Stop people pleasing by asking who the “yes” is really for. Most of the time it protects your comfort, not theirs: you’d rather do the hard thing yourself than watch someone else feel awkward doing it. Hand back one hard job this week and sit through the squirm without rescuing anyone.
The polite advice is “just set boundaries.” Lovely. Where do we buy those? Target? (Aisle nine, next to the candles nobody needed.)
Why it’s harder than it sounds
People pleasing rarely looks like pleasing. It looks like being nice. You take the dull jobs so the team keeps the fun ones. You redo the slide at 11pm instead of sending it back. You organize the office party because someone has to, and somehow someone is always you.
Serena owned up to her version on the show: “I kind of take on the crap jobs, the shit jobs, the jobs I wouldn’t give to other people on my team.” The reward? “I’ll be sitting there looking at bookkeeping that I hate and doing invoices.” Glamorous.
It isn’t all in your head, either. A study in the American Economic Review found that women, more than men, “volunteer, are asked to volunteer, and accept requests to volunteer” for tasks with low promotability. People ask because you say yes. You say yes because people ask. Neat little loop. Nobody wins it.
What actually works
Ask who the yes is for
This one stings. One founder who ran an agency of about 30 people worked out that her rescuing was mostly for her own benefit. In her words, “my people-pleasing behavior was more about me feeling comfortable than it was about wanting them to feel comfortable.”
Ouch. Useful, though. If the yes exists so you can dodge a bit of awkwardness, it’s a no wearing a cardigan.
Hand back one hard job
Pick the task you’ve been hoarding because it’s “quicker if I just do it.” Give it to the person whose job it is. Explain it once. Then step away from their desk.
The same founder saw the cost at home first, when her eight-year-old was the only kid on the soccer field who couldn’t tie his own shoes. Doing hard things for people, she said, “does people a disservice.” It stunts them. It stunts you too, because you’re still doing the invoices.
Sit through the squirm
Nobody warns you about the silence after you hand something back. They sigh. They ask a question you think is obvious. Every cell in your body wants to say “oh, leave it, I’ll do it.”
Don’t. In her experience, when people do the hard thing themselves, “their level of ownership, their level of confidence actually goes up.” The squirm is temporary. The invoices are forever, unless you stop.
Audit a week of yeses
Write down every yes for five working days. Next to each one, mark whether it moves your business, your team or your career forward. The ones that don’t are your first candidates for “Thanks for thinking of me. I can’t take that on.”
Say it once, then stop talking. (The over-explaining is the people pleasing sneaking back in through the side door.)
Hear it from someone who’s done it
Andrea Engstrom ran an agency with around 30 team members and now runs the Bold Coaching System. She gets into protecting her team’s feelings, doing the hard jobs so they didn’t have to, and what that cost everyone. Jump to 22:23 for the moment, or catch the audio on the episode page.
FAQ
How do I stop people pleasing at work?
Start with the tasks, not your personality. List what you do that belongs to someone else, hand back one item a week, and decline the office chores that never show up in anyone’s review. Changing what you do is quicker than waiting to feel brave.
Why is it so hard to say no?
Saying yes feels kind and saying no feels risky, and plenty of us learned early that love looks like doing things for people. One founder traced hers straight to her mom, who would bring her dad food on the couch rather than let him get up. Spotting where you learned it makes it easier to unlearn.
How do I say no without sounding rude?
Keep it short and warm: “Thanks for thinking of me. I can’t take that on.” No essay, no invented dentist appointment. The rudeness people worry about usually lives in the over-explaining, not the no.
Will my team resent me if I stop doing the hard jobs?
In that founder’s experience, the opposite happened. When her team did the hard things themselves, their ownership and confidence went up. Expect some grumbling on day one. It passes.
Want the whole conversation, including how she untangled the old beliefs behind it? Listen to the full episode.