How to Enjoy Your Job Hunt

Use informational interviews to cut through the BS to the job you WISH existed.

Let’s talk about why your job search is killing your soul.

First of all, it’s not your fault. It’s not because you are in some way lacking, or value-less. Someone out there wants exactly you.

The problem is that our current system is built in a way that makes it an exhausting, demoralizing slog for you and your dream employer to find each other.

I blame job postings. And here’s why…

Put yourself in the shoes of a business owner or manager:

You want to hire someone to work for your company. You need them to have X, Y and Z skills/experience. What’s step one? If you’re like most people, you begin from within your company and your network. You ask around, in your company, your family and your friend groups, “Does anyone know someone who would be great for this role?”

If that doesn’t work, you branch out a little to networks with more tenuous connection to you. BNI groups, Chambers, facebook groups… stuff like that.

If THAT doesn’t work… THEN you create a job posting. You list X,Y, Z skills – and also A, B, C, skills while you’re at it….

AND THEN you get inundated with hundreds of faceless resumes, none meet your crazy requirements perfectly (because who could) – and you’re now facing a giant pile of faceless emails and hours of work trying to find some solid candidates.

Now let’s jump back to you, the potential employee who just tailored a cover letter and resume to tell the story of why you’re perfect for this job. What are the chances that the hiring manager is even going see your resume? Let alone recognize the care you’ve put into it?

BUT WAIT – there’s a better way. And when I say it, it’s going to seem so obvious.

Get in front of them earlier in the search. Be the person someone thinks of when they’re asked if they know someone.


Let me introduce you to my super power – the informational interview.

What if this week, instead of putting 10 hours into researching companies, tailoring resumes and crafting cover letters, you put the same amount of time into having coffee with awesome people.

Yeah, it sounds pretty great to me too.

Step 1.

To begin, make a list. Start with anyone you know who is sort of in your field, or area of interest. Include people who inspire the crap out of you. People who are well connected in your community or who you’d just like to spend an hour talking to.

Step 2.

Then send them an email along these lines (tailor the tone so that it’s appropriate to your audience, of course):

Hey _,
I really admire _ about you! Here’s a sentence about me. I’d love to find out more about what you do. I’m also curious about (insert a specific question or two here). If you’d be open to grabbing a cup of coffee, I’d love to take you out. Let me know some times that might work for you and I’ll set it up!
I look forward to hearing from you/talking in person.
– ME

Do not ask to pick their brain – it’s a red flag for people, and a vague request that requires more cognitive energy than being asked a specific question about their role or day.

Then book those coffee dates. Send email confirmations, share information so that you can find each other – you know the deal.

Step 3.

Before you step into that coffee shop, get yourself into the right mindset. This isn’t a job interview, you don’t need to prove anything, you don’t need to put on a front. Just be your amazing and valuable self, and know in your bones that the right gig is heading your way as fast as it can. Your job is just to make sure you’re findable.

Then step into that conversation with as much genuine curiosity and enthusiasm as possible. If you need some help here are some questions I lean on when in doubt (What’s your favorite moment in your work day? What is your day to day experience like? What is the most challenging aspect of your work? What inspired you to get into this field/role/company? What would you do if you had 20 more work hours a week? Where are you/your company heading in the next 5 years?)

There’s a certain point near the end of this chat where either your guest will ask you how they can help you, or it’s your chance to bring that up (feel it out, you’ll know when the time is right). Depending on the conversation you can ask things like

“Well, I love everything you’ve said about your work, is there any chance you’re hiring for something I might be able to help with?” or

“You mentioned that your company has _ need, that happens to be the kind of problem I love to solve. Would someone at your office be interested in talking about some contract work?” or even

“Well it’s too bad you’re not hiring, but now that you know a little more about me, who might you know that I should talk with next?”

Ending any good conversation by asking for more conversations is a great way to keep the ball rolling, and keep meeting new, more interesting people.

The worst thing that can happen is you don’t click with this person, and then you’ve only wasted an hour or so and the cost of coffee.

Step 4.

Send a thank you note, card or email. It means a lot. Maybe even follow up with a book or article they might be interested in.

Here are some of the “but’s” I hear most often.

But I don’t know anyone!

First of all, bologna, you know someone. Whether you went to school with them, they’re an old teacher, or they’re your Aunt’s ex-boyfriend – you know someone interesting and worth talking to. But let’s pretend, for the sake of argument, that you don’t… Take a different approach. Start by finding your dream companies, then look for the position you would love to do there (or want to know more about). Then try to find someone at that company who currently works at that level or one or two notches above – ideally they’ve been at the company 3-5 years – long enough to know the ropes and have connections, but new enough to still be flattered that someone wants to talk with them. If their email isn’t listed on their company’s site, shake the social media tree. Send them LinkedIn messages, tweets, Facebook messages – whatever platform they appear to be most active in.

If you craft a message with the right combination of flattery and genuine interest, you’ll get a response 9 times out of 10.

But I’m an introvert!

Think of a way you could reach out to people and still feel safe. Video conferences are great, or phone calls. You can wear your pajamas, drink tea and snuggle your dog. If you really struggle (and I’m talking diagnosed social anxiety issues level of struggle), try just corresponding via email.

But not in my field!

There are some fields where this can be a lot more difficult – specifically fields where people get a lot of random emails asking for some of their time. My challenge to you is – how can you approach these people as a breath of fresh air? Not as another person taking something from them. How can you remain resilient in the face of a higher-than-normal level of rejection?

They didn’t answer… now what?

Only a no is a no. If they don’t answer, maybe they were just too busy that day. Your email crossed their desk at the wrong moment. You’re not going to bother them if you ask again. Keep trying. They will either remember your persistence with admiration or not notice it at all. No one will hold it against you.

So I hereby give you permission to get off the job post sites, and instead have a lot of great coffee dates. Let me know how it goes! If you have any questions or comments, or tweaks that have really worked for you – share them here!