Ask HaviNote: it is almost impossible to get on the Ask Havi list. This person got in by a. being one of my clients or students, b. flattering the hell out of my duck, and c. making life easy on me by being clear about what the question was and what details I could use.

“I need to become better at hiring people.

What do you do before hiring someone? Do you have a process? Do you go with your gut? What do you look out for? How do you make sure that this person will be a good fit working with you?”

Oh honey. Yes. This is probably the hardest part of being in business and biggifying what you do. Seriously.

Let’s see …


Hahahahahaha. Not really.

I write a personal ad. I think about the qualities and values that are important to me. I put a wish out there.

And then I ask everyone I know for recommendations. That’s how I’ve found most of the VAs (virtual assistants) on my pirate crew.

Go with gut?


I really have to get a hit that I can trust this person.

Of course, I’ve worked with plenty of people who were absolutely trustworthy and it still wasn’t a good match … sigh.

What do you look for?


A sense of humor.

Someone who is at least as weird as I am.

My wonderful friend Kelly Parkinson says that you really have to “match your values”, and I think she’s right.

So what I value is kookiness, personality, passion and hard work. Maybe for you it’s something else. If you look at what isn’t working, that might give you a better idea about what could work.

How do you make sure that this person will be a good fit working with you?

Okay, this is not exactly where I excel, but I will share the absolute all-time best information I’ve ever received on this.

Story time! Plus the best advice I can give you (that’s not even mine).

Remember when I flew to Vancouver for Michael Port’s Beyond Booked Solid seminar?

(flashback to September 2008, weird scooby doo effects)

This is me in a state of complete and utter desperation because my business was turning into the world’s biggest headache.

On top of that, I couldn’t get the VA thing to work. And I was starting to think that I would never find someone who would be able to really help me in my business.

Also, I was terrified that I was turning into Aryeh, the worst boss I ever had. Seriously. Worse than the fall-down drunks who ran the bars I used to work at.

The worst boss and the person I am afraid of becoming.

Always upset with you. Always screaming at you in front of the entire company.

Oh, and he expected you to be able to do three people’s jobs cheerfully, efficiently and flawlessly. Also, without any explanation whatsoever about what those jobs entailed or how to do them.

Perspective? This guy had gone through fourteen executive assistants in the course of one year. Half had gotten canned and the other half had (understandably) run away.

I worked for him for three months, making me by far the one with the most seniority. I know.

And somehow, he managed to think that it was always “them”. Never him. He wasn’t the asshat. They were incompetent.

Now all of a sudden I was the CEO* and — even worse — I had turned into the one complaining about how it’s “impossible to find good help”.

Disaster. And embarrassing. So by the time I got to Michael’s seminar, I was really at a loss.

Luckily he was full of wisdom and smartnesses, which I will pass along to you.

*CEO = Chief Eccentricity Officer

Healthy relationships take time.

Michael reminded me that any good relationship is something that is built over time.

He reminded me that I’m not a horrible person if some of them don’t work out.

Just like with falling in love. You don’t fall in love with everyone you have a coffee with.

Same goes for finding a good therapist or the right yoga teacher. Most combinations aren’t going to work.

Anyway, I was incredibly relieved to learn that Michael had also gone through a very long period of trial and error, emphasis on error.

It gave me permission to keep trying.

Training is everything.

Michael also taught me that it’s my responsibility to train people very specifically in terms of what I want them to do and how I want them to do it.

So I had always looked for a VA who knows my shopping cart system, and then would get annoyed when she’d make ridiculous mistakes.

She said she knew the system, but then she’d get things wrong.

To me it seemed irresponsible and incompetent. But Michael helped me realize that not everyone uses the same systems in the same ways, and that it’s my job to be very clear on how I want things done and why I want them done that way.

His analogy: even Michael Phelps is screwed if he’s out alone in the middle of the ocean.

Skill sets alone are meaningless without instruction, guidance, boundaries. That was useful for me.

Also, I hired the brilliant Cairene to help me clarify and organize my systems, which has helped me enormously. Understatement. I would be lost without her.

Look for someone you like.

The other huge piece of advice I got from Michael –and this was my lightbulb thing— was this:

I should stop looking for a VA … and start looking for someone I really like who gets my business. Someone who really, really gets it.

To look for qualities over skills, personality over ability and willingness to learn and get dirty over experience.

Find the person you like and then train them to do what you want them to do.

And very, very, very soon after that, I found my dear First Mate Marissa.

I never would have approached her before because she wasn’t branded as the thing I was looking for.

But in the meantime I was filling out long and complicated forms for these fancy VA sites and they weren’t even getting back to me.

If you love them and they get it, you can figure out the rest.

All along I’d been hiring these super-fancy, super-expensive, assistant-to-the-stars, works-with-all-the-biggifiers sort of VAs, and it wasn’t working.

Yes, they were competent, but they didn’t get me or what I was trying to do.

Realizing that I need someone in my business who really and truly gets the feeling and the essence of what we do and who my Right People are … that was what changed everything for me.

And hooray for that.

Because without Marissa, I wouldn’t have been able to go on email sabbatical or to take an emergency vacation or to run my business with repetitive stress stuff that doesn’t allow me to type.


Well, definitely write a personal ad.

That’s always a good thing.

  • If you have a holistic good-for-the-world business, I recommend that you talk to Joy Slaughter (she’s @JoysLaughter on Twitter).
  • If you need someone who is super social-media savvy (and also a total sweetheart), I recommend that you talk to Michelle Wolverton (she’s @ChelPixie on Twitter).

  • And of course I highly recommend Marissa (she’s @MarissaBracke) but just make sure to leave about 60 hours a month for me because I can’t live without her.

Hope that helps!

I’m sure there’s more, though. So … thoughts? Suggestions? Things I forgot to add?

The Fluent Self