Breaking free from people-pleasing as a leader

Executive overview

Wanting everyone to like your decisions sets you up to fail — someone will always disagree. Laura Henshaw, co-founder and CEO of the Kic app, traced her people-pleasing to a deeper need for respect, not likability. Working through this shifted how she leads and how she delivers difficult feedback.

Being clear is kind — clarity beats cushioning every time.

Why people-pleasing backfires

• Trying to be liked by everyone is an unachievable goal, especially as a CEO
• Avoiding hard truths damages trust more than honesty would
• Fear-driven feedback is unconvincing — if you don't believe what you're saying, neither will your team
• Over-softening a message (too much "bread" around the "ham") means no one gets it

Shifting from liked to respected

• The real goal isn't likability — it's respect
• Respect comes from leading well, not from making everyone comfortable
• Being dismissed as "the marketing girl" fuelled a need to prove herself; therapy helped her see that was on others, not her
• Reframing "tough conversations" as "important conversations" changes the mindset going in

Giving feedback that lands

• The shit sandwich approach (praise → criticism → praise) dilutes the message
• Feedback delivered from fear fails — the speaker's doubt transfers to the listener
• Prioritise clarity over kindness in delivery; clarity is the kindness