It Isn’t Working Doesn’t Mean It Won’t Work

making mistakes

One of the reasons people and organizations will never transform themselves is because they’re afraid of making mistakes. Either they never take risks, or they back out on the first sign something doesn’t work if they do make mistakes.

On this last point, “It isn’t working” or “it doesn’t work”, these three words usually mean the end of most ideas.

A client of mine uttered these words to me last year after we implemented a chatbot for his real estate business. He did so even though we had walked him through the process we needed to go through in order to get to a point where the chatbot could potentially take on more complex tasks.

If you’ve worked with machine learning, you know that it takes time to gather and label data so an algorithm can make sense of it, chatbots aren’t that different. Therefore we started off slowly since we needed to train the chatbot to identify certain words and cluster of words. People would get frustrated trying to talk to it in either english or spanish; this drove the client crazy!

After having a discussion with the client, I decided to cut the project because he was not really committed to going through the process and making mistakes.

Innovation is the opposite of certainty

People and organizations who started off doing what already works elsewhere will have a hard time innovating because they’re in the business of avoiding mistakes; not making new ones. They were born with a “best practices” manual that eliminates all sense of uncertainty from their heads, giving them a sense of security that everything will work out fine if they follow an established template.

But innovation is the opposite of existing best practices. You are creating new ones, a process which takes time and learning from mistakes.

Remember, everyone wants to be seen as forward thinking, being first, but are not willing to make the mistakes that comes with actually doing it. So these established businesses operate by the two deadliest words in business: prove it.

Ideas take time to evolve, there’s no way around it. You have to try stuff, learn what works and what doesn’t, and iterate from those insights. This is common sense for innovators, so much so the innovator’s mantra is we’ll figure it out.

As a leader of an organization, it is your job to model the way. This means loosening your addiction to certainty by shifting your mindset from “prove it” to “let’s figure it out”.


Bottom line: “It isn’t working” or “it doesn’t work” does not mean “it won’t work”; it means you haven’t figured out how to make it work.

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