Imagine you’re leading a strategy meeting. Your team is split on a major decision. Half are pushing for a bold, expensive pivot, half are advocating for a safer, proven approach. Everyone’s looking at you to make the call.
Your instinct screams for the bold option. You could shut down the debate right now and move forward with confidence. But what if you did something else?
“Before I share my thoughts, I want to make sure I truly understand both sides. Joe, you’re advocating for the conservative approach. If I were completely convinced that option B is right, what would my strongest arguments be? What risks am I seeing that others might be missing?”
Then to the other side: “And Caitlin, if I were absolutely certain that option A is wrong for us right now, what would I be most worried about?”
Instead of a tug-of-war where everyone digs deeper into their positions, you get something more productive: people reveal their real concerns and genuine insights. They feel heard. And you make a decision with complete understanding of every angle.
This isn’t indecision. This is what real assertiveness looks like.
The Practice That Changes Everything
Learn to argue both sides of every important issue.
Before advocating for any position that matters, spend time genuinely understanding and articulating the strongest possible version of the opposing viewpoint. This isn’t about playing devil’s advocate. It’s about doing the intellectual work to comprehend why reasonable people might see things differently.
Why This Works
Most assertiveness training teaches us to be more confident in our own position. But confidence without understanding often comes across as arrogance. When leaders can argue both sides of an issue:
- We become more credible. People trust leaders who’ve considered multiple perspectives before reaching conclusions.
- We become more persuasive. Understanding real concerns means you can address them directly instead of talking past them.
- We become more collaborative. Teams feel safer challenging leaders who’ve already challenged themselves.
- We become more decisive. Decisions made with full understanding of trade-offs are stronger and more sustainable.
How to Practice This
- Choose Your Issue: Pick something you’re advocating for: a strategic direction, policy change, or resource allocation.
- Build the Opposing Case: Spend real time researching the strongest arguments against your position. What legitimate concerns exist? What risks might you be overlooking?
- Practice the Opposition: Articulate the opposing viewpoint out loud until someone who holds that view would say, “Yes, that’s exactly what I believe.”
- Integrate What You Learn: When advocating your position, acknowledge legitimate concerns: “I know some of us are worried about X, and that’s valid. Here’s how we can address that while moving forward with Y.”
The strongest leaders aren’t those who never doubt themselves. They’re those who doubt themselves privately so they can be confident publicly.
Instead of: “We need to implement this strategy because it’s clearly the right approach.”
Try: “I know there are legitimate concerns about the risks and costs of this strategy. I’ve considered alternative approaches, and here’s why I believe this path gives us the best chance of achieving our goals.”
The difference is night and day. One approach shuts down conversation. The other opens it up.
When leaders combine thoughtfulness with the courage to speak up for what they believe, they become leaders worth following.
