Strategies for Handling a Disagreement with a Superior

"I have a bone to pick with you." That's how I opened a recent conversation with an executive. Spoiler: It didn't land well. 🫠 (𝘐’𝘮 𝘴𝘸𝘦𝘢𝘵𝘪𝘯𝘨 𝘴𝘩𝘢𝘳𝘪𝘯𝘨 𝘵𝘩𝘪𝘴 𝘰𝘯 𝘓𝘪𝘯𝘬𝘦𝘥𝘐𝘯, 𝘣𝘶𝘵 𝘐 𝘣𝘦𝘭𝘪𝘦𝘷𝘦 𝘪𝘯 𝘯𝘰𝘳𝘮𝘢𝘭𝘪𝘻𝘪𝘯𝘨 𝘮𝘪𝘴𝘵𝘢𝘬𝘦𝘴, 𝘴𝘰 𝘩𝘦𝘳𝘦 𝘪𝘵 𝘨𝘰𝘦𝘴.) I came in with a strong point of view, ready to advocate for my position. It was in opposition to a decision she made but that could still be changed. "She'll appreciate that I have conviction!" I thought confidently. But instead of sparking a productive debate, I miscalculated. The executive gently stopped me. She offered advice I'll never forget and have been thinking about days since: "Consider the context around how I made this decision." In that moment, I realized I'd skipped a crucial step: curiosity before challenge. Here's what I learned about challenging up, why my approach was all wrong, and what you can learn from my mistake. This advice is great if you're a current or aspiring #chiefofstaff but also applicable to anyone working to improve their persuasion skills. 1️⃣ 𝗟𝗲𝗮𝗱 𝘄𝗶𝘁𝗵 𝗰𝘂𝗿𝗶𝗼𝘀𝗶𝘁𝘆 𝗯𝗲𝗳𝗼𝗿𝗲 𝗰𝗼𝗻𝘃𝗶𝗰𝘁𝗶𝗼𝗻. Instead of jumping in with a firm stance, start with, "I'm curious how you landed on this decision." This simple shift creates space for dialogue. It might even change your perspective before you voice your challenge. (In my case, as soon as I had more context, I changed my tune. If only I had led with curiosity...) 2️⃣ 𝗞𝗻𝗼𝘄 𝘄𝗵𝗲𝗻 𝘁𝗼 𝗯𝗿𝗶𝗻𝗴 𝗮𝗻 𝗶𝗻𝗳𝗼𝗿𝗺𝗲𝗱 𝗼𝗽𝗶𝗻𝗶𝗼𝗻 𝘃𝘀. 𝗮 𝘀𝘁𝗿𝗼𝗻𝗴 𝗣𝗢𝗩. Here's how I think about the difference: An informed opinion means you've thought critically but remain open to learning; a strong point of view (POV) usually means you've already decided the best course of action and are looking for buy-in. Generally, if the decision is in your domain/area of expertise, it's good to have your recommendation (POV) ready. For broader strategic decisions, almost always seek to understand first. 3️⃣ 𝗙𝗿𝗮𝗺𝗶𝗻𝗴 𝗺𝗮𝘁𝘁𝗲𝗿𝘀 — 𝗮 𝗹𝗼𝘁. Compare "I disagree with this approach" to "Here's something I've been thinking about. Could I share my perspective?" Both convey your conviction, but one does it WAY more effectively. The former shuts down dialogue; the latter invites discussion. This experience taught me an important truth: The most effective persuaders aren't just those with strong convictions. They're the ones who master the dance between inquiry and advocacy. 💃 And even in an AI-driven world, persuading other humans will continue to be an in-demand skill. Whether you're early in your career or sitting at the executive table, understanding this balance can transform how your points are received. It might even change some strong opinions you thought you had. It did for me. (𝘛𝘩𝘪𝘴 𝘱𝘰𝘴𝘵 𝘸𝘢𝘴 𝘸𝘳𝘪𝘵𝘵𝘦𝘯 𝘣𝘺 𝘢𝘯 𝘰𝘷𝘦𝘳𝘵𝘩𝘪𝘯𝘬𝘪𝘯𝘨 𝘩𝘶𝘮𝘢𝘯, 𝘯𝘰𝘵 𝘈𝘐.)

