Teachable Moments: Life Lessons From a Park Bench

Matt Jackson wants to live in a world where people live fearlessly and technology takes care of the mundane so humans have more time to connect. As the President of Jackson Consulting, he’s worked with some of the nation’s best-known software companies and has spoken about, contributed to, and authored numerous white papers and blog posts on software operations, leadership, project management and turnarounds. You can find some of his work on LinkedIn, The Guide to the Product Management and Marketing Body of Knowledge (ProdBOK), and the Jackson Consulting blog.

 

Teachable moments are formed when you have done something--regardless of the outcome--and learned from the experience. Learning makes us better at what we do and provides a great opportunity to develop others and sharpen skills. We’ve compiled our best Teachable Moments from our community members for you to learn from and share with other project managers.

We all have pivotal moments in our career that stick with us and form the storyline of who we are. I’m a mash-up of many such stories.

Early in my career while working for a software startup in Seattle, we had an opportunity to make a sale to a client that would put our tiny business on the map. The risk was we didn't yet have the product features they wanted to buy, and they were far larger than any prior customer. So my area, software implementation, would be a real challenge.

Our CEO convened a meeting of all of his direct reports to get input and weigh the pros and cons of the opportunity. We all gathered around the table. Each person took their turn discussing how their department might handle the challenge, then making a go/no-go recommendation about the deal. Everyone was aware of the challenges, but were in favor--everyone except me.

Yep…I was the one to rain on the parade. Logical and rational points about why it was too great a risk, but still the only “no” vote.…

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