
You were an excellent salesperson, constantly achieving your targets and knocking them out of the park.
Now that you’re a sales leader, it’s a whole new ball game, and you’re facing one of your biggest challenges:
Your sales reps are struggling to meet their quotas.

You’ve assembled a great team and have a sales pipeline full of potential clients. So, what’s going wrong? Why are your reps struggling to achieve their quotas?
Is it you? Or is it them?
Do you wonder if you should revise the sales targets to make it easy on your team? Or should you give them a stern talking to, for the not meeting quotas saga has been going on for a while?
If your sales organization is struggling to achieve its business goals, this article is just for you. We’ve compiled a list of five critical strategies to improve sales performance and optimize the sales cycle so that your team can achieve their quotas and you can get back to being a rockstar sales manager in no time.
#1: Identify the root cause of the issue
If your car breaks down, what do you think is the best course of action? Do you open the hood and try replacing the engine, or get it checked by a qualified mechanic?

You cannot fix your car unless you know what’s broken. The same applies to improving sales underperformance. You need to identify the core issue(s) to find the right solution.
The 5 Whys is a powerful analysis technique that helps you dissect a problem and reveal the underlying issue(s). Developed by Sakichi Toyoda, a Japanese industrialist and inventor, this iterative interrogative technique asks ‘why’ five times to identify the core issue, ultimately arriving at the right solution.
Here’s an example of the 5 Whys technique in practice:
Problem: “My sales team members aren’t achieving their sales goals.”
- Why isn’t my team achieving their targets?
“They aren’t closing deals.”
- Why aren’t they closing deals?
“They don’t have the right information and insights to close deals.”
- Why don’t they have the right information and insights to close deals?
“They have to manually enter customer data into the CRM, which they forget to do.”
- Why do they forget to enter crucial customer data?
“It’s a tedious process and is practically impossible to record each snippet of customer data manually.”
- Why is it a tedious process?
Because we don’t have an automated system for tracking customer calls, identifying and qualifying prospects.
Well done! You have uncovered the solution to your problem. Whether you ask ‘why’ two or twenty times, persistently asking the right ‘whys’ helps you dive deep into your core issues and identify the right solutions.
In this scenario, a conversation intelligence tool (like Wingman) can help in sales enablement by arming sales professionals with crucial customer insights, thereby helping them build customer relationships, increase their conversion rates, and close more deals. Moreover, as a sales manager, you can seamlessly garner actionable insights for identifying the sales coaching needs of your team and creating data-driven coaching templates.
#2: Master the art of active listening
One of the most underrated traits of a successful sales representative is their ability to actively listen to a prospect to understand their pain points and needs. Reps in your sales team may be experts in reciting product features and imparting industry knowledge, but they’re bound to miss out on crucial selling opportunities if they don't listen.
The ultimate goal of the sales team isn’t to sell.

At the outset, the above statement might be hard to accept, but it’s one of the biggest mantras of the sales world.
A sales team doesn’t sell. Instead, their primary responsibility is to solve a problem for the customer. When they address the customer’s pain points, they no longer have to stress over persuading the prospect to close. The prospect realizes the impact and benefits of your product or service, and selling happens automatically.

Mastering the art of active listening during the sales process is a crucial skill and a decisive advantage. Unfortunately, it’s the most challenging skill to implement, especially when your sales reps have a zillion other sales activities to handle in the background when they are on a phone call with a prospect.
A conversation intelligence tool helps your sales team participate in active listening. They can replay customer conversations conveniently and identify the little details and emotional nuances they missed during the call. They can then proactively take the right actions, solving the client’s needs, thereby getting the client to convert.
#3: Be flexible and agile

One of the most successful strategies for sales quota attainment is the ability to adapt and learn on the go.
Too often, sales companies take a “let’s wait and see approach.” They execute a sales strategy and stick to it for the whole month or quarter, even when the plan fails to achieve the desired results.
This approach rarely ever works. Blockbuster is an excellent case study of what could go wrong when you fail to take timely actions. For all of you gen-z folks reading this, here’s a bit of history that you might not be familiar with. And, for you millennials, let’s head on a quick trip down memory lane.
Before the advent of OTTs and streaming platforms, Blockbuster was THE biggest video rental store in the US. Customers could pop in, rent their favorite movies on DVDs or VHS tapes (it makes us feel so old, just saying that word), and watch from the comforts of their homes.

