Early in my career, I used to avoid playing devil’s advocate. It always felt a bit negative, like I was slowing things down or questioning momentum when everyone else was ready to move forward. But after a few projects didn’t go the way we expected, I started noticing a pattern that was hard to ignore.
The decisions that failed weren’t the ones we spent too much time debating. If anything, those usually turned out fine. The ones that caused real problems were the ones nobody really challenged. Everyone agreed in the room, the plan sounded reasonable, and we moved ahead with a lot of confidence. It felt smooth in the moment. And then a few months later, the cracks would show up. Usually in places we could have spotted early if we had just asked slightly harder questions.
Since then, I’ve tried to change one small habit. Before committing to anything meaningful, I take a step back and try to stress-test the idea a bit. Nothing formal, just forcing myself (or the team) to answer a few uncomfortable questions.
Things like: if this fails in six months, what probably caused it? What assumption here are we taking for granted? What would someone who strongly disagrees with this say?
It’s not about being pessimistic or slowing things down for the sake of it. It’s more about creating a moment where it’s okay to surface doubts before they become expensive problems later. I ended up building a small internal tool to make this easier to run consistently, but I’m less interested in the tool itself and more curious about how others approach this.
Do you actively try to challenge decisions before committing, or do most of those questions only show up once things start breaking?
I’m a solo maker and I built this after repeatedly running into the same problem in planning sessions. No matter what framework we used: RICE, ICE, voting, scoring, nothing actually got removed. Everything had a solid justification. The roadmap just kept growing.
It wasn’t a prioritization problem. It was a subtraction problem. So I tried reversing the rule. Instead of asking people to vote on what to keep, I made everyone cut three items. You couldn’t move forward until something was actually removed.
The tone of the conversation changed immediately. It forced real trade-offs instead of polite agreement. I turned that exercise into a small web tool called Less Is More. It’s intentionally simple, no accounts, no scoring system, no analytics. Just structured subtraction. I’m curious how others here handle “priority inflation.” Do you enforce caps? Time box initiatives? Something else?
Happy to clarify anything here. This isn’t meant to replace roadmaps or frameworks. It’s more of a conversation trigger something to surface disagreement early instead of discovering it weeks later in execution.
Curious how others here handle prioritization when multiple stakeholders are all “right” at the same time.
I’ve seen plans fail that were technically solid. Clear goals, reasonable timelines, capable people and full agreement in the room.
Yet execution slowed weeks later. Not loudly. Quietly.
What I eventually realized was missing wasn’t alignment or process. It was confidence. People had agreed, but they didn’t fully believe the plan would work. After decisions are made, doubt rarely gets voiced. It feels late, political or unproductive. That doubt goes underground and shows up later as hesitation, delay or quiet disengagement.
I’m a solo maker and built a very small experiment to surface that signal early, essentially a lightweight confidence check before execution. I’m less interested in the tool itself and more curious about the practice.
How do you handle this? Do you explicitly check confidence before committing?
Or do you rely on signals that appear during execution?
Would appreciate perspectives from people who’ve lived this.
Fair point and I agree. The intent isn’t to make anyone “die on a hill” or perform loyalty. What I kept running into was people accepting decisions without really feeling ready to own or back them in execution. That gap usually only showed up later as delays or fuzzy ownership. The wording is one way to surface that but the goal is clarity, not confrontation. Appreciate you calling it out.
After meetings, everyone agreed but execution still drifted. People had different interpretations of the same “yes.” I built Same Page, a 60 seconds check where everyone independently writes what was decided, what happens next, and what risks remain.
Answers are grouped by meaning so misalignment shows up immediately.
It takes about 60 seconds.
No accounts.
Free to use.
I’m sharing this to learn:
- Does this problem resonate with you?
- Where would this feel most useful (or unnecessary)?
- What would you change about the questions or flow?
Would love feedback on whether this problem resonates.
Maker here. Built this after repeatedly mistaking agreement for commitment in real projects. It’s free and intentionally minimal. Happy to answer questions or hear where this breaks down in real teams.
We kept running into the same issue after decisions where everyone agreed in the meeting but execution slowed later. The problem wasn’t disagreement, it was unclear commitment.
All In is a small, free tool I built to quickly check whether people actually stand behind a decision or are quietly unsure.
After a decision, participants answer a single question independently. You see where support is solid, where it’s weak and where follow up is needed.
No accounts, no setup, no facilitation overhead.
It’s intentionally simple. Meant to be used right after decisions, before silence turns into delay.
Before you write any content, you want to know what questions people ask on Google, Who is ranking on the top 10 and what other keywords do they rank for?, and 'Google Suggestions' for the phrase. So I created a tool that does that based on all the interest I received.
The decisions that failed weren’t the ones we spent too much time debating. If anything, those usually turned out fine. The ones that caused real problems were the ones nobody really challenged. Everyone agreed in the room, the plan sounded reasonable, and we moved ahead with a lot of confidence. It felt smooth in the moment. And then a few months later, the cracks would show up. Usually in places we could have spotted early if we had just asked slightly harder questions.
Since then, I’ve tried to change one small habit. Before committing to anything meaningful, I take a step back and try to stress-test the idea a bit. Nothing formal, just forcing myself (or the team) to answer a few uncomfortable questions.
Things like: if this fails in six months, what probably caused it? What assumption here are we taking for granted? What would someone who strongly disagrees with this say?
It’s not about being pessimistic or slowing things down for the sake of it. It’s more about creating a moment where it’s okay to surface doubts before they become expensive problems later. I ended up building a small internal tool to make this easier to run consistently, but I’m less interested in the tool itself and more curious about how others approach this.
Do you actively try to challenge decisions before committing, or do most of those questions only show up once things start breaking?