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How to Make Every Sales Conversation Better From the Start

How to Make Every Sales Conversation Better From the Start

Liston Witherill
Liston Witherill
10 min read

“Thank you for your proposal. After careful consideration, we decided to go a different direction.”

That overly formal and wholly impersonal message is one we’ve all heard before. Which is to say, a losing proposal is the result of a sales conversation that didn’t yield the result we wanted.

Your first inclination may be to ask “how can I write a better proposal?” It’s a good question, but most deals are lost long before you ever write, let alone send a proposal.

A sale is a process. It’s not a snapshot in time. Selling isn’t something you suddenly turn on or shut off. Whether you make a sale is the result of the collection of experiences that a prospect has with you, and their decision is their ultimate judgment of that experience.

Perhaps the most critical of all sales experiences is the initial sales conversation. The initial chat has the potential to be the most awkward of any other selling interaction for a simple reason: in many cases, you and your prospect are complete strangers!

Unlike sales at large consulting firms or product companies, your sales process as a services provider has much higher stakes. You’re the product and the salesperson, so prospects make judgments about you personally that will also color their decision about your ability to provide the services you sell.

You also have a vested interest in everything that happens in your sales process. Of course you do: this is your livelihood. But you can’t control how people buy; you can only control how you present yourself and run your process.

And I’d contend that focusing on having productive and friendly initial sales conversations is the first step to sales excellence. The reason is that your initial sales conversation will have the most lasting impact on your prospect. If a prospect gets a negative impression of you from the outset, it’s unlikely you’ll recover.

Start Without the Awkwardness

Sales don’t have to be awkward. In fact, it can be a fun and engaging process for you and the buyer.

There, I said it. I say this from experience because I enjoy selling, and my clients enjoy buying from me. Weird, I know, but it’s true.

The reason is that my goal is not to sell anything at all. Instead, my goal is to learn about the person I’m speaking with, then assess whether I can help them. If I can, I tell them. If I can’t, I tell them that, too.

Under no circumstances can I or anyone else “make” someone buy. Sorry, it doesn’t work that way, and it shouldn’t be your goal. Mutual gain is the foundation of successful business relationships. When a shared benefit is not apparent, it probably doesn’t exist.

What to Learn, and In What Order

Okay, say it with me: the goal of selling is to learn, not to sell.

What we want to learn is very specific, focused, and useful for both parties. Our goal in learning isn’t to passively sit back and hope that the right information uncovers itself, or that our prospect is so adept at buying services like ours that she knows what to do. She won’t.

As professionals, we must help our buyers buy. Sometimes that may mean telling our buyers that they should not buy from us or others like us. In that scenario, rest easy knowing you have a moral compass that’s fully operational. You’re considering your buyers best interest. You’ll also see something surprising: a real relationship! People like others who have integrity, and it’s pretty clear you have it if you defy your self-interest.

So what do we want to learn in our initial sales conversations? Four simple but highly targeted things:

  1. The problem the prospect is currently experiencing
  2. The business goals they have in solving the problem
  3. The value of solving the problem
  4. Determining whether there’s a fit to work together

Initial Sales Conversations Don’t Just Happen on the Phone

You have the right goals in mind. You have four things to learn. You have a goal of helping your prospect.

You’ll do all of this by following a short process that includes research, the initial sales call itself, and follow up activities. If you take nothing else from this article, I recommend you pay extra-special-scrutinizingly-close attention to the next section.

Research to Prepare for Your Initial Sales Conversation

Your initial conversation will be a total bust without research.

There. I did it. I don’t like making sweeping generalizations, but in this case it’s true.

Consider this example: imagine turning the clock back to the days when you were gainfully employed. You’re looking to make a lateral move to a new company to secure a more impressive title and higher pay. You apply for a job and get a callback to go in for an interview. When you sit down in the boardroom with your interviewer, you ask:

Remind me again…what does your company do?

Next! You would never do this because you’d obviously have zero chance of getting the job. And yet some initial sales calls start like this (and end immediately in your prospect’s mind).

