Originally published April 2021. Updated March 2026.
There are a lot of articles out there about how to shorten sales cycles. While many share helpful and clever ideas, they often require company-wide buy-in or long-term planning that will take some time. Chances are, if you’re Googling “how to shorten the sales cycle,” you want something that can immediately impact velocity in sales.
A list of ways to trim the sales cycle I read suggested making sure prospects could sign contracts from any device. Is this a good idea? Of course. Is this something you, as a sales professional, can do right now to shorten the sales cycle? Probably not. It would likely involve changes being made by your IT people and possibly your legal team. It’s not an action you can take right now on your own. But we know how important velocity in sales is, so what can we do?
At Maestro Group, we are all about useful tips and suggestions that can be implemented right away and that can make measurable differences. If that’s the kind of sales-cycle-shortening list you’re interested in, then read on.
GET INFORMATION AS QUICKLY AS POSSIBLE TO SHORTEN THE SALE
The biggest risk we have in sales is not having enough information. This lack of information is responsible for a lack of velocity in sales and a lot of the pitfalls that salespeople encounter throughout the deal. That’s the reason we developed and use the DRIVE information-gathering framework. It provides a blueprint for building a relationship with your prospect, one in which you have the information you need to move toward a sale faster.
There are several key components of DRIVE that can help you shorten the sale right now.
GAIN VELOCITY IN SALES USING OPEN-ENDED QUESTIONS
No matter what kind of information you’re after, it’s best to get it through asking open-ended questions. Why? Because the more information we have, the better off we are, and open-ended questions yield the most information.
Instead of asking, “Are you happy with the software you’re using?” try, “What do you like about your current software?” Instead of, “Are you making this purchasing decision?” try, “Who besides you and your department is involved in the decision-making process?” Your goal in asking questions is to uncover every pain point, objection, and possible bump in the road. Asking open-ended questions and actively listening to your prospect’s responses is the best way to do that. Getting ahead of those obstacles helps shorten sales cycles.
UNDERSTAND DECISION-MAKING TO SHORTEN SALES CYCLES
To accelerate the sales process, it is crucial to understand your prospect’s decision-making process. You might have had several calls and meetings and think you’re on your way to a sale, only to discover there are three other people who need to be involved. Now you have to start all over with them included. We all like to hear that someone likes our product or service, but don’t let your “happy ears” keep you from discovering that you need other people on board in order to actually have a deal.
ADDRESS OBJECTIONS HEAD ON TO INCREASE DEAL VELOCITY
We’ve written before about how it’s helpful to reframe objections as opportunities. While it might seem easier to avoid objections, this doesn’t make them go away. Instead, it just means that they come up further along the funnel and have the potential to derail all of your hard work.
It’s always best to address objections as soon and as often as possible. This will help you build trust with your prospect as well as prevent your deal from coming to a screeching halt later on.
The importance of addressing objections right away is one reason we suggest asking your prospect what they like about their current solution first, instead of what they don’t like. If your product does everything they value about their current solution, you can assure them of such. If it doesn’t, find out which of these missing features are deal breakers. Addressing objections early is key to maintaining velocity in sales.
USE DRIVE TO RECAP INFORMATION
Not only is DRIVE a great information-gathering framework—it also provides a great format for recapping information. After meeting with a prospect, send an email sharing what you heard their needs are, who needs to be involved in the next meeting, when they want to have a solution in place, etc. This will give them a chance to clarify anything right away so that you don’t move forward with any false assumptions that slow deal velocity. Recapping your meeting in this way also shows them that you truly listened to what they had to say. You understand their pain points and can help them solve their specific problem. Finally, if there was a key decision-maker missing from your initial meeting, this email can give that person a good overview of what they missed.
SPEED UP YOUR RESPONSE TIME TO SHORTEN SALES CYCLES
It pays to be the first to respond. According to OptiFai, leads contacted in less than five minutes achieve a 32% close rate—2.6x higher than those contacted after 24 hours. However, the average B2B lead-response time is 47 hours. WHAT. ARE. WE. DOING???
The farther along you are in your relationship with a prospect, the less likely it becomes that they are considering a lot of your competitors. Early on in the process, however, being the first to respond to a call or email could be what makes you stand out from the competition.
It also helps to think about what your prospect’s day looks like. If you’re communicating with a C-suite decision-maker, chances are she schedules set times to look at emails and is booked with meetings the rest of the day. If she emails you and you can reply right away while she is still at her desk, not only will she be impressed, but you’ve also cut down on the time between communications, a great way to shorten sales cycles.
A DEAL IN MOTION STAYS IN MOTION
The worst thing that can happen to your sale is that it stops moving completely. A deal in motion stays in motion, while a deal at rest is likely dead. It’s up to you to make sure your deal keeps moving forward.
FREQUENT TOUCHPOINTS
Plan a cadence for reaching out to your prospect, and stick to it. Don’t let more than a few days go by between touches. A touch could be a call, an email, or reaching out on social media. You want to keep your prospect engaged without being a nuisance to them. Remember that gifting can be a great way to reach out to a prospect as well. Something as simple as sending an article you think would be of interest can keep up deal momentum.
TRACK MICRO CONVERSIONS TO BOOST VELOCITY IN SALES
A sale can’t be your only way of measuring your success with a prospect. That would be like a doctor waiting to see if their patient gets better without ever monitoring vital signs along the way. Micro conversions are a good way to check on deal velocity.
Micro conversions, as the name suggests, can be quite small. Something as simple as responding to an email or scheduling a meeting can be a micro conversion you choose to keep tabs on. These would be positive micro conversions that indicate your deal velocity is healthy.
A lack of a response, or someone leaving your meeting early (even though you did a time check at the beginning and they didn’t say anything) would be examples of negative micro conversions. These are important to track and address as they are symptoms of an ailing deal that’s slowing velocity in sales.
Like objections, negative micro conversions need to be addressed head-on. Be bold. “I noticed you left before our call was over. I wanted to make sure everything was okay. What questions do you have about the information that I shared?” Even if it turns out that this prospect is no longer interested, it’s better to get to a definite “no” and move on than to nurse a slow maybe.
THREE IS THE MAGIC NUMBER
This last strategy is so simple, but it has the potential to shorten sales cycles dramatically when used consistently. When you propose a meeting, provide three time windows that your prospect can choose from. It makes it much easier for them, and you’ll avoid all of the back and forth that normally goes into picking a time. Choosing times that are coming up soon—in the next 24–48 hours—provides another nudge that adds velocity in sales.
It seems so easy, right? And it is. But avoiding the half-day of back and forth to schedule a meeting for every prospect and for every meeting adds up to a lot of time shaved off of your sales process. Plus, as with all of the tips mentioned here, you don’t need any other departments or specific software to put it in motion. Go on, boost your deal velocity now.
Do you want to learn more immediately actionable sales strategies? Contact mastery@maestrogroup.co to learn more about our engagements!