How to Know Your Customers and Improve Sales Success

If a job was easy then anyone could do it. 

Take sales and selling, for example. Few have the knack for or desire to put it on the line each day to make the calls and close the deals. It’s a tough job most people can’t do. 

Another adage says there’s a right and wrong way to do things. In the context of selling that means doing your research homework, being prepared, and making the effort to know your customers before making a pitch. By not getting to know your clients, it makes a hard job that much tougher - even impossible. 

It is a too-common mistake made by sales professionals and it’s happening in many organizations - even ours. Case in point: Vendasta sales leadership routinely reviews recorded sales conversations to gauge performance, coach for success, and share learning. Below are the cringeworthy highlights of a recent call.

Discover a great selling conversation starter - check out SnapShot Report.


The Conversation Killer 

To set the stage, the conversation was a follow-up with a prospect who clearly did his homework and recognized the potential between our offerings and his needs. He’s reached out, looking for help. The call begins as most do, with a warm and friendly greeting, a brief bit of small talk, and a seemingly innocent first question posed by one of our sales representatives: 

Sales rep: The reason I’m giving you a call is because I wanted to learn a little bit more about what you’re interested in from Vendasta.

The prospect quizzically responds: That’s really why you called?

Already sounding perplexed and a tad exasperated, the prospect answers and calmly goes on to explain he wants to grow his business and that his clients could benefit from digital marketing help. He thinks we may have the solution he seeks.

Rather than delving deeper into what he’s just heard, the sales rep circles back to his initial question and repeats - I’d like to learn more about your business, what you do, and what solutions you use today - and whether there is a partnership fit.

The prospect now skeptical asks: Do you know anything about my business? 

Sales rep: Ah, briefly...I have the website here (seemingly indicating he’s looking at it now). That’s about it. So I’d love to hear it straight from you.

Prospect: Can you tell what I do from my website?” 

There’s an uncomfortable pause. The sales rep nervously chuckles and says: “Well...that’s what I’m calling for...”

A perplexed prospect is now agitated and calls him out: 

“You haven’t seen my website. I know you haven’t looked at my website. I know you have a list of questions you’re going to ask me. And I know you don’t know anything about me. You haven’t put that effort into it.”

He continues:

“I learn about my customers before I call them. I know about them. I know how I can help them. I know what they need. “I know tons about YOUR company. YOU don’t know anything about mine.”

Things have quickly moved from bad to worse. The rep stumbles and makes the attempt to go through a high-level pitch about offerings. But the prospect stops the rep cold and, in a calm, but exasperated tone, he tells him - “I know all that.” 

Finally, the rep is aware of the precarious situation he’s in and backs away from the precipice. He gathers himself and suggests an immediate next-level conversation with a product expert. The prospect agrees, a bullet is dodged, and good fortune prevails. 

It’s a sales Lazarus effect - a seemingly dead corpse miraculously brought back to life.

The Price of a Lead


Know your customer

How easily this could have been a lost and wasted opportunity and how simply such risk could have been mitigated with a bit of prior homework. Lack of basic preparation to get to know your customers is bad business and wastes significant investment made to acquire and move prospects to a sales conversation.

This was a singular example, but no doubt it’s happening too often for many organizations. How often do sales conversations fail to launch because simple research wasn’t done, customer needs and requirements weren’t understood, connections between challenges and business solutions were not made, and a prospect got frustrated and discouraged? It’s likely worse than most realize.

“You’re probably losing deals and you just don’t know it,” says seasoned sales professional Ron De Appolonia, the global head of account development performance at OpenText Corp. “Prospects might be saying, ‘thanks, I’ll be in touch,” and you never hear from them again.”

It’s a tragic waste when you consider what’s required to warm up a lead.

Research shows it takes at least eight touches to engage a prospect and drive a sales conversation. A touchpoint can be a combination of contact activities like an email, voicemail, social media message on LinkedIn, and even a voicemail. All this happens prior to a sales call with a prospect who by then is already 57 percent sure of a purchase.

