How To Land Your Dream Job

Updated: Aug 29, 2019

Okay folks, I’m not going to sugarcoat this: I really needed that job as an Executive Assistant.

I had been a work-at-home Mom managing a 70-unit apartment complex for two and-a-half years, and it was driving me slowly insane. For those who haven’t experienced it: being a work-at-home parent is the worst of both worlds. Because you are home, your child expects your undivided attention. Because you are working, you cannot provide it. Constant mutual frustration ensues.


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ACTUALLY, more like:


So, I set out to find work “outside the home.” This proved to be a far more difficult task than I recalled it being back in my pre-graduate school days.

To be fair, many things had changed since those halcyon days: the job market had shriveled to a sliver of its dot com bubble glory, and tech companies now dominated the local economic landscape. Meanwhile, I was no longer an adorable Fulbrighter with a bright future ahead of her. I was an overeducated mom with a PhD in Dramatic Arts. And what the hell was I supposed to do with that?

Get creative, that’s what.

Step One: Focus

At first, I applied for anything and everything for which I was even peripherally qualified. Turns out casting a wide net comes off as, well, desperate. And “desperate appeal” is an oxymoron.

Meanwhile, not having a specific role in mind made it rather difficult for my friends to help me (we’ll come back to that in step three). I mean, how annoying is it when someone says, “I’m hungry,” but when you ask what they want to eat they just shrug and say, “Anything.” Answer: incredibly annoying.

So I said to myself: all these tech companies have executives. Executives need assistants. A life in the theatre had prepared me well for both taking and giving direction, keeping things on schedule, and perhaps most importantly, people pleasing. So I took the plunge and narrowed my focus to a single role: Executive Assistant.

Step two: Tailor

Armed with a specific job title, I could mine job descriptions under similar titles for duties and buzzwords to work into my resume. This is enormously important since HR folks have a huge pile of resumes to get through, and you make their job much easier by using the exact keywords they are skimming for.

But even more importantly, this helped me clarify, both for myself and for prospective employers, what exactly I bring to the role in question.

I made a list of my “superpowers” – the specific skills within the relevant set that set me apart from, and above, my competition.

For example, while I may not have been the most experienced EA on the block, I am a remarkably quick study, and can tolerate an enormous amount of uncertainty, chaos, and sudden change. In short, my flexibility is phenomenal, if not actually superhuman.

This, as it turns out, is a major advantage in a start-up setting.

And nobody, but NOBODY beats me at bringing the fun. Wherever I go, fun follows. Whether anyone likes it or not.

And that’s an advantage in any setting.

But peppering my resume with keywords and my cover letter with superpowers was only useful if I could get those materials into the right hands…

Step three: Network (a.k.a. “It’s who you know”)

Despite my supernatural social skills, it did not immediately occur to me to leverage my network of friends to help me find a job.

Looking back, my reasoning was ludicrous. I thought I would be burdening my connections by asking for their help when, in reality, everybody loves to feel like they’ve been of help to a friend. So if you make it easy and pleasant to do so, then you’re basically doing them a favor.

No, seriously.

And how do you make helping your job-quest easy and fun?


A. Make a list of every company you think you could stand working for. In my case, this meant going to the Geek Wire website and combing through the list of the top-200 start ups in the Seattle area.

Don’t limit yourself to companies that are actively hiring! Often the juiciest positions are not even advertised externally.

Don’t be afraid to aim high! Turns out the main concern at the kinds of companies that are the most fun to work for is whether you’re a good fit in terms of personality and ability, not necessarily experience or education.

B. Log onto LinkedIn and methodically go down the list looking for first- and second-degree connections working at those companies.

C. Write to any first-degree connections, and ask them if they can introduce you to someone working there who does what you’d like to do (in this case, any executive or administrative assistants). Offer to provide copy so that all they have to do is send a pre-written email, which will take all of 30 seconds out of their day.

