The Whole Messy Story
Okay, let’s be real. Finding someone actually good to handle your stuff when you’re busy making money? It’s way harder than anyone admits. I learned this the painful, expensive way. Don’t make my mistakes.
First Wake-Up Call: I realized I was drowning. Seriously. My calendar looked like alphabet soup, emails were a horror movie, and trying to book a simple dentist appointment felt like negotiating world peace. I was wasting 40 hours a week on nonsense. That’s a whole work week! Insanity. I needed help, fast.
The Dumb Mistakes I Made (So You Don’t Have To)
Mistake #1: Thinking “Experience” Was Enough
I went straight for the fancy agencies. Found candidates with star-studded resumes working for big-shot names. Interviewed this one woman – flawless suit, spoke three languages, knew exactly what fork to use at Buckingham Palace lunch. Hired her instantly. Big. Mistake.
- She knew protocol, but couldn’t improvise if her life depended on it.
- Freaked out when my flight got canceled suddenly.
- Her idea of “urgent” was… not mine. Missed a critical deadline because she stuck rigidly to “process”. Fired her after 3 months. Wasted time and a hefty fee.
Mistake #2: Hiring Someone I “Liked”
Next time, figured I needed someone I clicked with personally. Found a guy – super chill, great to chat with, seemed to “get” me. Interviews felt like hanging out. Hired him.
- Turns out “chill” meant “sloppy”.
- Forgot to renew my passport. FORGOT.
- Details slipped through cracks constantly.
- Tried being “friends,” got resentful when I gave direct feedback. Had to let him go. Awkward as heck.
What Actually Worked (Finally!)
The Lightbulb Moment: Needed both brains AND backbone. Someone sharp who wouldn’t crumble under pressure. Someone discreet above all else.
Step 1: Gut Check with Myself
Sat down and forced myself to answer honestly: What tasks made me want to scream? What things did I never want to think about again? What kind of personality actually meshed with my (admittedly sometimes chaotic) work style? Wrote it all down, brutally honest.
Step 2: Ditch the Fancy Agencies (Mostly)
Went niche. Word-of-mouth became my bible. Asked everyone – lawyer, accountant, even my pilot – “Know anyone exceptional? Someone you’d personally trust?” Found a small, specialist recruiter through this who actually understood “discretion” wasn’t just a buzzword.
Step 3: Testing, Testing, Testing
Stopped caring so much about the resume polish. Started caring about:
- The Chaos Test: Gave candidates a real (but anonymized) nightmare scenario during the interview. “Flight canceled, VIP client demanding immediate reschedule, passport expiring, and the dog needs vet pickup. Go.” Watched how they thought, not just the answer.
- The Discretion Drill: Talked about confidential but minor past issues we’d “faced” (made up). Fished hard. Did their eyes light up? Did they pry? Or did they just nod, note the issue, and move on?
- The “See Them Work” Trial: Hired the top two contenders on a paid, one-week trial project. Gave them actual, real, non-critical tasks with messy details. Watched like a hawk. Who spotted the hidden conflict? Who double-checked the fine print without being told? Who asked the right clarifying questions?
Step 4: References? Dig Deeper!
Called the references they gave, sure. But then I politely asked those people: “Off the record, completely confidentially… is there one weakness, one thing they might need coaching on?” Got the real scoop. Found out one top candidate was amazing but notoriously slow with expense reports – crucial for me.
The Gold I Found
The winner wasn’t the fanciest CV, wasn’t the smoothest talker. She asked me hard questions too. During the chaos test, she didn’t panic, just methodically listed steps A, B, C, then paused and said, “But honestly? First I’d call you directly to confirm Client X truly is the priority here before bumping the medical specialist.” Boom. Understood urgency AND the need to clarify my priorities.
Her trial week? Impeccable. Spotted errors everyone else missed. Anticipated needs I didn’t even voice. Handled a minor schedule hiccup gracefully. Discreet? Like a vault.
Been with me 18 months now. Saves me at least 30 hours a week, handles things I don’t even know need handling. Worth every penny and then some. Took messing up twice to figure it out, but getting the right help? Priceless. Be brutal in your search.
