Work Through a Problem and Decide Whether to Escalate
Think through a work issue step by step, decide whether to handle it or escalate, and draft a clear summary for your manager.
Overview
You have a work problem and you are not sure what to do with it. Handle it yourself? Loop in your manager? This template connects Slack, Gmail, and Google Docs so your AI assistant can walk you through the issue step by step, help you figure out the right call, and -- if you decide to escalate -- draft a clear summary your manager can act on in under a minute.
How it works
Describe the issue you are facing. The AI asks clarifying questions one at a time: what is happening, what you have already tried, what resolved would look like. Then it helps you explore options you could handle yourself. If you decide to escalate, it drafts a short summary with the issue, context, your proposed solution, and what you need from your manager. Send it directly via Slack or Gmail, or save it to Google Docs to refine first.
Who this is for
Anyone who hits a work blocker and wants to think it through before reacting. Especially useful for individual contributors navigating process, priority, or resource issues where the line between "I can handle this" and "my manager needs to know" is unclear.
Suggested prompt
I have a work issue I need to think through. Here is what is going on: [describe the situation]. Help me clarify what is really happening, explore whether I can handle this myself, and decide if I need to escalate to my manager. If I decide to escalate, draft a short summary I can send them with the issue, what I have tried, my proposed solution, and what I need from them.
Frequently asked questions
What kind of work issues is this for?
Any work-related issue where you are unsure whether to handle it yourself or bring in your manager: process blockers, priority conflicts, resource constraints, decisions above your authority, interpersonal friction, or unclear ownership. It is not for career coaching, performance goals, or feedback conversations.
Does it just tell me to escalate everything?
No. The workflow walks you through clarifying the issue, exploring what you could do on your own, and then making the call yourself. Many people realize they can handle it once they think it through. Escalation is only one outcome, and the template helps you make that decision with more clarity.
What does the escalation summary look like?
A short, scannable draft you can copy into Slack or email. It includes: what the issue is and why it matters, what you have already tried, your proposed solution, and what you need from your manager. Your manager should be able to grasp the situation and respond in under a minute.
Can I save the summary instead of sending it right away?
Yes. The draft can be saved to a Google Doc if you want to refine it before sending, or sent directly to Slack or Gmail when you are ready. You control when and how it reaches your manager.