How Coaching Can Shorten Sales Cycles

how to shorten your sales cycle

Once you identify that your team has a sales cycle length problem, it’s time to do something about it. Here’s everything you need to know to create sales coaching programs to shorten your sales cycle.

What is sales cycle length?

Sales cycle length is how long it takes you to close an opportunity. It’s measured from when the opportunity is created to when it closes, regardless of if it ends up being a won or lost deal.

Opportunity creation is slightly different for every organization, but as a rule starts around the time of the first meeting.

Most CRMs will calculate your cycle length automatically. It’s measured in days.

How sales cycle length is calculated

Sales cycle length is the number of days between when the opportunity is created and when it’s closed.sales cycle length

How to know if you need to shorten sales cycles

When you’re calculating how much revenue you can generate for your annual planning sales and sales forecasting, you take into account how long each opportunity takes to close.


You need to shorten sales cycles if your cycle length is a problem if, when you look at your Salesforce or CRM data, you see:

  • Your cycle length is longer than your forecast, but it’s not being offset by higher win rates
  • Your cycle length is longer than your forecast, but your deal size is in line with your projections.
  • You notice that your reps continually push the close dates out multiple times during the sales cycle.

How coaching can shorten sales cycles

There are two main coaching levers to pull here.

First, increasing urgency. This is where most VP Sales will start, since it’s a fairly controllable thing to do. They can exert internal pressure on their team as well as creatively increase urgency on prospects.

One tactic is to offer limited-time pricing, usually in line with the end of the month or the quarter.

Here are a few sales coaching techniques you can use to coach your reps to increase urgency to shorten sales cycles length:

  • Offer incentives to buy early, like discounts
  • Reiterate the timeline reps have agreed with the prospect, and reiterate the consequences of missing it
  • Make additional customer success or implementation resources available if the deal is closed in a set timeframe
  • Coach your reps to decrease their follow up time for prospects throughout the cycle, and measure the cadences of emails in and out between your team and your prospects.


These are your basic “build urgency” tactics. And while valuable, they tend to come in at the end. To really shorten sales cycles, coaching needs to happen much earlier:

  • Increase the value you bring: your reps need to sell on value rather than selling on price, product, or availability. By focusing on value, you increase the difference between the current-state and the future state, effectively creating opportunity cost of moving slowly.


  • Get your assets in order: Every time one of your sellers has to build a custom asset is time wasted. Especially for longer sales cycles, these 1-2 day delays add up significantly. Make sure your sellers are equipped with the assets they need to do the job.


  • Understand why now: Your prospect probably isn’t talking to you because they like you (though I’m sure they do). They’re talking to you because they have some reason to talk to you now. But getting to that why means taking the time to really understand their world. Basically, your reps need to ask good questions in the discovery so they understand.

Action plan

Here’s how you can turn these concepts into reality quickly and easily with sales coaching.

Focus on your discovery

If you want to bring more value to your prospects and understand how to close, you need to understand their problems at the personal and organizational level. So go back and listen to your teams’ sales calls. Are they asking enough questions? Are they prying into the real reasons for the discussion?

Call intelligence software that can track your interactions can help you understand which reps in particular should be questioning more to help you focus your previous coaching time where it’s needed most.

Establish compelling events

If there’s no compelling event established early, then it’s harder to apply pressure to shorten sales cycles later on. Good questions for uncovering and establishing compelling events include:

  • Why do you want to have this discussion now?
  • When ideally do you want this launched? Why that date?
  • What happens if you miss that deadline?
  • How are you impacted by this timeline?

Force harder questions

It’s tempting to hang onto deals long after they should have been closed, eating up time and resources and making forecasting a total nightmare for the organization.

So you need to coach your reps to ask hard questions about the future of the deal as it moves into the later stages (especially if the close date starts being pushed out regularly).

Good coaching questions include:

  • This deal keeps pushing. What can we do to stop this from happening?
  • You’ve committed to [critical event] and said A, B, and C will happen if you miss it. We’re not currently on track to hit that deadline. Are A, B, and C still important to you?

Red flags to watch for

Sales is a balance. If your cycle length is suddenly much shorter, then you need to check your other metrics to make sure they’re still in line.

First, has your win rate dramatically decreased? Are reps closing deals which aren’t ready to close / lost just to get them out of their pipeline?

Second, has your deal value decreased dramatically? As you coach to shorten sales cycles, it’s going to be tempting for reps to only work smaller deals they’re more confident they can get across the line fast. Make sure the new deals being piped are on par with the deals piped before you started your coaching sprint.

Wrap up

Everyone knows sales managers are going to coach more.

That’s just not going to happen. Instead, focus your coaching where it’s needed most. Identify where the gap in your velocity equation is, then coach specific reps around that to get the most from the coaching hours you can put in.

If your problem happens to be sales cycle length, then you now know how to deal with it.

If not, take a look at our other posts:

  • How sales coaching can increase your deal size
  • How sales coaching can increase your win rate
  • How sales coaching can improve your sales efficiency

Image credit: Charles Deluvio via Unsplash