How To Fire Your Daughter
Firing an employee is hard enough. But what if that employee is your child? Separating personal relationships from business decisions can be uniquely challenging in a family business—especially when you’re ready to step away, and your child isn’t ready to step up.
On this episode of Slate’s How To! podcast, Wingspan Founder and Harvard Business School professor Christina Wing advises Kyle, a 65-year-old small-business owner in Texas, who wants to retire and sell his family-run insurance agency to his employees. The complication? One of those employees is his daughter Natalie. While she excels at sales, Kyle doesn’t see her as capable of running the business—and their strained working relationship is making it even harder to plan his exit.
Christina talks Kyle through how to approach this moment with clarity and care. She encourages him to separate his goals into three distinct categories: what’s best for the business, what’s best for his daughter’s personal development, and what’s best for their family relationship. “Right now,” she says, “you’re trying to talk about all three at once. And that’s why every conversation goes in circles.”
Christina suggests a phased strategy: rather than selling the business immediately—or excluding his daughter outright—Kyle might ask Natalie to step away and gain experience elsewhere for a few years. This would give her a chance to build skills and confidence outside his shadow, and possibly return ready to lead. In the meantime, Kyle can continue growing the business with his trusted employee Brooke, who is prepared to take on more leadership.
She also challenges Kyle’s communication style. Instead of lecturing or sending articles for his daughter to read, Christina urges him to flip the script: ask Natalie what she needs to thrive. “Help me help you,” she suggests he say. This kind of listening opens the door to more honest dialogue—and a chance to rebuild trust.
Finally, Christina offers a candid reality check: if Kyle doesn’t make a decision soon, he risks losing both the business and his daughter. “Ten years is too long to leave things unresolved,” she says. “A little tough love earlier would have been better. But it’s not too late.”
This episode is a compelling example of what many family enterprises face—tension between legacy and leadership, loyalty and letting go. Christina’s message is clear: with structure, empathy, and the courage to have the hard conversation, families can navigate even the most delicate transitions.
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