How to Have Tough Conversations When You’re a People-Pleaser

Erica Lee

Does holding up the line at the grocery store make you anxious? Have you ever been stressed about creating a music playlist all your friends will like? Do you refuse to complain about your food in a restaurant so as not to upset your server?

If you can relate to these situations, you're likely a people-pleaser. Wanting to bring happiness and fulfillment to others is not a crime, but in excess, it can get in the way of your own success and joy. An Aug. 2017 article from Psychology Today, “10 Signs You're a People-Pleaser”, outlines the major characteristics (and pain points) of people who tend to put the happiness of others before their own:

  1. You pretend to agree with everyone.
  2. You feel responsible for how other people feel.
  3. You apologize often.
  4. You feel burdened by the things you have to do.
  5. You can’t say no.
  6. You feel uncomfortable if someone is angry with you.
  7. You act like the people around you.
  8. You need praise to feel good.
  9. You go to great lengths to avoid conflict.
  10. You don’t admit when your feelings are hurt.

Personal life people-pleasing brings its own challenges, but perhaps nothing as challenging as workplace conflict resolution. In business, there is a lot more on the line: job security, employee safety, legal limitations, etc. With that, the pressure to keep the peace can be exponentially greater for extreme empathizers.

As an expert in leadership communication, Sandler Training Owner & CEO Lisa Nausley said being proactive is the healthiest way to reach a resolution, despite anyone’s people-pleasing instinct to avoid the issue.

“A lot of people think that if they upset the team, they will not be liked as a leader,” Nausley says. “However, as a leader, it is our job to help them with continual growth and learning.”

According to Nausley, going along with the majority’s opinion or avoiding a conflict with a subordinate is not the right thing to do. Instead, offering honest feedback and contributing ideas leads to healthy corporate growth and improved team member relationships.

“If we do continue to sugar-coat everything, they’re going to discount you as a leader,” she says. “It is one of those strange dynamics. They’re really leading you more so than you’re leading them.”

There are two approaches that Nausley often advises her clients to use when handling an uncomfortable conversation. The first is to “fall on the sword.” This simply means that you take responsibility as a peer or leader. This approach is prime example: “I failed you by not giving you the tools/information/training that you needed, but here is what I’m going to do going forward to help you reach your fullest potential.”

The second approach is to “give them an out.” This method gives the other individual more ownership in the situation so they don’t feel intimidated. In a sense, permission for criticism is being requested: “If I were to notice something that might be holding you back, would you want me to share that with you?”

Regardless of the approach that’s used, Nausley emphasizes that these discussions should always be held “on the sidelines”.

“When there is some sort of issue, the customer does not want to see it or know about it,” she says. “We just fix it. It makes us and them more comfortable with this relationship continuing. Otherwise, it doesn’t make us look like team players.”

From a human resources perspective, HR Designs Founder Jamie Nabers and her Chattanooga-based team offer these additional conflict resolution considerations for their clients as part of their consultative services:

  1. Do not assume you know the full story. Always start by asking questions.
  2. Do not make your mind up about how to address the issue (i.e. consequences) before talking to the employee. Employees who are given the chance to speak before being disciplined will normally respond more constructively. For example, listen and then tell them that you will get back to them later today/tomorrow. Sometimes, it may even be appropriate to ask them what they would do if they were in your shoes.
  3. Do not make it a “he said/she said” type of conversation. Take ownership, try to preserve anonymity and use discretion as much as possible.

High-friction situations, such as sexual harassment and discrimination claims, can be tense for everyone on the team, not just people-pleasers. The biggest mistake Nabers says people tend to make in these scenarios is delaying action, therefore overlooking the urgency or severity of the situation. In turn, avoidance can exacerbate the existing issue.

“Managers might let a week or two pass before starting to handle the issue,” she says. “A lot can happen when an employee thinks their complaint has fallen on deaf ears. So, act promptly. Keep the employee informed along the way with the steps you are taking and try to set their expectations accordingly. Be discreet and try to protect anonymity. Ask individuals you are speaking with to do the same. If it is of a serious nature, you may need to remove an employee from the situation while you continue your investigation.”

In addition to these highly personal matters, there are occasions where simple infractions become hot button issues for employees. Cell phone use and truancy are two prime examples. While it’s necessary to address the concern with the employee who’s a repeat offender, taking a big-picture look at your entire team’s behavior might be the wiser approach.

“Think through and observe how other employees are using these same benefits,” Nabers says. “Sometimes as managers, we only notice certain employees taking advantage of the system. When that employee is confronted, he/she will normally cite others that are doing the same thing and they automatically think that you are singling them out. There are always extenuating circumstances, but managers who are fair and consistent will have less heartache over these types of issues. It’s also always a good idea to have specific examples (dates/times) of when you witnessed the employee’s behavior.”

Getting the word out isn’t difficult either. Nabers added that simply pushing out a reminder message via email or at a team meeting is enough to reinforce an existing policy or reiterate your expectations.

One of the simplest ways for people-pleasers and all business leaders to avoid and prevent conflict is to establish a culture of open communication, often referred to as having an “open door policy.” By voicing this opportunity for sharing ideas and opinions, leadership welcomes employees to approach them and establishes more respect between supervisors and subordinates. Walking the walk is also a critical component; the entire leadership team should abide by policies.

“If a manager is known for not listening, never acting or making excuses, employees will not see the benefit of an open-door policy and will not use it,” Nabers says. “A manager can set specific office hours that he/she is free, can practice just keeping their office door open and welcoming visitors or even set specific times to physically leave their office and visit with employees. A manager can also hold informal roundtable discussions to learn about various concerns throughout the year or ask for feedback through a comments box or anonymous inbox. There are many ways to show employees that you want to listen and that you care. It’s just picking a few and sticking with it.”

How To Prioritize Your Own Happiness and Success

  • Don’t always be agreeable: As a subject matter expert, politely express your thoughts. Customers and co-workers will appreciate your honesty.
  • Be responsible to your commitment: Don’t focus on making a customer or co-worker happy so much as empowering them with information or opportunities.
  • Make it right: Apologies are OK, but fixing the problem is what people want.
  • Say no: Not every piece of business is worth your time. Not every opportunity or request either.
  • Make time for you: The only way to be a better leader for others is if you take care of yourself. Be with family. Exercise during lunch. Find a balance.
  • You’re not perfect: Understand that you’ll make people upset, but if you have their best interests at heart, you’ve got nothing to be upset about.
  • Share your feelings: Don’t confess your angst to customers; lean on your team when you’re struggling with a project. They know what you’re going through. Also, discuss interpersonal conflicts calmly and with sensitivity, and the resolution won’t be far off.
  • Be yourself: You have unique talents and ideas. Don’t copy others. People will like you more for your authenticity.
  • Question the norm: Conflict or a difference of opinion, when approached the right way, can resolve animosity and confusion. It can also instigate positive changes for your team, campaign and company.

Want to dive deeper into this topic? Tune into the related podcast episode “People Pleasing and How to Make it Work for You in Sales & Marketing” from the Flywheel Brands podcast, “Momentum Marketing: Fulfilling Your Urgency to be Great.”

Flywheel Brands, Inc. is a leading brand marketing agency that has been generating momentum for its clients with creative solutions like custom promotional products, apparel, graphics and print items since 1981 in Hixson, Tennessee. For more information on Flywheel, visit our website at, or follow us on Facebook, Twitter and Instagram.

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