The 4-Box Job Searching Grid

So you want a new job? Great. Hold your nose and start applying, right?

No. Absolutely not. Unless you’re looking for the clearest path to resume purgatory and the most likely option to put yourself back on the job market again in 18 months.

A job search is a strategy game of chess that you must play accordingly if you want to win. This doesn’t mean only looking for companies that will hire you, but looking deep within and asking yourself, “What is it that I want now?” And perhaps more important, “What is it that I don’t want?”

To help me stay organized, the last time I approached my personal job search, I made this handy grid to help me stay on track:

How to use the grid

Look at the grid in two ways. The top two boxes relate to your actual job description and the work you as a person will be doing.

The bottom relates to the company itself — this is the squishy stuff like the culture and the team and your manager and how much they’ll pay you.

It’s important to isolate these things when considering a job so that you have a better understanding of what you want and why.

Digging into job stuff

Job titles mean nothing. Let’s get this out of the way right off the bat. So before you even consider falling into keyword hell on a job search on a website like Indeed or LinkedIn, it’s important for you to break your current job apart into its component parts. What do you like? And what don’t you like?

Start your grid with these two questions:

• What things do I like doing the most (and what to keep doing / do more of)?
• What things I dislike doing the most (and want to stop / avoid doing)?

Here’s what this looked like for me in 2015, the last time I started sniffing around for my next thing:

Each of these gives you a clue as to how you might consider approaching your next job search. At the time I approached this search, my title was “Customer Happiness Marketing Manager.” Prior to that point, I had roles in sales, marketing, content creation, and consulting in my career. I worked alongside sales, marketing, and product teams. Which meant to me that the scope of my possibilities was a lot.

After making this list, I knew I wanted to lean away from certain things (like Digital Marketing or straight Sales / Account Management Jobs) and more toward other things (skewing heavily on the external connections and partnerships piece).

Jobs I looked at (and I looked at a lot of jobs) included titles like this:

• Business Development Manager
• Product Marketing Manager
• Strategist
• Partnerships Manager
• Program Manager
• External Affairs
• Communication Specialist
• Community Development
• Engagement Manager

I point this out only to show that job titles mean nothing. Every organization has a different name for the thing you might want to do.

Unless you’re really looking at the pieces of the work that you want to be doing, it’s very likely that you won’t be able to find the thing that matches your skillsets and your needs.

Demystifying company stuff

Once you’ve figured out what you like and don’t like about your current job (and what roles you’re looking for), you can start to think about companies that might lead you to jobs like that.

This is often an even harder half of the grid to complete. You need to be honest with yourself about what you want.

Here’s a short list of things that might be important to you in a culture, company, or job:

• Smart team
• Good manager
• Big paycheck
• Remote / flexible schedule
• Opportunities for advancement
• Friends in workplace
• Close to home (short commute)
• Management potential
• Big brand name
• Going through important growth stage with a business
• Has figured out product/market fit
• Still figuring out product/market fit
• Raised a ton of VC money

It will be hard to narrow it down to only three things. But it’s really important to do so. In fact, when I look at all of the elements that made up my job search process in 2015, this box was the most difficult for me to fill in my grid. I started to get a little dejected that I wouldn’t be able to find all three of my priorities in one place. But having articulated them all clearly upfront made it so much easier for me to recognize the right thing when I did come along.

Equally important however are your deal-breakers. These might be things you experienced in a previous job that you want to avoid again — or they may just be elements of workplace environments where you know you don’t succeed as much. But it’s so important to articulate these deal-breakers before you go into an interview process. Because these deal-breakers will help you figure out what questions to ask in the, “What questions do you have for us?” section of your job interview. That’s your time to put your dream job to the test and see if it passes.

There are a million other things that might make you interested (or disinterested in a company), and it’s important to be honest with yourself about why you want that and how you will flag them in the interview process.

For reference, here’s approximately what my list looked like back in 2015:

And by the way, just like job titles have no standardization, neither do companies. Back in 2015, I was looking at everything from enterprise tech and startups to political campaigns, consulting agencies, and yes, even venture capital.

Bringing it all together

It’s likely that going through this exercise will not be fun for you. But just think about how much more fun it’ll be to have a job you really enjoy. The upfront effort is worth it.

After I went through this thought process in 2015, I made a list of people who might be able to point me in the right direction of one or more of these areas. I was targeting people who I felt had some analogous characteristic or quality to one of my own workplace strengths.

I literally titled the list, “Smart People I Know.” I had about 20 people on it. And then I started emailing them one by one to invite them for coffee.

To be clear, my list was not titled, “Smart People I Know (Who are Currently Hiring).” In fact, many of them were not in a position to hire anybody at all. But before I honed in on the specific job, I wanted to figure out what company, industry, or general role might make the most sense for me.

The next period of time was a grueling process of crossing things off the list. This is actually the least fun part of the whole process. But you have to remember that saying “no” to something is just as important a decision as saying “yes” to something else.

Maybe it won’t take you as long as it took me, but suffice it to say, this took me a really long time. At some point throughout it all, in the fall of 2015, I realized I had crossed off just about everyone on my list and had only one thing remaining. I was pretty despairing about having crossed off basically everything else as a viable option and felt a little bit crazy about throwing all of my eggs in one basket… but guess where I ended up working?

Whether you’re just starting out or in the midst of a job search, maybe this grid approach will help you like it helped me find a job I really love. I’d love to hear how it goes.