By
Partner, Next Step Partners
Sam*, the CEO of a national retail chain, found himself in a dilemma. His Head of Operations, Kristin, had been with the company for over a decade, playing a key role in shaping its operational backbone. But as the retail landscape shifted, Kristin* struggled to adapt. Sam knew it, but hesitated to act. She was well-liked, had built strong relationships, and had helped foster a culture that firing her could disrupt. Sam’s delay in taking action allowed operational bottlenecks to persist, which stunted the company’s competitive growth in the digital age.
This story is all too familiar. We see it in our CEO practice regularly, but it’s a subtle trap that’s easy to miss until it’s too late. Positive emotional bonds—built over months or years of shared wins, problem solving, and mutual respect—can become obstacles to making tough decisions. The result? Organizational stagnation, frustrated leadership teams, and compromised performance.
In the high-stakes world of executive leadership, this over-affiliation can be costly.
CEOs naturally invest time and energy into cultivating trust with their executive team. But this investment can sometimes cloud judgment when it’s time to hold someone accountable. This is especially prevalent among first-time CEOs or those with long-standing relationships with their team.
CEOs who over-affiliate with their executives often feel emotionally conflicted when faced with the need to let one of them go. They worry about damaging relationships, disrupting team culture, and betraying the trust they’ve spent years building. The affiliation trap makes it easier to rationalize a delayed decision, hoping that the underperformer can turn things around, even when the evidence suggests otherwise.
Most CEOs develop personal connections with their executives. Firing someone can feel like a betrayal, especially if that person played a key role in the company’s success. In startups, this emotional loyalty is compounded by guilt—especially when the original team can’t keep pace with the company’s evolving needs.
Long-tenured executives are often cultural cornerstones. CEOs may fear that firing them will destabilize the team. However, we’ve found that once an underperformer is removed, feedback from the organization often overwhelmingly confirms that the decision was long overdue.
CEOs often convince themselves that an underperforming executive can improve. They selectively focus on small improvements while ignoring ongoing red flags, driven by a desire to avoid conflict or admit hiring mistakes.
CEOs are, by nature, optimistic. This can lead to unrealistic expectations that an underperforming executive will improve, prolonging the inevitable.
Failing to remove an underperforming executive in a timely manner doesn’t just affect the individual in question; it ripples through the entire organization and changes the CEO’s standing. Here’s how:
Loss of Credibility
A CEO’s every action or inaction sends a message. Tolerating subpar performance tells the rest of the organization that accountability isn’t enforced at the highest levels. Other leaders and employees may begin to question the CEO’s judgment and commitment to performance standards. Over time, this erodes trust and diminishes CEO authority with the team. At one insurance company we worked with, members of the executive team all expressed repeated frustration over one of their colleagues not being held to the same standard of performance by the CEO and started to question his judgment. If the Board starts to notice the issue, directors may also second guess future talent decisions.
Damaged Team Morale
When an executive can’t execute, the rest of the leadership team feels the burden. Left to pick up the slack, which breeds resentment, they collaborate less effectively under increased stress. Top performers look elsewhere if they feel their efforts are being undermined by CEO inaction. At one tech firm we worked with, problems with a senior Product Development leader had gone unaddressed for years, damaging the company’s offering and positioning in the market. This caused another key executive to eventually leave.
Organizational Drift
An underperforming executive doesn’t just impact one department or set of direct reports; they affect the company’s overall trajectory. Strategic initiatives stall, operational efficiencies flail, and important opportunities are missed. The longer the CEO waits to act, the further the organization can drift from its goals.
One CEO of a mid-sized tech company we worked with faced this very challenge. She had hired her CMO early on, in the startup phase. They had weathered long nights and numerous product launches together, building a close friendship along the way. Five years later, though, the CMO struggled to adapt to the increased demands of scaling the growing business and executing more complex marketing strategies. The CEO’s loyalty clouded her judgment, and despite repeated signs that her CMO wasn’t keeping up, she couldn’t bring herself to make the tough call. By the time she finally acted, the company had already lost market share to competitors who were more nimble in building their brands.
There’s often an interpersonal basis for the affiliation challenge. The solutions require some inner-personal awareness.
1.Recognize Your Affiliation Bias
CEOs who are highly relational or conflict-averse are more prone to over-affiliation. Recognizing this tendency is crucial for maintaining objectivity when evaluating executive performance.
2. Set Measurable Expectations, and Check Your Gut
Establish clear performance standards from the start, tied to specific, measurable outcomes. Regularly review these metrics to ensure decisions are based on data, not just personal feelings.
If you find yourself mulling quiet doubts or frustrations about a direct report, review performance against key success indicators. Assign a grade and look at trends. Have they gotten better or worse? Stayed fundamentally the same? What will the impact of, say, of this leader’s B-grade performance have on the company in the next year? Two years?
3. Listen to Repeated Concerns and Name Your Fears
Do you find yourself repeatedly addressing the same performance issue? It’s time to reassess. Ask yourself: “Would I hire this person today?”
If you’re starting to suspect an unfixable performance issue, complete this sentence: I need to replace my direct report with someone who can ___________. The thing holding me back is ___________. The way I can get over that is _________. Once you identify the fear that is in your way, you can reality-check it. Our experience is that once a subpar performer is replaced, 100% of the time CEOs wish they had done it sooner.
4. Seek Outside Perspective
Engage an external advisor, board member, or coach to provide an unbiased view, untangle emotional attachments, and clarify when action is necessary. As coaches, we often catch repeated concern patterns early and can help CEOs cut them off at the pass.
5. Prioritize Organizational Health
Ultimately, a CEO’s responsibility is to the organization’s long-term success. Shift your focus from the immediate difficulty with one of your people to company goals. Is this executive preventing you from meeting them? It may be that simple.
When emotional bonds or misplaced optimism hinder executive accountability, the CEO must refocus on the big picture. Use that clarity to take decisive action so the organization can quickly move forward.
CEOs are human. They connect with their people. Disconnecting is hard, but over-affiliation can trap any organization in stasis or decline. While building strong relationships is essential to leadership, allowing emotional ties to cloud judgment does a disservice to everyone—including the underperformer. Executives who are held accountable, even when it’s uncomfortable, will rise to the occasion or realize the job is no longer a fit, leaving room for those who can drive the company forward.
By knowing and managing affiliation trap risks, CEOs can make the tough calls when they’re needed most, protecting both their credibility and their company’s future. It’s not about being ruthless. It’s about tough love.
What is tough love, exactly? It’s balancing head and heart. It’s using your full humanity to hold accountable those who depend on it for discernment as well as emotional connection. That’s a responsibility no CEO can afford to ignore.
*Name changed for confidentiality