What’s the line between productive pushback and problematic refusal to disagree and commit? Especially when it’s your manager you disagree with? I’ve seen this debate go in both extremes. On the one end, you have people who push so hard, it becomes a performance issue. They’re so focused on proving their manager wrong that they start bottlenecking processes instead of realizing that either: 1. They’ve become the problem, or 2.This isn’t the right place for them any more. On the other end, you have people who are so eager to be agreeable, they never push back at all — even when they can see a million red flags signaling that the team is headed in the wrong direction. So what‘s the right answer? Here’s what’s worked for me in the past: 1. Be clear about your opinion, but be equally clear about the severity of your pushback. This can be a simple, “I personally wouldn’t take this approach, but on a scale of 1 - 5, the risk of doing this feels like a 2, so not the hill I’m willing to die on…” or a more emphatic, “I think this is a mistake. I am meaningfully concerned this will cause X problem. Ultimately, this is your decision to make, and I’m prepared to disagree and commit, but I want to be clear about why I think we shouldn’t do this.” 2. Be open to experimenting, but be quick to communicate if it isn’t working. “I know you asked me to try X process despite my reservations. I’m 2 weeks in, and candidly, it’s not working. I can keep this going for another few weeks, but transparently, I think we need to pivot. I’d love to walk you through where I’m running into issues and how I think a different approach could solve this.“ 3. Get clear on your deal breakers and be direct in asking about your options. This one’s important — I’ve seen far too many people make themselves sick trying to win an argument that wasn’t actually that important. I’ve also seen people run themselves into the ground fighting important, but losing battles instead of accepting the hard truth and redirecting their energy more productively, ie finding a job better suited to their ways of working. I’m not ashamed to admit I’ve fallen victim to both. And I can tell you that: 1. Life is a whole lot better when you stop treating every disagreement like a fight to the death, and 2. As hard as it can be to realize your team is no longer right for you, stepping away to find the right team that *is* is 1,000% worth it. Try: “I’ve realized X is a deal breaker for me, and I want to know if you see a world in which this realistically changes any time soon.” Sadly, I was far less articulate in working through my thoughts on this week’s podcast, but you know what? That’s okay. A little word vomit is good for the soul. And honestly, it helped me get to this point. So if you want to watch me awkwardly fumble my way through this thought process while Roxanne Bras Petraeus provides a much needed reality check and shines like the low ego rockstar she is, check it out. Link below.👇🏼

Want to stop triggering defensive reactions in critical conversations? Brain science reveals a simple technique that's transforming how top companies communicate: As an executive coach, this is the first thing I teach founders who are struggling with critical relationships. Why? Because it's consistently the most powerful tool for transforming toxic communication into productive dialogue. When you're fighting with your co-founder, your brain's threat response system activates. This shuts down the exact parts of your brain needed for effective communication. But there's a way to keep those neural pathways open. It's called speaking inarguably - using only facts that can't be disputed. Instead of "You don't care about this company" (judgment) Say "When you missed our last three meetings, I felt worried about our partnership" (fact) The first triggers defense mechanisms. The second creates psychological safety. There are two types of inarguable statements: • External facts: Observable behaviors, metrics, documented events • Internal facts: Your sensations, emotions, thoughts ("I feel frustrated") I've seen this technique help to transform toxic co-founder relationships into thriving partnerships more times than I can count. Here's how to start: 1. Pause before responding to emotionally charged situations 2. Strip away interpretations, focus only on observable facts ("You arrived 15 minutes late" vs "You're disrespectful") 3. Own your internal experience ("I felt anxious when that happened" vs "You're stressing everyone out") 4. Practice radical honesty about your feelings (This builds trust faster than pretending to be perfect) The hardest part? Letting go of being right. Your interpretations might feel true, but they're just stories you're telling yourself. This is where inner work meets leadership. When you master this, difficult conversations become growth opportunities. Your leadership emerges naturally from who you are, not who you think you should be.

What do you do when you disagree with your boss?   Somebody told me the other day, “Tom, you don’t remember what it’s like to have a boss and to disagree with him since it’s been so long for you.” In fact I’ve had several bosses along the way, and I remember vividly what it was like to disagree with them. In one particular episode, my boss – let’s call him Henry -- was on the cusp of a call I knew was the wrong one for the business and our team. But he was torn and reluctant to make the call. We all waited breathlessly for the smoke signals to clear the roof of the Vatican, the final signal that he’d finally made up his mind.   I think there are four things you can do when you disagree with your boss.   1.     You can stay mum, keep your dissent to yourself, and wait like a lamb for the hammer to drop. It’s likely a job-preserving move since too many bosses recoil when underlings dare take a position that strays from their party line. But if you do this, I worry it’s ultimately a career-limiting move because it deprives you of the agency you need to have if you’re going to grow and learn and level up over the course of your career. 2.     You can take the opposite course and tell your boss, “Look, I understand your decision, but let me diagram all the ways and reasons YOU’RE WRONG.” That's also likely a career-limiting move because it negates the possibility that your boss might know something you don’t yet understand. I’ve been there many times: a boss knew something I’d yet to appreciate, but in my zeal to be right – or perhaps just to indulge my own sense of righteousness – I shut down intellectually and resisted the opportunity to learn. Maybe my boss didn’t have the vocabulary to explain it to me properly at the time; perhaps I wasn’t in a frame of mind to receive it. 3.     You can grin-f*#k your boss and say, “Sure thing, boss, I’ll get ‘er done,” and then quietly proceed to subvert her decision. If you’re artful, you’ll enroll colleagues in a campaign to put pressure on the boss and let her know that she’s about to screw the pooch.   The fourth path is to Disagree and Commit. In my own situation years ago with Henry, I decided to let him know what I thought we needed to do. I marshaled all the facts, data and logic within reach to persuade him.   He made the call, which is exactly what bosses are supposed to do. I put my back fully into doing what I believed was the wrong course of action. Yep, that's what you do sometimes when you're part of a team. There wasn’t a moral dimension to it – it was just a bad business call. Predictably, it ended in failure and a stomach full of acid for everyone. I wrapped it up, exited six months later, and started building the next thing. Life is long, after all, and careers are ripe with possibility. Which is to say, if you disagree with your boss and he keeps making bad calls, you can always choose another course *after* doing everything you can to implement his decisions. #DisagreeAndCommit