§ 02.1Leadership field guide

The Sales Leader's Field Guide

Three jobs decide whether a sales team hits its number: the pipeline it builds, the people who work it, and the forecast the leader puts their name to. This guide gives you rules, questions and working tools for each, plus a weekly rhythm that ties them together.

For first- and second-line sales leaders · teams of roughly 4–12 sellers

01Pipeline

Shape the pipeline. Don't just inspect it.

A pipeline is a portfolio of bets. Most reviews ask whether there is enough of it. The better question is whether it is the right mix: real deals, at the right stage, old enough to close and young enough to still be alive.

Define stages by what the buyer has done

Stages built on seller activity (“demo delivered”, “proposal sent”) measure effort. Stages built on buyer action measure progress. Every stage should have an exit test that a skeptical peer could check from the CRM record alone.

StageExit test: the buyer has…Evidence in the recordTypical stall
1 · IdentifiedAgreed to a first conversation about a named problem.Meeting held; the problem written in the buyer's words.Interest with no problem attached.
2 · QualifiedConfirmed the problem has a cost, an owner and a reason to act this period.Owner named; cost estimated; trigger event and date."Nice to have" with no date.
3 · ValidatedAgreed your approach solves it and named who else must agree.Decision group listed; success criteria written down by the buyer.One enthusiastic contact, nobody else.
4 · Business caseSeen pricing and accepted the value case internally.Proposal sent; budget source confirmed; economic buyer engaged.Price is "under review" for weeks.
5 · Commit to buyAgreed a dated plan through signature, including legal and procurement.Mutual close plan; paper process started; signer named.Close date moves without a reason.

Rename the stages to match your CRM. Keep the exit tests.

Five hygiene rules worth enforcing

  1. 01No next step, no deal. Every open opportunity carries a dated next step that the buyer has agreed to. A step only the seller has planned does not count.
  2. 02Two pushes and it is re-qualified. When a close date moves twice, the deal drops back a stage until the buyer gives a new reason and a new date.
  3. 03Age limits per stage. Set a maximum days-in-stage at roughly 1.5× your median for that stage. Anything past it is reviewed or closed out.
  4. 04Close it lost on purpose. Treat a clean “closed lost, reason recorded” as good work. Inflated pipeline protects the seller’s feelings and wrecks the forecast.
  5. 05Amounts follow evidence. The value on the record matches the last number the buyer has seen. Upside lives in a note, not in the amount field.

The numbers that tell you what is really happening

MetricWhat it tells youWarning sign
CoverageWhether there is enough pipeline for the period at your real win rate.Raw coverage looks fine but half the deals have no next step.
CreationWhether next period will have enough pipeline.Weekly creation below target for three weeks running.
Stage conversionWhere deals die.One stage converts far worse than the rest, team-wide.
Days in stageWhether deals are moving or parked.Median days in stage rising quarter on quarter.
Win rateHow good the pipeline is, not just how big.Win rate falling while pipeline grows.
Average deal sizeWhether sellers are chasing the right accounts.Size drifting down as sellers fill the pipeline with easy small deals.

Build pipeline every week, not every quarter

Pipeline created this quarter closes next quarter or the one after. A dry month of prospecting shows up as a missed number months later, when it is too late to fix. Track creation weekly against a simple target:

Weekly creation target = next period’s target ÷ win rate ÷ weeks in the period

With a $1.2M quarterly target, a 25% win rate and a 13-week quarter, the team needs to create about $370K of qualified pipeline every week. Split it by seller and by source, and review it with the same seriousness as the forecast.

TOOL 01

Pipeline health check

Raw coverage flatters a weak pipeline. This check discounts deals with no agreed next step and deals that have gone stale, then compares what is left with what you need at your real win rate.

Coverage needed

3.6×

Raw coverage

4.0×

Healthy coverage

2.2×

Healthy pipeline short by

$1.20M

Result · Looks fine, isn't

Raw coverage of 4.0× looks enough, but only 2.2× survives the next-step and age checks. Fix the records before you trust the number.

Run the pipeline review as a portfolio review

Walking every deal in order turns a pipeline review into a recital. Review the shape first, then go deep on the few deals that change the picture.

TimeAgenda item
10 minShape. Coverage by period, stage mix, aging, and creation versus target. Where is the pipeline thin?
20 minThree deals that matter most. The largest, the most at risk, and the one the seller is least sure about. Use the deal questions in section 02.
10 minCleanup. Deals to close out, re-stage or re-date, decided in the room.
5 minCreation plan. Named accounts and actions for the coming week, by seller.
02Team

Coach the people who carry the number.

Most managers spend their week inspecting deals and call it coaching. Inspection tells you where a deal stands. Coaching changes what the seller does on the next one. You need both, and you need to know which one you are doing.

Diagnose before you coach

When a seller is behind, the cause is usually one of four things. Each needs a different response, and coaching a skill gap that is really a territory gap wastes everyone’s time.