D. Write to any second-degree connections and ask for an introduction to the person they know who works there. Again, offer to provide copy.

If you get that intro, go back to C.

E. Once you get an introduction to someone in a relevant role/department, reach out with a specific ask: can we meet up for coffee at [place] on [date/time] to chat about your work at [company]? Don’t put the onus on the person who is taking time out to chat with you to come up with something. If the suggested meetup doesn’t work for them, they’ll simply counter with something that does.

If you don’t hear back within 3 days, move on to the next connection AND send a follow-up email, just in case the first message got buried in their inbox.

At these casual coffee meet-ups, your goal is three-fold:

  1. To establish whether or not it’s a good fit (Would you want to work at this company? Would you be a good culture fit there? Do you have the skill set they are looking for?)

  2. To be yourself so that they can assess whether or not they think you’re a good fit.

  3. To make note of the language they use, the unique problems they have, etc., for use in your cover letter, resume, and any interviews.

Close by thanking them for their time and asking if they’re open to you following up with them. Chances are (provided they think you’re a good fit), they’ll say yes. If not, it probably wasn't a good fit for you, so be grateful they just saved you a lot of time and heartache down the road, and be on your way.

If they were open to a follow up, then FOLLOW UP with them 10-30 days later. Mention something helpful they did, or progress you’ve made. Note any open positions at their company and ask if they can recommend someone you could reach out to for more info.

Meanwhile, don’t just rely on friends, or friends-of-friends, who actually work for the companies you’d like to work for. Reach out to EVERYONE in your network. Let them know you’re looking. You never know who might know someone who can help you out.

This is essentially an opportunity factory. Just keep cranking them out until you can ride one all the way to the end.

I cannot stress this enough: The job hunt can be depressing. It can sap your will to keep trying. Having a system in place that keeps your forward momentum going even when you are SO not in the mood is essential. Trust the process. It works.

Step four: The phone screen

The first phone screen is generally casual. They’ll ask you to tell them about yourself, what you’re looking for, what you bring to the table, etc. They might have you walk them through your resume and describe your skill set.

Here’s what they’re trying to establish:

  • Are you in any way risky as a new hire? (Don’t volunteer any information that could be construed as a risk factor. They can’t ask, so you shouldn’t tell.)

  • Are you a good fit within the culture of the company? (Do your homework! Most companies have their values and/or mission statement available for public viewing on their website.)

  • Is your skill set useful and relevant to the specific position? (You are responsible for making that connection explicit. Make sure they understand what you bring to the table and how it will help them succeed.)

  • Here’s what you need to have at the ready:

  • Your “elevator speech,” a quick (30-60 second) introduction to who you are and what you’ve been up to for the last few years. For example, I tend to lead with, “I’m a bit of an odd duck, in that I’m a deeply creative person but also a highly organized one. I got my PhD, but I got it in Theatre, so that tells you something right there.”

  • Why you’re interested in this company and this position (be sure to weave in verbiage that hits on their core values and mission. For example, Amazon often refers to a “customer obsession,” and Google loves “outside the box” thinkers. Use words and phrases that communicate to the company in question.)

  • What you can do for them. For example, one of my superpowers is resourcefulness. I can find you a fabulous new wardrobe at Value Village for a couple hundred bucks, or make you a gourmet meal from what’s left in the fridge. So one of the things I can do for a Startup in particular is to efficiently and effectively stretch a limited budget and use a wide range of resources to get the job done.

Your job in this interview is to let them know who you are, and to reassure them that you are not a risk, but an asset, meaning you will bring more value than you will cost them.

Step Five: The second interview

In the second interview, they are likely to ask you behavioral questions to get a sense of how you think and act. Behavioral questions are generally phrased like this:

“Tell me about a time when you…”

The answer they are looking for a is a narrative which describes your methodology for problem-solving. It should follow this general pattern: STAR

Situation (give some backstory so they get the sense of why this problem matters)

Task (the problem that needed to be solved)

Action (what steps you took to solve the problem)

Result (how your actions helped solve the specific problem and how that solution helped the organization as a whole)

Or they will give you a hypothetical situation and ask how you would handle it.

