What To Do When Your Prospect Pulls The Blog Feature
Molly D Protosow

By: Molly D Protosow on May 24th, 2018

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What To Do When Your Prospect Pulls The "Boss" Card: How To Assess the Opportunity

Sales Training | Sales Management | Sales Meetings

Have you ever been in a situation where a customer has said to you, “I like what you’re selling, I like the product or service, and I’m all in favor of it. I’m going to talk to my boss, and I’m going to tell her that I think this would be a valuable investment. Let’s see where that goes.”

So often, we hear these kinds of things and we assess how much potential this new opportunity has, how much time we should be spending on it, and how many resources should be applied towards it.

But let’s consider this for a moment:

50% of sales time is wasted on unproductive prospecting, according to B2B Lead. And it takes 50% longer on average to lose a deal than to win one according to research by TAS Group.

Sales reps can spend valuable time managing prospects who either aren’t qualified or simply aren’t interested in buying. And to add insult to injury, these types of prospects tend to linger.

This means you need to be ruthless in how you assess and prioritize the sales opportunities in your pipeline. But, very often, we find ourselves misled by words.

People say things and make promises they have no intention of keeping. A prospect can tell you they will buy from you but until their behavior and actions coincide, you’re probably not going to believe them.

So, what can you do?

Play Defense

Salespeople, like basketball players, need to know how to play defense. Basketball players are taught to look at the opponent’s hips, not their feet because "fancy footwork" can be deceiving.

The opposing player wants you to think he’s going one way, when in fact, he’s planning to go the opposite.

"Fancy footwork" (aka misleading words and vague promises) can be tricky to navigate. But we know hips don't lie (thanks, Shakira) and a player can’t move without leading with their hips because your hips indicate what you’re really thinking and which direction you're really headed.

In sales, hips equal actions and feet equal words.

When a prospect or client says certain things using their “fancy footwork,” it’s important to distinguish their words from their actions.

A prospect may tell you that the sale isn’t going to happen unless one or two important people within their organization approve. While this may appear to be a gesture of transparency, you cannot be 100% sure how to interpret this information.

Is this the truth? Are they stalling? Are they afraid to say “no”?

Actions speak louder than words. Your pipeline and forecasts should be based on actions and behaviors, not on the promises people make.

If you've ever had the "boss" card pulled on you, then consider the following 3 things to help you assess the realistic nature of that sales opportunity.

  1. Why?

  2. At This Moment

  3. Collaboration


If the customer lets you know that he or she must speak with the boss, ask them what they think the boss will or won’t like, and why. Show them that you’d really like to know the reasoning behind their thinking. This shows the prospect that you are curious and interested, and also provides you with more information to add to your deal-closing arsenal.  The best way to execute this is to find a conversational way to do it. If you don’t feel comfortable asking why, then find a new angle to approach it. Just make sure that you find one way or another to ask.

This is your chance to really understand, from your prospect’s point-of-view, how important it is for you to meet their boss and how that will influence the momentum of the sale.

For example, suppose you meet with your prospect’s boss and she doesn’t like what you have to say.  Does that mean the sale is over? Is that a deal killer?

Remember to ask, “Mr. Prospect, if your boss doesn’t like the pitch, is that a deal killer?” If so, then every single thing that you need to do next hinges on accomplishing a successful meeting with the boss.  

On the other hand, if your prospect says, “Well, actually, if my boss is not 100% behind it, I could still buy from you, but I’ll need to change either the pricing model so it fits within my budget, or get some other departments involved.” If this is the case, then at the very least you'll have a plan B.

At This Moment

Next, you’ll want to consider asking, “What do you think your boss would say at this moment?”

The boss is likely to already have a pre-existing bias, either for the kind of solution you’re selling, or against it. Understanding what that pre-existing bias may be is extremely important for landing a deal.

The boss may not even care that much about this issue, or the problem you’re solving for may not be a priority for him or her. Therefore, the contact and his boss may not be inclined to act with urgency or "at this moment". This is why you need to delve deeper and find out what current priorities and projects are top of mind for both your contact and his boss. 

For example, if your contact says, “Well, I like your solution and I know my boss would see the value our people would receive. But we've just started another new initiative.”

This signals a positive perception about what you're offering, however, it may also mean they aren't willing to place any importance on your solution at this time because the immediate need is on this other new initiative. 

On the other hand, if your contact says, “Well, I like your solution and I know my boss would see the value our people would receive. It will also help us look good as a company, make us more money, and I’ll get that promotion I’ve been working for. ”

This signals personal and professional motivation, which increases the probability of them wanting to work with you in a timely fashion.


How open is your prospect to collaboration? Are they willing to let you help them sell your solution internally?

You can find out by asking second-level questions such as:

  • Can we work together to get your boss on board?
  • Can we either present to your boss together, or meet with your boss in advance of the presentation?  
  • Can I help you create a presentation that, when you present it to your boss, will address any pre-existing biases, and more likely, gain their support?

Your prospect’s willingness to collaborate with you to create a compelling argument and presentation for their boss and internal stakeholders is another gauge to help you assess the opportunity.

The more receptive they are to your help, then the more willing they are to fight for your solution, and the better your chances will be of closing the deal.

If they aren’t so willing to accept your help, then you may consider asking something like: “If you’re going to be talking to your boss without me, and I really appreciate you doing that, will you be recommending me?”  

Again, find the comfortable, professional, and consultative way to go about asking that, but find out whether you’re going to be recommended, versus “spread sheeted.”

Either way, what’s said about you behind closed doors can make or break the deal. By having an internal champion to help you navigate the ins and outs of the organization, you'll be well on your way to handling the "boss" card like a real boss yourself!


Don't let the "boss" card throw off your sales momentum. When it comes to assessing the potential of a pending sales opportunity, your ability to interpret both positive and negative cues as well as the spoken and unspoken word, will allow you to take a more objective look at your pipeline and only focus on real opportunities.

Express your curiosity early and often by asking why. Understand the reasoning. Why is it important for you to meet with your contact's boss? Why is something happening or not happening? Asking why helps you further assess the opportunity and adjust your sales approach accordingly.

Learn what the priorities are at this moment in time. What's their timetable? Is this an urgent decision, or are they just starting their research? Learning how their decision making process works and if there's any timeline associated your solution will help you determine how to prioritize this opportunity.

Leverage your prospect for collaboration. How will you know what their boss or other key stakeholders are saying? Work with your prospect to convert them into an internal champion who is pulling for you and your solution. The more collaboration and agreement you have, the better your relationship will be and the more comfortable your contact will be when the time comes to recommend you. 

Looking for more sales tips? Learn more techniques for managing your sales opportunities with our Pipeline Management Made Easy Guide. You'll learn additional steps and strategies to take when analyzing your pipeline.


*Originally published May 20 2013, updated May 24 2018.


About Molly D Protosow

Molly Protosow is the COO and Training Strategist for DMTraining. She manages the day-to-day business and training operations while helping research and develop new training programs as well as refreshing signature programs to reflect the newest sales trends, technology, and best practices. Molly utilizes her wide-range of skills to create sales and marketing assets focused on delivering value to DMT’s clients. Molly has a passion for learning and leveraging new knowledge and experiences. Outside of DMTraining, Molly is a hard core Pittsburgh sports fan, enjoys staying active by running and golfing, and unwinds by reading and playing the piano.

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