The Founder’s Paradox: How Do You Listen to People You Trust Tell You It Cannot Be Done?

It is important for founders to learn the skill of listening with resilience.

The brother of a friend — I had spoken with him in the past and he was thoughtful. Plus, I knew he was an experienced product manager who had built a number of important products. So after we launched our new company in 2013, I thought he would be interested in a private beta. Well, he ended up stopping me about two minutes into my demo of our roadmapping software. This is what he said.

“No one needs Aha! — spreadsheets work well for roadmap planning. Besides, there are tons of bug tracking systems that product managers already use to enter their requirements.”

I smiled, thanked him for his time, and closed the web meeting.

This is the quintessential founder’s paradox — heed the caution of those you trust or trust yourself to make the seemingly impossible possible?

I know this paradox well. Aha! is not the first company that I have launched with my co-founder and good friend Dr. Chris Waters. In 2007, we launched Paglo, one of the first IT management companies built on a SaaS platform. Paglo was acquired by Citrix in 2010.

Chris and I have been building products most of our careers — at traditional Silicon Valley startups and at multibillion-dollar public companies. When we founded Aha! five years ago, we wanted to do something different. We knew the pain points of product managers based on our own experiences.

We wanted to build software that would help create a world of awesome products and happy product builders — with no outside funding, no sales team, and no offices.

The good news is that there were only a few vocal naysayers, like that brother of my friend. Did we hear them? Yes. We listened. But we did not let the vocal few disturb what we trusted. We knew deep in our souls that we were building a product of real value.

You may think that it is easy for me to say now. After all, Aha! is very successful and still growing fast. What about in those early days? What gave us the fortitude to smile, close the web meeting, and then demo the beta of Aha! to the next likely customer with conviction?

It is important for founders to learn the skill of listening with resilience. Too many entrepreneurs I talk with question their fundamental beliefs and sway from conversation to conversation.

Here is how I suggest you start:

Go back to your core premise
Skepticism is more powerful than defensiveness. So do not jump to defend. Be skeptical of both the feedback you are hearing and your own assumptions. Do you still believe the core premise of why your product is needed? Is there some key new insight that you can learn from this person? Is the negative response actually a positive one — an indicator that your core premise is a deep pain point? A strong response means that your ideas matter. Apathy is far worse.

Find other people you trust
You probably would not drastically change your product based on just one customer’s feedback. Right? So why would you allow one trusted source to disrupt your forward momentum? Validate. Get in front of another trusted source. And another. Pitch your story and the product and see where themes emerge. For example, after a few conversations, we realized that we needed to change how we explained why Aha! was needed — even though it was obvious to us.

Stay strong
No one will believe in your new view of the future if you do not. So now that you have confirmed your core premise and gathered key insights from multiple people — there is one more question to ask. Does any of it change your assumptions? If the answer is no, here is where the fortitude gene that all founders must have kicks in. It is time to double down on your gumption.

Remember that it is easier to destroy than build up
I am not so foolish as to suggest there will not be moments of doubt. Staying strong can be exhausting. Especially when you are just getting rolling and building a company and product simultaneously. Negativity can be easy and comfortable for people — many are drawn to destruction rather than building something up.

Remember that we live in a world of contradictions
That brother of my friend said he was happy using a spreadsheet and a bug tracking tool. Really? I knew it could not be true. I knew this because I had done it for a long time. Now that Aha! serves thousands of customers and hundreds of thousands of users, I know it even more deeply. People will tell you things that do not make sense. And even better, trusted people will tell you the exact opposite of what others suggest and what you know to be true.

Get up the next day
We are more fortunate than most — if your biggest problem is that someone has tried to sideswipe your thinking on your new product, you are doing fine. Every day is a new opportunity. Even the worst days will end. Get up the next day. And get up the day after that. Keep getting up because the work is never done. It is your work, so get up and make it exceptional.

Listen to people you trust when they tell you it cannot be done. But listen with resilience. And go back to what you believe in.

Good, smart people will tell you lies — lies that they believe to be the truth. You cannot control this. You cannot hold it against them. And whatever you do, you cannot let it stop you.

All founders live with contradictions. And those who make peace with the fact that even their most trusted advisers will sometimes be wrong have the best chance of building something meaningful and lasting.

Originally published on the Aha! blog

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