Wingspan Founder Christina Wing joined Travis Chappell on the Travis Makes Money podcast for a conversation about relationships, leadership, and the topics most of us would rather skip. Christina, a faculty member at Harvard Business School and author of Unspeakable: The Taboo Topics We Avoid and How to Talk About Them, covered a lot of ground, from how she ended up at HBS to what really sinks a business.
Travis opens every episode by asking guests about the first dollar that meant something to them. Christina’s answer was a first for the show. As a young lifeguard, she pulled a struggling kid out of a deep-water pool, and the parent pressed a $100 bill into her hand. She admits she isn’t completely sure he was drowning, but he was flailing, and Travis agreed that’s not the moment to wait and see.
Raised at the boardroom table
Christina’s father went to West Point, served in the military, and then went to business school and became a serial entrepreneur. From about age six, she grew up at the table listening to conversations about what to invest in and what to try next. The family moved 13 times before she started high school, and being the new kid every year pushed her to pay close attention to business and to how people interact.
That curiosity carried her to SMU, where a professor who had come from Harvard Business School introduced her to the case method, learning through real stories instead of textbooks. She went on to Wall Street, then to HBS, and eventually joined the faculty. She’s quick to say none of it was planned. It came through relationships.
Who you know gets you in the room
That led to one of the best exchanges of the episode. Travis, whose show used to be called Build Your Network, asked how much of success comes down to relationships versus competence. Christina didn’t hesitate. “What you know demonstrates capability. Who you know gets you in the room to use that capability.”
Knowledge has to keep evolving, she said, but trust is what drives action, and trust comes mostly through relationships. She credits the people who invested in her, and the people she invested in, for where she is today.
Unearth the elephant
Her years doing M&A on Wall Street left her wanting longer, closer relationships with companies instead of one-off transactions. What she has seen since then is pretty consistent. The businesses she works with rarely fail because of bad business decisions. They fail because of poor communication and because no one addresses the elephant in the room. “If you can get in the room, unearth the elephant, and talk about it, you’re more likely to survive.”
Why she wrote Unspeakable
Christina wrote Unspeakable because the list of things we don’t talk about keeps growing. When Christina was growing up, the off-limits topics were politics and religion. Now the list gets longer every year, and she sees it in her classroom. When she asks executives what they talk about at work and at home, the answers are Netflix, vacations, and sports. What they avoid is money, promotions, fertility, religion, and plenty more. Her hope is that every reader finds at least one chapter and thinks, I should try this. She’d much rather people start there than try to tackle everything at once.
She also drew a line between a difficult moment and a difficult conversation. Firing someone or ending a relationship is a difficult moment. A difficult conversation is one where you want the other person to keep moving forward with you. For those, she offered a simple playbook:
- Think, but not too long. Stew on it too long and you get what Christina calls “pre-pissed.” If that happens, go for a walk first.
- Don’t ambush anyone. Skip the phone call. Send an email that names the topic and suggests a neutral spot, like Starbucks.
- Set the norms up front. Explain that you’ll talk, then listen without interrupting, and that if it gets uncomfortable you can stop and pick it up another time.
- Follow up. These rarely get solved in one sitting, so keep the conversation going.
A firm that would have helped her family
Christina described Wingspan as “a firm that would have helped my family.” Her father was very successful, but the family never talked about anything real, and he never would have hired an outside advisor. Wingspan listens to big problems, works with the team on a solution, and then stays to help carry it out, whether that means rebuilding a leadership team or helping a family decide whether to keep or sell the business.
She called starting Wingspan the biggest risk she has taken, and said it doesn’t feel like a job. It’s part of her life. That includes a lot of travel, because she believes you can’t advise a client in Turkey, or in Austin, Texas for that matter, from a desk in Boston. You have to put boots on the ground and see how people live and work.
There’s a lot more in the full episode, including the places Christina most wants to visit next. Give it a listen below and check out Unspeakable.
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