Deep Sales Wins Today. Here Are 3 Ways Sales Managers Can Instill It into Their Teams.

Deep sales wins today.

A new analysis from LinkedIn and Ipsos of 2,000+ sellers found that deep sellers – meaning those who adopt the three habits of deep sales – are nearly twice as likely to exceed quota as their peers. Why?

Deep sellers are more intentional with who they reach out to and when, conduct deeper research on those they do reach out to, and do a better job of building key relationships. This leads to them being seen as strategic advisors buyers want to partner with.

Meanwhile, shallow sellers – defined as salespeople who ignore deep sales habits – give generic pitches and they’re seen as transactional. As a result, they’re more than six-times more likely to miss their quota.

Companies want (and need) more deep sellers. To achieve that, they often offer more training, they leverage AI to generate better customer research, and they prioritize long-term relationships with their buyers. All of that matters 

But there’s a crucial component that’s often overlooked when an organization is trying to develop a team of deep sellers: sales managers. 

The challenge is, traditional sales coaching often overemphasizes immediate revenue opportunities while underemphasizing deep sales skills. In our decade of coaching sales teams, we often see sales managers unintentionally sabotaging long-term growth because their conversations with their teams are exclusively focused on immediate opportunities.

Here are three ways sales managers can avoid that trap and encourage more deep selling:

1. Don’t confuse pipeline meetings with coaching. Instead, ask questions that focus on customer impact. 

Traditional pipeline meetings are necessary, but they’re not sales coaching. A pipeline meeting with questions like, When are you going to close it? and, How much revenue will it be? does not drive deep sales behaviors.

While these questions are needed for predicting revenue, they can unintentionally promote shallow selling because the rep and managers are only focused on the immediate transaction.  

The questions sales managers ask their reps become the questions reps ask customers. Asking reps some version of, When can we collect the revenue? often results in a sales team that asks their customers similar transactional questions like, When can you sign? Who has purchase authority? 

While this information matters, it’s hardly a compelling conversation for the customer — and it doesn’t differentiate the sellers from any other person trying to close a deal.

Instead, managers can point the rep’s brain toward customer impact by adding in questions like, How will this sale impact the customer? Or, our favorite, How will the customer be different as a result of doing business with us?

Asking reps to articulate the impact the sale will have on the customer (versus just the revenue-win for the sales team) prompts sellers to think more deeply about how their solution is helping the customer achieve their goals. Asking about customer impact also helps reps identify who else beyond the buying committee might be impacted; they automatically start to do more multithreading.

It also encourages them to do deeper research to identify the issues their customer cares about. What matters to them and what’s happening within their industry?

This type of thinking is the basis for deep selling and establishing great competitive differentiation.

2. Take a longer view on account planning, so sellers become more intentional with their outreach. 

A critical aspect of deep sales is prioritizing high-potential accounts, as top-performing sellers focus on organizations that are the best fits for their solution and are ready to buy. This comes down to each seller adopting a long-term, strategic view of which accounts they’ll focus on and when.

How can sales managers reinforce this practice?

Start by asking sellers to self-identify the highest-potential accounts in their book. Encourage them to look for signals, such as accounts that are hiring quickly, have higher buyer-intent, and/or have a higher percentage of warm connections and hidden allies within them.

Sellers, you can play a role here too. Share your ideas for account prioritization and long-term account expansion with your manager — even if you aren’t asked.

The ideal state: manager and seller working together to proactively identify cross-selling and upselling opportunities and creating a long-term account strategy (in addition to what you need to deliver this quarter). 

Too often, “coaching conversations” end up looking more like report-outs. Both parties, manager and rep, have the power to elevate that conversation. Taking a long view in account planning solidifies a deep selling mindset.

3. Reinforce deep customer and industry intelligence through questions about both.

Managers can further reinforce deep selling by leaning into deep customer and industry intelligence. Regularly ask sellers, What’s going on in this customer’s industry? What are the key business issues facing our customers?

This prompts sellers to think holistically about the overall business landscape. And to look at issues through the eyes of their customers.

Shallow sellers tend to focus on their own solutions. Sales managers can help sellers go deeper by asking them to look outside the buying committee to understand the key issues facing the industry as a whole, and engage with larger networks of people.

Leaning into greater breadth and depth of both customer and market intelligence helps sellers create more urgency with customers, because they’re speaking the same language. And it also leads to trust, as buyers – more than anything else – want sellers who understand the challenges they face.

Bottom line, in sales, we all want to make our number. We also all want to have a positive impact on the lives and businesses of our customers. 

For more on this topic, see our LinkedIn Learning course ‘How to Motivate Your Sales Team.’ You can also listen to our audio course called ‘Sales Fundamentals,’ where prominent sales leaders and salespeople share how they leverage these deeper, more purpose-driven selling practices.

Coaching your team to lean into deep selling makes them more likely to meet quota, it enables them to have better conversations with customers, and ultimately provides a more fulfilling work experience.

Want to learn more about the habits of deep sales and how to get your team to adopt them? Explore ‘Deep Sales: The B2B Sales Playbook to Boost Revenue in 2024’.