How to Sell Smarter than Automated Communication and Artificial Intelligence

Cars can drive themselves.

Cars can drive themselves. Filmmakers can replace actors with CGI. Conversations can be automated with a computer program. For years, we’ve needed a human element to get where we want to go, to build connections with people, and to communicate with others, and everywhere you look, that human element is becoming more and more irrelevant. What’s more, it’s starting to wreak havoc in the sales industry.

If you’re like me, you’re already starting to see artificial intelligence and automation making human sales reps more and more superfluous.

Think that sounds a little wild? I bought a Tesla last year online. I didn’t talk to a single sales rep. I went online and configured it, they drove the car to my house. That was it. Artificial intelligence and automated communication took over the sales part of buying a car. There was zero human intervention.

With the technology to automate conversations with customers and the logistics of a sale, what’s the value of a sales rep anymore?

The most compelling answer that I know of is that the value of sales reps is closely tied to their ability to provide context. Pulling from a presentation I recently did for Visualize Summit for Sales, sponsored by Lucidchart, and a keynote I did recently at the Sales Assembly Summit, I’ll share my insights on how to use context to make yourself more valuable than the sales robot.

What is context and why is it important?

One of my favorite influencers is Gary Vaynerchuk (and if you’re not following Gary Vaynerchuk, I highly recommend you do). Everybody talks about how content is king, but Gary’s response to that statement is “Fine. If content is king, then context is God.” And that statement got me thinking about the role of marketing versus sales.

Marketing’s job is to provide content, relevant information that customers can reference as they learn about a product. Sales’ job is to provide customers with context, tailoring generalized messages from marketing to be specific to individual customers.

But that’s not what sales reps are doing these days. If you think about it, the average sales rep is starting to look more and more like a marketer: blasting out template emails, pressing play on scripted demos, sharing stuff on social without an opinion. That is just providing content, and I do not need a human being to do that anymore. Providing content is where the average sales reps will meet their downfall.

So how do sales reps rise above average to provide context instead of content? I want to dive into some tactics for email writing, for building social presence and your personal brand, and for presenting and demoing so that you can walk away and apply context to your sales during your day-to-day activities.

Providing context for emails

There are plenty of cool tools out there right now like SalesLoft,, and Yesware that are supposed to be sales efficiency tools. The problem is that average sales reps are using them as sales automation tools. They’re just taking template emails that marketing gives them, putting them into cadences, and pressing play, without putting any thought behind them. That’s providing content.

Personalizing emails with “why you, why now”

In my training, I build off of Jeff Hoffman’s email technique called “Why you, why you now” to help sales reps learn how to provide context in their emails.

The technique is pretty self-explanatory. You need to find a way to answer the two essential questions: why I am contacting you and why I am contacting you now.

In order to answer these essential questions, you need to visit the company’s website and do some research. For your top accounts, it’s also helpful to do some listening via social media (I like to use social listening tools like LinkedIn Sales Navigator and Owler) to find out what big initiatives are driving the company forward. As you do your research, you are looking for buying triggers. Did they open up a new office recently? Launch a new product? Merger or acquisition?

Once you have some context to provide around the two essential questions—”Why you, why you now”—you can craft your email. Here’s a quick example where I start with the “why you?” (context) and then show the “why you now?” (buying trigger):

I know what you’re thinking: “I can’t spend a half an hour writing every email that I want to write. I have to do 20, 30, 40, or 50+ dials a day, so I can’t spend a half an hour writing every email.”

Here’s a way to make these emails efficient: Pick five specific events or triggers that commonly occur across your customer base where your business typically adds value. Some examples include:

  • Opening up a new office
  • Launching a new product
  • Merging with another company
  • Growing quickly

Then come up with messaging about how your solution addresses those triggers specifically.  When I hear about one of these triggers through social media or information on the website, I open up my trigger template, scrub it up a little bit, and fire it off. I’ve just done some really high-quality prospecting in a very efficient way.

Also, try out these tips to make your emails shine:

  • Don’t start your emails off with “I’d like to introduce myself to you” or “We’re the leading provider of…” Nobody cares about that. The only thing readers care about is themselves.
  • Add a call to action. Tell them what you’d like them to do next.
  • Keep your emails short—under one or two scrolls on a smartphone.
  • Sign up for marketing email blasts so that you know what your prospects are already getting from you/your company in their inbox, especially if those emails have your name on them.

That last point is especially important. I don’t want a client to get inundated with templated emails from me when they are already receiving marketing emails, only to hear from me a couple weeks later in a more personalized way.

Using mass marketing emails to your advantage

When I see a piece of content that marketing sends to the masses, whether it’s a newsletter or a webinar invite, I find the 5 to 10 clients in my territory who I want to stay top of mind with and who could get value out of that piece of content. I send the content to these clients directly and say something like this:

“I’m sure you probably saw this from our marketing department. I was reading through this piece the other day, and I thought it was interesting because it addressed [insert relevant information here]. Based on our previous conversations, I thought you might want to take a look at it.”

It’s even better when you can point out specifically where they’re going to find value. For example:

“Based on what I know about your company, at around minute 15 to minute 32 is really where the core value of this webinar is. The presenter was talking about some very tactical things there. Thought you might find that interesting.”

If a rep would ever send me something as valuable as that, I would fall out of my chair.

So as you personalize your emails and show your customers exactly where to draw connections and find value, you’re well on your way to adding the valuable context to content from an email standpoint.

