By: Natalie Johnson
The board wants to know why the company is not moving faster. The management team wants to know how much more it can realistically deliver. Between them sits the CEO, who must turn those competing pressures into a plan and answer for the result.
It can be the loneliest position in the company. The CEO must be candid with the board without undermining confidence in management, and candid with management without making the board sound like an adversary. Neither necessarily sees everything the CEO sees. When their expectations collide, the CEO still has to make a decision and own what follows.
Most CEOs know that seat well. Fewer stop to count how many versions of it exist across their organization. A sales manager sits between what customers were promised and what operations can deliver. A finance leader sits between investment proposals and cash discipline. A technology lead sits between new systems and the people expected to use them. Plant supervisors, project managers, and department heads spend their days between groups that want different things from them.
These positions can feel like friction, something to manage or endure. William Paiva has built his career on a different view. A person who understands what both sides need can draw on the knowledge, relationships, and priorities of each. That combination gives them a perspective neither side has on its own and a place from which to recognize opportunity.
CEOs need to make sure their organizations recognize and reward people who connect teams, translate competing priorities, and turn those differences into opportunities, even when that contribution falls outside their formal job descriptions.
From Molecular Biology to Venture Capital
Paiva’s path runs from a Ph.D. in molecular biology through healthcare investment banking at J.P. Morgan to venture investing and university leadership. He is Founder and Managing Partner of OLSF Ventures and Executive Director of Oklahoma State University’s Center for Health Systems Innovation.
Science, finance, and academia each have their own language and priorities. Rather than choosing among them, he has drawn on all three, and each has strengthened his work in the others. His philosophy, Life in the Middle Seat: Put Yourself Where Opportunity Can Find You, comes from that experience.
An Early Lesson in Opportunity
While earning his MBA at Dartmouth, Paiva made himself a rule: he would attend every alumni dinner he could, whatever the speaker’s industry. If the school had invited an executive back, that person was worth meeting.
At one dinner, the guest ran a large air conditioning business in Columbus, Ohio. Three students came. Paiva was a molecular biologist hoping to break into healthcare investment banking, and he had no obvious reason to be there. At the end of the meal, the executive asked him why he had come.
When Paiva told him, the executive said his best friend from business school ran the healthcare investment banking group at J.P. Morgan, and he would call him. The next day Paiva had a message from that banker. Two weeks later they had dinner in Hanover, and that conversation began the process that led to his job at J.P. Morgan.
The dinner committed Paiva to nothing more than a conversation. The opportunity came from walking into a room most people skipped. He did not need to know the whole path to begin walking it.
“Sure, Why Not?”
Paiva’s shorthand for that willingness is “Sure, why not?” For CEOs, it means disciplined exploration. An opportunity from an unlikely referral may warrant an initial meeting. An idea disputed between teams may be best tested in a limited pilot. Across the company, it encourages employees to take a bounded next step, such as a conversation with another department or a proposal to address an unmet customer need. None of these steps is a commitment to the full destination. The useful question is whether the next step offers enough learning to justify its cost and downside.
Choosing Which Risk to Carry
Organizations rarely account for the cost of the step not taken. A failed pilot shows up as an expense. A partnership no one explored leaves no record at all, and neither does an idea a manager never raised because it crossed a departmental line. Paiva puts it plainly: “Action has risk. Inaction has risk. Choose which risk you are willing to carry.”
What Managers Can See From the Middle
For managers, the Middle Seat can be an advantage: access to the knowledge and perspective of different teams, and the ability to combine them. A manager who understands both sides can spot an unmet customer need, redesign a handoff, or find a solution that neither department would have developed alone.
Two questions can bring that possibility into a team meeting: Where are you sitting between competing expectations, and what opportunity can you see from there? What support would let you test it?
The next step is to define the question, limit the exposure, and agree in advance on what the evidence will mean. For CEOs, the goal is a workforce more willing to bring forward ideas that cross departmental boundaries, with managers using their position between teams to solve problems.
Putting the Ideas to Work
Progress often starts with one person willing to bring an idea across a department line. A sales manager might propose a small pilot with operations to fix a recurring delay in customer onboarding. How leadership answers that first proposal tells everyone else whether leadership means what it says.
Paiva encourages leaders to be ready for that moment. That means recognizing contributions to shared outcomes and giving managers the time and authority to test ideas across team lines. If managers are rewarded only for their own department’s results, work across boundaries becomes a distraction.
It also means recognizing useful learning from a well-designed experiment, even when the idea does not work. Leaders can ask what the team learned and whether that evidence supports continuing, changing, or stopping. The response helps establish whether people can bring forward the next idea honestly.
Making the Seat Less Lonely
The Middle Seat does not require isolation as a leadership style. CEOs need relationships in which they can examine uncertainty without performing confidence. A trusted board chair, experienced mentor, peer, or outside advisor can challenge their thinking candidly. Within the company, a management team that brings forward difficult information can help share more of the thinking, even when accountability remains personal.
The Middle Seat will still be uncomfortable. A CEO who learns to work there and helps managers embrace their own positions between teams, priorities, and perspectives can turn that discomfort into clearer decisions, stronger trust, and opportunities the organization can act on.
CEOs and their executive offices can contact William Paiva through LinkedIn to discuss building a culture that helps managers embrace the Middle Seat, or explore a speaking engagement for a leadership team or executive gathering.
