How to Go Over Your Boss’s Head

Welcome back. Last week, I shared a story about a major disagreement with a boss that, luckily, ended well. But more often, the outcome isn’t so easy. The boss makes their decision, and you're left with the choice: let it go or keep pushing. But what do you do when you've given it your all, yet the power-holder is still set on a decision that endangers worker safety or jeopardizes a project?

Imagine if my story from last week ended differently and my boss insisted we not hire security personnel in a conflict zone. What could I do? I would definitely document the discussions and decision, but the high stakes would lead me to escalate the issue.?

First, I’d assess the risks. Could I handle a tense relationship with my boss? What about retaliatory behavior like getting fired or passed over for promotions? While there are ways to minimize these risks, it’s vital to understand the limits of your influence and the potential consequences of continuing to push. Even with the right tone and a valid point, power often doesn’t listen.

If you've weighed the risks and still choose to disagree, start by maintaining the same informed, supportive, and firm stance you’ve held throughout the disagreement. Stay professional—even if you feel justified in being sarcastic or rude, matching disrespect is likelier to undermine your position. It’s challenging to navigate this power dynamic without becoming meek or overbearing, but there are strategies to find that balance. (Let me know if y’all would like an article with more on that!)?

Next, involve your boss in the escalation process. Start by saying, "Boss, we have the same information but different views on how to proceed. Given the high stakes, I'd like to involve more of our team." Then, set up a meeting with your team and your higher-up, inviting your boss to both. In these meetings, present your perspective while fairly representing your boss’s viewpoint. Encourage input from teammates across the chain of command, allowing all leaders to understand and collaborate on a solution. Once you’ve advocated for your position and documented everything, your influence will have reached its limit. At that point, you’ll need to either accept the final decision made by those with the most power or decide if it crosses your boundaries enough to consider resigning.

This requires a lot of repetition, patience, and openness – it is a lot of work to push past your boss’s decision. It may help you to keep in mind you’re problem-solving and teaching others how to handle disagreements with integrity. You’re also demonstrating how to refocus on relationships when tensions rise, which is something even seasoned leaders struggle with. This challenge is an opportunity to practice and model your capabilities and values.

There’s much more to say about this complicated topic but for now, I'll leave you with a few reminders I’ve relied on in similar situations: 1) If you have no positional power or are at the bottom of the hierarchy, you can always build relationships with your peers. 2) Humanize your leader—putting them on a pedestal or fearing them only amplifies their outsize power. 3) Reduce the pressure on yourself and understand your limits; you could do everything with solid intentions and still not achieve your desired outcome.

Finally, for those of us with significant influence and control in the workplace: If our employees don’t feel comfortable disagreeing with us or if we don’t create a path for disagreement, we’re missing a crucial element of leadership. The best leaders know that disagreement isn’t disrespect. They see their team’s ability to safely disagree as a sign of strong relationships and trust. Ultimately, retaining talent and delivering the best work should guide us — this is what makes us worthy of our positions, not the absence of mistakes.