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Should I Fire a Senior Leader?

By Stan Tscherenkow · Published September 2025 · 6 min read

Quick Answers

Should I fire a senior leader? If you are asking this question seriously, the answer is probably yes. But diagnose the structure before concluding the problem is the person. A senior leader operating in a poorly designed role with unclear authority and misaligned accountability may look like a performance problem when the actual problem is the structure they are operating in. Once the structural diagnosis clears, the answer is yes in four specific situations: sustained underperformance with no trajectory change, a values or judgment failure, a capability mismatch produced by scale, or organizational confusion that exceeds the individual contribution.

When is the answer yes to firing a senior leader? Four situations. One, sustained underperformance beyond ninety days where feedback and an improvement plan have not produced a trajectory change. Two, a values or judgment failure that feedback cannot correct. Three, the role has scaled past the person's capabilities, the COO at $8M is not automatically the right COO at $25M. Four, the person is producing more organizational confusion than their contribution is worth. Each situation has a clean decision even when metrics are mixed.

What is the cost of delaying a firing decision at the senior level? The cost of delay is not just operational. Every month a known underperformer remains in a senior role is a signal to the organization about what is tolerated at the top. Senior leaders observe how founders handle senior-level underperformance and draw conclusions about standards and accountability. A founder who holds frontline staff accountable while allowing senior leaders to underperform for extended periods creates a visible double standard that erodes the culture more effectively than almost anything else.

When is the answer to wait rather than fire? Two situations. One, the structural diagnosis is not complete. If the role design, authority clarity, and resource adequacy have not been assessed, you owe the leader and the organization that diagnosis before making the decision. This takes two to three weeks of honest assessment, not three quarters of performance management. Two, the person is in the middle of a high-stakes deliverable that only they can complete in the next thirty to sixty days. Sixty days is the outer limit.

If you are asking this question seriously, the answer is probably yes. And the more important question is why it has taken this long to get here. The hesitation around firing senior leaders costs more than the decision itself in almost every case I have observed.

Structural diagnosis first

The direct answer to whether to fire a senior leader requires a prior question: is the problem structural or personal? A senior leader operating in a poorly designed role, with unclear authority and misaligned accountability, may look like a performance problem when the actual problem is the structure they are operating in. The structural diagnosis must come first. Not to protect the leader from accountability, but to protect the organization from replacing the person without fixing the situation that produced the failure.

Once the structural diagnosis clears, once you can confirm the role was designed correctly, the authority was real, and the person had what they needed to succeed, the question of whether to fire has a clear answer in four specific situations. The related framework sits in how do you build leadership authority without losing control.

When the answer is yes

Four situations in which the decision is clear once the structural diagnosis has cleared.

Four conditions when the answer is yes

Sustained underperformance with no trajectory change. The leader has been underperforming for more than ninety days, the problem has been named directly, and the trajectory has not changed. The standard performance management response (feedback, improvement plan, direct work on the gaps) has been applied. The improvement has not materialized. At this point, continued investment in performance management is not a management strategy. It is delay management.
Values or judgment failure. The leader has demonstrated a values failure or a material judgment failure that cannot be corrected. This is distinct from a performance failure. It is a question of who the person is, not what they can do. Dishonesty with the founder or the board. A decision that prioritized personal interests over organizational ones. Treatment of direct reports that is incompatible with the culture the organization is trying to build. These situations do not improve with time. They compound.
The role has changed and the person has not. The business has scaled past the capabilities the current leader can offer. The person who was the right COO at $8M is not automatically the right COO at $25M. This is not a performance failure. It is a capability mismatch produced by growth. It is the kindest and most honest version of this conversation: the role has changed, you have not, and continuing is not fair to either party.
The person is producing organizational confusion. The leader's presence is creating more dysfunction than it is solving. Decision authority disputes with peers. Senior team attrition attributable to the relationship with this leader. Conflicting direction being given to shared reports. When the cost of the organizational friction exceeds the contribution of the individual, the calculation is clear even when the performance metrics are mixed.

If this decision is live, a direct conversation can get to clarity faster than continued deliberation.

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The delay problem

In my experience working with founders on this decision, the most consistent mistake is not making the wrong call. It is making the right call six to twelve months after the evidence warranted it.

The cost of delay is not just operational. Every month a known underperformer remains in a senior role is a signal to the organization about what is tolerated at the top. Senior leaders observe how founders handle senior-level underperformance. They draw conclusions about standards and accountability from what they see. A founder who holds frontline staff accountable but allows senior leaders to underperform for extended periods creates a visible double standard that erodes the culture more effectively than almost anything else.

The team already knows. They made the decision about this person months ago. They are waiting to see if you will.

When to wait and how to execute

There are two situations in which the answer is not yet. One, the structural diagnosis is not complete. If you have not confirmed whether the failure is personal or structural, if the role design, authority clarity, and resource adequacy have not been assessed, you owe the leader and the organization that diagnosis before making the decision. This takes two to three weeks of honest assessment, not three quarters of performance management.

Two, the person is in the middle of a high-stakes deliverable that only they can complete. This is genuinely rare at the senior level, and founders overestimate it frequently. If the assessment is that only this specific person can complete a specific deliverable in the next thirty to sixty days, and the failure of that deliverable would be materially damaging, a short delay is defensible. Sixty days is the outer limit.

The execution of a senior leader exit requires three things: legal and HR process handled correctly before the conversation happens, a clear and brief reason given directly and without softening, and a clean separation that does not leave the relationship or the role in ambiguous status. The brief reason matters. Senior leaders who are given vague or conflicting reasons for their exit carry that ambiguity into the organization through their networks, especially if they remain in the industry. A specific, direct, honest reason is kinder than a soft one, even when it is harder to say. The documented case of the exact delay pattern lives in the CEO who waited too long to fire.

If this decision is live, get it to clarity. Continued deliberation costs more than the conversation does.

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Stan Tscherenkow Private Business Advisor Two decades operating across Europe, Russia, Asia, and the United States.

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