One of the most important qualities a sales rep must possess is knowing how to prospect.

Many argue that due to the number of tools available to sales professionals, prospecting is as easy as ever. But sadly, many still continue to call their prospect list and ask questions that could have easily been avoided had you performed proper sales prospecting.

In this article, I will go through expert tips on how every salesperson should approach their ideal prospect and how by using personalization and storytelling, your sellers will be able to create sales engagement.

The Importance of Knowing How to Prospect

If this COVID addled 2020 has taught us anything, it’s that experts’ predictions of the world going completely virtual, happened way before any of us expected.

Countless organizations have had to adopt virtual selling and improve their sales prospecting skills to reap the benefits of all of the readily available information.

Old school sellers prior to the internet didn’t have the luxury of locating anything from company size down to a trigger event and even competitors. On the contrary, a salesperson from the pre-web era had to rely on good old’ fashioned phone books to get most of their information. It surely is a wonderful time to be in sales.

With prospecting and other sales tools being introduced left and right, sales leaders have a plethora of options to ramp up their teams and design a great sales plan. But can these tools be overwhelming? Of course.

Sales Automation Tools When it Comes to Prospecting

In this episode of Modern Selling Podcast, I speak to Ed Calnan. Ed is the co-founder and CRO of Seismic, where he leads the company’s go-to-market efforts. Ed brings more than 20 years of sales leadership experience from ADP, Thomson Financial, S&P, and EMC to Seismic. In 2016, he was named a Top Boston Startup Founders Over 40 by

This episode highlights the sales tools that are part of every sales team’s arsenal as well as how incorrect usage can do more harm than good.

That’s right, we receive countless emails and phone calls where it appears that proper prospecting wasn’t done. This in turn, instead of being beneficial, it leaves the sales team looking lazy by not using all of the readily available information.

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Lazy Reps Yield Poor Sales Engagement Results

It’s an interesting time to be in sales. Those who have been in the game for 15+ years are excited to see that new age reps have access to so much information prior to any call. Before picking up the phone, previous research is pivotal to create a real conversation with your sales leads.

If your sellers call a lead asking what problems they’re facing, they’re likely going to waste both parties’ time. Instead, if they leverage the information found on social platforms, even if it’s just flattery, they’ll spark the interest of prospects.

This happens way too often and it makes tenured sales leaders look like they haven’t coached their team properly. Great insight from @ecalnan & @M_3jr in the @GoModernSelling. Click To Tweet

They should use what I like to refer to as, “show me that you know me.” This is at the very minimum what prospects expect out of any call they take.

A correct prospecting plan is all about using the tools at your disposal but not relying on them entirely.

Ed says that “automated tools get reps headed in the right direction but there is a point where the system ends and people need to take over.”

In layman’s terms, tools like Xant are fantastic sales engagement platforms but it’s up to sales leaders to ensure their team is humanizing them.

The Concept of Personalization

In the B2C world, some of the world’s biggest brands are already where they need to be. Brands like Netflix, Spotify, and Amazon grab what they know about you and people like you (thanks to similar interactions within their platforms), and provide their users with recommendations.

For example, Netflix knows how to prospect by displaying what shows you watch, grabbing similar titles that other people have watched, and provide you with a list of suggestions. The same goes for Spotify with their weekly playlist for every year. And Amazon knows that you have an infant at home and tells you when you need diapers and or formula.

Sales automation will eventually get to that level of intuition but we’re not there yet, but that doesn’t mean it can’t be done manually. Here’s a great example of a conversation Ed proposes.

“I understand you, I think I know what your organization is going through and I’ve helped organizations and people very similar to you. Here’s what I’ve done and here’s how their problems were resolved.”

It’s not quite as intuitive as Netflix, Spotify, and Amazon but it does create real conversations that will let your prospects know you understand them. It will also ensure you’re talking to the right people because let’s face it, you don’t want to be speaking to a leader whose problem you can’t solve.

What Does it Take to Book a Sales Meeting with a Top CIO?

I wanted to share an interesting anecdote about a business relationship I had once upon a time with Mckesson Corp., one of the world’s largest pharmaceutical and medical supplies companies and current fortune 6 company.

My relationship was with the then CIO, Randy Sprad. I decided to open up a can of worms and ask why out of all of the calls he received on a daily basis, being prospected by just about everyone, did he decide to take my call? What did it take to have him become a potential customer?

Randy succinctly answered, “everyone seems to be in a hurry to explain product specs and how they can save me money. Sure, these are things that are important, but those who go out of their way to explain to me what my competitors are doing and what they can do to give me the competitive advantage, that’s what I’m looking for.”

Interesting advice from a top CIO. Too many cold callers are focusing too much on product specs and pricing. In this episode of @GoModernSelling with @ecalnan and @M_jr3 Click To Tweet

But how is this done? Through the art of storytelling.

