The Failure Gap

A Conversation With Chris Baird, President & CEO OptConnect


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Chris Baird is the President and CEO of OptConnect, and his leadership story starts far from the corner office. He joined the company in 2009 as an ATM repair specialist, kept volunteering for the “extra mile” work (where, as he put it, there’s no traffic), and stepped into a bigger responsibility when ownership transitioned and a leadership gap opened. Along the way, he learned his path is hard to copy, but the behaviors behind it are simple: say yes, stay curious, and be humble enough to take feedback without treating it like a personal attack.

Julie and Chris dig into the Failure Gap, that familiar space where everyone agrees something is a good idea, but nothing changes. Chris shares a real example from his leadership team: “false alignment,” when people nod in the meeting and then operate their own plan afterward. Naming it helped them stop “going along to get along” and start getting honest about how they would actually execute together. They also explore how misalignment shows up with customers, like teams optimizing for the lowest price instead of the true cost, then being surprised when “cheap” comes with a side of missing features.

Chris also connects leadership to endurance events, sharing lessons from training for (and surviving) a 70.3 race: grit matters, but systems matter more. Preparation, structure, and team support beat willpower alone, especially when conditions get hot, and your assumptions start melting.

Episode Takeaways

  • Curiosity and saying yes create leadership momentum, even when the path is unplanned
  • “False alignment” is agreement with unchanged behavior, and it quietly wrecks execution
  • If teams optimize for the wrong problem (price vs. total cost), misalignment multiplies
  • Grit helps, but disciplined systems, feedback, and preparation carry you farther
  • Humility and vulnerability make alignment easier because teams solve problems together

Alignment to big goals often starts with a small moment: raising a hand and asking, “Are we actually aligned, or just being polite?” Bonus: it’s cheaper than another reorg.

Episode Resources

  • Ken Thompson, AlignOrg: “Death by a Thousand Good Ideas: The Power of Strategic Clarity”

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The Failure GapBy Julie Williamson, Ph.D.