How Will This End?

Why Talking About the End of a Work Relationship Shouldn’t Be Taboo

What If We Talked About the End at the Beginning?

In today’s workplace, discussing the end of a professional relationship feels as forbidden as talking politics at the dinner table. This taboo approach is surprising given that executive roles, even under ideal circumstances, have an average lifespan of 4.6 years. Add a new CEO, a market shift, or a board pushing for change, and that timeline might shrink to two years. So, why don’t we talk openly about “How will this end?” from the start, especially in leadership roles? Why is there such hesitation to discuss a structured, respectful exit strategy?

The Reality of Executive Tenure

While terms like “onboarding” and “culture fit” flood HR vocabulary, few conversations include, “What happens when this isn’t working?” When relationships fall short of expectations, executives often end up enduring a long, awkward process rather than a straightforward exit. Leaders may be reluctant to make a decisive choice due to fear of confrontation or reputational damage. And HR interventions, like coaching or counseling, can feel like Band-Aids, delaying the inevitable.

The Fear Factor: Why the End is Painful

Many leaders, especially CEOs, find it excruciatingly difficult to have an honest conversation about an executive’s exit. The conversation can feel as dreaded as passing a kidney stone. Instead of directly saying, “I don’t see you as part of our team anymore,” CEOs sometimes sidestep, dragging out a process that leaves everyone involved stressed and insecure. The prolonged uncertainty can breed distrust across the organization, and before long, resumes start circulating and LinkedIn notifications begin to buzz.

But why is it this way? Could it be that our litigious culture discourages tough conversations? Or perhaps it’s an “I did nothing wrong” mentality, where both sides avoid addressing a misalignment, expecting the other to take responsibility.

What If We Talked About the End at the Beginning?

Imagine if, during the hiring process, we were upfront about how a departure might look. It might seem as odd as bringing up a “breakup plan” on a first date, but clarity about exit expectations can actually foster healthier relationships. It can make the departure, if it happens, less traumatic and more structured.

For example, setting a clear severance plan could provide reassurance. For staff-level roles, a 30-day notice with benefits could suffice; for senior leadership, a six-month severance after three years of tenure would allow time to regroup financially and emotionally. This approach not only eases the stress of departure but also reinforces a culture of honesty and mutual respect.

Avoiding the Emotional Roller Coaster

When we avoid the conversation about “How this will end,” we create a toxic cycle. It’s an emotional game of gaslighting, where neither party is willing to blink, and everyone around them suffers. Prolonged ambiguity raises fears among other employees, who begin to wonder, “Could I be next?” This uncertainty can trigger an exodus of talent, with LinkedIn connections lighting up and resumes polished during lunch hours.

In contrast, open communication about potential outcomes can remove the sting of uncertainty and build a stronger foundation of trust. While it may not make the conversation easier, it certainly makes the process cleaner and more professional.

Confronting the Truth: The Value of an Honest Goodbye

HR counseling, when managed with a 60-day period for growth and adjustment, should be a standard first step. But when things still aren’t working, it’s time for a real conversation. CEOs, as leaders, need to be courageous enough to have these difficult discussions and avoid dragging everyone into an emotional standstill. Ending a professional relationship should be a straightforward, respectful process—not a prolonged ordeal.

The real question isn’t about if we should talk about “How this will end,” but when. Embracing this conversation early can prevent the drawn-out “Sunday Stress” and the “Monday Blues” that come with ambiguity and avoidance. Ending a working relationship doesn’t have to be a taboo subject; instead, it can be the cornerstone of a healthier, more transparent workplace.