Are You Embarrassed to Admit You’re a People-Pleasing CEO?

Every once in awhile, a CEO or business owner will share something with me they loathe to admit.

It’s a problem, and it causes issues with profitability, job satisfaction and productivity.

Worse yet — hardly anyone is talking about it.

It’s being a people pleaser –and it’s possible you might be one without even knowing it.

Let’s take a look at what “people pleasing” is and talk about why it can cause problems in your business. Then I’ll give you a step-by-step method for putting this behind you.

The Symptoms of Being a People Pleaser

What exactly is a “people pleaser”?

If you’re a people pleaser, you most likely:

  • Try to be the nice guy (or gal) most of the time
  • Want to be liked
  • Like making other people happy, because that makes YOU happy
  • Feel good when other people need you
  • Tend to avoid conflict
  • Feel uncomfortable or awkward when dealing with people issues (like performance issues or holding people accountable)
  • Have a difficult time setting boundaries, especially with your time
  • Find it challenging to say no to other people
  • Think of other people first, and tend to put their needs before your own

Of course, there’s nothing wrong with being nice, and most of us want to be liked.

But when you’re too much of a people pleaser – when you are too susceptible to the pressing demands of others – it can make it extremely difficult for you to be an effective business leader.

How Being a People Pleaser Can Hurt Your Business

You can lose sight of your vision.

When everyone in your company (including your own family members) has differing opinions on how you should grow your business – and you’ve gotten in the habit of saying “yes” to everyone – it’s practically impossible to achieve the growth you really want.

Wondering why your team takes so long to implement? With too many irons in the fire and no real sense of direction, you strain your resources and diminish your team’s ability to execute. A chaotic environment of constant firefighting and numerous unfinished or abandoned projects is usually the result.

Employees and/or family members may take advantage of you.

If you struggle with holding people accountable, certain people will pursue their own agendas, disregard deadlines and not turn in projects – all the stuff that drives you crazy. And they do it because they know they can. They know you probably won’t stop them for fear of the conflict or confrontation and so they manipulate you into getting what they want at your expense.

Even worse, when this kind of behavior becomes a pattern and you don’t put an end to it, it can come across as favoritism to the rest of your management team.

Perhaps you’ve never thought about it this way (or you don’t want to think about it), but trust me – your team members aren’t stupid. They see what’s going on. And when you don’t deal with “The Manipulator,” this perceived favoritism can have a big impact on morale and motivation, to say nothing of team cohesion.

On the flip side, when you have healthy boundaries, your employees will respect you more. They’ll have more faith in you as a leader, and will be more likely to stick to deadlines and actually implement the decisions you make in management meetings.

When you stop being a people pleaser and start following through on your plans for the business, you’ll also see a “trickle-down” effect in your organization. Your employees will learn how to say “no” in a healthy way by watching you, and your entire company will benefit.

You may make poor business choices and sabotage your own business’s growth.

If you’ve hit a plateau in your business growth, and you can’t figure out why you can’t seem to break through a particular income point, your people-pleasing problem might be partly to blame.

Pushing your agenda forward and keeping the business moving toward your vision takes perseverance and commitment. You have to stay focused and see things through. If you can’t say no to others, alignment and commitment to the over-riding goal, which you are responsible for, is lost.

Additionally, not being able to say no can cause you to take on more projects and responsibility than your team can handle.

You probably put off dealing with under-performing or toxic employees.

It’s tough dealing with under-performing or toxic employees when you’re desperate for everyone’s approval and you’re consistently trying to avoid conflict.

But again, to the rest of your team, this is exceptionally frustrating and confusing.

They’re aware of the problem, they’re tired of dealing with the person, and they don’t understand why you won’t do something about it. This can have devastating consequences on culture, productivity and morale.

By keeping your people-pleasing habit in check, you can get those lackluster employees back on track (or dismiss them, if you have to).

Strategic planning fails to achieve its goals and feels like a waste of time.

People-pleasing is the kiss of death for strategic plans.

Effective planning requires timely execution of action items. If you can’t hold people accountable and no one respects your deadlines, nothing is going to change and your organization will stay stuck in old, unproductive patterns.

When you learn how to communicate more effectively with your employees and hold people accountable, your plans will get implemented and real change can happen. Your deadlines will be meaningful, and you’ll see a big increase in productivity and progress as a result.

You feel frustrated and resentful – and you’re probably hiding it.

When you’re the CEO and you’re continually trying to please everyone, you end up being pulled in multiple directions. I find this is particularly common in family businesses. 

When family members are constantly telling you how to run the business – and you can’t say no to any of them – it’s going to lead to massive aggravation. Half the time, you’re just trying to keep the peace and keep everyone talking to one another. Frankly, it’s a no-win situation.

