Innovation and the Digital Enterprise

The episode contains a handful of genuinely actionable operational insights - gamifying post-mortems with awards, deploying to 10% of client base to fail cheaply, the 'I vs. we' interview heuristic - but roughly a third of runtime is consumed by host anecdotes, sports analogies, and recycled leadership maxims that add no density.

“we actually started having like monthly awards for the best post-mortem. And we actually would celebrate failure.”

“I hire athletes. Period. Full stop. I mean, I look for the best athletes. And what I mean by that is I don't spend a lot of time assessing specific technical skills.”

A few tactical wrinkles are genuinely useful - the contextual 'I vs. we' language probe, post-mortem gamification, and the AI-assisted five-whys agent - but the episode leans heavily on well-worn slogans ('culture eats strategy for breakfast,' 'bad news doesn't get better with age') and standard leadership frameworks with no meaningful reframing.

“if they're talking about a failure, are they using an 'I' word? Those are the things I start to look for.”

“I actually created an agent like just this last week with some of the Microsoft tooling that actually now walks people through a 'five whys' conversation and helps produce a great like post-mortem document from that.”

Ehlers is a legitimate practitioner who scaled Paylocity from ~$100M pre-IPO to ~$1B over eight years and has held real engineering leadership roles across Hewitt, Benefitfocus, and Xerox; his insights come from doing the work, not from speaking circuits, though he is not a marquee name.

“eight years later, I helped this company from IPO go from a hundred million in revenue to close to a billion dollars in revenue”

“I ended up joining Xerox Services from Hewitt. So by the time I left Hewitt, I had been there 12 years.”

The episode is well-stocked with concrete numbers and named examples - dollar overruns, revenue figures, headcount, SLA windows, a specific Polish-language app request, and an MFA rollout that broke an auto-body shop's workflow - giving the abstract points real grounding.

“we were a year behind schedule, we were a million dollars over budget”

“the total size of PlanSource as far as number of employees is about 440 people... it's really all we have dedicated to this is about a quarter of an FTE to kind of manage that program”

Shelli lands the sharpest follow-ups ('Is there a customer conversation that changed a roadmap decision?') and the post-mortem accountability question is well-timed, but Patrick frequently interrupts the guest to share his own anecdotes, insert sports analogies, and finish sentences, reducing the depth of answers the guest is allowed to give.

“Is there a customer conversation you had that maybe even changed a roadmap decision?”

“You know, when you made that comment about your career progression is not a straight line, I'm like... It is if it's a flat line!”