8 of the Most Difficult Types of Prospects

actionable advice from real sales leaders

8 of the Most Difficult Types of Prospects: Are you ready for a shocking, next-level revelation that’s going to turn your world upside down? Here it is: Prospects aren’t always easy to deal with. Boom! That’s the kind of astute, game-changing insight you can only find here at The Pipeline, baby. You’re welcome.

But in all seriousness, difficult prospects are a fact of sales life, and dealing with a difficult buyer who makes a sale harder than it needs to will always suck—aand from time to time, you’re bound to deal with an especially difficult buyer who makes a sale even harder than it needs to be, and that experience will especially suck.

So to help you get a sense of the kinds of buyers you need to look out for (and what to do when you‘re dealing with them), we asked some sales leaders for their takes on the most difficult types of prospects to work with and how to engage with them effectively. Let’s hear what they have to say.

Baidhurya Mani,

The founder of Sell Courses Online suggests that particularly preoccupied prospects can pose real challenges for salespeople. She says, “Prospects who are always too busy are some of the most frustrating to deal with. These are prospects who are genuinely interested in the product and really want to talk to you, but just have so many things going on that they can’t seem to spare time for you. As a result, meetings are always either postponed or no-shows.”

How to Handle Them: Create urgency.

Mani suggests that “the best way to deal with prospects like this is to enforce a sense of urgency. Offer them an exclusive discount that’s time-based or on a first-come, first-served basis. Put a deadline on your offer so that they will make it a priority to close the deal with you on or before the said date. Without a deadline, they get too comfortable postponing things because there’s no urgency.”

2. The Prospect Who’s Afraid to “Sell in”

When we asked Patty Radford Henderson, CEO & Founder of Annum, about some of the most frustrating prospects she deals with, she referenced buyers who were a little sheepish about bringing potential offerings to company leadership.

“It is challenging when a potential user sees the value of your solution and wants to put it into practice, but they are afraid of having to convince their boss and the head of finance,” the speaker says.

How to Handle Them: Guide them on how to present a business case.

Henderson suggests that salespeople offer some additional guidance to these kinds of prospects. She says, “We’ve found success by guiding them on how to present a business case. To ensure clarity, persuasiveness, and alignment, we recommend tailoring the presentation to the priorities of your audience. Senior executives are often more interested in high-level strategic implications and financial outcomes, while operational managers prioritize feasibility and implementation details.

“Or, tell a compelling story. Clearly articulate the problem or opportunity, the proposed solution, and the expected benefits and outcomes. You can also present evidence-based insights. Support your recommendations with firsthand or industry data that demonstrates the feasibility and potential impact of the investment.”

3. The Overly Demanding Prospect, 8 of the Most Difficult Types of Prospects

Jason Hunt, CMO and Co-founder of Merged Media, mentioned running into trouble with buyers who ask too much of salespeople. According to him, “The most difficult type of prospect to deal with has always been the overly demanding buyer who seems impossible to please. In my experience, these prospects ask for the moon — customized solutions, deep discounts, unlimited revisions — often before establishing any relationship or value provided.”

How to Handle Them: Address them diplomatically.

Hunt says, “It’s tempting to simply avoid them, but I’ve found the best approach is to address concerns directly yet diplomatically, clearly explain standard offerings, and try to find some common ground. If that fails, walking away may be the wisest path to maintaining trust with other, more reasonable clients in the long run.”

4. The people-pleaser: 8 of the Most Difficult Types of Prospects

Michael Alexis, CEO of teambuilding.com, suggests that sometimes buyers who falsely present as a little too enthusiastic can be the toughest to deal with. He says, “As a sales leader, I think one of the most difficult types of prospects is the people-pleaser. Sales reps might shudder at the thought of an outwardly challenging lead who shares unfiltered honesty, but the opposite is more insidious.

“Some potential customers respond positively to your pitches and outreaches not out of genuine interest or product fit but out of politeness, aversion to conflict, and a desire to be amenable. It can be tricky to tell when these folks are truly considering your solution and when they are giving lip service out of a need to appear nice or avoid uncomfortable reactions.

“However, no matter how agreeable your prospect might be, there are still warning signs. For instance, the customer may avoid answering your questions directly or giving concrete timelines. They may also agree with everything you say and fail to ask any questions of substance.

