I had tremendous problems with this. I hired a friend of mine who is intelligent and recently graduated from a highly reputed engineering school.
I told her that she was there to save me time, and that she should act with maximum initiative. One day I asked her to arrange a meeting for me within a certain time-span tomorrow, at a café with wireless Internet. She emails me back several hours before the requested time-span with a list of possible cafés and with everyone's availability -- thereby leaving it for me to arrange the meeting!
I also gave her a copy of my password database, and told her she was responsible for this. We go over everything and I make sure she knows how to open the password vault program. Later, I hired someone to do some Wordpress stuff for me, and emailed them both, explaining that the Wordpress contractor was supposed to coordinate with my assistant for all of the relevant access and passwords. I wake up one morning to see an email from my assistant to the contractor saying, "I don't know anything about that password." I end up having to send another half-dozen emails to my contractor and answer as many calls, while I was onsite and supposed to be billing hourly to another company.
Days later, I find out that she lost access to the password db file, and she never told me.
The problem you are having, I think, is that you are hiring someone who is not trained as an assistant, and expecting them to become an assistant with little training.
This would be like hiring a smart guy right out of law school and then complaining that he didn't know bash or something. I mean, if you can make it through law school, I think you can pick up bash, but it is irrational to think the person will be good at it the first day, you know?
I mean, I'm not saying you made a poor choice of assistant; I've had luck with people of similar backgrounds; but if the person hasn't done the particular job you need done before, well, you are going to have to train that person; training takes time and effort.
I know you want someone who "gets things done" - the problem is, everyone wants a different level of control in different situations. I mean, personally, I like someone else to 'just deal with' the money side of things. If we're running out, lemme know and I'll go get some contract gigs. But first, most people are pretty uncomfortable spending other people's money, so reassurances need to be made. And next, even I have some strong opinions once it gets down to the wire; (I mean, until you run out, money doesn't matter... but at that point? it becomes a very big deal) I had one assistant who would pay debt before payroll. So it's like "yeah, I want you to 'just take care of it' but I also want you to do what I think is the right thing."
I repeatedly gave instructions, like: If I don't specify it, I want you to come up with something that works. It will be my fault if I don't tell you. I want you to act with maximum initiative.
I still got massive amounts of my time wasted by assistants not completing things and asking me "cover your ass" questions.
I totally agree that it's a specialized skill set.
I know. It drives me crazy, because the only complaint I had was that she didn't get things done and act on her own initiative, and I tried for her to get the idea for a few weeks. I think some people are just socialized that way.
It takes a long time to build up the sort mutual trust needed for something like that to work. Most people have some sort of experience with being told something like that, yet still getting into trouble when they made the "wrong" decision.
There is a reason why many executives hang onto their personal assistants for decades, insisting they also get hired each time they change jobs job.
I think school is especially bad in this regard; you are expected to perform only tasks that you have been taught to perform. It's hard to make the adjustment to more goal-oriented work.
I still think it's often worth working with someone like that and the effort of training them up because school teaches people to be good at things I'm not very good at. Like follow through. And following the rules.
Why on earth would you pick an engineer to be an assistant? Engineers are usually people who want to build things, and being a good assistant has nothing to do with that. I don't know what fields are ideal for this sort of position (MBA would be my guess), but I can't imagine any engineering field to be one.
Why on earth would you pick an engineer to be an assistant?
Because I could also tell her to do stuff like "Set up an Amazon EC2 instance" and she could just look up instructions and do it. (I know, because exactly this happened!) She could do geeky, she just didn't understand "assistant." I wanted someone who could do both.
I'm not going to say that you're wrong to want to hire a person like that, but I will say that most people who hire "assistants" don't expect them to coordinate password databases with contractors or spin up EC2 instances.
I can see why it would be particularly hard to hire the kind of assistant you seem to be looking for.
Correct, most people don't do this but there's a class of 'assistant' where technical skills are worth more than secretarial skills.
For example, research assistants are expected to help with the tedium of econmetric studies (e.g. performing regressions, collecting data, etc.) and this requires at least a masters level education.
Right, but you don't call those 'assistants', they're professional staff. 'Assistant' = title inflated way of saying 'secretary'. Who with a master's degree wants to have 'assistant' on their business card, unless it's very clear that it's a short stepping stone towards becoming whatever is after the 'assistant'?
From the writings others who have advocated assistants, like Tim Ferris, it seemed possible to find someone with a modicum of technical ability, but who also could generally "Get Things Done."
I may have a skewed view of what constitutes trivial technical things.
I may have a skewed view of what constitutes trivial technical things.
I think perhaps you are right :)
System Admin and Office Admin are distinct jobs. You should expect an office admin (ie, an assistant) to work out how to use your phone system (but not to install it) or to drive Excel and your payroll system.
Honestly this sounds kind of strange to me. It's almost like, "I need someone who can code Ruby and also take out the trash." Making appointments isn't quite the same, but it's certainly not using the skills of a technical person and seems insulting.
