Playbook · Diagnostic

How to run a pipeline health review in week one

Pipeline value is the wrong headline number. Pipeline health is the right one. This playbook gives a new revenue leader, sales director or fractional CRO a structured five-day review that surfaces whether the pipeline will convert, before week two.

Audience

Revenue leader, Sales leader, Founder / CEO

Time on task

Five working days

Context

Written by Rich Evans from advisory engagements with founder-led and PE-backed SMEs. Most pipeline reviews are recitations of value by stage. This playbook replaces that with a structured assessment of coverage, concentration, velocity and stage health, scored against thresholds.

Before you start

  • Read-only CRM access with stage and close-date history
  • Last four quarters of closed-won and closed-lost outcomes
  • Stage definitions and exit criteria as currently defined
  • Quota and target by rep for the current quarter

What you will have at the end

  • A structured pipeline health memo covering coverage, concentration, velocity and stage health
  • A scored RAG verdict on each of the four dimensions
  • Three to five immediate actions for the sales leadership team
  • An honest forecast of the current quarter against the published target

The steps.

Step 01One day · Revenue leader with RevOps support

Day one: pipeline coverage against target

Coverage is the ratio of qualified pipeline to remaining target. Without coverage of three times the gap, the quarter is at meaningful risk. Without coverage of four times for a long-cycle business, the quarter is unrecoverable.

Checklist

  • Calculate qualified pipeline value (mid and late stage only) against remaining target.
  • Set the coverage threshold against your historical conversion rate.
  • Score green at three-plus, amber two to three, red below two.
  • Document the coverage by rep and by segment, not just at the aggregate.

Failure mode this step prevents

Counting early-stage pipeline in the coverage calculation. The number flatters the quarter and the leadership team is misled.

Step 02One day · Revenue leader

Day two: concentration risk

Concentration is the share of the forecast that depends on the top one, three and five deals. A quarter where the top three deals carry seventy per cent of the forecast is one phone call away from a miss.

Checklist

  • Sort the qualified pipeline by deal value and by close-date confidence.
  • Calculate the share of forecast carried by the top one, three and five deals.
  • Score green below thirty per cent in top three, amber thirty to fifty, red above fifty.
  • Identify the concentrated deals by name and assign a leadership stakeholder to each.

Failure mode this step prevents

Reporting an aggregate forecast without concentration analysis. The board hears a comfortable number; the leader knows it stands on one deal.

Step 03One day · Revenue leader with sales managers

Day three: deal velocity by stage

Velocity is how long deals take to move from one stage to the next. Stalls predict losses long before close-date slippage shows up in the forecast. Compare current cohort velocity to the trailing twelve months.

Checklist

  • Calculate average days-in-stage for each pipeline stage from the last twelve months.
  • Compare the current open pipeline against the trailing average.
  • Flag any deal more than fifty per cent over the trailing average for that stage.
  • Score velocity green if cohort within ten per cent of trailing, amber within thirty per cent, red beyond.

Failure mode this step prevents

Treating an old deal as still alive because it has not been closed-lost. Stalled deals are losses with later paperwork.

Step 04One day · Revenue leader with sales managers

Day four: stage health and exit criteria

Stage health is the discipline with which deals enter and exit each stage. Without exit criteria, stages are aspirational and the forecast is a hope. Audit a sample of deals against the current exit criteria.

Checklist

  • Pull the published stage definitions and exit criteria.
  • Sample twenty open deals across the pipeline.
  • Score each deal against the documented exit criteria for its current stage.
  • Flag any stage where more than thirty per cent of sampled deals fail the exit criteria.

Failure mode this step prevents

Accepting the CRM stage as truth. Reps move deals forward to look productive; the audit is the only check on that drift.

Step 05One day · Revenue leader

Day five: write the memo and call the forecast

The output is a one-page pipeline health memo with a RAG verdict on each of the four dimensions, three to five immediate actions, and an honest forecast for the quarter. The memo is read at the leadership meeting in week two.

Checklist

  • Draft the one-page memo with verdict, actions and forecast.
  • Walk the memo through the CEO and CFO before publishing.
  • Present the memo at the leadership meeting in week two.
  • Re-run the same review monthly, against the same template, for trend.

Failure mode this step prevents

Producing a forty-slide deck rather than a one-page memo. The leadership team disengages and the actions do not land.

Common questions.

What pipeline coverage ratio should I aim for?

Three times remaining target for a typical SaaS or B2B services business with one to three-month sales cycles. Four times for industrial, capital-equipment or enterprise sales cycles longer than six months.

How often should the pipeline health review be re-run?

Monthly against the same template once installed. The week-one review is the baseline. Re-running monthly surfaces drift before it shows up in the forecast.

Should the sales reps see the pipeline health memo?

Yes, in summary form. Hidden diagnostics breed mistrust; transparent diagnostics drive accountability. The named-deal detail stays at leadership level.

How does this review feed into the commercial scorecard?

Pipeline coverage, concentration and velocity are typically three of the eight metrics on the weekly commercial scorecard. The week-one review establishes the baseline and the thresholds.

Talk to Evara.

Sales recruitment, GTM recruitment and revenue advisory for SMEs UK-wide. We reply within one working day.

Email Rachel Lunn