Providing context for social and brand building

Another way sales reps can go above and beyond robotic selling is to build their personal brands, especially on social media. Again, I’ve seen automation be the enemy here: marketing departments sometimes tie a marketing engine to every sales rep’s Twitter account and blast out robotic tweets from all of them. I don’t need a live sales rep for that.

So how do you do social the easy way? When social selling first came out, I was not at all excited that there was yet another thing I had to do to be successful in sales. It flipped for me when I started looking at social selling as self-education. I started using tools like Feedly to send me content that improves my business acumen and helps me learn about my clients and the industry that I focus on or even about the personas that I sell to.

When I read an article that I think is actually valuable, I take an extra two seconds to:

  1. Put some context around the article that explains why I think it’s interesting.
  2. Share it on LinkedIn and Twitter.

For example, I might write something like:

“Really good ebook here. If you’re a VP of sales in the SaaS industry trying to integrate social selling into your routine, you should take a look at pages 3, 8, and 12. There’s some tactical stuff that you can do immediately after reading this article.”

This approach saves you the time it takes to create your own content. You can just provide people with great content that is already written. You’ll still be the one your clients will thank when you provide them with valuable context around the content.

Providing context for presentations and demos

My least favorite part of the sales process is the demo because every single demo is exactly the same. I listen to three to five demos every week because all of these sales technology companies want to pitch their products to me so I can potentially introduce the technology to my client base.

Here’s what to avoid in the standard sales demo:

  • Asking “Is this still a good time?”—What kind of a response are you expecting? “Please hang on a minute while I check my email?” The client scheduled this time for you to spend with them. Get started with the conversation.
  • Going through every single slide—Sales demos should not simply be you reading through all of the slides. Clients don’t need you for that; they can do that part themselves.
  • Constantly saying “Does that make sense?”—People will generally say “yes” to this question, and then at the end of the demo, they’ll say, “I’m gonna need a little time to digest what you said.” If you ever hear that, stop and apologize to the person because you just wasted their time. It is our job to help people digest information.

How do you make your demos outstanding? You provide context. Here’s how:

Email your prospect the day before the demo

You can get the essential information you need to tailor a demo if you learn first about your prospect’s goals and priorities. Provide an agenda for the demo and ask if your prospect would please add to the list of items to cover. This initial email is also a great opportunity to confirm the qualification information you received from your SDR or BDR.

Here’s an example:

“I’m looking forward to our meeting tomorrow. To get the most out of our time together, I’ve put together a brief agenda that will cover [insert key presentation points] items. I heard from my colleague that [BDR/SDR information] is also important to you and wanted to confirm if that is still the case.

Could you do me a favor and email me back to let me know what else you’d like to add to the agenda and to confirm that I understand your priorities?”

It doesn’t matter whether or not they respond. The important thing is that I can later use this email to start our conversation with goals, priorities, initiatives, and the bigger picture so that I can tailor my demo (more details below).

Figure out when you’re going to lose their attention

When you start the demo, you want to know when people are going to start tuning you out. So just ask them.

“Do you have a hard stop at 2:00?”

If they have a hard stop at 2:00, around 1:50 or 1:55 they are going to start thinking about their next meeting. Plan to get the essential material in early.

Use the agenda email to drive a value-based conversation and tailor your presentation

Because you sent an agenda email, you can set expectations for the content of the demo and start the conversation as a big-picture, value-based discussion. I usually start by saying something like this:

“You may or may not have seen the agenda I sent out yesterday. I just want to make sure that we get the most of our time together. I have a 30-page slide deck here to show you, and it usually takes about 30 minutes. Instead of going through the whole deck with you, I would like to focus on what’s most important.

If we could start here by talking about what you want to get out of today’s presentation, that would be very helpful. Help me understand from a business standpoint where are you trying to go. How are you trying to scale?”

Based on that 5- to 10-minute preface conversation, you can start going through your presentation with the customer’s priorities in mind. You can highlight the areas that they were most interested in, and you can diminish or skip the ones that weren’t as important for helping them achieve their goals.

Check for understanding by asking the client to put your solution into their business context

Instead of asking “Does that make sense?” every few minutes, you can pause intermittently and say:

“Okay, this component of our solution is actually something that you said was a priority for you. Could you explain to me how you see our solution fitting into your existing workflow? Or could you share with me how our solution compares to what you’re doing now?”

If your client struggles to explain how your solution fits in, you know you haven’t communicated your solution clearly enough. Ask some more questions to understand where the gaps are and fill them in to make sure your message comes across crystal clear.

Adding value with context

Your email cadence approach, personal brand building, and demoing tactics are huge areas of opportunity for any sales rep, but they can also be danger zones if you’re one of the reps who continues to just push play, providing content instead of context.
I don’t have all the answers about what it will take to stay relevant long-term. Start thinking about how you can improve and how you can stay relevant in today’s world. Look at every single aspect of the sales process, of your business, of the tools that you use, and ask yourself, “Is this content? How can I put my context around this to add a valuable human element there?”

To learn how other thought leaders are answering these questions, check out other sessions from the Visualize Summit for Sales.

During the event, Lucidchart made an exciting announcement about the Lucidchart Sales Solution, which is designed to drive success for sales reps, technical sales, sales operations, and sales leadership at every stage of the sales cycle. The solution includes Lucidchart for Salesforce, a brand-new integration that allows you to automatically import your Salesforce contacts into Lucidchart to easily build account maps. Account maps can be a great way to enable collaboration with marketing, customer success, and sales leadership so that your customers receive consistent, personalized communication. Give it a try!

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