Wingspan Founder Christina Wing sat down with Alison Beard on HBR IdeaCast, Harvard Business Review’s weekly podcast, to talk about the things most of us think about at work and almost never bring up. Money, age, politics, family obligations, ambition, fear. The conversation was based on Christina’s book, Unspeakable: The Taboo Topics We Avoid and How to Talk About Them, which looks at why we avoid these subjects and how to start talking about them.
Her starting point is simple. People already talk about these things, just with the wrong people, usually in side conversations. The person who could change something never hears it, decisions get made without the right input, and the list of off-limits topics keeps getting longer.
Privacy is fine. Secrecy is not.
Alison raised the old idea that home life should stay at home. Christina drew a line between privacy and secrecy. Telling your manager you need time off for a medical issue, without sharing every detail, is privacy, and that’s perfectly fine. Asking for time off with no explanation at all is secrecy, and it doesn’t build trust. She described an employee who would rather quit than ask whether she could wear a headscarf at work, and a colleague who can’t explain why they’re out for a religious holiday. Neither one can bring their whole self to work.
Christina grew up in Texas and went to a big public high school with only a few Jewish students. She didn’t understand many religious holidays until she worked alongside colleagues of different faiths. Her advice to managers is to do more than approve the day off. Ask why the day matters.
Politics at the office
The episode was released on the day of the 2026 midterm elections, so politics came up early. Alison asked whether it’s better to keep it out of the office altogether. Christina disagreed. If a company does business in Egypt and tariffs might change, leaders need to talk about what that means for the business. When leaders pretend politics doesn’t exist, every decision ends up in the C-suite and everyone else just carries it out.
After an election, she suggests a short, non-partisan acknowledgment from leadership and a few words on how the company is thinking about what comes next. Leaders don’t have to weigh in on every issue, but they should be consistent. Employees notice when a company holds a meeting after one event and says nothing after another.
She also had a warning for anyone who assumes the people around them agree: “When you feel you’re in the majority, you’re probably wrong.”
When a conversation goes sideways
Christina’s prep advice will sound familiar to anyone who has heard her speak. Role-play first (Alison suggested AI as a practice partner). Come in with empathy and a shared goal, and if you don’t have both, don’t start. Never go in agitated. Invite the other person to a neutral spot instead of calling them into your office, and have the conversation in person, not over text or the phone. She also separates a difficult conversation, where you share a goal like growing sales, from a difficult moment like firing someone.
And if it goes badly, don’t get up and leave. “You never get up and walk away because then you really went backwards.” Say it isn’t going well, take a break, and set a specific time to pick it back up right then, before it drifts.
Age, ambition, and pay
The second half of the episode got very practical.
- Separate age from succession. Assuming someone is slowing down because of their age is a projection. Maybe they’re bored, maybe they’re unwell. Ask about their plans. If you’re the one thinking about stepping back, laying out a multi-year plan gives the organization time to prepare and gives a younger colleague a path. In Christina’s words, “Clarity is kindness.”
- Say what you want. Of the six fears Alison listed, Christina sees fear of ambition most often, especially in women. Her suggested question is “What do I need to do to get to the next level?” If a leader judges you for asking, she says, it may be time to look elsewhere.
- Talk about pay early. Most people only bring up money at review time. She’d rather they raise it at the start of the year, with a plan for how they’ll add value. She also favors transparent pay bands for each level, with where you fall discussed privately with your manager. “Transparency is kindness.”
- Be honest about AI. Silence creates fear. Tell your team AI is coming and roles will change, then bring them into figuring out how. What people imagine is usually worse than the reality.
- Ask about caregiving. Offices celebrate a new baby, but hardly anyone talks about caring for aging parents, even though so many people are doing it. Christina suggests leaders ask each team member once a year what they expect to need.
Owning your mistakes
Christina models this herself. She tells her team when she sends an email to the wrong person, and she tells her students she was once fired, which hurt at the time and turned out well for her later. Hearing those stories makes it easier for others to own up to theirs. Her advice to anyone who has been let go is to communicate quickly, own the story, skip any criticism of your former employer, and focus on what you’re good at and how people can help. “We have to get rid of the stigma.”
There’s a lot more in the full conversation, including how to check in on a colleague who seems to be struggling. Give it a listen below.
