According to The Harvard Business Review and an article “How to Tell Your Boss They’re Wrong – Tactfully,” by Rebecca Knight, telling your boss you disagree with them can feel risky, but when done right, it can foster trust, not tension. The key is to push back thoughtfully, with clarity and care.
How to have a production conversation with more awe and less awkward:
- Reframe your pushback as a contribution. As an EA, you may have felt that silence feels safe, but it can lead to wasted time and poor outcomes. Saying something shows your commitment to shared goals, that you are thinking strategically, and are outcome-oriented.
- Know your influence—and use it wisely. Before sharing your thoughts, consider your credibility, the timing of your feedback, and the urgency of the issue at hand. You may want to wait for the right moment. A one-on-one conversation matters more than ambushing someone in the hallway.
- Tailor your approach. Each executive has their own style, priorities and way of working. Adapt and frame any concerns you have around what they care about. For example, if they’re after results, morale or efficiency, ask if they would be open to another perspective; thereby leading with curiosity.
- Offer solutions, not just criticism. When possible, a compromise or alternative may be proposed. If they resist, clarify your intent with: ‘I’m sharing this to help us succeed.’ Then let it go if needed.
What the experts say
Amy Gallo, contributing editor at Harvard Business Review, writes: It’s a natural human reaction to shy away from disagreeing with a superior.
“Our bodies specialise in survival, so we have a natural bias to avoid situations that might harm us,” says Joseph Grenny, the coauthor of Crucial Conversations and the cofounder of VitalSmarts, a corporate training company. “The heart of the anxiety is that there will be negative implications,” adds Holly Weeks, the author of Failure to Communicate. We immediately think, “He’s not going to like me,” “She’s going to think I’m a pain,” or maybe even “I’ll get fired.” Although “it’s just plain easier to agree,” Weeks says that’s not always the right thing to do.
And remember to stay calm
You may feel your heart racing or your face turning red, but do your best to remain neutral in both your words and actions. When your body language communicates reluctance or anxiety, it undercuts the message, Weeks says. It sends “a mixed message, and your counterpart gets to choose what to read,” she explains. Deep breaths can help, as can speaking more slowly and deliberately. “When we feel panicky, we tend to talk louder and faster.” Staying calm is staying
