How to Manage Up to a CEO Who Oversteps
A people-pleasing CEO can be hard to navigate
Ritika Vijay
, Fri 5 September 2025
When Aiden, the Chief People Officer (CPO) of a rapidly scaling tech startup, first joined the leadership team, he was excited to bring structure and strategy to a company that had doubled in headcount in less than two years. But within months, he noticed a troubling pattern: teams were bypassing their functional leaders and going directly to the founder and CEO, Michael.
At first, Aiden assumed this was the natural growing pain of a founder-led organization. But as he looked closer, the issue was more complex. Michael, though visionary and deeply invested in his team’s happiness, had a tendency to be a people-pleaser. When a group of engineers disliked the CFO’s directive requiring partial in-office work for regulatory and financial reasons, they didn’t raise the concern with the CFO. Instead, they went directly to Michael. Wanting to avoid conflict and preserve goodwill, Michael agreed with them on the spot, unintentionally undermining the CFO’s authority.
This cycle repeated across departments. Leaders would establish policies aligned with the company’s strategic needs, only for those decisions to be overturned, sometimes in casual hallway conversations, because Michael wanted to reassure employees. While well-intentioned, the CEO’s overstepping left the leadership team fractured, credibility strained, and employees confused about which rules actually applied.
The Core Challenge: The People-Pleasing CEO
People-pleasing tendencies in CEOs are not uncommon, especially in founder-led organizations where loyalty and culture are prized. But without boundaries, these habits can unintentionally destabilize the very leadership structure designed to support growth.
For business leaders like Aiden, the challenge isn’t just about managing their own function—it’s about managing up. The question becomes: how do you support a CEO who oversteps in the name of employee satisfaction, while ensuring other leaders maintain credibility and the company doesn’t drift into chaos?
Because objectivity diminishes the higher anyone goes in an organizational hierarchy, Aiden wasn’t getting objectivity. Fortunately, Aiden is in an executive mastermind group and those executives encouraged him to pursue the following steps:
Strategies for Managing Up Effectively
- Clarify Decision Rights Publicly
High-performing leadership teams thrive on clear ownership. One effective approach is to create a “decision rights map” that makes visible which leader is accountable for which areas. For example, workforce policies might sit under the CFO’s purview, while the CEO provides input only at set review points. Codifying authority in this way helps employees understand where to direct concerns and reduces the temptation to bypass functional leaders.
- Reframe Employee Requests
When a CEO agrees too quickly to employee requests, leadership peers can step in to reframe the moment as an opportunity for alignment. A useful response is something along the lines of: “That’s an important concern—let’s make sure the relevant leader is looped in so it fits into the broader plan.” This keeps the CEO connected to employees while reinforcing the authority of the leader responsible for the decision.
- Create Feedback Loops
To avoid conflicting directives, organizations can set up systems where employee concerns raised directly with the CEO are logged and routed back to the appropriate leader. This preserves the CEO’s role as approachable and empathetic, while ensuring that input is integrated into structured decision-making rather than creating confusion.
- Highlight Long-Term Impact
Sometimes a CEO needs help connecting the dots between short-term reassurance and long-term leadership credibility. Leaders can surface real examples—such as policies being ignored or authority eroding—to show how quick promises can undercut strategic goals. Framing the issue as a trust and alignment challenge, rather than a personal flaw, helps CEOs recognize the importance of consistency.
The Outcome
When these practices are in place, CEOs learn to respond differently: “I hear your concern, and I want you to know we value it. Let’s make sure the right leader is brought into the conversation so we can get this right.”
The result is a healthier leadership dynamic: credibility is preserved, employees know which channels to follow, and the CEO maintains their approachable style without undermining the authority of their team. Ultimately, these guardrails allow fast-growing companies to scale without sacrificing trust or clarity.
The Takeaway for Business Leaders
Fast-growing startups depend on both visionary leadership and operational discipline. When CEOs lean too heavily into people-pleasing, they risk undercutting the very leaders who drive sustainable growth. Business leaders who find themselves in Aiden’s position should remember: managing up isn’t about controlling the CEO—it’s about protecting leadership integrity and creating structures that allow empathy and authority to coexist.
