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How I hired an executive assistant that I'm happy with
I wanted to hire an assistant to help me with the workload for my business. After many failed attempts (and hence lots of paralysis), I'm happy to say I found a person who's a joy to work with. Her name is Jen.
I want to talk about the hiring process and what I learned about each step — mostly to consolidate my learnings. It'll be a bonus if this helps you work through any kinks when you're in that stage.
Note: these are my opinions and don't reflect what other hiring managers or employers think.
I split the hiring process into 3 stages:
Completing the entire process took about 2 weeks. I ended up hiring 2 people even though I only looked for one.
Here are some brief notes about the timeline.
Note: timings stated here are estimates
I realized you only have to say three things for a good job description:
Here's my job description in case you were wondering what it looked like.
Writing the job description is the most challenging part of the hiring process. Everyone wants to hire a rockstar for their team — it's tempting to add high requirements to find these people.
This is a big mistake.
The biggest problem with a "rockstar search" is you're not being honest about who you're hiring for your job. This dilutes your ability to filter candidates in the application process.
Second, high requirements deter people from applying. You may receive less quality candidates by setting your requirements too high.
Third, why would a rockstar want to work with you? What do you have to offer them? If you don't have much to offer, you won't be able to hire one, much less keep them.
So it's better to discard your fantasies and look for someone real — list your minimum requirements instead of your ideal requirements. (That's why they're requirements and not ideals).
When you can be honest with yourself, you can set good expectations that others can honour. This one step removes a lot of candidates that don't align with what you offer.
Here are a few examples from my job description:
It's tempting to copy other people's job descriptions to simplify the process, but it doesn't work.
It doesn't work because the intention and energy put forth into their role doesn't match the role you're advertising. Sometimes you find qualities you think are "good to have", but they detract you from what you originally wanted.
So it's best to brainstorm what you actually need and list the requirements yourself. This gives you a chance to create the written application and any tests to suit the role you want to hire for.
I started with a written application that contains only two questions:
I used these two questions because they're easy to answer so candidates don't overthink — which is important for doing jobs effectively and efficiently as an assistant.
I kept the process simple with Google Forms. Through the process, I noticed I loved two features of Google Forms.
First, I can cycle through responses individually by clicking the individual tab.
Second: I can delete people people who don't make the mark during my first pass.
I filtered the responses heavily since I only let myself interview 10 people. This is an arbitrary limit I imposed on myself to train myself to filter properly.
I filtered people out when:
From there I picked people (first come, first served) who seemed to have the ability to communicate effectively. Eventually, I invited 12 people for interviews. It's a little bit over my self-imposed limit, but I think this is good enough.
Of the 12 candidates shortlisted, 10 turned up for the interview.
I limited each interview to 30 minutes (again, an arbitrary number) because I wanted to keep things tight. I wanted to see if I could find out enough about a person within the first 30 minutes.
I set up the meeting so it's more of an informal chat between us — I want to get to know each other better and whether we have a good chemistry to work together.
There were only two questions I asked everyone:
I looked out for a couple of things:
Notice I wasn't looking for ambition here: I wanted someone who's not very ambitious so I can rely on this person for a long time. (So ambition isn't always good!).
The interview isn't only about finding the "right" person for the job. The purpose is to find out who this person is and whether they can support you. If you find someone perfect for the job, great! But don't discount anyone who isn't a perfect fit.
In this case, I found a few gems:
So be open minded. You never know who you speak to and how they can help you in various ways!
I offered each promising candidate a mini-project. I gave them two tasks:
I also gave them the following instructions:
This paid project simply tells me how they work and whether the quality of work is what I intend to have.
I hired two people through the interviews. I onboarded them together and shared my expectations with them:
We held one meeting each week as a team, beginning with a weekly review of four questions
These four questions allowed me to see how each person is able to be honest with themselves about the jobs they were asked to do in the previous week. They also allowed me to improve from the feedback that I gathered from the team.
After the weekly review and some social chit-chat (about 30mins total), we would break into individual sessions where I delegate tasks and explain what these tasks are for.
I spent an average of about 2 hours per week on the meetings themselves.
I wasn't ready to hire two people — hiring two people would drain my finances and create more stress — but I thought I would give it a go anyway.
I hoped the extra person could grow quickly and become someone I could rely on to become a great product manager. I had confidence that I would be able to train someone up relatively quickly.
I was wrong — the person didn't show a good trajectory towards what I needed within our 30-day paid trial. I ended up letting him go (with much heartache).
Upon reflection, I realized I jumped onto three fantasies/delusions:
My greatest mistake is taking a gamble on the candidate without filtering him for the skills I needed him to have. I relied on blind faith that his positive and will-do attitude will tide him through.
Although I have no doubt that his attitude will serve him in the long term, I realized I was unable to train this person up.
Why?
Two reasons:
I ended up letting him go because his presence was creating a lot of negative energy for me and all I could think about was how to handle this person, and not expanding my business or pouring energy into my work.
Hiring this person, although wrongly, was a good learning experience since it allowed me to take a closer look at the delusion I had – that I needed to help people grow. I realized I wanted to help people grow, but I could not fulfil this delusion of mine for everyone.
We need to know why we're hiring and what we're hiring for. We can only find the right (or best-fit) person based on complete honesty of the criteria we set.
We cannot have delusions and fantasies about who we hire. We do not run charities and we cannot afford to support people at the expense of our business and lives.
We need to vigorously test and filter people out accordingly. I cannot expect myself to be great at interviews and sniffing people out at a glance because I'm not trained to do so, and I shouldn't have that delusion either. So a paid trial is necessary.
If the paid trial doesn't work, I need to fire the person and face the fact that I hired the wrong person for my business. I also need to understand where I was wrong so I won't make the same mistake again.
If you're looking for employment, please remember that employers look for people to help them — you will have a much better chance if you demonstrate you can help them, instead of saying you want to learn from them. (This is just my opinion, of course).
Thanks for reading. This article was originally posted on my blog. Sign up for my newsletter if you want more articles to help you become a better frontend developer.
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