# Pipeline Coaching 1:1 Conversation Guide

> The exact questions to ask in a weekly pipeline 1:1 so you're coaching the deal forward in real time, instead of doing a status readout of numbers that already happened.

Free guide for sales managers. Topic: [Pipeline, Deal Management & Forecasting](https://www.peerlab.ai/library/topic/pipeline-deal-management-forecasting/). Published by PeerLab in the [Sales Enablement Resource Library](https://www.peerlab.ai/library/). Source: https://www.peerlab.ai/library/pipeline-coaching-1on1-guide/

## How to use it

Run this every week, picking 3-4 priority deals rather than the whole pipeline, and always close with the written commitment recap, it's what turns the 1:1 from a status update into accountability.

## What's inside

- The prep checklist to run before every pipeline 1:1
- The opening question that sets a coaching tone, not an audit tone
- Stage-specific coaching questions for New/Early, Qualification, Proposal/Late, and Stalled deals
- 3 pipeline-generation questions to ask every week, not just at quarter-end
- The single question that catches sandbagged or inflated deals
- A closing commitment script with a written follow-up format

**The shift this guide makes:** a pipeline review asks "where's this deal at?" A pipeline coaching conversation asks "what needs to happen this week to move it, and what's in your way?" Use the questions below, not a report screen-share, to drive the 1:1.

## Before the 1:1: manager prep (5 minutes)

- [ ] Pull the rep's pipeline sorted by close date, then flag anything with no activity in 10+ days
- [ ] Note any deal that has slipped a close date more than once
- [ ] Pick the 3-4 deals that matter most this week (biggest, most at-risk, or closest to close), you will not review the whole pipeline every week
- [ ] Write down one pattern you've noticed across this rep's deals over the last month (e.g., always stalls after proposal, always under-multithreads)

## Opening question (sets the tone)

> "Before we get into individual deals, what's the one thing that would make this week a win for your pipeline?"

This puts the rep in the driver's seat and tells you where their head is at before you start probing.

## Stage-specific coaching questions

### New / Early-stage deals
- "What made this worth qualifying, what problem did they actually describe?"
- "Who have you talked to so far, and who haven't you reached yet that you need to?"
- "What's your plan to get to the economic buyer, and when does that happen?"
- "If this doesn't move in the next two weeks, what's the reason likely to be?"

### Qualification-stage deals
- "What's the compelling event here: and did they tell you that, or did we infer it?"
- "Walk me through their decision process as you understand it right now."
- "What's the biggest open question you still can't answer about this deal?"
- "Who else needs to be in the room that isn't yet?"

### Proposal / Late-stage deals
- "What did they say, in their words, when you sent the proposal?"
- "What's the one objection or risk that could still kill this?"
- "Is the close date on the record their date, or the date we want?"
- "What's the mutual close plan look like: do they have it too, or only we do?"
- "If I called your champion right now, what would they say is left to figure out?"

### Stalled / at-risk deals
- "When was the last time the prospect, not you, took an action on this deal?"
- "What changed since this looked healthy? Be specific."
- "Is this still real, or are we holding onto it out of hope?"
- "What's the one thing you're going to do differently this week versus last week on this deal?"

## Weekly pipeline-generation questions (ask every 1:1, not just at quarter-end)

1. "What's your pipeline coverage looking like against this month's number: are we ahead, behind, or on pace?"
2. "Where is your next deal coming from if [biggest deal] slips?"
3. "What's one prospecting action this week that wasn't just 'more of the same'?"

## The sandbagging / inflation check

> "If you had to bet your own money on this closing by [date], would you still call it [Commit / Best Case]?"

Asked plainly, most reps will self-correct the category on the spot: use their answer, not the CRM stage, to set the real forecast number.

## Closing the 1:1, commitment script

> "So to recap: on [Deal A] you're going to [specific action] by [date]. On [Deal B], I'm going to [manager action, e.g., join the next call / loop in our exec]. And this week's pipeline-generation target is [X new qualified opportunities]. Anything I'm missing before we close?"

Write this down and open next week's 1:1 by checking it, not by starting fresh.