What Generalists Bring, and How to Make It Count at Work
There is a person on almost every team I have ever worked with. They connect the dots nobody else connects. They see the pattern three moves before it becomes obvious. They can walk into a room of specialists, translate between them, and somehow move the whole thing forward. Yet, when performance review season comes, they are the hardest person to describe. They don’t fit the job description. They don’t map cleanly to the org chart.
For most of my career, I watched these people quietly carry teams and quietly get overlooked. It turns out they have a name. They are generalists. In a recent conversation on the Flourishing Edge podcast with Siobhán O’Riordan, I was reminded of just how much this moment belongs to them.
Siobhán is a life-long generalist, the founder of Big Sea Strategies, a certified Gallup CliftonStrengths coach, and the author of Reframe: How Generalists Thrive in a Changing World. She has partnered with hundreds of leaders and more than 100 organizations. But what makes her work land is that she is not describing generalists from the outside. She is one, and she has lived both the highs and the crashes.
Flourishing Is a Fit Problem, Not an Effort Problem
I have said for years that so much of our wellbeing at work comes down to being in the right role, in the right context, doing work that is genuinely ours. Siobhán put language to why that is so hard to get right.
“The idea of flourishing is really connected to fit,” she told me. “And I think we don’t really understand fit until we really understand ourselves.”
That sequence matters. Fit first requires self-knowledge and most of us are trying to fit into a model before we have understood who we actually are.
Here is the number that made the case impossible to ignore. In a 2023 OC Tanner survey of 36,000 people, more than half identified as generalists. Many of them reported the same quiet ache: unsure if they were in the right role, unsure if they were doing what their job description said, shut out of promotions and the salaries that come with them. As Siobhán put it, generalists are “so ubiquitous and yet unseen.”
Then consider the other half of the picture. In one Harvard Business Review analysis of 10,000 CEOs, roughly 40% clearly owned being generalists. So the trait that so often reaches the very top is the same one our systems are built to overlook on the way up.
What a Generalist Actually Is
We throw the word around, so it helps to be precise. Two things define a generalist, and both showed up again and again in our conversation.
The first is ranging curiosity. A specialist goes deep and becomes an expert, and we need that. A generalist wants to know about a lot of things, and often a lot of people. The second is lateral, non-linear problem solving. Generalists connect dots across industries and functions. They notice that a solution which worked over here might just work over there.
This is not abstract to me. It sits at the heart of the work I did at McKinsey. When you joined the firm, you effectively chose your shape. You could join an office and take a more exploratory route across industries and problems, or you could join a practice and go deep. Both routes led to partner. What mattered was that people chose the one that fit them, and that we guided them when they had chosen wrong. The distinction Siobhán draws is the same one that quietly determined who thrived.
The problem is what happens after the choosing. “The HR structure does not exist for generalists,” she said. Job titles, descriptions, performance assessments, and promotions are almost all built around specialization. The generalist roles that do exist, like chief of staff, are so individualized that no two look alike.
The Hospitalist: Why Adaptation Needs Generalists
If you want one image to understand why generalists matter right now, Siobhán offered a beautiful one.
A century ago, you had a doctor. One person who knew you from birth to death and knew enough about everything. Then medicine specialized, gloriously, into cardiology and pediatrics and gerontology and a hundred fields more. But a patient is not a collection of separate issues. Someone arrives after a car crash with a head injury, a leg injury, a cardiac history, and diabetes, and suddenly five brilliant specialists are each pulling in their own direction.
So the hospital invented the hospitalist. “The generalist of the hospital,” Siobhán said, “working in partnership with these specialists to really prioritize the right steps in care.” The hospitalist knows just enough about every specialty to connect them around one whole patient.
That is the role I see going unfilled in company after company. The pace of change today is external and relentless. Specialists, precisely because of their depth, can carry two blind spots: it becomes harder to shift, and they often want more data before they move. In a world where you frequently do not have the time or the full picture, you have to fail your way forward. Generalists, Siobhán argues, are the “expert practitioners” who test ideas, take the risks, and absorb some of the risk that specialists feel. This is convergence with everything I believe about adaptability being the core leadership capability of our age. A great generalist on the team is the one who might have questioned Motorola’s bet on satellite phones as cell phones exploded, or seen Netflix coming while Blockbuster counted DVD sales.
Crushing It or Crashing Out
What made this conversation more than a framework was Siobhán’s honesty about her own arc.
Her mother jokes that she was born with the confidence of two people, and she used it to jump into opportunities with both feet. In some roles she was excelling, winning fellowships, named a 40 Under 40 in Boston. Then she would show up in a different role, the exact same person with the exact same energy, and be shown the door. “I was either crushing it,” she said, “or crashing out.”
The difference was not talent. It was context. In the roles where she thrived, people who knew her handed her freedom and gave her cover to run. In the roles where she crashed, she was hired by reputation into a senior seat to fix a culture, doubled down on her catalytic energy without any cover, and watched the resistance grow stronger. “The more you give, the more freedom you give to a generalist, the further they can range,” she reflected. “And they can range too far, and also sometimes too fast.”
I find this liberating rather than discouraging. If the same person can crush it or crash out depending on context, then the failure is diagnosable and fixable. It is not a verdict on your worth.
How Generalists Turn Range Into Value
Curiosity and lateral thinking are superpowers, but overused or undisciplined they become distraction and nuisance. So how does a generalist convert range into value?
Siobhán’s answer starts with strengths. As a CliftonStrengths coach, she is blunt about it:
Either you are in control of your talents, or they are going to boss you around. And when they boss you around, they’re never in your favor.”
Someone high in ideation can flood a room with a hundred ideas. The discipline is to know the room, write the rest down, and bring the best three.
The second move is partnership. “Generalists cannot work alone,” she said. “We are dependent on the learning and expertise of others in order to be effective.” And this is where the present moment tilts in the generalist’s favor. AI is becoming the ultimate thinking partner for offsetting your weaknesses while you lean into your strengths. Siobhán uses it to pressure-test ideas before a meeting. When people debate the one-person “unicorn” company, I think they have it backward: what enables it is not a specialist, but a generalist orchestrating deep expertise through AI and stitching it into something that works.
Three Moves to Thrive in a Specialist World
I always say that if you live on Earth, don’t fight gravity. We operate in a predominantly specialist world, and pretending otherwise helps no one. So I pressed Siobhán for what a generalist can do right now, even without a team to lead. She offered three.
- Know your value, and remember that generalists are defined externally. Ask five to ten colleagues what you actually did for them.
- Manage up. Tell your manager, in plain language, what your role is and the value you bring as a generalist.
- Get smart about what you say no to, because saying yes to everything is the classic generalist trap.
To that I would add a fourth: augment your gaps. Build enough specialization to earn your seat, then use technology and people to compensate for what you are not good at. As Siobhán said in the line I keep returning to,
If you’re not self-aware, you can’t self-manage and you can’t grow.”
If you have ever felt like you didn’t fit the mold, I hope this reframes it. You may not be broken. You may simply be a generalist who has not yet found the right context, named your own value, or built the partnerships that let your range become a gift. And if you lead people, look again at the connectors and pattern-spotters on your team. They may be the most adaptive talent you have.
There is much more in our full conversation, including how Siobhán coaches generalists to name their value out loud and what leaders can do to stop losing their most adaptive people. Listen to the conversation on the Flourishing Edge podcast.
Learn more about Siobhán O’Riordan on LinkedIn.
Listen to the podcast with Ashish and Siobhán O’Riordan. above, You can also listen on Apple Podcasts.
Access and subscribe to all of the episodes of the Flourishing Edge Podcast here.
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