Ask HN: Advice on Hiring an Assistant?

20 points by And1 4 years ago | 7 comments

I run a small business and I'm totally swamped. I've outsourcing the standard stuff (bookkeeping, financial ops, most writing) but I'm still drowning in a lot of one-off tasks.

I've tried one virtual assistant service, but I've been underwhelmed with the help I've been getting (been through 2 candidates so far). I'm really trying to not expect too much, but it would be nice to not field a million questions on what seems like a straightforward task.

I'm open to the idea that I'm doing a bad job of formulating tasks, and that this is a skill I need to get better at, but has anyone found success with hiring an assistant? Local/virtual? What worked? How long does it take to have someone get your style? Do you know if its not a fit right away?

Any wisdom appreciated.

elasticventures 4 years ago |

Finding a good assistant is rough, it requires patience, initiative & chemistry. Once you find 'the one' reward them, because a good assistant is like having a 3rd hemisphere to your own brain -- it sucks when you lose it.

Retooling for an assistant is the most important thing you will ever do for your company, it is what will ultimately allow you to perhaps grow or exit someday.

For new assistants - start them writing down your processes as an operations manual. Every day, they should be making updates and journal entries in the operations manual. The primary purpose of this is to see they can write in a way you can understand, if they can't do this - then fast fire.

If you find somebody who can write/edit/update -- Make sure they know "this role temporary, until it is permanent" and their role is to make themselves indispensable by anticipating your needs.

review your inbox, edit your documents, organize your calendar, and do research, follow up with clients, billing/collections, whatever tasks they can identify and offload from you.

A good assistant once fully trained will be 80% right, 20% wrong, .. you need to accept they aren't you - but eventually you'll both find how to make sure they do the 80% .. and defer/check with you for the other 80%.

A good assistant will write things down for your next assistant. We call this the "BUS" (or Tram) factor.

I know this seems cold & harsh, but having/updating an operations manual should be the first week of any new person as they are training.

tdfx 4 years ago |

I highly recommend Notion for building a knowledge base at your organization. We have one section dedicated to company-wide knowledge, and another section dedicated to various tasks. Any recurring task should be documented fully, with screenshots or a screen recording. The upfront time investment of doing this allows you to really let go of the burdensome stuff. For any work that isn't creative or specialized, you really shouldn't do it yourself longer than it takes to document and delegate it.

Once you've got the workflow in place, finding an assistant is really just a process of elimination. You can easily find someone with C1 English skills for less than $10/hour on Upwork.

You'll need to filter through a bunch of bad ones to get to a good one, but again, this is an upfront time investment. Establish expectations early and fire quickly at the first sign of issues. Trying to "make it work" is worse than accidentally losing a good candidate.

I would also encourage you to post it as a full-time position, as you don't want to be competing with other clients (you still will, but if you're their primary professional focus that pays the rent, you won't lose out in most deadline situations).

e1g 4 years ago |

I'm considering doing the same and found this tactical guide from a serial founder to be helpful and well-structured: https://review.firstround.com/a-tactical-guide-to-working-wi...

Arrath 4 years ago |

>I'm doing a bad job of formulating tasks, and that this is a skill I need to get better at, but has anyone found success with hiring an assistant?

I would start with this point. Take some time, be it weeks or a month, and every time you come across one of your one-off tasks that you would love to delegate out, note it down.

Later on, try to document or at least bullet point those tasks into something more well described, workflow, deliverables, average time to complete, etc.

Once you have a stable of such tasks you can then condense them back down to a job description that will help your search a lot. I did this prior to hiring an assistant and it worked great. I had a list of tasks to post, and to discuss through the interview. I knew which programs I would be asking the interviewee to have experience in, and I had an idea for further tasks to be added to the workload if things worked out, which they did!

sinac 4 years ago |

Ramit Sethi has a good course that goes over these specific issues. It’s called Delegate and Done and it includes a guide on how to hire a good assistant.

I’d also suggest reading Michael Hyatt’s Your World Class Assistant.

His Free to Focus book is also quite helpful to map out what you need to delegate away after you get an assistant

bryan_w 4 years ago |

Note, the internet is full of scammers, so I would opt for a part time PA that you can meet in person before handing over the keys to the kingdom

(Or maybe I'm too paranoid)

tucaz 4 years ago |

What kind of tasks?