Pipeline Coaching 1:1 Conversation Guide

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.