Episode 25: Why the disease to please is blocking your next level (and what to do instead)

When we don't know what we want and need, we have lost direction. And without clear direction as a leader, everything else collapses.

You know I believe as within, so without. How we lead ourselves is also how we lead others.

The Pleaser saboteur makes providing and holding direction almost impossible, because direction requires disappointing people. It requires choosing and saying “we're going THIS way, not that way.” It requires anticipating risks and communicating when there is something not working.

And when we're constantly in fear of being judged, it's very hard to take this role.

I remember one of my clients. She was managing a team of 6 people in an international company, but she told me she felt they liked her as a friend and she didn't feel she was treated as their leader. She would think a leader is someone you follow, you respect, while she had to beg people to do their job.

When we started digging into how she was showing up, we noticed so many ways where she was diffusing her authority to be more likeable. In simple things such as the way she asked them to do things, using phrases like “When you have the chance could you please make me the favour to…”

She was teaching her team that her requests were optional. That she wasn't really their leader. That they were doing HER a favour, not doing their job. And then she felt resentful when they didn't prioritise it. But how could they know to prioritise it when she framed it as “when you have the chance”?

We worked on managing her people-pleasing saboteur, on clarifying where she was headed and what she needed from her team, and on the guilt that came every time she thought someone might get offended. She started showing up as a powerful leader. And her team not only respected her more, they also appreciated the new level of clarity.

While you are trying to be nice, you are not being clear. And by not being clear you're also making it harder for people to do good work.

I've seen this at even higher levels. I worked with a client who was the only woman on her executive team. Her Pleaser made her over-explain every decision to gain consensus, while her male peers simply stated their position and moved forward. She was working twice as hard for half the authority.

Being a people pleaser is exhausting. The Pleaser saboteur drains you because you're constantly:

• Reading every room for signs of disappointment
• Replaying conversations to see if you upset anyone
• Managing everyone else's emotional state
• Suppressing your own needs and opinions
• Crafting every message to minimise potential offence
• Saying yes when you mean no, then scrambling to deliver
• Carrying guilt about boundaries you can't set

Women already do more emotional labour at work. The Pleaser multiplies this by 10.

The first step is awareness. Start noticing when the Pleaser shows up. Ask yourself:

• Am I about to say yes when I mean no?
• Am I softening my message to avoid someone's discomfort?
• Am I managing someone else's emotions instead of stating what I need?

From Positive Intelligence, we know that labelling the saboteur weakens it. So when you catch it, literally name it: “That's my Pleaser talking.” Or even better, choose a funny name. This creates space between you and the pattern.

And here it is important not to judge this part of ourselves. Belonging is a basic need for humans. Being liked and accepted is something our primitive brain craves.

We have been so conditioned to think about others that many times we don't even ask ourselves what we want in our careers. Or if we do, we don't give ourselves the space to say it out loud.

Get clear on what you are building. Where are you going? What do you actually want your career to look like? What kind of leader do you want to be? What projects excite you? I dedicated Episode 5, “Let's Talk About Unrealistic Dreams”, to exactly this.

And then, and this is the crucial part, when you are in a safe space, say it out loud.

“I want to lead the new product launch.” “I want the promotion.” “I want to write a book.”

Saying it out loud makes it real. It takes it out of the realm of “selfish thoughts I shouldn't have” and into the realm of “legitimate desires I allow myself to pursue.”

Many of my clients tell me this is the hardest practice, and also one of the most impactful parts of our work together. Because when you give a bigger space to your dreams, you naturally start taking more actions towards them.

Here's the beautiful irony: you're already an expert at empathy. You know what your team member needs before they ask.

Now turn that superpower toward yourself.

You're in a meeting. Someone asks you to take on another project. Your Pleaser wants to say yes immediately. Pause. Use your empathy on yourself. Ask:

• What do I feel right now? (Overwhelmed? Resentful? Excited? Afraid?)
• What do I need right now? (Space to think? To say no? To negotiate scope?)

Make it a daily habit to ask yourself these two questions. Don't underestimate it because of its simplicity. As I always say, simple is divine, complex is human. We often overcomplicate things.

An excellent way to practise this is the 24-hour rule for non-urgent requests. When someone asks you for something that's not urgent, practise saying: “Let me check my calendar and get back to you.” It gives you space to check in with yourself about what you actually want and need, and it breaks the automatic “yes” pattern.

When you start managing your people pleaser, guilt will show up. A lot of guilt. But not all guilt is the same. There are two types:

• Type 1: Real guilt. You actually did something that is against your values or hurt someone unnecessarily. This guilt is useful. It tells you to apologise, make amends, do better.
• Type 2: Identity-shift guilt. You did something aligned with your vision and values, but it FEELS wrong because you're becoming someone new. This guilt is just the discomfort of change.

This guilt is not telling you that you did something wrong. It's telling you that you're changing your identity. And what nobody tells you is that this will happen at every new level of leadership you reach.

So check with your vision. Ask yourself: is what I just did aligned with the leader I want to be? Is it aligned with where I'm going? If yes, the guilt is identity-shift guilt. It's growth, not wrongdoing. Name it: “This is growth.”

You don't have to make the guilt go away. You don't have to fix it or apologise your way out of it. You can feel guilty AND know you did the right thing.

In the beginning of a new identity, expect it. Welcome it. It's a sign you're on the right path.

You need to practise saying no to get comfortable with it. And here's what helps: every time you want to say NO, ask yourself, what am I saying YES to?

No to that meeting = yes to focused work. No to solving their problem = yes to their growth.

Start small. Skip one unnecessary meeting this week. Don't respond to a message immediately. Let someone solve their own problem.

Notice what happens. Usually? Nothing catastrophic. And sometimes people actually respect your time more.