Instead, do your homework on the person and their company. The information you seek to uncover in your research depends on your service offering. At a minimum, you should check out the company website, LinkedIn, and review the context of your interactions before your initial sales conversation.

Note that you should only spend about 10-20 minutes on the research phase.

Website Research

There is so much you can learn from your prospect’s website. I look for their target customer, a description of their suite of offerings, any marketing materials they have (which reflect their understanding of their customers), and their team.

If you’re selling marketing or web services, you can also look at their funnel, website quality, and lead generation activities. To understand scale, I also check out their web traffic using Similar Web. It’s easy to figure out the tech they have installed, too, with a tool like BuiltWith. And if you want bonus points, you can get more information about their marketing channels by looking up traffic sources in SimilarWeb, and check estimated spend and keywords on SEMRush or ads they buy on Spyfu.

I always look at a few individual pages on the site, too. I like to review the Careers page to see who they’re hiring now, which gives me a sense of company priorities. I also scan the About page to learn about the company’s history and culture. For instance, if the About page is all about the Founders and their otherworldly genius, I’ll be less inclined to work with the company because there’s probably more narcissism than I can handle. On the other hand, if the About page showcases employees and customers, then a healthier, more collaborative culture is likely to exist.

LinkedIn Research

LinkedIn is the best source of professional information that I’ve found. It’s extraordinarily powerful, and a few of its lesser-known features can help your research.

I start with research about the prospect. I’m looking for their career history, promotions within their current company, education, and where they’re from. Shared connections are another useful data point. In short, I’m looking to understand more about who they are, what motivates them, and what kind of story is told by their career trajectory.

I then move on to learning about the company. Note that if you have a Premium or Sales Navigator account, you’ll get much more data on company targets. On the regular LinkedIn page, you can see things like employee headcount by department, changes in total headcount, and hiring trends. On Sales Navigator, it’s easy to see updates and news about the company.

Communications History

Before your first call, you’ve had communications with your prospect. Maybe they filled out a form on your website, or emailed you, or were introduced by a past client. What is the context and content of those communications?

Capture it, because it’ll help you steer the conversation in the most productive direction.

Having the Initial Sales Conversation

We finally made it to the point you’ve waited for, and so patiently! Before I move on, take a moment to reflect on just how much you can learn before you ever talk to your prospect.

It’s almost time to have your initial sales conversation, but first…

Send an Agenda

About 24 hours before your chat, send an agenda so your prospect can prepare for your discussion. The agenda helps you control the flow of the call, sure. But it also shows that you’re a professional who knows what you’re doing. You are, aren’t you?

Want a script for your pre-call agenda? Download the guide now.

Having a Productive Call

Remember that the goal of the call is to learn about your prospect. To do that, you have to create an environment that allows for a productive call, without wasting any time.

To do it, you need to cover the five following steps in your call:

  1. Build Rapport
  2. Review Agenda
  3. Discovery
  4. Summarize
  5. Decide on Next Steps

Get the Initial Sales Call checklist.

Build Rapport – 5 minutes

Building rapport is a little-understood art. I’m not a natural at this, so I’ve analyzed times when people like me, and times when they don’t (i.e. I didn’t build rapport properly). What I’ve learned is a time-tested axiom: everyone’s favorite subject is themselves.

When you build rapport, the goal is to showcase your personality while allowing your prospect to talk about herself. I always inject a bit of humor and show that I’ve done my research by asking a question that reflects what I learned. So for example, I may say something like “So you went from a Fortune 500 to a startup…how are you holding up?” A question like this almost always gets a chuckle, and it’s focused on my prospect and her current experience.

Review Agenda – 1 minute

Remember that pre-call agenda you sent 24 hours before the call? Review it now, so that you have a chance to establish the goals of the call clearly and create a reference point in case the conversation gets off track. After you state the agenda, ask if there’s anything your prospect would like to add or change.

Discovery – 40 minutes

Discovery is where the majority of the learning happens. Since it’s called Discovery, your job is to discover. The only way to do that, of course, is to ask questions and listen. As a general rule, you should be listening 80% of the time in your initial sales call.

