considered at least three options, however, I’ve examined enough alternatives to be confident I’ve picked the best one.”

“What if you don’t have time to find those other options?”

“In my experience? That’s when it’s even more critical to search them out. As the cliché says: if I don’t have time to do it right the first time, how will I ever have time to do it over?”

“Hmmm. I’m not convinced. I get your point, though. Just because I have a good plan doesn’t mean a little more effort won’t find an even better plan. Or, at least, an idea that will make my plan better. That’s worth examining.”

Use these questions to gain confidence

“Did these questions help?” Mary asked Bob.

“They did, thanks. First, I’ll record myself explaining my plan for next year. That will show whether I have an actual plan or just a random collection of ideas. If the latter, I’ll iterate until I have a for-real plan.

“Then, I’ll check how I’m feeling about that plan. Again, I’ll iterate here until my feelings indicate my plan is good enough.

“Finally, I’ll do all this for at least two other plans. Then, I’ll either pick one of those plans or synthesize them into a new plan. Finally, I’ll go through the first two questions yet again with the final version of my plan.”

“Sounds like a plan,” Mary said laughingly.

Jerry Weinberg first taught me that “one option isn’t an option; two options are a dilemma; and it’s only three or more options that are truly options” many moons ago.

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