At one point, the company had over 9000 stores and 50 million regular customers. Fast-forward to today, the company has filed for bankruptcy and serves as a cautionary tale for corporations that don’t adapt and change to meet evolving client needs.
While Blockbuster made several crucial missteps in the late 90s, one of the biggest reasons for its failure was its inability to pivot quickly and introduce new products and services to keep up with the changing times.
Netflix, then a small-time competitor, had started renting DVDs to customers via mail. Customers who enjoyed the convenience of ordering DVDs online and receiving them at their doorstep quickly moved away from Blockbuster. Netflix was agile and was able to change its strategy to keep up with the times. The company started offering streaming services in 2007, and the rest of the story, as they say, is history.
Reid Hastings, the co-founder and CEO of Netflix, described the crux of the situation perfectly when he said, “Companies rarely die from moving too fast, and they frequently die from moving too slowly.”
The key takeaway here is that you’ve got to adapt, be flexible and revise your strategy to keep up with changing customer needs. If your current sales strategies aren’t working, you’ve got to act fast to put Plan B and C into action. As a sales leader, you’ve got to closely monitor your sales data, pay attention to any red flags and act proactively.
#4: Focus on the quality of your leads
Marketing teams are often focused on the number of leads that they fail to concentrate on the quality. Attracting a large number of leads is a good thing, but the quality of the leads is what determines the conversion rates.

The famous adage, “a bird in the hand is worth two in the bush,” is apt. It’s better to have a dozen qualified leads who are likely to invest in your product than hundreds of leads who have only a passing curiosity about your products and services.
This is where sales and marketing teams have to break free of their silos and come together to agree on a qualified lead generation strategy. Their goals should be in sync and communications spot-on to improve lead quality. We’ve previously written about how sales and marketing teams can benefit from using call recording software to generate leads and close deals.
PS: If you’re struggling to generate leads, a quick and efficient tactic is, to begin with, cold calls. Yep! Cold calls are still effective in initiating conversations and help to get prospective clients interested in your products and services. Here are our proven strategies to ace cold calling and win more deals.
#5: Refine and optimize your sales call scripts
Making cold calls and reaching out to prospects is one thing. But the calls are likely to fizzle out unless your sales team is prepared. Your sales team probably uses a sales call script to structure their pitches and convince prospects to close.

But when was the last time you updated the script? Do you know if sales reps stick to the script, or do they deviate from it (for better or worse)? How effective is the script in achieving your sales plan? Does it address customer pain points? Do you use the right keywords?
You can find the answer to all these questions and more by using conversation intelligence tools like Wingman. Wingman is an AI-powered conversation intelligence tool that records, transcribes, and monitors your sales call. Think of it as the secret weapon to improve your sales team’s performance.
With Wingman, you can:
- Automatically analyze sales calls and use the insights to push your prospects down the sales funnel and get your sales team to exceed their sales quotas.
- Record sales calls, assess all relevant sales data points, track AI-enabled metrics like talk-to-listen ratio, the likelihood of conversion, etc., to help your sales team better understand prospects and identify the best ways to close deals.
- Get a visual snapshot of your team’s performance. Identify the top performers; you can also spot struggling sales reps and offer them personalized sales training.
There’s a lot more Wingman can help you with, like identifying call dynamics, game tapes, battle cards, real-time sales coaching, etc. Reach out to us for a free demo to see how Wingman can help your sales teams achieve (and consistently exceed) sales quotas.
Meeting your sales targets doesn’t have to be something you stress over. Now that you have five powerful sales quota strategies under your wing, it’s time to optimize your sales strategies and knock your sales quotas out of the park!