For many leaders, finding joy at work can sound like a soft aspiration. For Rich Sheridan, CEO, Co-Founder and Chief Storyteller at Menlo Innovations, embedding joy in the workplace is a practical choice about how people work, learn and perform over time.
That conviction came from disillusionment, not idealism. After he spent years trying to solve problem after problem, Sheridan says he began to see that the real issue in software was not technical talent but the way humans were organized around the work.
The answer, he says, was to build simpler systems based on measurable, visible outcomes that could replace chaos with consistency. At Menlo Innovations, that long experiment has produced a striking result – just two software emergencies in 25 years.
“Leadership requires understanding the people around you and making sure that you are connecting with them at a very deeply human level.”
What changed first was not a metric on a dashboard but the energy in the room.
“If you can give people an environment where they can go to work and get meaningful things actually done every single day, it increases their spirit,” Sheridan says on CEO: Behind the Scenes.
That belief helps explain why Menlo Innovations returned to an in-person environment after the early years of the COVID-19 pandemic had passed. Working shoulder-to-shoulder, he explains, restores the energy of people solving problems in real time.
It also shapes how Sheridan thinks about leadership itself.
“Leadership requires influence,” he points out. “Leadership requires understanding the people around you and making sure that you are connecting with them at a very deeply human level.”
That same human-centered lens extends to the company’s software design philosophy, which Sheridan describes as high-tech anthropology. Instead of treating users as obstacles to engineer around, Menlo Innovations studies how people actually work, what frustrates them and where design can remove errors before they happen.
The goal is not to teach people to tolerate clumsy systems.
“We really work hard in our high-tech anthropology practice to design the errors out of the system,” he reveals.
Underneath all of it is a rejection of hero-based organizations, a model Sheridan once embodied himself. He realized that when one person becomes the hero, the whole system depends on overtime, exhaustion and a fragile concentration of knowledge. Menlo Innovations counters that with paired work.
“Two people together, sharing a computer, shoulder to shoulder, keyboard and mouse, floating effortlessly back and forth between the pair of developers or the pair of high-tech anthropologists, is our fundamental unit of work,” he says.
“Leadership requires understanding the people around you and making sure that you are connecting with them at a very deeply human level.”
Sheridan argues that learning accelerates when people think out loud, challenge each other and rotate often enough for knowledge to spread across the team. That shift demanded a deeper change in mindset.
“I was looking at the fear of staying the same,” he says, recalling the period that forced him to choose transformation over familiarity.
Now, when leaders ask where to begin, Sheridan doesn’t point them toward a sweeping reinvention, but encourages them to step outside of their comfort zone.
“Everybody’s busy. We have to go to our next meeting, we have to get our next email answered,” he acknowledges.
“I want to arm people with a simple phrase, when that happens, look them in the eye and say, ‘I get it. But why don’t we try it before we defeat it? Let’s run the experiment.’”
Listen to the latest episode of our CEO: Behind the Scenes podcast with Rich Sheridan on Amazon, Apple or Spotify.
