5 Questions I Ask Before I Bend a Rule
When red tape feels like handcuffs I check my map and pick my moment
👋 Hey it is Jimmy. One afternoon I watched our team stall for 2 full days just to swap a homepage logo. Meanwhile a customer-facing bug raged in production. We needed action not approval. That moment flipped something for me. Since then whenever the rulebook slows me down I run these 5 questions in my head before I rewrite the rules
Read time: 6 minutes
Where we are headed
This is not about being careless. This is about being clear and responsible while still moving forward. These 5 questions help me lead with speed and conviction when the process tells me to pause
1 “What was this rule meant to solve”
Start with purpose before you start bending anything
Some rules were written in response to one painful incident 5 quarters ago. That moment passed but the rule stayed forever. I ask what the rule was created to fix and whether that threat is still real
How I handle it
I trace the rule back to its origin I ask who created it and why then check if that reason still applies
🚫 “We need 3 approvals before anything goes live.”
✅ “That rule saved us from a bad rollback last year. But this time we are patching a typo. I will take the risk and ship”
2 “Who gains and who loses if I bend it”
Every rule you bend helps someone and costs someone else
Skipping a process might help my deadline but break someone else's calendar. I look past my task list. Who does this decision serve and who might it put at risk
How I handle it
I map the benefits and tradeoffs and ask which matters more right now
🚫 “No one will notice if I push this through.”
✅ “The marketing team hits their timeline. The legal team is still in the loop. My team stays out of burnout. That is a win across the board”
3 “Am I ready to own the fallout”
You do not get to bend the rule and dodge the blame
The moment I skip a step I raise my hand as the person accountable for the outcome. That is the price. Speed in exchange for responsibility
How I handle it
I write the apology note in my head before I take action to make sure I can live with the consequences
🚫 “They will not know if something goes wrong.”
✅ “If this breaks I will take the heat in the team meeting and own the fix. No excuses”
4 “Is there a quieter way to bend the rule”
Not every act of judgment needs to be loud
Some rules deserve open challenge. Others need quiet adjustment. I ask myself if I can move around this rule while still keeping trust intact
How I handle it
I follow all the meaningful steps. I skip only what blocks progress and I leave a record in case someone asks later
🚫 “Let us escalate this to leadership.”
✅ “I will explain my decision after we land the release. People will see the logic when they see the result”
5 “What is the next rule I should bend”
If 1 rule no longer serves us there are likely more
This is not about breaking the system. This is about evolving it. Each smart exception is a sign that the rule needs an update
How I handle it
I keep a list of the blockers we had to bypass then bring them back later to fix the root cause
🚫 “Let us act like that never happened.”
✅ “It worked. It helped. Let us build it into how we work from now on”
Summary – here is what to do next
“Ask what the rule was originally made to solve”
“Think through who wins and who loses if you break it”
“Make sure you are willing to take the heat if things go wrong”
“Keep track of what steps you followed and be ready to explain your choice”
“Look for patterns and update the system where needed”
Let me know which one you are going to try first. Talk soon
—Jimmy