In that case, the important thing is to SHOW YOUR WORK. Talk them through how/why you came to that answer so they get a sense of how you tackle problems more generally.

All of the questions will be pertinent to the kinds of tasks you would be expected to handle in this position, and to the values of the company as a whole. Again, do your homework and think about relevant work you’ve done in the past so that these questions don’t throw you off your guard. I recommend actually writing out narratives in the STAR format ahead of time.

Sometimes you get lucky, and they ask a question you’ve already prepared a well-thought-out answer for, but even if not, the practice will help you improvise on the spot.

Step Six: The on-site interview

If you’ve made it this far, they think you are capable of doing the job in question. Now they are trying to establish three things:

Are you the best fit, personality-wise, for this particular team/person? How do you perform under pressure? What are your limitations? In other words, what are the outer levels of your knowledge and skill set?

Expect that there will be some hard-hitting questions in this round. But recognize also that all you reallly need to do is to accurately represent yourself and your skill set. Showing your limitations won’t necessarily disqualify you; you don’t know what their expectations are, nor where your competition falls on the spectrum. And if this isn’t a job you can do well, then this isn’t a job you’re going to want in any case.

By the same token, if these folks don’t adore your personality just as it is, then these are not the folks you want to spend every day with for the foreseeable future. Don’t put on an act. Just be the you that you know you can happily, sustainably be. The one YOU like, and who the kind of person you like would like.

Here’s a little mental trick I use for auditions and in-person interviews: pretend you already have the job. Imagine you’ve been told by someone on the inside that you are a shoe-in and this is just a formality they have to go through to make HR happy. So really, this is just an opportunity for you to meet and greet your new co-workers and to show off a bit of why they’re so glad they hired you.

Works like a charm.

Step Seven: Adjust

Listen to feedback. It can be hard to accept even the best advice when you’re failing at something. It can feel like they’re kicking you when you’re down. But believe me, any and all feedback you get from friends and potential employers is worth its weight in gold. Wherever appropriate, ask. Then bite your tongue, swallow your pride, do whatever you need to do to make yourself shut up and take it in. That one change may mean the difference between success and failure the next time around.

And remember to pay attention to non-verbal feedback as well. That look on the interviewer’s face when you gave that one answer you weren’t so sure about?

Yeah. The interviewer wasn’t so sure about it, either. Fix it.

Listen to your own feedback, too. Go with your gut and change what doesn’t feel like it’s working. Make a list each week of 3 things that went well and 3 things to improve on. And improve on them.


Step Eight: Fight for it

If you aren’t advocating for yourself, don’t expect anyone else to.

At my final interview for the EA job at PlayFab, I knew it was down to me and one other gal. I also knew that she was vastly more qualified for this position than I was. She had been an Executive Assistant for 20 years, and was currently working under one of the big wig VPs at Amazon, which could mean a major strategic advantage for her new boss. She would require little to no training, whereas I was starting from essentially ground zero. It would have been easy enough to simply tell myself that she was a better choice for him and give up on the idea of getting the job.

Instead, I dug deep and came up with genuine and compelling reasons why I was a better fit despite my relative lack of experience. I explained in painstaking detail how my unique skill set was an ideal match. I emphasized the importance of chemistry and a compatible personality in a working relationship, particularly given how much time we would be spending together. I reminded him that experience doesn’t always translate into competence, and that he would have to un-train all the habits she had accrued that he wasn’t so fond of, whereas I was a blank slate, ready to be molded into his ideal EA.

In short, I sold him on the idea of hiring me.

And that, my friends, is what you will need to do if you want a job worth fighting for. Learn what you bring to the table, and TELL THEM. Loudly, clearly, shamelessly, and repeatedly.

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