7 Reasons People Pleasing Sinks Sales (And How to Fix It)

We are social animals.

The thoughts, emotions, and actions of others have an enormous effect on our thoughts, our emotions, and our actions. And this deep connection is, in part, why we’ve been so successful as a species.

But when that connection only goes one direction (or is outright ignored by the other party), that’s when things take a turn for the worse.

People pleasers are a direct result of this disconnect. And if you’re a people pleaser in sales, you’re destined for a career of exhaustion, frustration, and in all likelihood, only moderate success.

But it’s not all doom and gloom. You can in fact get rid of your people pleasing tendencies—with the right guidance.

This guide looks at the definition and drawbacks of people pleasing. Then, we dive into how to stop people pleasing in sales using a simple yet effective three-rule framework. And with it, you can start closing more, earning more, and loving your job—you guessed it—more.

What Is a People Pleaser?

People Pleaser – A person who has an emotional need to please others, often at the expense of his or her own needs or desires.

We’ve all met a people pleaser before.

They’re the ones running around parties and refilling drinks rather than sipping on their own. Standing in line alone for hours so their “friends” can make it into the show. Or constantly giving rides to the boss, even though they’re arriving two hours before their shift.

Know the type?

In sales, these people pleasers tend to be a little harder to spot. But the same core principle is true—they give up their own well-being for the sake of others. And usually, that sacrifice isn’t ever returned.

For example, a people pleaser in sales may:

  • Stay late to finish up a project their superior should have been handling themselves.
  • Stick around with bad clients because they’re afraid of cutting them loose.
  • Avoid conflict (both with buyers and colleagues) like the plague.
  • Be willing to pass on potential clients to other sales reps.
  • Not live life to their true self and don’t have healthy boundaries.

If any of this is hitting just a little too close to home, I’ve got bad news for you—you’re probably a people pleaser.

And consequently, you’re going to have a tough time in sales (and even issues with mental health) unless you figure out how to change.

7 Reasons Why Being a People Pleaser Is Bad in Sales

You’d think making everyone around you happy would be a good thing.

But in reality, people pleasing behavior in sales is often disastrous. Here are seven reasons why.

1. Wasted Time With Bad Clients

People pleasers hate conflict.

Raised voices, poked chests, and even simple “I don’t think so”s can end up haunting them for weeks. As a result, a people pleaser in sales will find it difficult—if not impossible—to cut off bad buyers before they turn into more of a problem.

We’re not just talking potential buyers. Although that certainly comes into play since proper lead qualification can make your job infinitely easier down the line. And if you can’t say goodbye to buyers that aren’t a fit, you could waste weeks on closing a deal that was never going to happen.

But I’m also talking about buyers that are already moving through the buyer’s journey. Buyers that are sucking up too much time. Too many resources. And although you might close the deal, the amount of energy you need to invest to get them there (or maybe even their low purchase value) just doesn’t justify the payout.

People pleasers will always struggle with weeding out bad buyers early on. And as a result, that means more work for less money than if you’d found the right buyer.

“People who are excessive people-pleasers, which is actually a lot more people than certainly I ever realized, is incredibly limiting to doing well in sales because they’re not willing to ask for what they really want. They’re willing to spend far too much time with people who have no value to their business whatsoever because they’re too nice to say, “I’ve got other things I should be doing that are more important.” – Interview with Matt Anderson, Author, Coach, & Speaker

2. Great Relationships Are Built on Equal Value

Value begets value… or at least it should.

And in the world of sales, the best relationships are those that bring equal value to the table.

For you, the value offered could be industry insights in early conversations, educational content, or even social connections to other industries. For buyers, it’s usually a bit simpler—a commitment to learn about your product or service and then to make a purchase.

But when you share people pleasing behavior, you’re offering all this value without any clearly communicated reciprocity. Instead, people pleasers operate off of what’s known as covert contracts, a concept we’ll discuss later in this guide.

Ultimately, that means all the work you’re putting in—the insights, the content, the connections, the effort—is wasting time by not effectively locking in the sale.

3. Finding the RIGHT Solution

One of the more serious problems with people pleasers is that they’re bad communicators.

As sales reps, our job is to connect the right buyers with the right solution—our solution. But since a people pleaser’s so avoidant to conflict, they may end up misleading the wrong buyer to believe our solution can fix their problem rather than risk disappointing them.

And that, as you can imagine, can lead to some very serious problems.

