Sales · Chapter 3 of 5
Pipeline, forecasting and the number
Named in 84% of postings. The mechanics, reported from what employers describe.
Everything in a quota-carrying role reduces to a funnel: enough qualified opportunities, progressing at a known rate, closing at a known proportion. Postings ask about the inputs far more than the outcomes, because inputs are what a candidate controls.
What postings ask for
- Self-generated pipeline. Outbound and prospecting appear in 84%, so relying on marketing-sourced leads is not the expectation at this level.
- Qualification discipline. Whether or not a named methodology is used, the underlying questions are constant: is there a real problem, is there budget, who decides, what is the timeline, and what happens if they do nothing.
- Forecast accuracy. Repeatedly named, and it is a distinct skill from selling — a rep who calls their number accurately is more valuable to a business than one who occasionally beats it and is unpredictable.
- CRM hygiene, named in 49%. Unglamorous, and it is how the business plans.
The interview question that recurs
“Walk me through a deal you lost.” This appears across the corpus's seniority range, and the strong version names a specific reason — a competitor's existing footprint, a champion who left, a procurement gate nobody mapped — and what changed in how you qualify as a result.
“We lost on price” is the answer that says nothing, and it is the most common one.
The mechanics, and where the number comes from
Pipeline is not a list of interested people. It is a set of deals with a stage, a value and a date, where the stage is defined by something the customer did — not by how the seller feels about it. That single rule is what separates a forecast from optimism.
- Stages must have exit criteria that are observable. ‘They are interested’ is not a stage. ‘We have met the economic buyer and confirmed budget exists’ is, because someone else can verify it.
- Coverage is the ratio of pipeline to quota, and the common rule of thumb is roughly three to four times — but the number is meaningless without knowing your own historical win rate. Coverage is quota divided by win rate; if you close one in five, you need five times, and a borrowed multiple is somebody else's win rate.
- Stage-weighted forecasting multiplies each deal by its stage's historical close rate. It is better than a gut number and it is still a model — and it degrades badly when sellers park deals in a favourable stage.
- Commit is a promise, not a probability. The distinction between commit, best case and pipeline only works if commit means the seller will personally be wrong if it slips. Where commit is treated as 80% likely, the forecast is noise.
- And pipeline decays. A deal that has not moved stage in two cycles is usually dead and is inflating your coverage. Aging by stage is the report that finds it, and almost nobody runs it.
The forecast question that reveals discipline
“What made you move a deal back a stage?”
Anyone can describe moving deals forward. Moving one backward costs something — it is an admission in front of your manager — and a seller who has never done it is either extraordinarily lucky or is not applying the exit criteria.
The related one: “walk me through a deal you expect to lose, and why.” A pipeline in which everything is progressing is not credible to anyone experienced, and presenting one signals either inexperience or a willingness to forecast optimistically — which is the most expensive trait a sales hire can have, because the whole company plans on that number.
What good looks like is a seller who can say: this one is committed and here is why I am confident; this one looks good and I have not met the buyer who signs, so it is best case; and this one has not moved in six weeks and I am taking it out.
The underlying point generalises past sales: a forecast is only useful if being wrong has a cost attached to it. Where it does not, everyone forecasts optimistically and the number stops carrying information.
Check yourself