There’s a simple bottom line to the financial cost of gathering a sales lead. The easiest way to figure it out is by applying this basic formula, below, to calculate cost per lead (CPL): 


  • Total dollars spent on marketing / # of leads from a campaign = CP


Research from Linchpin shows the following CPLs:

How to Know Your Customer

The amount of preparation for a sales discussion with a prospect depends on many factors. You might ask - should it be proportionate to the potential size of a deal? According to Vendasta Chief Customer Officer, George Leith, you shouldn’t necessarily think about it that way because you can’t be dismissive of any potential sale.

Leith says you need to understand the outcome you want to achieve, and then determine the prospect questions required to get you there.   

De Appolonia says preparing for a sales conversation can literally be as easy as a three-minute check on what a prospect’s company does and how they make money. Then consider what are the problems they are experiencing and ladder back to what your company does to solve those challenges.

But you might not easily find research on a business through online search, particularly if it’s smaller. So look to understand the industry or business vertical itself by researching and understanding the typical challenges of businesses in those domains. For example, a small retail business may not think it is directly competing with a giant such as Amazon, but by researching Amazon and learning about their strategies and plans, you can provide valuable and meaningful insight to a potential customer.

With the most basic "know your customers" conversation template you might start by telling a prospect about trends or something newsworthy in their industry to spark a conversation. By doing so you’re demonstrating that you have familiarity with their industry or business type. And it shows a prospect that you’ve earned the right to a conversation.

“Dial into what the prospect is thinking - get to the pain,” De Appolonia says. “You want to make an impression quickly.”   

When researching specific industries, create brief playbooks for each that outlines general trends, pain points or challenges, opportunities, and best practices. Then prior to a prospect meeting, look over your playbook as part of your preparation. In addition, always do a Google search of a company and of the individual with whom you’ll be speaking. 

“Search for pain points on a company by name or topic,” De Appolonia says. “Go hunting for pains and challenges. If you can’t find anything on LinkedIn or Google, then go back to your industry sheet. The goal is to have an intelligent and insightful conversation - demonstrate to the prospect that you’ve done some homework.”

Check out a prospect’s biggest competitors. Research what they do and perhaps make that part of a conversation, too. Then engage - “I notice a competitor of yours grew its business this way or had these challenges. Are you doing/noticing the same things?” They might ask: How do you know so much about my competition? You respond by saying, “I did the research.” The prospect is impressed!

The point of research is to demonstrate you’re the right person with whom to speak. By not taking the time to know your customer and being prepared, a prospect doesn’t see value in you and they’ll likely make their own decision. They’ll pump you for information, then do likewise with your competition, and finally make their own evaluation and choice. 

“A good sales person never wants that to happen,” De Appolonia says. “They don’t want you to move on. A great salesperson wants to make the best impression so that you engage. Then you start telling me what your real challenges are and I look to fit my solution - show you that (my company has) the answer. And you’ll think, ‘I don’t need to go anywhere else.’”

Recovery and Asking Questions

Let’s go back to that cringy sales call. Is it actually possible to recover when a sales discussion goes off the rails? Maybe, but what should you do? 

“On the spot - apologize,” De Appolonia says. More importantly, learn from the hard lesson you’ve just received - come prepared next time, always knowing your product, and how it helps the business with whom you’re speaking.

Leith says it’s also a matter of owning up to your mistake, being authentic, and admitting when you’re wrong. “Perhaps tell a prospect you appreciate being called out because it will help you improve,” he says. Leith even suggested a sales professional might consider starting the call from the beginning - tell the prospect, you want to hang up, begin a new call, and this time you’ll be prepared. 

“Do it right,” Leith says. “What’s wrong with that? The customer will either bail on you or they will be impressed and tell others about the interesting call they had.”

Realistically, even when you’ve done your homework to know a customer, you can’t know everything. Sometimes a customer will expect you to know a lot more about them, but public information may not be available. In that case, it’s important to be a listener.

“The smartest people I’ve met don’t talk very much,” Leith says. “They ask a lot of questions. So always be listening and learning. Your job is to take them on the tour they want to go on. To do that, you need to listen and ask the questions that will help you figure out where they want to go.”

Think of it as a diagnosis. You need to do some digging then make an assessment. De Appolonia uses the extreme analogy of a doctor who gives a diagnosis through a comprehensive examination to understand your pain and problem.  

“If you’ve done your homework and understand a prospect’s business then you’re asking questions that are relevant to you and the customer,” he says. You validate your understanding, asking the prospect, “am I getting it right? Is this the pain you’re feeling? Let me show you what we can do and can’t do.”