Scathing reviews, refunds, battered brand image, even termination. When a buyer’s been misled about your product’s capabilities, you better believe you’ll have hell to pay.

4. Inauthenticity Breeds Contempt

Nobody likes a suck-up.

Sure, they’re ultra-agreeable, shower you with compliments, and never bring up any negative news. But even still, you can tell they’re not coming at it from a place of authenticity. Instead, they’re putting on a show.

When you can tell someone isn’t acting authentically, you don’t trust what they’re saying. Even when there’s no real reason for them to lie in the first place.

Combine that with the fact that just 3% of people think reps are trustworthy in the first place, and you’ve got a winning recipe for losing in sales.

5. Extra Work = Risk of Burnout

Being a people pleaser is exhausting.

On the one hand, you’re relentlessly focused on what others are thinking and feeling. Not just in the moment, but throughout the day, week, and month. And all that fixating on others comes at the cost of serious mental energy.

On top of that, there’s the physical energy.

  • Going through the extra work to keep buyers and colleagues happy.
  • Staying late at the office to finish up someone else’s project.
  • Neglecting your personal life to better the life of someone else.

It’s all so draining on your emotional well being. And if you aren’t careful, it’s going to quickly leave you a burned-out husk of your former self.

“I do research around a survey with B2B sales professionals, and of those, 67% of the respondents strongly agreed that they are currently close to burnout or experiencing burnout. There’s another survey that said 95% of human resource executives think that burnout is hurting efforts to retain workers.” – Interview with Tim Clarke, Co-Founder & CEO of UNCrushed

6. People Pleasing Plummets Positive Self-Perception

Self-esteem is also at risk here.

When you’re only thinking about the well-being of others, you’re constantly neglecting your own. Eventually, your own self-worth is built entirely on the external validation you get from others. And that can make it absolutely devastating when you don’t get the external validation you crave.

The problem here is a bit of a vicious spiral too. Those with low self-esteem tend not to value their own desires and needs. And as a result, they may seek out approval from others. But self-esteem plummets when that approval isn’t granted, making the problem even worse.

The only hope here is breaking the cycle—and that’s what the framework in this guide is for.

7. Miscommunication Sinks Sales

Finally, there’s the issue of miscommunication.

As we noted earlier, people pleasers don’t communicate their own needs well (or at all). They’re rarely share their true feelings. But miscommunication throughout the sales process can quickly sink a deal. And that’s especially true for high-ticket B2B products or services.

More so than typical B2C sales, B2B deals go through only when all the details are noted, checked, and double-checked. After all, a buyer who bungles a six-figure purchase is going to get the boot if the product ends up being incompatible.

If a people pleaser miscommunicates essential product details, deal terms, or use cases, a prospect won’t just abandon the deal—they’ll steer clear of the company for years to come.

The How to Stop People Pleasing Framework

Alright, out with the bad and in with the good.

Being a people pleaser can lead to some seriously disastrous scenarios in sales. But there’s still hope. Because once you know how to stop being a people pleaser, you can reverse this detrimental personality flaw entirely.

And that means you can enjoy:

  • Better close rates
  • Higher earning potential
  • More authentic relationships
  • Greater personal time to do the things you love
  • Improved sense of fulfillment on the job
  • Easier to set boundaries
  • Faster career advancement

The first step is making your way through The How to Stop People Pleasing Framework. This framework is built specifically for those in B2B sales. And it’s made up of just three rules.

  1. Make Your Needs a Priority
  2. Stop Seeking External Validation
  3. Communicate “Yes” & “No” Clearly

Rule #1. Make Your Needs a Priority

“We’re all selfish. In Maslow’s hierarchy of needs, serving other people isn’t right there at the top. So, get your needs in the right order first. Look after yourself, not in a selfish way, but look after yourself, be the best version of you.” – Interview with Michael Heppell, Customer Service Expert & International Sunday Times No. 1 Best-Selling Author

Humans are, to put it bluntly, selfish. We are!

We’re usually more interested in ourselves than we are in other people. Which is why it’s so strange that people pleasers exist in the first place—why even waste your time trying to please someone that rarely thinks about you?

If you don’t make your needs a priority, someone else will inevitably come along and take advantage of you. That’s just a fact. And it’s just how we’re wired.

That’s why the number one rule of the framework is to take stock of your needs and start prioritizing them.