GapWhat you seeWhat to do
SkillDeals stall at the same stage. Good activity, weak conversion.Pick one behavior. Model it, practice it, then watch them do it live. Review in two weeks.
WillActivity has dropped. Forecast calls get vaguer. Commitments slip.Ask directly what has changed. Agree weekly commitments in writing and review them every week.
TerritorySolid skills and effort, but too few accounts with a real reason to buy.Re-check account assignment and potential. Fix the patch before you judge the person.
ProcessThe whole team stalls at the same point: legal, pricing, a handoff.This one is yours. Escalate it, fix the process, and stop coaching around it.

The weekly one-to-one

Thirty minutes, same time every week, and the seller’s agenda first. Cancel it rarely; move it if you must. (Template in section 05.)

MinutesAgenda item
0–5Their agenda. What they need from you this week. Blockers you can remove.
5–15One deal, in depth. Their choice. Work it with the deal questions below. Leave with one specific next action.
15–25One skill. The behavior you are working on together. Review a recent call or email against it.
25–30Commitments. Two or three, written down, checked at the start of next week’s one-to-one.

Ten deal questions that do the coaching for you

  1. 01What happens to the buyer if they do nothing this year?
  2. 02Who loses something if this project goes ahead, and what are they doing about it?
  3. 03Who signs, and when did you last hear from them directly?
  4. 04What did the buyer say, in their own words, about why now?
  5. 05What has the buyer done in the last two weeks that they did not have to do?
  6. 06What would make this deal slip one quarter?
  7. 07Who else are they talking to, including their own team building it?
  8. 08What does the buyer's approval process look like after they say yes?
  9. 09If we lose this, what will the reason be?
  10. 10What is the one thing you could do this week that would change the outcome most?
Ask, then wait. The seller’s first answer is usually the one they have rehearsed. The second answer is the one you need.

Reviewing calls without killing confidence

  • Ask the seller to pick the moment they would do differently before you say anything.
  • Give one piece of feedback per call. A list of seven gets none of them acted on.
  • Tie the feedback to the behavior you are already working on together.
  • Say what worked first and mean it. People repeat what gets noticed.

Ramp new hires against evidence, not time

MilestoneThey can show you…You check by…
Day 30The top three problems your best customers bought to solve, explained in customer language.A ten-minute role play with you as the buyer.
Day 60A territory plan: priority accounts, why each one, and the first route in.A written plan and a 20-minute review.
Day 90Pipeline they created themselves, at stage 2 or later, with clean records.The pipeline health check, run on their numbers.
Day 180A forecast call they can defend deal by deal.Their commit list put through the commit test in section 03.

When performance has to be addressed

  1. 01Write the expectation down. Specific, measurable and dated. “More pipeline” is not an expectation; “$400K of new stage-2 pipeline by the 30th” is.
  2. 02Show the evidence. Numbers and examples, shared before the meeting so it is not an ambush.
  3. 03Offer real support. Name what you will do differently: time, introductions, deal help.
  4. 04Review on the date you set. Every time. A plan that is not reviewed tells the seller it was never real.

Involve HR early and follow your company’s process. This section is about the conversation, not the policy.

03Forecast

Call the number you can defend.

A forecast is a judgment you sign. Adding up what sellers hope for is not forecasting. The leader's job is to set strict categories, test every committed deal against them, and track how accurate their own calls turn out to be.

Four categories, strictly defined

CategoryMeaningEntry testLeader's question
CommitYou would bet your own credibility on it closing this period.Passes all five required items in the commit test."What would have to go wrong for this to slip?"
Best caseCould close this period if the remaining gaps close.Economic buyer engaged or a dated buyer event, plus a close plan in progress."Which gap closes first, and by when?"
PipelineA real opportunity, not this period.Stage 2 or later with a buyer-agreed next step."What makes it move up, and when?"
OmittedKept open, excluded from every number.Anything that fails the above."Why is it still open?"

Commit test

TOOL 02

Commit test

Tick what the record and the buyer can actually prove, not what the seller expects. The first five are required for Commit.

R = required for Commit · 4 of 7 ticked

Result · Best case

1 required test(s) still open. Name the owner and date for each before this can be committed.

Run the forecast call on changes

Only discuss what has moved since last week. Every change to a committed deal needs a reason the buyer gave, not one the seller inferred.

  • What moved in? What did the buyer do that earned it?
  • What moved out? What did we learn, and when could we have known?
  • What changed in amount or date? Who on the buyer side said so?
  • What is your call? One number, from each seller, said out loud.

TOOL 03

Forecast range

Turn categories into a floor, a call and a ceiling. Use your own track record for the two conversion rates: how much committed business actually closed in past periods, and how much best case converted.

Floor

$907.00K

Your call

$1.10M

Ceiling

$1.54M

Call vs target

91%

■ Closed■ Floor■ Call▢ Ceiling| Target

Result · Gap

Your call is $104.00K short. Hitting target needs more best case than you normally convert. Say so now, not in the last week.

