The Conversation You're Avoiding: How to Fire Someone You Actually Like
Nov 25, 2025You've been putting it off for weeks. Maybe months. Every time you think about having "the conversation," your stomach knots up. They're such a good person. The team likes them. You like them. But the performance issues keep piling up, clients are affected, and you can't ignore it anymore. How do you fire someone when you genuinely care about them as a human being?
Anna and Kendall address this emotionally fraught situation with brutal honesty, sharing wisdom from their own difficult experiences. Right from the start, Anna acknowledges: "Kendall's a much better firer than me" – a vulnerable admission that most alternative healthcare providers aren't naturally built with this skill set.
The conversation begins with a crucial reframe. As Anna explains: "You take yourself out of the equation. It's not about you. It's not about whether you're friends. It's not about whether the person sucks even. It's simply, it's not a match for the company at this time." This shift from personal rejection to business reality makes the impossible feel possible.
But reframing alone isn't enough. The practical execution matters enormously. Kendall shares a critical tool – creating and using a script: "Thanks for meeting today. I have some bad news. This is difficult for me. This is a really difficult conversation for me. So I wrote some things out and I'm actually just going to read it." This approach accomplishes multiple goals: it keeps you on track, protects you legally, and signals the seriousness of the situation.
The harder part? Sticking to the script when the person on the other side starts pushing back. As Kendall describes: "They're going to come back with, well, why? You said it's performance based. What do you mean? I need examples... And then they have a rebuttal for everything... then it becomes a breakup conversation." The solution is staying firm with "That's all I'm able to share. It's performance based. And we will be parting ways."
Perhaps the most painful reality addressed is what happens to the relationship afterward. Kendall states clearly: "Very rarely are they going to welcome or initiate a relationship forward." This is often the biggest source of hesitation for practice owners – the fear of losing not just an employee but someone they genuinely enjoy.
Anna acknowledges another common fear: "Potentially, you know, incur some, I don't know, get a reputation in the community." But she counters with an important truth: "If somebody is not a fit, then it's more egregious to keep them in that position than it is to terminate the relationship and then get somebody who's amazing for that role in there."
The conversation takes an important turn when discussing the loneliness of leadership. Kendall reflects on why she'd never hire a close friend now: "I know that at the end of the day there's a strong possibility that we will no longer have a relationship." This represents a hard-won wisdom that comes from experience – the realization that employer-employee relationships, no matter how warm, require boundaries.
Anna captures the grief inherent in this reality: "We want to hire the best, and so we want to be friends with the best... I adore my team. I wouldn't have hired them if I didn't think they were completely awesome." Yet maintaining those boundaries is essential for sustainable leadership.
The episode concludes with an important reminder about finding peer communities where practice owners can process these challenges with others who understand. As Kendall notes, "The more I step into leadership and the more that our business grows, the lonelier it feels."
If you're avoiding a difficult termination because you like the person too much, or if you're grieving the reality that you can't be close friends with your employees, this episode offers both practical strategies and validation for one of leadership's most painful realities.
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About Anna Rudel
Anna Rudel, L. Ac is the owner and founder of Lokahi Acupuncture Clinic in San Jose California, founded in 2003. Anna is a master organizer and clinician, and as a Coach she specializes in working with Clinic Owners in the state of California, and Acupuncturists and Acupuncture Clinic Owners, or groups wanting to add Acupuncture worldwide, as well as teams that need support with employee retention and satisfaction. Born in the UK, Anna has traveled extensively in Asia and now has a thriving multi-practitioner clinic in the US!
Anna's Website and Links
- Website: https://lokahiacupuncture.com/
- Learn Group Coaching: https://www.wellnesscentercreators.com/group-coaching
- For info about Individual Coaching: https://www.wellnesscentercreators.com/individual-coaching
About Kendall Hagensen
Kendall is a Somatic Mental Health Therapist, Multidisciplinary Clinic Owner and Business Coach. She specializes in, and is passionate about, working with healthcare professionals to create the businesses of their dreams. Big goals always have a psychological component beneath the surface, so Kendall uses her background in Somatic Psychotherapy and EMDR Therapy mixed with Business Coaching tools to help clients develop a healthy relationship with their business and their strength as a leader.
As someone who lives with a chronic illness herself, Kendall feels that health happens best within community, which is why she takes a holistic, integrative, and collaborative wellness approach to her personal and professional life.
Kendall’s Web/Social Links