4 Questions That Scare Salespeople

I can appreciate the job's difficulty. But I swear, at times, it seems like salespeople are intentionally making their job harder.


It’s not so much that the questions scare salespeople; it's the lack of answers they find terrifying.

As someone who coaches salespeople and makes selling a part of my everyday activities, I can appreciate the job's difficulty. What I can't respect is not doing everything possible to make the job simpler. I swear, at times, it seems like salespeople are intentionally making their job harder.

Here’s what I mean

Open your customer relationship management (CRM) system and answer the following questions for each active prospect…

But wait. Hold on a minute. Before we get to the questions, let’s address the two key elements in my request.

First, let's make sure we agree about what constitutes a prospect. A prospect is not a name on a wish list or on the list you just purchased. Those are suspects, someone you think you may want to have as a client.

You don't have an actual prospect until the person is aware of your interest in potentially doing business and agree to participate in that exploration.

Now your CRM. To be clear, I’m talking about the technology you use to track prospects. This is the system that you bitch about to your sales manager because "entering stuff in the system gets in the way of my valuable sales time.”

Do you know why salespeople avoid using a CRM? It allows them to avoid owning up to the reality of not having a healthy pipeline.

Tracking prospects in a consistent, centralized manner is a prudent practice. Enough with the bitching and moaning about data entry.

Back to the questions

Yes, selling is difficult. Nobody likes to be sold to, right? So, look at the opposite side of this coin. Instead of thinking about how you can sell to the opportunities in your pipeline, focus on how you can help them make better buying decisions.

The path to them making better decisions comes with clues that lead to an engagement with you. If you can answer the following questions, there is an excellent chance you will help the prospect make a better buying decision. There is also a good chance that a better buying decision will include you.

1. What does this opportunity value most?

This question is both the most obvious and the most ignored. It is obvious because, of course, you have to show prospects more value. The problem is that most salespeople assume the answer to this question on behalf of the prospect. Salespeople assume the prospect wants a lower price, more free stuff or better service.

Maybe they do. But the path to lost opportunities is littered with wrong assumptions made by salespeople.

See also: Trusted Adviser? No, Be a Go-To Adviser

Don’t make this difficult. Just take the time at the beginning of the sales process to ask the buyer what they value. But ask it in a way that expands their expectations beyond price, product and service.

Ask, "If we were getting together for dinner to celebrate what we have accomplished by working together, what are a couple of non-cost-related things we would be celebrating?”

2. What have I done to deliver on that value?

Once you have identified what a prospect values, start delivering it. I mean, like NOW, while they're still a prospect.

I laugh at one of the cornerstones of way too any producers’ value propositions. They will say, "What sets us apart is the level of service we provide."

WTH?! 😳

Here’s my problem. A prospect can’t experience your service until they become a client. You have ZERO chance to demonstrate that value during the sales process.

If you want to make the buying decision easier for a prospect, nothing will move the needle faster than delivering ideas and advice on what they value. This completely removes the concern they have over whether they would get any meaningful value from working with you.

A prospect in motion

The following two questions are yet more examples of why following a sales process is so important. If you have a consistent sales process in place, the steps of moving a prospect through the pipeline become apparent. To ensure productive movement, you must be able to answer these questions for each opportunity.

3. When will our next meeting take place?

The one thing worse than an empty pipeline? One that is filled but stagnant. Prospects must keep moving forward (and I don’t mean on the two- to three-year timeline so many producers believe it takes to earn a new client).

If you have identified what a prospect values and are already providing proof of your ability to deliver, you have their attention. And, if you have shown them a path that leads to even greater value, they will be eager to schedule the next conversation and move forward with you.

Interested prospects are almost as excited for the next meeting as you are.

4. What is the purpose of the next meeting?

Every meeting must have a purpose, a defined goal. When you and the prospect agree on what you will discuss next and why it is meaningful to the buyer, meetings stop feeling like a burden and start to look like the growth opportunity they need to be.

When you have defined the purpose of a meeting, they become productive, meaningful and valuable to the buyer.

Purposeful meetings build momentum, trust and confidence.

The questions move your KPIs

The average time it takes a typical producer to acquire a new client is way too long in our industry, and the close ratios are woefully low.

Answering these four questions with confidence will lead to more new clients in dramatically less time.

Closing more deals isn't rocket science, guys. You have to be able to answer the right questions.

See also: What COVID and 43 Years Taught Me

Back to your CRM

Look back at each prospect in your pipeline. If you can positively and definitively answer each of these questions for a prospect, you are likely looking at a future client.

If you can't, well, your gut has already been telling you that answer.

Kevin Trokey

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Kevin Trokey

Kevin Trokey is founding partner and coach at Q4intelligence. He is driven to ignite curiosity and to push the industry through the barriers that hold it back. As a student of the insurance industry, he channels his own curiosity by observing and studying the players, the changing regulations, and the business climate that influence us all.


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