Presenting your forecast upward

  1. 01The number. One figure. Not a range, not “it depends”.
  2. 02The range. Floor and ceiling, so they can see your confidence.
  3. 03The risks. The two or three deals that would move the number most, and what would move them.
  4. 04The ask. What you need from them: an executive call, a pricing decision, a resource.

Keep score on yourself

Write down your call every week of the period, then compare it with what actually closed. After two or three periods you will see your own bias: whether you call high early and correct late, or sandbag and finish ahead. Both cost you credibility with the people above you. Knowing which one you do is how you fix it.

  • Record the call, the date and the three deals that drove it.
  • Measure the gap between call and result at week 4, week 8 and the final week.
  • Do the same for each seller. Coach the bias, not just the number.
04Weekly rhythm

One week, three disciplines.

The guide only works if it runs on a calendar. This is a starting rhythm for a team of six to ten sellers. Keep the order and adjust the days.

DayMeetingLengthWhat happens
MonForecast call45 minChanges only. Each seller states a number. You submit yours by end of day.
TuePipeline review45 minShape, three deals, cleanup, creation plan for the week.
WedOne-to-ones30 min eachTheir agenda, one deal, one skill, commitments.
ThuDeal and call workAs neededJoin live calls or review recordings. Strategy sessions on the largest deals.
FriScore and plan30 minCreation versus target. Record your forecast call. Note what to coach next week.

Monthly and quarterly

  • Monthly, stage audit. Pull ten random deals and check them against the exit tests. Fix the definitions, not just the deals.
  • Quarterly, win/loss review. Speak to three lost buyers yourself. Their reasons rarely match the CRM.
  • Quarterly, territory check. Is each seller’s patch big enough to hit their number at your real win rate?
Protect Wednesday. When the quarter gets tight, one-to-ones are the first meeting to be cancelled and the one that matters most.
05Templates

Copy, paste, run.

Plain text so they drop into any doc, CRM note or calendar invite.

Weekly one-to-one

ONE-TO-ONE · [Seller] · [Date]

1. YOUR AGENDA (5 min)
   - What do you need from me this week?
   - Anything blocking a deal that I can remove?

2. ONE DEAL, IN DEPTH (10 min)
   Deal: ____________   Stage: ___   Close date: ________
   - What happens to the buyer if they do nothing?
   - Who signs, and when did we last hear from them?
   - What has the buyer done in the last two weeks?
   - Next action (owner, date): ____________________

3. ONE SKILL (10 min)
   Focus behavior: ____________________
   Example reviewed: ____________________
   What to try next time: ____________________

4. COMMITMENTS (5 min)
   - [ ] ____________________  by ________
   - [ ] ____________________  by ________
   Last week's commitments: done / not done (why)

Commit deal review

COMMIT REVIEW · [Deal] · [Amount] · [Close date]

REQUIRED (all five for Commit)
[ ] Economic buyer confirmed decision and budget directly
[ ] Buyer-agreed close plan with dated steps to signature
[ ] Legal / procurement / security steps known and started
[ ] Price and terms proposed, not in dispute
[ ] Close date tied to a buyer event: ____________

SUPPORTING
[ ] Champion has moved the deal without us in the room
[ ] No open competitor or credible "do nothing"

What would have to go wrong for this to slip?
____________________________________________
Category: Commit / Best case / Pipeline / Omitted

Pipeline review prep

PIPELINE REVIEW · [Team] · [Week of]

SHAPE
Coverage this period: ___x  (needed: ___x)
Deals with no buyer-agreed next step: ___
Deals past stage age limit: ___
Creation this week: $_____  vs target $_____

THREE DEALS
1. Largest:            ____________________
2. Most at risk:       ____________________
3. Least sure about:   ____________________

CLEANUP (decide in the room)
Close out: ____________________
Re-stage:  ____________________
Re-date:   ____________________

CREATION PLAN (by seller)
[Seller] · accounts / actions: ____________________

Forecast call log

FORECAST LOG · [Team] · [Period]

Week | Date | Closed | Commit | Best case | My call | Drivers (top 3 deals)
-----|------|--------|--------|-----------|---------|----------------------
  1  |      |        |        |           |         |
  2  |      |        |        |           |         |
 ... |      |        |        |           |         |

Final result: ________
Gap at week 4: ____  week 8: ____  final week: ____
Pattern I see in my calls: ____________________

Red flags to catch early

  • Close dates on the last day. Many deals closing on the period’s final day means the dates come from your calendar, not the buyer’s.
  • The single-threaded deal. One contact who likes you, and nobody else has replied in a month.
  • Pipeline that never closes lost. A seller with no lost deals is not winning everything. They are keeping deals open.
  • Stage 4 without a budget source. A proposal with no named budget is a quote, not a business case.
  • “They’re just waiting on legal.” Ask who in legal, since when, and what they are reviewing.
  • Creation falls off mid-quarter. It always does when everyone chases the number. It is also next quarter’s miss.
  • Forecast that only moves in the last week. The calls were hopes for eleven weeks. Test commit deals earlier.
  • Coaching that is all deal inspection. If every one-to-one is a pipeline review, nobody is getting better.

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