5 Advanced Selling Skills (& the Techniques to Nail Them), According to Coursedog's Director of Sales

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Zach Drollinger
Zach Drollinger


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Exceptional salespeople don't separate themselves from the pack by doing what everyone else is doing and hoping for the best. They go above and beyond, and you can't do that if you lean exclusively on conventional sales skills.

No, the best reps demonstrate advanced sales skills — ones that can help frame you as an authoritative, helpful, empathetic guide with expertise relevant to your prospect's circumstances. Here, we'll review some of those skills and go over the techniques you need to know to demonstrate them.

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Advanced Sales Skills

1. Being Helpful Without Being Too Friendly

Cold as this might sound, your prospects aren't your friends. Any sale is a professional engagement and must be treated as such. That doesn't mean you have to bully potential customers, roll your eyes at their questions, and be visibly frustrated every time they take too long to answer.

But it also doesn't mean that you can roll over to their every demand, agree with all of their objections, and let them run the conversation. The best salespeople can strike a balance between those ends of the spectrum — they help their prospects without giving up control of the sale.

Advanced Sales Technique: Guiding Without Dominating

So how do you get there? Well, if you want to find that middle ground between overly friendly and excessively confrontational, you need to take a consultative role in the sale. You're the expert here. You know what you're talking about, and you want to apply that insight to help them — not just sell to them.

You have to lead with thoughtful, relevant questions. Quickly and thoroughly respond to objections while acknowledging you know where they're coming from. Make sure you keep the focus on their business, its specific pain points, and how your offering is the best possible remedy for them.

You're there to walk them through the process of understanding their pain points, seeing the value of your product or service, and ultimately finding where those two elements intersect. That comes from an advisory perspective — not an overly friendly or confrontational one.

2. Conveying Value Specific to Your Prospect

This point ties into the one above. You can't take an advisory role if you have no idea who you're advising. Exceptional salespeople don't sell on general sentiments and generic "bells-and-whistles" pitches.

They offer tailored value propositions that consider the specific circumstances the prospect is operating within, the implications of those circumstances have had on similar businesses, the range of outcomes those implications might lead to, and how their offering can make those outcomes as ideal as possible. All of that takes precedence over touting the neat features their product or service has.

For instance, let's say there's an edtech company that sells a solution for curriculum planning. That business wants to sell its product to a community college in Northern California that still mostly tracks and coordinates its course registration manually. The value proposition shouldn't be "Our product has an accessible interface that makes curriculum planning easier."

It would be something to the effect of, "At an institution of your size, manual registration tracking leads to routine under- and over-enrollment in required courses, stalling degree velocity. Our program can provide information to cut unneeded sections and expand overfilled ones — accelerating degree velocity."

Advanced Sales Technique: Conducting Extensive Research

The perfect value proposition doesn't come out of nowhere. You can't just read the front page of a company website and figure something out on the fly. You need to have extensive knowledge of a business, its leadership, its industry, its market position, and its current performance — among other factors.

That takes extensive research — whether that be through company marketing collateral like case studies, industry publications, public financial reporting, background information on company leadership, or any other resources that can give you a closer look at what a business does and the challenges it faces. From there, you can start to string together a thoughtful value proposition that will register with your prospect.

3. Teasing Out Pain Points Your Prospect Might Not Have Even Considered

Pain points are the basis of all things sales. If they didn't exist, sales wouldn't either, so if you're going to sell successfully, you need to be able to find and address them. Sometimes, pain points are obvious — ones that your prospect understands going into the conversation.

But the best salespeople go beyond that — they know how to unearth very real issues that the prospect hasn't even thought about. Being able to identify unconsidered issues, bring them to light, and thoughtfully address them in a single conversation is one of the trickier, most advanced skills a salesperson can have in their repertoire.

By nailing this process, you can earn a special degree of trust with a prospect. In doing so, you're effectively demonstrating that you thoroughly understand their businesses, have a strong feel for the challenges it faces, and can solve problems for them as they arise.

Advanced Sales Technique: Taking a Consultative Approach

Consultative selling is an approach to sales where a salesperson focuses primarily on building value, trust, and rapport with a prospect before offering a solution. It's a relationship-first methodology — once you've built one, then you can actually start selling.

The methodology involves balancing questions with insights, expressing knowledge, keeping conversations genuine, letting there be some back-and-forth, being receptive to feedback, and listening intently.

If you follow those steps, you can put your prospects at ease and get them talking. They can use you as a sounding board, and ultimately voice issues they might not have considered in the process.

4. Relaying Industry-Specific Knowledge

Trust is a recurring theme that has a place in every point on this list — exceptional salespeople know how to quickly and convincingly develop it with prospects. A lot of the time, trust is a byproduct of specificity.

Prospects want a specific value proposition that implies specific actions to suit their specific pain points. One way to nail that element is by conveying extensive knowledge of their industry in your correspondence with them.

Show them you're well-informed and on top of the trends that are going to shape how they and their competitors operate. Again you want to demonstrate that you're not just a salesperson, you're an expert — one who knows both what they deal with and how those broader issues dictate how they operate.

Advanced Sales Technique: Passing Along Relevant Content

Like the second point on this list, this one starts with research — but how you relay your knowledge to your prospect is key. One way to get there is by passing along relevant, industry-specific content to your prospect at different points in their buyer's journey.

It takes some finesse, but this technique can give you some serious clout as you work your sales process — when done right. You don't want to inundate your prospect with dozens of articles from industry publications, heavy-handedly trying to say, "Look how much I know about what you do!"

Instead, try to see if you can find content that relates to certain industry-relevant points you might have discussed in an email or phone call. For instance, let's say you're selling a construction project management solution to a regional fast-food chain that's deciding whether to upgrade its tech stack.

You might want to pass along an article detailing how popular franchises are leveraging cutting-edge tech to let your prospect know you're keeping an ear to the ground within their industry and give them more perspective on the rising tide of digital transformation among fast-food chains.

5. Maintaining a "Contrarian Mindset"

Maintaining a contrarian mindset rests on your ability to find gaps and hiccups in your prospect's operations. It's a matter of staying skeptical, scrutinizing, and being mindful of faulty logic, overlooked opportunities, or sub-optimal execution.

Exceptional sales reps with this mindset look for places where the customer might have got it "wrong." Did they overlook an opportunity for savings? Do they leverage any processes that deliver subpar results? Are certain components of their tech stack redundant or inefficient?

Salespeople with this mindset can turn these hiccups into viable "ins" that give them a basis for an effective value proposition. From there, they can offer an alternative perspective to raise questions and answer unique questions — as opposed to confirming already established ones.

Advanced Sales Technique: Conducting Extensive Research and Actively Listening

Like the second point on this list, "maintaining a contrarian mindset" is a function of how well you can research your prospect — specifically how their business is faring.

See if you can find out what solutions they're currently leveraging. Review their public financials to see if they could be doing better in that arena. See if you can find some insight into their clientele.

One way or another, drill down how they're performing and what's influencing that performance. On top of that, you need to actively listen throughout your conversations with them. Be hip to any tidbits they might drop about where their business is lacking and why that's the case.

Maintain your contrarian mindset, and find the "in" you need.

Being an exemplary sales rep takes more than doing whatever everyone is doing better than everyone else — you need to branch out and master less conventional skills to get there. Obviously, this list of advanced sales skills is far from exhaustive, but it's a good place to start if you're looking to take your sales game to the next level.

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