It’s helpful to recap the four things we want to learn during the initial sales conversation:

  1. The problem the prospect is currently experiencing
  2. The business goals they have in solving the problem
  3. The value of solving the problem
  4. Determining whether there’s a fit to work together

Uncovering the problem starts with a simple question: “So tell me…what’s goin’ on?” This question is open-ended and assumes nothing. It helps the prospect remember why they contacted you, and it gives them the freedom to tell you anything that’s on their mind. If they get off track, just remind them that the goal of the call is to understand where they are now.

Tying the problem to business goals creates a context for the journey the prospect is attempting to complete. The business goals should be SMART and agreed upon before you move any further in the process. A good business goal may look something like this:

“I need to increase sales revenue by 5% by the end of Q3.”

It’s clear, easy to understand, and we’ll all know if we’ve achieved it. On the other hand, an insufficient goal may look like this:

“I need more sales.”

How much more? And do you need a higher volume of sales transactions (and therefore more customers), or more sales revenue? By when?

Once you establish goals, it’s your job to translate goals into value. That is to say, there has to be clarity on what it would be worth to solve the problem. There are two ways to establish value: quantitative and qualitative.

Quantitative value means you can put a number on it. Numbers are ideal for sales or marketing efforts, like the goal example above. In that case, I’d go a step further and figure out the dollar value of a 5% increase in sales. That number would serve as an anchor for the price I’d charge for my services.

In many cases, qualitative value is the primary driver of the project value. This means you can observe a change, but you can’t put a number on it. If you provide coaching for speakers, the primary benefit you bring may be increased confidence and more positive audience reactions. Even so, I’d contend that you could quantify it in some way, you’d just have to get creative. If you’d like to learn more about this subject, I highly recommend the book How to Measure Anything: Finding the Value of Intangibles in Business by Douglas Hubbard.

Summarize – 5 minutes

At this point in your discovery call, you’ve established your prospect’s problem, business goals for solving it, and the value it would create.

Summarize your understanding of all three. The purpose of providing a summary is to ensure that you have the correct understanding of the problem, goals, and value. Invite your prospect to tell you if they agree.

The summary provides another checkpoint in the conversation. That checkpoint is an explicit agreement about what’s going on, what you will achieve, and what it’s worth. This information is critical to you and your prospect, so be sure to have complete agreement on the summary.

Decide on Next Steps – 5 minutes

By now you should know enough to determine if there’s a fit to work together. Either way, tell your prospect what you think. That may sound something like this:

“Based on your situation, I’m convinced I can help you get to a 5% increase in sales revenue by Q3. Would you like to continue the conversation?”

Notice I haven’t pressed for a pitch, or a sale, or even assumed the prospect agrees that we should keep talking. The reason is simple: I believe that allowing your prospect to decide for themselves is the most potent and ethical way to sell. No one wants to be deceived, persuaded, or have their arm twisted. You wouldn’t want that, so don’t do it to your prospect!

Instead, invite them to continue the conversation. That way, you and your prospect will mutually decide to continue, or not. It’s okay to stop the discussion at this point. Not every opportunity should end in a sale.

If there’s agreement to continue, the conversation must continue! Set a meeting right then and there, and send a calendar invite to your prospect.

What to Do On Your Next Initial Sales Conversation

Having a productive initial sales conversation is the best way to improve your probability of winning new business. But more importantly, it helps contextualize why and whetheryou and your prospect should do business together.

Do This

  1. Take charge of the conversation by providing leadership through your process.
  2. Do your research and send an agenda before every call.
  3. Don’t pitch on your initial sales call – just learn!
  4. Keep your prospect talking so you can soak up more information.
  5. Summarize, summarize, summarize!

And also…

  1. Don’t put pressure on yourself to implement everything at once. The most accessible place to start is with the agenda and research, then build from there.
  2. Don’t be inauthentic. The key to creating rapport is to be yourself.
  3. Don’t sell. It’s not the point, so get it out of your mind!