That kind of getting-to-know-your-client conversation becomes genuine and real for your prospect and encourages them to open up and share more details. That’s how to create a great sales fit between their challenges, pain, and needs, and your products or services.

“That’s why you need to go in prepared. You can’t custom-fit something if you don’t take measurements,” De Appolonia says. “Taking measurements is going in prepared then asking questions to fill in the information that’s missing.” 

Vendasta Snapshot Report

Technology is a great tool to support meaningful conversations with prospects. The Vendasta Snapshot Report, for example, is a marketing needs-assessment solution that arms sales reps with automated insights into a business’s online marketing performance.  

Generating a Snapshot Report on a business provides a report card of a prospect’s online performance across a variety of channels, including social media, website, and advertising by “scraping” the internet for information, details, and conversations regarding that business. Snapshot Report performance metrics and grades allow a salesperson to concentrate on gaps in a prospects’ marketing. 

These metrics are ranked against industry benchmarks and when shared with your prospects gives them meaningful context into their marketing performance and an enticing target. Also provided is a breakdown of how a prospect compares to direct competitors when it comes to reviews and listings, giving them a deeper understanding of how they rank online.

With these insights, your salespeople can build trust as local marketing experts. Use the Snapshot Report to start the conversation with business owners, highlight gaps in their marketing, and propose the optimal solutions. The Snapshot Report aggregates data from more than 70 online directories to show your prospects:


  • Number of listings
  • Accuracy of listings
  • Missing sites


After sending the Snapshot Report to a prospect, your salespeople are alerted when it is opened and can follow up to provide a walkthrough, highlight weak areas, and close the sale.

Why You Now?

Here’s a sales outreach approach, credited to renowned sales consultant Jeffrey Hoffman, that De Appolonia among others has adapted as a teaching model for those with whom he works. Think of it as a template for an engaging sales discussion that demonstrates conviction, action, and benefit. It’s highly effective in email outreach and can be equally successful as a great way to think about a sales conversation. Here’s the model in its simplest form:


  1. Why you? The conversation or correspondence begins by establishing reasons behind your connecting with a prospect at this time. “Why am I reaching out to you now?” Perhaps it’s based on earlier sales touchpoints, but it may be prompted by research and knowledge gleaned about them - the fundamental reasons behind your outreach that basically says, “there’s something important and essential that matters to you that I need to share.” It could be specific - something about a prospect you’ve learned that represents a challenge they’re struggling with or an opportunity they’re trying to capture. Or it could be based on the industry in general - that businesses, including theirs, need to deal with. You’ve taken the time to investigate what matters to them and now you want to help.
  2. Why now? This speaks to timeliness and urgency. It’s explaining why they need to act now. “This is why I’m reaching out to you today.” Perhaps the competition is moving too far ahead of your prospect or there’s a short window of opportunity that they need to act upon, or that a business’s future success might be seriously impacted due to inaction. Here you might draw upon generally available research on a topic to prove a point. Be sure to let them know that change or action required is do-able and beneficial. Most importantly, let them know your business has experience helping others like them...and you can help them, too.
  3. Why us? Declares your value proposition and differentiation. Here you talk about your offerings, but rather than focusing on features and functions, you tie back to the business outcomes that can be achieved. You might briefly share highlights of a case study/success story or customer testimonials. Talk about why customers buy your products and the pains your business has succeeded in helping them solve.

Cold Calling


Let’s go to the other extreme of sales - cold calling, which is the most challenging of sales prospecting. It’s where you engage a conversation where few or no prior touchpoints have occurred. What can be learned from cold calling to help improve and enhance a customer conversation? Cold calling focuses on developing confidence by being prepared for the unexpected. Leith recently shared a series of top tips for being successful when making cold calls during an online discussion, entitled: Cold Calling Master Sales Series.  