How to Handle Them: Distinguish genuine interest from politeness.

According to Alexis, perceptiveness is key when handling these kinds of prospects. He says, “A key to dealing with this type of prospect is to engage in active listening and read between the lines of their responses.

“Watch body language, and stay alert for signs like lack of eye contact or fidgeting. During discovery, ask thoughtful questions that elicit a more thorough response (avoid yes-or-no questions), and be sure to listen to interpret the client’s most pressing needs. Also, give these prospects an easy way to opt out if they’re not interested so that you’re not wasting either of your time.”

5. The Tire-Kicker: 8 of the Most Difficult Types of Prospects

Gauri Manglik, CEO and Co-founder of Instrumentl, says salespeople should be wary of prospects who might not be serious about buying. She says, “In my experience, the most difficult prospects to deal with are the tire-kickers — those who seem interested but never actually commit or sign a contract. They ask thoughtful questions and get you to invest time preparing proposals and estimates, but then disappear or continually make excuses to delay actually moving forward.

“These prospects are challenging because they seem so promising at first. But after several rounds of follow-up, you realize they were never truly serious buyers in the first place. They were just gathering information or comparing options with no real intention to buy.”

How to Handle Them: Qualify them early on.

Manglik suggests that salespeople should try to catch these potential time-wasters preemptively with sound qualification. She says, “The key is to qualify these prospects early by asking targeted questions about their budget, timeline, and key decision-makers. Look for concrete signs that they are motivated to act, not just gather data.

“If those signs aren’t there, don’t invest too much time or resources until you see real commitment. Have an honest conversation about their intentions and let them know you need to see progress before providing more details. The best approach is to remain professional but cautious, rather than wasting effort on prospects who were never genuinely interested at all.”

6. The “Price Shopper”: 8 of the Most Difficult Types of Prospects

Mark Damsgaard, Founder of Global Residence Index, says salespeople should be mindful of overly cost-centric buyers. According to his account, “Some of the toughest prospects to deal with are those who don’t want to pay premium rates. Some call them ‘the price shoppers’ because they’re laser-focused on getting the cheapest deal possible.”

How to Handle Them: Shift the focus from price to value.

According to Damsgaard, “My tip is to avoid getting into a price war with them. Instead, do your best to shift the conversation toward value. Help them understand the return on investment they’ll get from putting their money into your solution. Help them see whether they’ll benefit through increased efficiency, cost savings, or revenue growth. Trust me, when people understand the true value of your offer, they won’t see your price as expensive.”

7. The Indecisive One

Johannes Larsson, Founder and CEO of JohannesLarsson.com, says buyers who can‘t pick a lane are tougher to deal with than most. He says, “Indecisive prospects are some of the trickiest to handle. They’re the ones who seem interested but just can’t seem to make up their minds. This can be frustrating because you can spend a lot of time and effort trying to close the deal — only to have them waffle or back out at the last minute.”

8 of the Most Difficult Types of Prospects: How to Handle Them: Guide them with patience.

“The key to dealing with these prospects is patience and persistence. You need to gently guide them through the decision-making process, making sure to address any concerns they may have along the way. It would also help to offer a little extra reassurance or incentives to nudge them toward a decision.”

8. The “Back-and-forth”

Beryl Krinsky, Founder and CEO of B.Komplete, says wishy-washy prospects have a tendency to give salespeople trouble. She says, “Following the pandemic, we have been dealing with prospects and clients who have gone back and forth with confirmed events, canceled confirmed programs, and asked for last-minute changes. This creates additional work, time, energy, and stress for our team, not to mention loss of revenue (and fulfilling our mission!)!”

How to Handle Them: Implement cancellation policies with empathy.

According to Krinsky, “We have made a few changes. First, we try to be as accommodating as possible with clients, demonstrating our empathy and allowing for one change or cancellation without a penalty. After this happens more than once, we do implement a small cancellation fee. I do recommend always having a service agreement in place prior to scheduling services to help mitigate a future issue.”

Like I said at the beginning of this post (when I blew your mind with the kind of mind-blowing insight that blows people’s minds), prospects aren’t always easy to deal with, and the prospects listed here fit that bill and then some. So hopefully, this guide will help you identify the kinds of prospects that will give you trouble and help inform more focused, effective strategies for dealing with them.