Ep.7 - The Questions You're Not Asking That Kill a Forecast in 5 Minutes

About This Episode

Your rep has a champion, a proposal out, a business case, and a close date. They're confident. You want to believe them. So the deal goes in the forecast.

That confidence is the problem. Because most reps aren't forecasting what they know — they're forecasting what they hope. And most sales leaders, under pressure from above, don't push hard enough to find the difference before it's too late.

In this episode, Richard Smith sits down with Chris Lingenfelter, VP of Sales and Customer Success at Level Up, and Nigel Arthur, former MD and SVP Sales across multiple enterprise SaaS businesses, to pull apart every layer of what makes forecasts fail — and then prove it live. The two guests take Richard through a real deal in real time, asking five questions. The deal doesn't survive.

The rep had a champion, a clear business case, and a quarter-end close date - and neither Nigel nor Chris would put it in the forecast.

You'll Learn:

• Why 90% of sales organisations have no clear entry or exit criteria on their CRM stages - and what that does to every forecast downstream

• The five questions Nigel and Chris asked in a live deal review that killed a deal with a champion, a proposal out, and a close date

• Why sandbagging is almost always a culture problem, not a rep problem - and the specific fear that drives it

• What an acceptable margin of error actually looks like across enterprise, mid-market, and SMB - and why obsessing over perfection misses the point

• Why monthly forecasting alone makes your reps more likely to discount deals, not less

Who is this for?

VPs of Sales, Heads of Sales, Sales Managers, and Revenue Leaders responsible for forecast accuracy and pipeline health. Especially those who have inherited a team with no shared qualification framework, are seeing consistent quarter-end surprises, or are trying to build a forecasting culture where reps take real ownership of their numbers.

Who are MySalesCoach?

MySalesCoach works with sales leaders to build the frameworks, coaching habits, and team accountability that turn forecasting from a guessing game into a discipline.

Book a call to find out more about how we can support you in building an elite, high performing sales team.