For years, high performers have been told there’s only one way to lead. Show no doubt, push through stress and keep proving yourself no matter the cost.
That formula tends to work until it doesn’t. Burnout, self-doubt and the pressure to keep pace with everyone else can quietly erode the confidence that got someone to the top in the first place.
Jaime Diglio built her career around a different approach. As Founder and CEO of The WIN Room™, she helps leaders find their own version of success instead of chasing someone else’s. Diglio joined ASBN’s Female Founder Show to talk about the burnout that reshaped her career and the coaching method she built to help other leaders do the same.
From the War Room to the Win Room
Diglio’s turning point came after 15 years as a top performer at Gartner and Microsoft. Following a stress-related health scare, she realized her success had come at the cost of her own well-being. That experience led her to develop a framework she calls the War Room and the Win Room.
The War Room, she said, is where self-doubt, comparison and self-sabotage take over. The Win Room is the opposite. It’s a mindset built on clarity about personal goals and values. Diglio said the shift starts with noticing the way people talk to themselves, since that internal dialogue shapes beliefs, and beliefs eventually drive results.
"The more you are you, the more successful you will be."
Train like an elite athlete
Diglio often compares business performance to athletic training. Athletes practice constantly before they ever compete, she said, but professionals are frequently expected to perform without ever rehearsing.
She builds that same discipline into her coaching, using role play to help clients prepare for high-stakes conversations before they happen. Diglio said that repetition builds the kind of calm under pressure that separates strong performers from the rest.
The new ROI: Revenue, Retention & Reputation on Interactions
Diglio also has a distinct take on ROI, one she calls the Interaction Economy. As AI levels the playing field on access to information, she said, the real differentiator has become how people connect with each other.
She breaks that down into what she calls the New ROI: Revenue, Retention and Reputation on Interactions.
"Our ability to interact with people... your value and your ability to be successful is not the information. It is your ability to build trust and connect with others."
Every conversation either builds trust or costs a leader credibility. Showing up with consistency and authenticity is what earns lasting trust with customers, teams and colleagues, Diglio said.
Moneyball Leadership
Diglio’s philosophy carries over into her book, Moneyball Leadership. The title draws on the same idea behind the film Moneyball: success often comes from recognizing hidden value rather than chasing a traditional definition of talent.
Rather than pushing a one-size-fits-all model, Diglio said her coaching helps leaders identify what makes them effective and build on it. Once leaders unlock that clarity in themselves, she said, they can pass it on to their teams and raise performance across the board.
The shift starts small, with the way leaders talk to themselves, but the impact compounds over time, Diglio said. As more professionals navigate burnout and rising workplace pressure, her message rests on the idea that authenticity, not perfection, is what builds lasting performance.
ASBN, from startup to success, we are your go-to resource for small business news, expert advice, information, and event coverage.