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I just have to be honest and mention, I once flatly told one of my reports "that won't work".

He said, "give me a month".

I said, "don't waste your time".

He said, "give me a week?"

I said, "okay, you can spend a week on it, but after it doesn't work, please do it my way".

Much to my surprise it worked, and much better than my way would have.



It works the other way too. I recently told my manager "that doesn't work like you think it does, so your proposal is a no-go."

After looking it up, I was surprised to find that, yes, it did indeed work like he thought it did, and his proposal was viable.

We all have to eat our hats sometime; no one can be right all the time.


Trying to be aware of your limitations and exposing those in your speech is one way of reducing the frequency of having to eat your hat. "If we do that, I think this would happen . . ." is so much more productive than "that won't work," because it allows you to start discussing the why, without the proposer feeling attacked.


That is why I think it's important we suffix our beliefs with a degree of belief. There's a huge difference between

- "that won't work, 60 %" (which could mean a healthy debate is the quickest way to settle the issue);

- "that won't work, 80 %" (which probably makes a timeboxed attempt the best way to settle the issue); and

- "that won't work, 95 %" (which signals something really wonky is at play. If two intelligent people have such firm yet different opinions, it's possible at least one of them has completely misunderstood the problem in the first place, or there's some other unexpected gap in knowledge.)

Of course, for that to work, we have to calibrate everyone's sense of uncertainty and keep validating their opinions to make sure 70 % really means 70 %.


50% of the time, works everytime!


I had a manager tell me "it won't work" after I'd done a proposal that involved an algorithm taught in undergraduate computer science. I expected most of the team would recognize the algorithm and see how it could be applied.

No one one spoke up to disagree with him. In fact, the CTO was in the room at the time. This guy (the CTO) was always evangelizing about innovation. Not a peep out of him after watching someone's idea shot down.

This event and others made me realize that "that won't work" was an integral part of my company's culture. I guess it's about risk. In a company culture like this, there is no upside for a manager to try anything new.


Maybe he genuinely believed it wouldn’t work. At this point, it’s important to engage and figure out why they don’t think it would work.


I don't disagree. I'm sure he believed it wasn't worth the time or effort. I'm sure the CTO didn't either. I was way behind them. They knew what I didn't know at the time: the company was not interested in investing in the project I was working on. They considered it finished.


Yeesh, after trying to block it multiple times and then telling them you still think it won’t work even if you’re letting them “waste” time on it, that’s some serious humble pie to eat! How did that go?


Yeah, I'm still embarrassed about it. Fortunately, we were all so excited about how well his crazy idea worked that he never held it against me. I was careful not to accept any credit whatsoever for how it all turned out, though.


> I was careful not to accept any credit whatsoever for how it all turned out, though.

While it’s easy to fall into that trap. 90% of people wouldn’t have given them the week in the first place. I think you deserve some credit for realizing that you ‘might’ be wrong.


I'm not the OP but I have had similar experiences along the way.

My approach to it happening has always been two-fold; Firstly when talking about it I would tell the story - I hated the idea, wouldn't work etc - but the other guy was better than me and made it work. I lean into the mistake, make sure others know it happened.

That leads to part 2 - everyone and most of all myself need to know I am not omniscient. Someone needs to tell me I also have bad ideas. Sometimes other people have good ideas I don't like.

Most of all I encourage people to have and share lots and lots of ideas. 90% are bad (mine included) but if we can isolate the good 10% we'll do OK.




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