In the modern workplace, the line between professional and personal conduct has blurred. We dine with managers, follow VPs on social media, and occasionally find ourselves invited to a pickleball game with the CEO and his partner. It feels casual. It isn’t.
Imagine you’re a sharp, 33-year-old executive with enviable rapport: affable, competitive CEO—the kind who smiles while dismantling your argument in a meeting. He hears you’re good at pickleball and suggests a match. Sounds friendly. Feels flattering. But immediately, you sense the undertow. Should you play? And if you do—win, lose, coast?
The answer isn’t etiquette. It’s performance psychology.
Play. Play fully. Play honestly.
Authenticity isn’t just a virtue, it’s strategic. People respect genuine conviction. Against a high-achieving CEO, showing up as your full self signals confidence, not arrogance; integrity, not vanity. The real risk is underplaying for his ego—feigned incompetence makes you look insincere and calculating.
Here’s the payoff: how he responds matters. If he loses and laughs, adapts or tightens his game—if grace or insecurity surfaces—you learn something valuable. Informal play can reveal more than any meeting.
If your boss needs you to lose to feel powerful, he’s not leading. He’s compensating. You’ll have to decide whether that fragility deserves your loyalty. Managing up sometimes demands confrontation, not appeasement.
Other times, restraint is wiser. Watch for signals. Some CEOs test for dominance; others just want to unwind. If he’s probing technique, teach. If he’s chasing laughter and sweat, ease up. Self-regulation isn’t dishonesty—it’s emotional acuity. Knowing when to soften your game shows you read the moment. Pickleball, like influence, is contextual. Treat it as theater when it is, and recess when it’s not.
Idea for Impact: When the invite comes, don’t overthink. Say yes. Stretch. Compete. Play hard and you’ll earn respect. Play soft and you’ll raise suspicion.
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