5 Common Reasons Your Sales Conversations Get Derailed

Written by
Aja Frost

1. You Stick to a Script

Having an outline in front of you while you’re on a call helps you stay focused and remember what you need to cover. The operative word being outlined, If you’re reading word-for-word from a script, you’ll sound rehearsed and robotic and turn buyers off.

In addition, you’ll miss valuable opportunities to learn more about your prospect.

Take this conversation between a prospect and a salesperson using a script:

Rep: “What’s holding you back from hitting your customer retention goal?”

Prospect: “I think the biggest problem is inconsistency. I’d love to get a representative from every department in a room so we can develop a strategy for consistent customer experience. Right now it feels like every team is doing something different.”

Rep: “Okay, got it. And have you explored any strategies for overcoming that obstacle?”

Prospect: “Well, as I said, I’d like to host a big meeting … ”

In this situation, sticking to her script made the rep lose credibility. Instead of delving into her prospect’s pain points, she recited the next question on her list. Even if he was interested in her product, the buyer will probably write her off.

2. You Start Selling Too Soon

Have you ever been on the phone with a prospect when they mention an issue that your offer is perfectly designed to solve? If so, you were probably tempted to jump into your sales pitch.

Selling too soon is detrimental for two reasons. First, it makes you look self-centred. Rather than talking about the buyer, you’re reeling off product features.

Second, bringing up your solution before the time is right also inevitably involves making assumptions. Your prospect might have more pressing priorities than the first one they mentioned, but you’ll never discover what they really care about if you talk rather than ask questions and listen.

3. You Don’t Properly Set the Agenda

Most salespeople provide some sort of agenda at the top of the call. Any agenda is better than none. However, if your itinerary isn’t clear -- or you don’t follow it -- your conversation will wander.

Make sure you include every discussion point you’d like to cover. In addition, your points should flow logically. It doesn’t make sense to move from the buyer’s strategy to your suggestions back to their current procedures.

Finally, incorporate your prospect into the agenda-setting process. If you don’t talk about the issues that matter most to them, they’ll inevitably be dissatisfied with the call.

Here’s an example of a poorly set agenda and how it could be improved:


“In the next 60 minutes, I’d like to talk about your goals for Q2 and how my team can help you achieve those.”


“I believe we have an hour. Let’s start with some quick introductions since there are some new folks joining us. After that, I’d love to learn more about your product team’s goals for Q2. Having more insight into your objectives and potential challenges will help me develop a tailored solution.

Mike mentioned you wanted to discuss how similar organisations have benefited from our services. I’m happy to do that. Is there anything else you’d like to cover today?”

4. You Don’t Have Enough Context

Nothing destroys your credibility faster than asking your prospect a question you could’ve easily answered with a quick Google search.

Nonetheless, some salespeople show up to calls with little to no information about the buyer and their company. This ignorance always reveals itself. 

For example, a clueless rep might ask, “Tell me about your company. What do you sell?”

Answering this question doesn’t help the prospect. In fact, it’s a waste of their time. Every minute a salesperson has with the buyer should be devoted to helping them or discovering information the salesperson couldn’t have gotten any other way.

When reps do research before their calls, they can immediately jump into high-value questions. An educated salesperson may say, “I know you offer toothbrushes at a range of price points. Have you had trouble reaching customers at the higher end of the market? Many of my customers have struggled to appeal to luxury consumers after branding themselves as affordable.”

5. You’re Not Speaking the Prospect’s Language

A successful salesperson acts as a translator, tailoring her message to her specific prospect so it’s relevant, comprehensible, and impactful. On a surface level, this means avoiding technical jargon the buyer probably won’t understand and instead using terms from the buyer’s industry. On a deeper level, it means focusing on the product features and benefits that’ll matter most to her prospect.

If the rep doesn’t customize her presentation, the buyer will tune out.

Let’s compare two sample conversations.

In the first exchange, the salesperson is giving a generic pitch:

Rep: “Our research shows most enterprise organizations are facing two major challenges with on-premise MTF: Rapid increases in average file size and a number of transactions, which burden legacy file transfer systems, and increasingly stringent regulations thanks to government concerns over data breaches. Do either of those challenges resonate with you?”

Prospect: “Uh … ”

In the second example, the rep has discovered her prospect is relatively unfamiliar with data storage. She’s also looked at the buyer’s blog posts to discover what language he uses.

Rep: “Since Glasshouse hosts approximately 2,000 different ATS systems, safe to say you’re dealing with a lot of data. Most of the organizations I work with that much data are struggling with their existing storage systems. Every day, the number of files they send and the average size of each file gets bigger. Does that sound familiar to you?”

Prospect: “Yes, the IT team has been saying something to that effect for the past year.”

It can be hard enough to secure time on buyer's calendars. Steer clear of these five errors so you don’t waste valuable time with your prospects.


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