Startup advice: Seeking the uncomfortable truths

We get emotionally attached to our ideas because they're a projection of our value – or so we may think. When someone questions those ideas, especially in a professional setting, it can trigger irrational responses that vary depending on your position of authority and leverage. As a company founder, you have the power to impose your ideas onto everyone around you and destroy dissent or seamlessly blend your ideas with those of others.

This doesn't just happen in startups or with founders. I've seen too many successful, promising projects fail because the squeaky wheels, that is, those in the organization who pointed out flaws, in logic and in execution, get promptly shut down. The truth is that customers are the squeakiest of wheels and they don't have a vested interest in protecting your ego, so if you want a terribly successful business, the way to start is to accept even the most robust ideas need a bit of blending.

A long time ago I collaborated with a startup with an unintuitive market – as 90% of the things I work on because apparently, I like suffering – and even finding "whiffs" of product market fit was incredibly hard. Those types of ventures require what I call "radical user interviewing", which most of the time means literally buying an IKEA desk and camping at a customer's place of work for weeks. After a lot of work, the team convinced itself the "whiffs" of product market fit were strong, ready-to-go market fit, even when the data suggested poor retention and qualitative feedback notes went from "meh" to "it's ok, I just don't need it".

Here's the thing: the team was good, it was so good. When you hire talented people, you have to expect them to have an opinion. If all you want is their time but not their criteria, you're in for a disappointing surprise. Members of the team started suggesting that maybe they had never really reached a solid product-market fit, and instead they had just convinced themselves that early traction data was all they needed. This was met with controlled rage by the founders, who accused members of the team of being non-believers. A couple of team members were let go for being "flippant". The few engineers left witnessed a couple of million dollars wasted on marketing and ads, to continue perpetuating what the data showed: retention was low.

This happens a lot in companies with a strong vision. That vision comes from somewhere – generally the founders – and they are in an unprecedented position of hard power in the organization. It's no surprise a lot of us admire Steve Jobs for his tenacity, but even the most single-minded leaders need to extract good ideas from their teams and blend them with their own.

Good, long-term successful leaders not only blend their vision and ideas with those they hire but seek the squeaky wheels in their organizations to zoom in frequently and check the individual trees in the forest are doing well. The truths closer to the customer are the most uncomfortable but are the most valuable. They may save you from untimely disasters and make your product better.