The Topics We Avoid at Work—and How to Start Talking About Them

Christina Wing says employees already discuss money, age, fear, family responsibilities, and other sensitive subjects—but usually in side conversations with people who cannot change anything. When leaders avoid those topics, decisions are made without crucial input, employees lack a safe place to explain what matters to them, and senior executives become increasingly isolated from the workforce. Cultural and generational differences affect how conversations should happen, but Wing argues that a company cannot credibly call itself values-based if it refuses to discuss employees’ actual values and concerns. Younger workers are also more willing to discuss salary and politics than older generations.

Wing rejects the idea that politics should never be discussed at work. If a company does business in Egypt and tariffs may rise, employees need to understand the political consequences and help assess possible actions; otherwise, the C-suite makes every decision while everyone else merely executes. She supports constructive expression, listening, respect, and finding common ground around the business. After an election, leaders should acknowledge that it happened, explain how the company may be affected, and invite discussion rather than pretend nothing occurred. Leaders should not make negative comments about opposing candidates or assume the majority agrees with them.

For conversations about controversial issues, Wing recommends role-playing, choosing words carefully, and approaching the exchange with empathy and a shared goal. She says AI can help by simulating an angry or unexpected response, though the real conversation should happen in person rather than by text. A script should guide—not control—the discussion, because learning what the other person actually thinks is the point. If the exchange goes badly, neither person should simply walk away: they can acknowledge the problem, take a break, and schedule a specific second attempt, since difficult conversations often require multiple meetings.

Wing says leaders should create a safe space for employees to explain the significance of religious holidays, food, race, or current events rather than treating differences as inconveniences. She models this by telling her diverse team that she has often been the only woman in a finance room, inviting others to discuss their own experiences. Earlier in her career, she discussed exclusion privately with other women instead of raising it openly. She now regrets not challenging basics such as a venue with only a men’s bathroom. At a women’s event, she found someone pumping breast milk at a bathroom sink and addressed the failure publicly afterward.

Wing contrasts the workplace celebration of having a baby with the silence around elder care: she says 75% of her generation also care for older people. Employees may need time for a teenager’s mental-health crisis, fertility treatment, or a family member’s needs, but often feel vulnerable because they cannot predict exactly what support they will require. She recommends that managers begin each year by asking whether anything on an employee’s horizon should be discussed. Employees raising such issues should request a calm meeting in a neutral place, explain what they can, and focus on a shared goal of improving the organization.

Wing argues for separating age from succession: an employee who appears to slow down may be bored or unwell, not necessarily ready to retire. Employees can give managers a gift by sharing a five-year transition plan, which lets leaders create paths for rising talent instead of making people wait for someone to leave. She identifies fear of ambition—especially among women—as the most common organizational fear; employees should say they want the next role or more pay and ask what it will take. Wing also tells students and colleagues about mistakes and having been fired, using personal stories to make honesty safer.

Wing says people tie money to self-worth and often wait until year-end raises or bonuses to discuss compensation. Instead, employees should raise the subject early—for example, in February if awards come in December—by explaining how they will add value and why they want to earn more. Organizations should publish pay bands, such as the range for a VP role, while leaving an individual’s position within the band private between employee and manager. Regarding AI and layoffs, leaders should acknowledge uncertainty, ask employees what AI can now do, involve them in redesigning roles, and provide daily upskilling. Laid-off workers should quickly tell their networks, own the narrative without attacking former employers, and focus on what they want next.