But to do that, it helps to understand a bit about the origins of why this happens and one of the most nefarious aspects of being a people pleaser—covert contracts.

People Pleasing Origins

For many, people pleasing starts during childhood.

At an early age, people pleasers were likely ignored or neglected, their needs not being met in a timely, healthy manner. Maybe it came from a neglectful parent. Or even cruel classmates.

But no matter where it stemmed from, the result was always the same—people pleasers came to believe they were “bad” for having needs in the first place.

As a result, people pleasers develop inaccurate interpretations of their genuine needs and use the following survival mechanisms to cope:

  • Trying to appear needless
  • Making it difficult for others to give to them
  • Using “covert contracts” to solve their needs in an indirect way

People pleasers will appear needless the best they can. They will either eliminate or hide all their needs because if you never ask for anything, you can’t be rejected for it.

For this very reason, people pleasers are terrible receivers of value. They become extremely uncomfortable when they do actually get what they want. And that creates a self-defeating prophecy where they’re stuck wanting but never getting. Clearly not ideal when your job relies on you taking cash in exchange for value from your potential partners.

So people pleasers turn to using “covert contracts” in an attempt to get what they need from life.

The Covert Contracts Trap

Covert contracts are unconscious, unspoken agreements that people pleasers use to interact with everyone around them.

A people pleaser’s covert contract might look like this:

Covert Contract – “I will do X for you, so that you will do Y for me. But I’m not going to tell you what the contract consists of. Instead, I’m going to hope that you understand what I want it and I’ll get mad if you don’t deliver on it.”

The problem here is of course that the stipulations for the contract aren’t clear to both parties. The people pleaser will assume they’re going to receive equal value in exchange. But the other party may never reciprocate.

Let’s look at what this might look like in the world of sales.

A rep finds a potential buyer and continually provides tons of value. They shower them with industry insights, point them to educational content, and even provide informed consulting to help them improve their business. The rep expects the buyer to return all this value by giving the rep their business.

But when all is said and done, the potential buyer goes with a competitor instead.

And it’s all because the covert contract in the head of the rep was never clarified, and they never asked for the sale.

The challenge, then, is to uncover these covert contracts and take responsibility for getting your own needs met. If you want an exchange in value, you need to be overt about this, especially to a would-be customer.

Remember, this is a business transaction, not a personal relationship. You have to understand that having your needs met in business is a part of the game. And being an adult means making your own needs a priority.

How to Stop People Pleasing Pro-Tip: Get comfortable asking for clarification and speaking bluntly about value exchange. Ask potential buyers outright, “If we can solve this problem for you, will you commit to giving us your business?” The only way to avoid the frustration of covert contracts is by being straightforward and direct.   

Rule #2. Stop Seeking External Validation

If you quizzed a hundred people and asked them, “Is being selfish a good trait to have?” almost every single person would say, “No.”

Being “selfish” has such negative connotations. And throughout our entire lives, we’ve been taught that selfishness is bad, antisocial, and downright immoral.

But I have a different perspective…

It may go counter to what you learned and were programmed with growing up. But if you’re willing to rethink what is good or bad, and you are ready to create healthy self-esteem, lasting and deep relationships, and B2B sales success, then this is going to be game-changing for you.

Be selfish. 

When you depend too much on others to build up your own self-worth, you’re at their mercy. You have no control over your life. And the goals you set, the dreams you have for what you can accomplish, those are all going to be under the power of someone else.

The result for you is feeling exhausted, anxious, and unfulfilled.

What’s more, other people are terrible judges of the value of your own work. They have their own lives to worry about. Their goals, their ambitions, and their endless thoughts and emotions are filling their heads every hour of the day. So if they don’t hand out the validation you’re looking for, it may not be because you aren’t worthy of it. But rather, it’s because they’re just concentrated on themselves.

How to Stop People Pleasing Pro-Tip: Focusing too much on what others think doesn’t make you look cool, sexy, or worthy. In reality, it does the opposite. Rather than fixating on the superficial (them-focused), aim for achieving your own goals and sense of fulfillment (me-focused).

“The one thing that we all know if people will follow you or not is the confidence that you exude. And so if you really believe in yourself and believe in what you’re doing from inside, not just superficially, I think people sense that you’re committed.” – Interview with John Bargh, Yale Professor of Psychology & Social Psychologist

Explaining the Selfish Spectrum

So let’s show what being selfish looks like visually.

