How This CEO Learned to Let Go

Aha! product roadmap management

“We no longer want to work with you.” I once had to say this to a well-known multinational technology company. Our team at Aha! had met with them eight times and they were still asking for an additional (free!) six-month product evaluation. The value exchange simply was not there. So, it was time to kindly say goodbye.

And yes, it was also a painful goodbye. Aha! was relatively young at the time and we were in seemingly no position to say “no” to that kind of business. But I knew that we wanted to build a company that would have the confidence to honor reality. This experience taught me an invaluable lesson.

If you want to build something lasting, you have to be willing to let go.

Letting go is about understanding that there is an opportunity cost for everything you work on. It is about valuing your own time and the time of the company. This gives you a powerful freedom to focus on what creates the most value. You are able to work with customers who respect you as you respect them.

Of course, there is something even harder than letting go of a customer or business opportunity — letting go of a teammate. Those decisions are not just painful, they can be downright heartbreaking.

But when someone is not able to deliver what the company requires — even when the goals are exceptionally clear and extensive training and feedback has been provided — the kindest thing you can do is let them go. It allows them to move on to someplace where they will be at their best. And likely happier than they were working with you.

Over the years, I have had to say a few tough goodbyes — both to customers and teammates.

And each experience has broadened the way I think about tough situations where a separation might be needed. The conversations are never easy. I would like to say that I learned a way to let go more easily, but that would be untrue.

I can tell you this: I have learned that goodbyes go best when you level with the person quickly and with dignity. You are transparent about the reasons behind your decision. And you are considerate with your word choice, kind in your delivery.

Letting go is not about a lack of caring. It is the opposite of that — you want the best for both parties.

So, care for your customers and your team well. Sometimes that means no longer working together. Acknowledge that not everyone can be a match. Let go when it happens.

It will not be easy — but the pain will be temporary. In the end you, you will move everyone forward to more fulfilling work and happiness.

How do you know when it is time to let go at work?

About Brian and Aha!

Brian seeks business and wilderness adventure. He is the co-founder and CEO of Aha! — the world’s #1 roadmap software — and the author of the bestseller Lovability. Brian writes and speaks about product and company growth and the adventure of living a meaningful life.

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  1. Mila Sevedge

    Poignant – and so very true. Diplomatic and direct conversations, though uncomfortable, are always for the best. In most cases, the interaction tends to leave each party with a higher level of respect. I’ve found this true of conversations that need to occur in order to move ideas forward as well!

    Ask the tough questions, have the awkward conversations while focusing on the vision. Knowing the ideal client ‘fit’ helps too ; >


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