Breaking these habits does take some work, but it’s going to make you a happier, more contented person. And a happy CEO is a considerably better leader than a miserable one.

The Step-by-Step Method for Changing Your People-Pleasing Habits

Step One: Figure out why you’re a people pleaser.

You’ve got to the get to the root of the problem before you can address it. Yes, this is difficult – I’m not going to lie to you. But you must figure out what’s causing your behavior (and what you’re getting out it) before you can begin to break the habit.

Ask yourself these key questions when you’re examining what motivates your people-pleasing behavior:

  1. What’s really causing my people-pleasing behavior? What’s at the heart of the problem? (Some common causes: fear of failure, trying to avoid conflict or awkwardness, trying to get everyone to like you, not wanting to be the bad guy, etc.)
  2. What am I gaining from continuing this behavior? What’s it giving me?
  3. What is it costing me? 

Step Two: Change your perspective by tackling one small and manageable change.

Pick one small situation where you’d like to learn to set a boundary, speak up, or confront something.

For example, if you run a manufacturing company and it bothers you there’s trash and scrap on the factory floor, have a conversation with your team about why it’s happening and why no one is picking it up.

Think about what you’d say to your team beforehand to get them to the issue. Make a list of the most important points you want to get across. For example, pride in the company, safety awareness and where else this kind of thinking shows up among employees. Make a script if it helps to get your thoughts down on paper.

Practice what you’re going to say several times until it feels comfortable and natural. Even doing some role-play exercises with a peer or a friend might be beneficial.

Dealing with small problems lets you practice saying no and setting boundaries, and helps build your confidence for tackling bigger problems. Build your confidence with some small wins, and you’ll learn that the world is not going to end when you say no to people or hold them accountable.

Making small changes is also better because it doesn’t shock your team. If you try to change too much at one time (and completely transform your management style in the process), your team members will knows it’s a temporary change, and they’ll know all they have to do is endure it until the old habits return.

Tackling these issues will likely feel scary at first, but it will get easier over time. Remember that it’s all about building new habits, so you just need to practice these skills and build new patterns.

Step Three: As your confidence grows, tackle larger issues with your staff, vendors and customers.

After you get some smaller wins, identify a couple of larger problems, and follow the same process.

If you’re feeling nervous about a particular conversation, you can even videotape yourself so you can objectively assess your style.

Remember, as you tackle bigger problems, your fear of conflict will likely kick in, and you might feel intimidated or unsure again. Don’t let that stop you.

Try to remember that if a person gets upset with you for saying no or setting a boundary, that’s their problem, not yours. If they get mad because they’re no longer the center of your attention, they can move on and take that attitude to a different company.

Tackle each situation as you identify it, and notice the changes you’re causing by breaking your people-pleasing habits. Are your employees treating you with more respect? Are you noticing that people are following through on the deadlines you set? Use that feedback as fuel to keep going with changing your people-pleasing habits.

Step Four: Make sure you don’t slip back into old habits.

As you break these old patterns, watch out for backsliding, especially in particularly high conflict or emotional situations.

If you find yourself slipping, remember the soul-searching you did back in Step One. Keep in mind why you wanted to make these changes, and what’s really at the heart of your people-pleasing habits.

Then go back to scripting your statements or responses, and carefully think through each situation ahead of time. Keep building new habits until the patterns are ingrained and you feel really comfortable with setting boundaries and saying no in lots of different kinds of situations.

Slaying the People-Pleasing Monster

Not all CEOs are people pleasers – but many are, and it can be a real problem.

Just remember that breaking these destructive habits (and learning to say no) doesn’t mean you’re not a fun person or an approachable leader. It also doesn’t mean you have to become dictatorial or take the “my way or highway” approach to leadership.

Compromise is okay when it’s appropriate. But leaders shouldn’t compromise the vision of the company by trying to please everyone else.

Start by getting to the root of the problem, then take small steps to set boundaries and say no in small, manageable situations. Then, once you’ve got some confidence, tackle the larger issues, and knock them out one by one.

Before long, you’ll set boundaries easily and say no with grace and ease – and you’ll start seeing major shifts in your profitability, your relationships, and your state of mind.

If you’d like help tackling your people-pleasing issues as a CEO, let’s have a conversation.

Photo: Tobin Akehurst/Shutterstock

Ready to get started with The Oken Company?

Brian Oken has helped dozens of business owners and CEOs become better leaders, build more effective teams and grow bottom-line profits.

If you're ready for some straight-line, actionable strategies that you can implement immediately to start getting better results, contact him today.

Get Started Now »