Storytelling: The Key to Personalization When Learning How to Prospect

Storytelling in sales is fundamentally important, it’s a skill that can be honed but can’t be left out of any sales process. A sales raconteur is someone who is skilled at telling stories and it is these individuals who can spark up immediate interest.

Tenured reps have a barrage of stories in their repertoire and some don’t even know it. From past experiences, stories and memories will inform your ideal customer of the experience you have in similar situations.

Buyer personas might not all be created equally, but letting qualified prospects in on what has happened in their peer group will create genuine interest.

The best reps will work with their marketing teams to leverage these stories to create compelling content. It isn’t just about sharing these stories with their prospects. It’s about creating content that will be used as resources on your company’s website to send new prospects to. It will also help your training team to teach incoming reps about what information attracts new buyers.

Here’s some great sales prospecting advice: decision-makers want to feel like they’re part of a movement. If you can show these companies (through stories and real-life examples) that you know what they’re going through, they’ll listen. Show a decision-maker that other companies in their peer groups are going through a similar predicament and they’ll surely want to be part of your solution.

Using video and social selling to improve your prospecting strategy

The modern buyer is as knowledgeable as they ever have been. With so much information available to them as well, a personalized email or text might not even be enough.

Adopting omnichannel is fundamental to getting ahead with today’s buyer. Social media, sales messaging, cold outreach, calls, they need to all be interwoven with your business strategy.

The best sales reps are masters at the social game. They have also mastered the art of video prospecting. Failing to recognize the importance of these as part of your current strategy will have you looking ancient.

Sales leaders need to learn what’s available and coach their teams to use every arrow in their quiver. If you don’t and continue to think the sales world hasn’t evolved, you and your business will become obsolete. Become socially engaged, adopt omnichannel and video-centric and you’ll pave the way for your team’s success. Both your potential client and existing customers will appreciate the extra effort.

How to train your team on sales engagement tools

With new sales engagement tools being released periodically, the sales world is looking bright for those high-performing sales professionals.

Organizations are forced to digitally engage, which makes training for this virtual world a lot different than it was 10 years ago.

I predicted 3 years ago that in 2022, the world would go completely virtual. Unfortunately for many, the COVID era has expedited this process and many are struggling to keep the lights on.

Every sales leader has a list of their favorite tools, but these tools aren’t as important if your team isn’t coached on how to prospect. Along with training them on how to best use these tools, as a leader you need to hone your team’s digital sales training skills. Social selling skills aren’t inherent to all millennials and before approaching any prospect they’ll likely have the following questions.

  1. How do I engage well on social media?
  2. What do I say?
  3. What’s the right way to say it?
  4. Who am I looking for?

If you’re going to be using cold calling, or cold emails it’s important to look for as much information about your sales prospect as possible. Make it a habit to find out 3 important things about each prospect before you call.

Getting someone on the other end to commit to a 2-minute call is hard enough work already. I really wish more reps would listen to this advice from @ecalnan and @M_jr3 in this episode of @GoModernSelling. Click To Tweet

When using video, don’t overdo it. You have 7-15 seconds to capture the attention of your prospects, make it count.

Lastly, we’ve seen countless individuals reach out to us on LinkedIn and even via emails with abysmal spelling skills. Ask your organization to invest in Grammarly, it might not close deals but it can break deals if your spelling isn’t on point.

Wrapping up By Teaching Reps How to Prospect

There’s an interesting idea Ed shared with me on this episode that I think is a great practice to consider.

Once a week, Ed likes to take a B2B sales call and listen to a rep’s sales pitch. Not only is it good sales karma for the universe but he also stresses the importance of rewarding creative young people. Of course, this is all predicated on correct prospecting but those who have done their homework and know where they want the call to go, deserve to be heard. Ed not only picks up their calls but also provides these reps with improved tips on how to prospect.

Content, storytelling, and personalization require a three-headed team. This team is marketing, sales leaders/reps, and sales enablement. Without these three teams in sync, it’s impossible to be effective in today’s sales world.

Think of these teams as an NFL roster. If offense, defense, and special teams aren’t working together, they can have the best players, but they’ll lose every game.


Outline of this Episode of How to Prospect

  • [1:04] About Ed: From Student of the Game to Founder and CRO.
  • [9:12] What is Prospecting? What do we consider prospecting to be?
  • [18:33] Why aren’t more sales leaders helping reps focus on bringing content that serves me up as a buyer.
  • [22:32] Learning to leverage sales content for storytelling
  • [23:53] Your prospects will react better to stories if they feel they’re part of a movement.
  • [32:02] What role does video play within social media for sales reps?
  • [42:06] Early predictions of a completely virtual world.

Resources Mentioned in this Episode

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