2023's Greatest Misses

I don’t “celebrate failure” in the over-hyped start-up sense. But I do believe we should deconstruct failures and reconstruct them into learnings that lead to personal and organizational growth.

Before we get too far into 2024, I want to look back at some lessons from 2023.

I don’t “celebrate failure” in the over-hyped start-up sense, especially when people’s jobs are at stake. But I do believe we should deconstruct failures and reconstruct them into learnings that, over the long run, lead to personal and organizational growth.

My intent is to help people avoid making the same mistakes I have, so let’s call this Crosby’s “Greatest Misses in 2023” and the lessons learned:

1. I moved the CCaaS provider for InflectionCX- not once, but twice. In spite of my intuition, I chose to migrate from Twilio to Amazon Connect instead of going to Zoom CC last February. I knew better, but acted out of fear that Zoom wasn’t ready yet and we couldn’t afford another Twilio type experience. But, as a result, we invested waaaaaaay too much time and money into making Connect work the way we needed. It proved to be an incredible waste of resources invested into non-differentiated heavy-lifting, which came at the opportunity cost of missing our own AI roadmap... I course corrected this in Q3 by migrating to Zoom CC and redirecting our team into developing value-added capabilities that can differentiate us in the market. I could not be happier with that decision.
   
   Lesson: Critical analysis mixed with a little intuition in decision making will always triumph over fear based decisions.
   

2. There’s a fine line between confidence and arrogance, and apparently I’m still learning it- I completely underestimated what it would take [ME] to develop an AI platform for the enterprise leveraging those lovely OpenAI APIs. Building any product with material dependencies on Other People’s Stuff (OPS) comes with inherit risk of getting burned somewhere. And when you’re pioneering into “unknown-unknowns”, you’re playing with gasoline and matches.
   
   Lesson: Stay clear-eyed and persistent. We’re all still learning this AI stuff and anyone that says otherwise is just believing their own bullshit.
   

3. “Culture matters” isn’t just a clever moniker- Over the course of 18 months, a culture of entitlement and toxicity took hold at Xaqt, mostly in the engineering team. This was a by-product of hiring during the peak of the job market and struggling to find great talent. Out of fear of not being able to replace people, I began to tolerate mediocrity and allowed arrogance to creep-in. This resulted in a major disconnect with our customers, constant bickering and crappy product. So over the course of 4 months, I terminated almost the entire team and hit reset.
   
   Lesson: There should be consequences for not upholding company values. Always follow through with it.
   

Next-up, 2024 is going to be the most exciting year yet.