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Run a weekly pipeline review in 30 minutes

Spot stuck and risky deals in minutes, then spend the meeting on the three deals that matter.

Sales managerFounder⏱ 30 minDifficulty: MediumUpdated 2026-11-09
What you'll have at the end

A list of risky deals with reasons, a short summary by rep and stage, three deals to discuss with questions, and a recap for the team.

Tools you need

Export open deals. Pipedrive, Salesforce or any CRM works.
Read the export, flag risks and summarise.
When you want forecasting and risk alerts running all the time.

Step-by-step workflow

1

Export your open deals

HubSpot Sales Hub

Export all open deals with deal name, owner, stage, amount, close date, last activity date, next step and date created. Remove contact names and emails you don't need before sharing the file with an AI tool.

2

Flag the risky deals

ChatGPT or Claude (with file upload)

Upload the export and ask the assistant to apply the same rules every week, so the review is consistent.

Prompt · Step 2
Attached is our open pipeline export. Today is [DATE].
Flag every deal that matches one or more of these rules, and say which:
1. no activity in the last 14 days
2. close date is in the past
3. no next step, or the next step has no date
4. in the same stage for more than [X] days
5. amount above [AMOUNT] and closing this month
Output a table: deal, owner, stage, amount, close date, flags. Sort by amount, largest first. Don't change or invent any values.
Free Companion Spreadsheet (.xlsx)

Pipeline review sheet

A spreadsheet where you paste your CRM export and risky deals are flagged automatically, plus a meeting agenda and every prompt from this workflow.

3

Summarise by rep and stage

ChatGPT or Claude (with file upload)

This gives you the shape of the pipeline before you look at single deals.

Prompt · Step 3
Using the same export, give me:
- total open pipeline and number of deals, by stage
- pipeline by owner, with how many of their deals are flagged
- deals closing this month: total amount, and how much of it is flagged
Keep it to one short table per item, then 3 bullets on what stands out.
4

Pick 3 deals and prepare questions

ChatGPT or Claude (with file upload)

Don't review every deal in the meeting. Pick the three where a decision this week changes the outcome.

Prompt · Step 4
From the flagged deals, pick the 3 where a manager conversation this week is most likely to change the outcome. Explain why in one line each.
For each, give me 3 coaching questions to ask the rep. Questions should help the rep think, e.g. "What has to be true for this to close by the 30th?", not accuse.
5

Send the recap

ChatGPT or Claude (with file upload)

Close the loop in writing so everyone knows what changed and what's expected.

Prompt · Step 5
Write a short recap of today's pipeline review for the sales team, based on these notes: [PASTE YOUR MEETING NOTES]
Include: pipeline this month in one line, the 3 deals we discussed with the agreed next step and owner, and one thing the team should do differently this week.
Under 150 words, direct and encouraging.

Turn this into a system

Once this workflow is working manually, connect it into an automated GTM playbook or stack.

Playbook · Agentic Operations
Revenue Forecasting & Deal Slippage Risk Detection

Evaluate pipeline engagement, meeting frequency, and email velocity to flag at-risk deals and support quarterly forecasting.

Open playbook →
Reference Stack · $590 – $680 / mo base software
The HubSpot AI-Native Stack

Augment your HubSpot instance with multi-source waterfall data enrichment, multichannel outreach, and customer retention telemetry.

Explore stack →

Want this running for you?

GPTify builds it on your tools, with a fixed scope and price.

CRM & Follow-up Automation →

Frequently asked questions

Is it safe to upload our pipeline to an AI tool?

Check your company's AI policy and use a business plan where your data isn't used for training. Remove contact details and anything you don't need for the review.

Why the same rules every week?

Consistent rules make trends visible. If you change them each week, you can't tell whether the pipeline got healthier or the rules got looser.

What should count as "stuck"?

Start with 1.5 times your average time in that stage. Adjust once you have a few weeks of data.

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