At the very least, administration is a different skill set. It's like "I need a salesperson / chef" or "I need an accountant / news reporter." What you need is 2 people.
Honestly this sounds kind of strange to me. It's almost like, "I need someone who can code Ruby and also take out the trash."
Adjusting a Wordpress site or spinning up an EC2 instance isn't the same as coding Ruby. (For values of "coding" that are really substantive.)
Making appointments isn't quite the same, but it's certainly not using the skills of a technical person and seems insulting.
She knew what she was getting into ahead of time. I doubt she was ever insulted by what I asked her to do.
At the very least, administration is a different skill set. It's like "I need a salesperson / chef" or "I need an accountant / news reporter." What you need is 2 people.
Actually, there is call for someone who has some culinary skill and some sales ability, and they can be useful for making money. (The guy who did the Miracle Blade infomercials, for example. There are others in boutiques I see around town operating on smaller scales.) Accountant / news reporter -- I could see a valuable business reporting niche!
Adjusting a Wordpress site or spinning up an EC2 instance sounds firmly within the job descriptions of an "IT operations manager", who clearly would not like the title "assistant".
Just for what it's worth. Nobody is saying you're crazy for wanting to hire that person.
This was a not yet employed recent engineering college grad who was contracting with me for $12/hr. And to be precise, she could spin up an EC2 instance, but couldn't keep my schedule.
Frankly, for most people in that situation, (highly educated, working in a low-paid contract job doing menial tasks unrelated to their education or interests) their first, if not only priority is going to be finding a real job.
This what she eventually did, but in the beginning, she seemed enthusiastic about having some kind of part time work. In just about the time she spent almost arranging a meeting, she could have just gone ahead and arranged it. I think acting on your own initiative is something not everyone quite knows how to do.
Yes, that's quite true. Most people are by nature reactive - even many high-level engineers. I've known many great programmers who can do amazing things once they get started, but simply can't seem to get going until they're told what to do. Employees who actively identify and solve problems are incredibly valuable.
The article title is technically ".. when to hire an assistant". It's an important distinction to make. The core point of the article is about how hard, but incredibly valuable it can be to let go of your baby.
I've been working with a virtual assistant for more than a year and it's really amazing. Saves me a huge amount of time, mostly booking travel but could be anything really.
I think the job of a CEO is to constantly develop systems such that you do not need to do the work, giving the work to other people or developing a process that doesn't require as much effort. A neverending battle to reduce the amount of work you have to do (and at the same time work more strategically on your business). An assistant is part of that process.
I think a virtual assistant in combination with sites like task rabbit is a good option as well (and an order of magnitude less expensive).
>This is a problem with job listings in general: They don't seem to describe an actual day's work. They're heavy on skills but not actions.
Ya. Job listings should detail exactly the work that the person will be doing.
I think part of the reason why this isn't done is because it may not sound as good.
But an employer should want someone who will enjoy their work.
So be honest and open about it. Employers should leave out the buzz words and marketing speak and just be straight forward. I wouldn't be surprised if doing so made hiring easier and better.
I'm really shocked that it took them that long to hire an assistant. It would be very difficult to think creatively with all of those trivial concerns in one's head.
Here's an idea, instead of "executive assistant" call it "office manager" or something. It seems like that would solve the "stepping stone" issue he ran into, while effectively being the same job. (I'm not saying the job titles are always related, but I AM saying that they could be the same thing.)
Huh. A little odd it wasn't in his article, but I guess it didn't help anyway.
Color me surprised. Perhaps the volume of responses they got were more from fans of 37signals rather than actual job seekers? Regardless, I don't have any ideas on how to combat that.
Many places solve the assistant problem by going through a temp agency and then offering the individual full-time employment if they work out at the end of their contract.
And I think there's an article waiting to be written about the dangers of the receptionist/assistant turned underqualified office manager. I've seen more companies go dysfunctional over that (fear to try to get more graph paper, kitchens that never get restocked, replacement keyboards/mice never get ordered, etc.) than even the dreaded IC-overpromoted-to-lead problem.
Not really, not until you need one (we have an office manager now, and she's awesome, but in years 1-2 the role would have been more trouble than it's worth today).
I told her that she was there to save me time, and that she should act with maximum initiative. One day I asked her to arrange a meeting for me within a certain time-span tomorrow, at a café with wireless Internet. She emails me back several hours before the requested time-span with a list of possible cafés and with everyone's availability -- thereby leaving it for me to arrange the meeting!
I also gave her a copy of my password database, and told her she was responsible for this. We go over everything and I make sure she knows how to open the password vault program. Later, I hired someone to do some Wordpress stuff for me, and emailed them both, explaining that the Wordpress contractor was supposed to coordinate with my assistant for all of the relevant access and passwords. I wake up one morning to see an email from my assistant to the contractor saying, "I don't know anything about that password." I end up having to send another half-dozen emails to my contractor and answer as many calls, while I was onsite and supposed to be billing hourly to another company.
Days later, I find out that she lost access to the password db file, and she never told me.
It's been hard to hire an assistant!