Your boss has a terrible idea. They are all excited about it and are about to kick off a workstream for it. You see some major flaws. 9 out of 10 people will fumble this situation in one of two ways. The first way is that they will say nothing. Afraid to confront their boss, many people will say nothing and let the bad idea proceed and gain traction while the flaws remain. The project then struggles, meaning you and your career struggle and slow down with it. The second way people fumble this situation is by calling out their boss directly, saying, “Here’s why the idea won’t work…” This kind of outright challenge forces their boss into a defensive position. They push their project through in order to not appear weak, so you end up working on the bad project anyway AND you have just made an enemy out of your boss. Not good. So, how should you go about raising your concerns in this situation? You need to challenge the idea, but you also need to be respectful and effective in your communication. I got a question on exactly how to do this in a coaching session, and I want to share my answer with you all. The question was, “When you’re challenging senior leaders (SVP and VP) or surfacing an uncomfortable truth, how do you balance that impact with respect?” You can read my answer in this week’s newsletter: https://buff.ly/Us5Wnls I go over how (and when) to challenge your leaders in a way that moves the best ideas forward and builds your reputation rather than destroying it. Readers - Let me know in the comments how you handle these situations.
And that’s how and why Agile was invented. 😄 Jokes aside, challenging someone’s idea when they’re at their peak excitement rarely goes well — especially with SLT. If possible, I’d rather ask for a follow-up discussion so everyone gets time to absorb the context, come back with sharper questions, suggest better alternatives, or think through ways to validate the idea with minimal effort. If a pushback has to happen in the moment, then I’d still engage with the same level of enthusiasm — but through questions that help uncover gaps, backed by past experiences or anecdotes on why it may not work as expected, while staying open to a deeper dive on how the idea could still be approached effectively.
In my mind there’s another strategy to deal with this. Using “difficult conversations” strategy is needed when you are providing a negative feedback, and it works well. But what if instead you would provide a constructive feedback? You can influence using an approach from “never split the difference” and ask a question that would force the leader spending their mental energy on solving, and as part of that adopting your position. I found it much more effective from my experience. In more general, if the leadership is not open for feedback, or treats it from defensive position, that’s probably something to think about on itself, and apply some “managing up” strategies on proactively managing those situations (which includes changing you job in extreme cases).
The moment your boss senses you’re slowing momentum, your logic stops registering as analysis and starts registering as resistance. “Here’s why this won’t work” - Fails. Once leadership publicly signalled certainty, the conversation is no longer about truth. Now your risk signal reads as hesitation after commitment has already been made. The conversation no longer asks: “What is true?” It asks: “Can I still stand behind this without looking uncertain?” You’re left with two choices: 1/ Challenge the idea. 2/ Protect momentum …while forcing the assumptions to survive scrutiny. Every risk signal you raise trains leadership on how to read your judgment. They either experience you as: judgment under uncertainty or as the person who slows momentum.
Most engineers I work with choose door one. Say nothing. Let it proceed. Not because they don't see the flaw. They see it clearly. They have already run the numbers three different ways. The problem is they think the flaw is the message. It is not. The real message is: I want this to succeed. Here is what I am seeing that could get in the way. Same data. Same logic. Completely different conversation. The engineers who learn to make that shift stop watching their best thinking get buried and start being the person their leader calls before the workstream even kicks off. Curious whether you see engineers defaulting to silence more than other roles. That is the pattern I notice.
I agree, that’s a really tricky situation. My take: 1) never fix your boss's thinking during the meeting. They will never admit it’s a bad one in front of the team. 2) ask clarifying questions about the idea to make the gaps emerge without pointing fingers. 3) if the idea remains on the table, suggest to test it in a small use case before full team commitment. What do others think?
Seems like dancing around an ego. Not really my style. If your idea is bad its bad. Take it like an adult and thank me for letting you know. Or push it through because of your pride and watch your bad idea fail? Im supposed to sugar coat it because you cannot take constructive criticism? Or you're the boss so clearly my advice isn't good and your idea is great. Tell them and let the fail. Only way to learn humility. Sure won't be a jerk about it but im not putting energy in not hurting your ego. Sometimes it shuts down entire businesses.
Strong leaders value, and seek, feedback and opposing viewpoints as this helps strengthen the idea and approach. A direct challenge is never going to be well-received. Seek to understand, ask questions, clearly align on what the idea is trying to solve and what success looks like. This dialogue will conversationally provide opportunities to curate the approach.
What you're describing as emotional intelligence is often actually a structural problem. When decision rights aren't explicit, any upward challenge reads as a political move rather than an operational input. The fumble happens before the conversation starts. Once the authority map is clear, knowing when and how to push back stops being a soft skill and becomes a straightforward call.
The reframe that's saved me more often than anything: don't challenge the idea, interrogate it with them. "Walk me through how we'd handle X if it comes up" puts you on the same side of the table, working the problem together, rather than across from them defending turf. The flaw surfaces on its own — and crucially, they get to be the one who spots it. People defend ideas they're cornered on. They abandon ideas they talked themselves out of. Your job is often just to ask the question that lets them do the second thing.