One-on-one meetings are a standard tool in most workplaces. When used well, they build trust, support career growth, and keep employees engaged. Research suggests that employees who meet regularly with their manager are roughly three times more likely to feel engaged at work. With only about half of all employees having regular one-on-ones, the case for consistent check-ins is strong. For managers and team members, a weekly 30-minute session or a biweekly hour-long conversation delivers real benefits: stronger relationships, timely feedback, and clearer career direction.
The trouble begins when this same culture is carried unchanged into senior leadership. When senior leaders rely heavily on private bilateral meetings — <strong>that is, two people meeting separately and repeatedly</strong> — the organization can start to break down in subtle ways. Similar topics get discussed in isolation, decisions made privately must be re-explained to others, and messages become inconsistent. Leaders also tend to develop a stronger focus on their own department rather than the business as a whole — a problem sometimes called functional bias.
Private executive meetings can also create unhealthy dynamics. When some leaders have more access to the top than others, informal competition and mistrust can develop. One large technology company addressed this by having its CEO manage 55 direct reports through group communication rather than individual meetings, ensuring consistency and shared learning across the organization.
A more effective approach at the executive level is to replace frequent one-on-ones with small cross-functional group meetings, sometimes called capability meetings. These bring together leaders from two to four related functions to work on a shared business priority, such as innovation or customer experience. One healthcare organization that made this shift shortened its go-to-market process by 20 percent while reducing duplication between teams. Experts recommend identifying five to seven critical business capabilities and building standing group meetings around each one, encouraging shared accountability and keeping strategic conversations visible to everyone involved.
This does not mean eliminating one-on-ones entirely at the senior level. <strong>Rather than serving as operational check-ins, executive one-on-ones work best as quarterly conversations focused exclusively on personal development, career reflection, and leadership growth.</strong> One COO who removed all operational content from these meetings saw improvements in both retention and succession planning. The key takeaway is that context determines the value of one-on-ones. For individual contributors and mid-level managers, they remain essential. For senior leaders, the right question is whether private meetings are driving better outcomes — or quietly fragmenting the organization.