Think of it as a how-to for handling the rejection when a prospect flat out says—no. According to Leith, rejection teaches that, among other things, you haven’t perfected and nailed down your conversation and pitch. Learning and preparation are key and Leith tips include:


  • Practice Makes Perfect: According to Leith, “one of my favorite places to practice is driving in traffic rehearsing at the steering wheel, and getting the elevator pitch nailed down with the various different value propositions.” Also look to hone your pitch by practicing with trusted advisors, colleagues, or mentors. Through practice and experience your cold-call technique will quickly improve. Leith also suggests being “Canadian-nice” - really nice. The person you want to be the nicest to is the gatekeeper because most times, the art of cold calling means getting by that gatekeeper to the person you really want to talk to. You need to put a value proposition in front of the gatekeeper and convince them to move you to the decision-maker.
  • Know When to Walk Away: Part of embracing rejection is also realizing when an opportunity just isn’t there or there’s not a fit. With only a finite amount of time, you want to spend most of it with the best opportunities. Cold calling can be an extremely effective way to figure out which prospects are the best fit for your organization.
  • Your Best References: Have reference customers ready to go. Things like: names, phone numbers, and email addresses that you can share to say, “Here’s someone I work with that will vouch for me.” Testimonials are vitally important, especially when dealing with potential buyers who know more about a product or service than a sales professional. Remember, in today’s digital age it’s easy for them to do comprehensive research on your company.
  • Ready-Set-Go Games That Perfect Your Pitches: These might include:
    • Sales Pitch Scattergories, where at the start of each round, a player choses a question from a Jeopardy-like category board, or spins a wheel to determine a random topic to speak about. Then you as a salesperson need to come up with a conversation explaining how your solution can help a customer. The topic might be search-engine optimization so you’d randomly come up with some sort of value proposition around SEO. It’s great practice for honing the ability to think on your feet and come up with answers off the top of your head.
    • What’s Up, where you sit with your team and they serve you up the scenario of a random lead and you need to make an immediate pitch. It’s a mock exercise in how to deal quickly and confidently with random opportunities that come your way, and how to effectively present a value proposition. 
    • Sitting on a Plane is an exercise where you envision sitting in first class on a flight next to the CEO of an organization you’ve wanted to recruit for years. Again, it’s all about thinking on your feet. The task is to create a conversation that’s compelling so that the CEO doesn’t go into a briefcase and to grab noise-canceling headphones?   

Some Final Tips

Here are other ideas for preparing for and knowing your customer:


  • Talk to your customer service or success departments. Learn about your existing customers, why are they buying your product, and what pains are they trying to fix. 
  • Understand how your prospect makes money - it’s probably why they’re interested in talking to you, because they want to make more. “You want to solve a problem that’s stopping them from making money, or the prospect is doing well and wants a springboard to make more money,” De Appolonia says. “You need to understand this in order to keep up with the conversation, and fit in the tools and products that you have in ways that a prospect hasn’t thought of.


Preparation is the value you give customers. As De Appolonia puts it, “You can’t just play the, ‘they show up and I just spit out the 12 points that I was told to spit out’ and then you sell yourself. That works for a couple of companies - like Apple, which is perhaps a product that you really want. But for the majority, that’s not going to do it.”

When a customer comes to you, it’s likely they are considering doing business with you versus engaging a competitor. So you need to show them why you’re better. It’s why you need to be prepared, be thinking on your feet, and connecting-the-dots.

And be real. Both Leith and De Appolonia agree it’s important to be forthright and genuine. 

“If you don’t know, you don’t know,” De Appolonia says. “Don’t make stuff up. A lot of people will rush to the answer instead of processing questions they don’t have an answer for - taking it away and getting the right answer. It’s OK to say, ‘I don’t know.’” 

Finally, you might need to be thinking, quality over quantity when it comes to your sales efforts. Higher closing quotas rather than measuring the number calls to prospects could be a more important metric. Increasing closing quotas may, in fact, drive sales professionals to up their game and be better, De Appolonia says.  

“With volume I don’t have time to do anything (to prepare). I’m really just spitting out the same story to every prospect and I’m looking for low-hanging fruit. I’m targeting those people who are almost at the close and are asking me, “does this come in blue?’”

“When you play the volume game, you’re really saying nothing,” he says. “Closing deals becomes harder and you need to keep adding more prospects to your pool. It becomes a vicious cycle.”

About the Author

Dan is a former Director of Content Marketing for Vendasta. He has spent more than 25 years as a marketer, research analyst, editor, and reporter in the IT industry. When not fervently writing his next blog, Dan enjoys reading, running, cyling, and watching classic movies.

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