This is what I call the selfishness spectrum.

On the left, there are the people pleasing behaviors (“ALWAYS you, NEVER me”). And on the right, the ultra self-absorbed behaviors (“ALWAYS me, NEVER you”).

In the middle green boxes, we have the middle ground, healthy self-interest. You’re able to put your own needs first at times and balance out things equally when necessary.

This middle ground is the behavior you should be aiming for in life if you want to get shit done. A healthy relationship is made of “Sometimes you, sometimes me.” And in that happy in-between, we can offer quality back-and-forth with the person we’re engaging with, whether it’s a colleague, client, or even a partner.

When you are building a business-to-business relationship, it might start off at “Sometimes me, sometimes you.” You give the value upfront, and then there is an exchange of value further down the conversation. You give them an insight at the beginning of a meeting, they promise to get you some inside information about the account before the next one.

Eventually though, once you’ve given enough value to a potential partner, you need to become more selfish and make it at least equal, if not them giving first and you giving second when it comes time to close the deal.

The sooner you become conscious of the giving that you’re doing while getting nothing in return, the sooner you’ll realize how much you’re spinning your wheels and wasting your time and energy every single day.

Rule #3. Communicate “Yes” & “No” Clearly

“I think ultimately, from the moment you’re born to the moment you die, you’re in some way communicating. And the quality of your life is determined by two things: one, the quality of your relationships, and secondly, the quality of your communication. You put those two together, and you are destined to have an absolutely awesome life.” – Interview with Paul McGee, Author, Motivational Speaker, & Conference Facilitator

Unclear instructions lead to uncertain results.

And if you’re not clear when you say “no” to people, it’s your fault when they pester you to do something that you don’t want to do.

Let’s look at three ways of saying “yes” and “no” effectively without any emotional baggage or stress.

How to Stop People Pleasing Pro-Tip: Stop saying “maybe” so much. It’s equally important to learn how to say “yes” clearly. If your answer to a question in your head isn’t an enthusiastic “yes,” then it should be a “no” and you should focus on something more important. Throwing out “maybes” leads to unclear expectations. 

Plan Out Your “Nos” Ahead of Time

It can be difficult to tell someone no in the moment. If you struggle with saying no because you’re afraid of disappointing, ask people to text or email you their request so you can get back to them.

Additionally, communicating over a written format rather than in person may help you be clearer and more concise in your response.

You’re a busy person, so it’s perfectly reasonable for you to say that you need to check your schedule before answering. Once they send you a follow-up, it’s much easier to send them a polite reply saying that you’re unable to agree to their request.

Don’t Offer an Explanation

Offering an excuse may seem like the polite way to decline a request. But it sets you up for an awkward situation. The problem with offering an excuse is it gives people the opportunity to change their request so that your excuse doesn’t justify your original no response.

For example, say you decline an annoying coworker’s invitation to go out for coffee because you already have plans on the day they requested. But then they ask you what day works best for you.

Now you’re trapped!

No matter what excuse you offer, people who are determined to get you to say yes can come up with a way to invalidate your communication.

By simply thanking people for their request and telling them that you can’t agree to it, you prevent them from trying to negotiate with you.

Provide an Alternative

If the person asking you for something is someone who you want to maintain a positive relationship with, you can lessen the impact of your no by offering an alternative that satisfies their want while being something that is more preferable to you.

Say someone wants you to collaborate with them on a project. If you’re not interested but still want to maintain the relationship, introduce them to someone else who might be interested as an alternative.

The goal is to offer compromise so they don’t take offense to you saying no, and you don’t feel guilty for turning down a request that would add unneeded stress to your life.

Wrapping Up

Being a people pleaser is no way to go through life. And in sales specifically, it can lead to wasted time with bad clients, misleading communication, and disastrous rapport. On top of that, it kills self-esteem, skyrockets anxiety, and is a surefire way to burn out quicker than ever.

But if you know how to stop being a people pleaser, you can save yourself tons of trouble. All it takes is:

  1. Make Your Needs a Priority
  2. Stop Seeking External Validation
  3. Communicate “Yes” & “No” Clearly

When you do, you’ll start closing more deals, building deep and engaging relationships, improving your work/life balance, and feeling more fulfilled on the job.

You’ve only got one life to live. So start living it on your terms.

And trust me—when you do, you’ll be on your way to being the best version of yourself possible.

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