Hold the line! [a sales coaching lesson]

“Don’t fire ‘till you see the whites of their eyes!” – Colonel William Prescott

History can often teach us important lessons. In our case, this infamous quote from the Battle at Bunker Hill can serve as a lesson of precision and diligence.

Hold the line! [a sales coaching lesson]For a B2B sales rep, patience is tough to maintain at certain parts of the sales cycle – especially for companies that offer free trials. We’re always trying to rush prospects through a sales cycle. But is that what is best for them?

As the sales leader, you should ask yourself if you’re giving away too much too easily. Are your salespeople wasting their precious time doing unnecessary demos, setting up free trials, filling out proposals and sending out contracts?

The answer is, yes.

I know what you’re thinking: “But Josh, we have a free trial on our website. Don’t we have to give it to them?”


Your sales reps must complete certain steps at each point in the sales cycle to move forward. Don’t let them rush to give demos or fill out proposals until they actually have everything they need to do so. As a platoon leader, you’d instruct them to hold the line. Firmly. As a sales leader, you’ll teach them not to fire off that proposal until they see the whites of their prospect’s eyes.

Let’s say you have an account executive on a hand-off call from a sales development rep. At the beginning of the call, the AE disqualifies the prospect. Should they still do the demo?

Of course not. Tell them to save their time.

The sales coaching strategy for due diligence

Define what steps need to occur at each stage of the sales cycle. Create a checklist for everything you know reps need to move forward.

Think of it this way: What typically happens when a sales rep’s prospect asks for a proposal?


*You look up and see said sales rep sprinting around the office*

Happy ears cloud the rep’s judgement. He’s so excited to move forward that he won’t take a step back and ask himself if he’s ready to write a kick-ass proposal to win the deal. Does he have baseline key performance indicators and ROI statements? Does his prospect agree with the calculated pricing? Can the rep work backward from an implementation date to create urgency around it?

Do this for each step of your sales process. After you’ve got your checklist, align it with your sales cycle or opportunity stages. Make sure each stage has a very clear definition. Here’s how that might look for an inside sales team:

  • Stage 1: Rep completes demo.
  • Stage 2: Rep kicks off free trial.
  • Stage 3: Rep sends proposal
  • Stage 4: Rep sends contract to procurement.

Reps might initially resist the idea of slowing down a sales cycle. Remind them that sales isn’t always a sprint. When momentum slows, help reps understand the prospect’s business objectives and build a use case. This type of sales coaching enables reps to create life-long customer advocates who know your company is invested in their success.

Use sales coaching to help reps take control of their sales cycle. Hold the line. If each member of your sales team completes their due diligence during each step of the process, you can see better CRM data, relationships and win rates.

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