Every business owner who hires an assistant hits the same wall. You can’t hand over the work without handing over the access. And you can’t know whether someone deserves that access until you’ve already given it.
That gap is uncomfortable, so most people try to close it with tools. A password manager. An NDA. Permissions set carefully on their own domain.
Those things matter. We recommend all of them. But they only solve half the problem, and it’s the cheaper half.
Two different fears wearing the same word
When someone tells us they’re nervous about trust, they usually mean one of two things.
The first is that a stranger will do something deliberate. Take client data. Misuse a credential. Walk away with something that isn’t theirs. One founder we spoke with this year asked about our vetting before anything else, because a previous contractor with access to their books had access to every client record in the business. They’d been burned once and weren’t interested in a second time.
The second fear is quieter and comes up more often once people start describing their actual work. It isn’t about theft. It’s about someone with good intentions doing damage because they didn’t know enough to catch a problem.
We talked to a business owner who’d had a customer-facing form set up by someone offshore. The dates displayed day-first rather than month-first. A small thing, technically correct, and completely normal where the person building it lived. His customers read it as an error and some of them didn’t complete the booking. Nobody did anything wrong. He still lost the sales.
These two fears need different answers, and only one of them has a technical one.
What screening actually covers
The first fear is a screening problem, and screening is mechanical. It should be, and you should expect specifics rather than reassurance.
Every person in our talent network is US-based and goes through a background check before they work with anyone: national, criminal, state and county databases, and Social Security validation. They sign an agreement with us covering confidentiality and the handling of client information. Anything they produce belongs to the client, not to us and not to them. If a client wants their own NDA signed on top of ours, that’s normal and we encourage it. If they want the background check documentation on file, we provide it.
That’s a real answer to the first fear, and you should insist on it. It’s also table stakes. Any agency worth talking to does this, and if one can’t describe its process in a sentence, that tells you something on its own.
Where it gets interesting is the second fear, because screening doesn’t reach it.
The part you only learn by working with someone
No background check tells you whether someone knows what not to repeat.
An executive assistant sees payroll. They see what people are paid, who’s being let go before it’s announced, which client is late paying, what’s happening in their principal’s personal life because it’s on the calendar. One founder described the specific shock of discovering that a working relationship she thought was mutual wasn’t, and it had nothing to do with data or credentials.
The quality you need there is professional maturity. Understanding that you’ll know things you don’t discuss with your friends, don’t mention on a call with another client, and don’t post about. There’s no software that produces it and no certification that proves it.
The same quality is what would have caught the date format. Someone who has spent time inside American small businesses knows how a US customer reads a booking form, what language is normal in a given industry, and when something technically fine is going to land wrong.
Here’s the honest position on both of those. You find out by working with someone. Not from a résumé, not from an interview, and not from a screening report. You learn it from how they handle a week that goes badly, whether they flag a problem early or sit on it, and what they do with information that was never meant for them.
So we try not to hand you a stranger
That logic points at us as much as anyone. If trust comes from having worked with someone, an agency introducing you to a person nobody has worked with is asking you to take the same leap you’d take hiring alone. You’d just be paying someone else to have taken it first.
So many of the people in our talent network have done work for us before they ever worked for a client. Our own projects, our own deadlines, our own briefs, including the rushed ones. We’ve seen how they operate when the work is real, which is a different kind of knowledge from anything a file can hold.
We can’t claim that about every person, and we won’t pretend otherwise. What we can say is that nobody joins our network without completing our onboarding course first. Everyone arrives having been prepared for the way our clients actually work, so no one lands in your business cold.
What that changes is the nature of what we can tell you about someone. A screening report says nothing turned up. Having worked alongside a person means we can tell you how they behaved.
The match is the second half of it. Knowing a person’s work is only useful if we also understand the business we’re placing them into: the pace it moves at, the tone it needs, how much context someone has to hold. The date format problem wasn’t a character failure. It was a matching failure. Somebody put a capable person in front of customers whose expectations they had no way of knowing.
The other failure mode: security that blocks the work
There’s a version of this that goes too far the other way, and we see it often enough to name it.
Someone gets careful about access, so they don’t give any. Their assistant has to come back for a login every time they need to do something. A code here, a password there, a quick approval before a file can be opened.
That isn’t delegation. It’s a slower version of doing it yourself, with an extra person waiting on you.
The point of handing work over is that it leaves your desk. If your assistant can’t act without you, the work hasn’t moved. It’s just queued behind you now.
What you want is access that’s real enough to be useful and structured enough to withdraw. In practice that looks like:
A password manager rather than shared logins. Credentials live in one place, get shared without being seen, and get revoked in a click. Every assistant we work with is used to onboarding into whatever system a client already uses.
Permissions on your own domain. An account you created, with the level of access the role needs and nothing beyond it. When someone leaves, you remove the account. You aren’t chasing down where your data went.
Admin-level access rather than full account access, where the tool allows it. One client working in a field with strict handling requirements is setting up a virtual machine his assistant logs into, so credentials never sit on a personal device at all. That’s further than most people need to go. It’s a good illustration of the principle: give access to the system, not to the keys.
Clear boundaries on what’s shareable. Say it out loud at the start rather than assuming it’s obvious.
Set up that way, extending access stops being a leap. You can give someone real reach into your business on day one and pull it back cleanly if the fit isn’t right.
What to ask, whoever you hire
If you’re weighing up an assistant, whether through us or anyone else, four questions get you most of the way:
- Where is this person based, and have they been background checked? What specifically was checked?
- What have they signed, and can I add my own agreement?
- Who owns the work they produce?
- Has anyone at your company actually worked with this person, and what did you learn about them?
The first three should get you fast, concrete answers. Any agency worth using can produce them in a sentence.
The fourth is the one to listen carefully to, because it’s the only one that can’t be answered by a process. Either someone has direct experience of how this person works or they don’t. If the answer turns into a description of their screening funnel, you’ve learned something useful.
You’re going to have to hand over the keys. That part doesn’t change. What you can decide is who you hand them to.
Whoever you end up hiring, the handover goes better when they aren’t guessing at your preferences. Our Working With Me worksheet gets that onto one page before day one. Download here →
