You have a “great” job offer… now what?

Interviewing for a new job can feel a lot like dating – and these days, with so many more opportunities out there than usual, you can be a little pickier about which way you swipe.

And much like someone might on a dating app, prospective employers are always showing you the best versions of themselves during the interview process: competitive salaries, company equity, generous benefits — whatever they can trot out for their mating dance. That’s all important stuff, but it’s also only part of the story. At the end of the day, a company is presenting a carefully curated image. 

So how can you get a read on what it’s like to actually work somewhere, day in and day out? How can you decide if you want to commit to a company for the next few years of your life? Who cares if a match makes great risotto if they’re going to have a screaming argument with your Dad every Thanksgiving about NAFTA? 

If you’re willing to do a little detective work and ask yourself some thoughtful questions, you can make sure a new team is just the right place for you — and avoid making a miserable mistake.

1. Reflect on your interview process.

Was your main contact easy to work with throughout the interview process? That doesn’t mean that they never asked tough questions, but it matters how they treated you as a prospect. Did they keep you up to speed about next steps? Are the team members you met people you’d actually want to work with? Did everyone show respect for your time?

It’s like Maya Angelou said: “When someone shows you who they are, believe them the first time.” Don’t ignore obvious signals just because somebody’s got a pretty face. Or a great 401k match. Whatever.

2. Check out their feeds.

Okay, so a social media page is probably not the only place you should look if you’re in search of authenticity. But that doesn’t mean it’s not valuable to look through social media content!  Sometimes you can really get a glimpse into a company’s character and glean useful info about what the day-to-day experience is like there.

Channel your inner Insta stalker — and this time, you don’t have to worry about accidentally liking something from 2017.

The same is true for opinion pieces, blogs, Medium articles or LinkedIn articles; it can be incredibly helpful to peek into the minds of the leadership team and understand what they care about. There’s an abundance of this stuff from the COVID era especially; it’s so important for companies to show up for their employees as people during tough times, and it’s hard to think of a tougher time than a global pandemic. It’s worth looking back to see if they stuck to a people-first approach during some of the darkest days of the last year and a half.

3. Dig into the company’s core values.


Do their values align with yours? It might seem corny, but a lot of work goes into identifying and codifying those. Company values are a reflection of what the company cares about and create a roadmap for how employees can be successful. If they’re done right, they’ll influence every aspect of your day-to-day working experience.

For example, take this Roadie value: “Just go.” We define that as: “We know objects at rest stay at rest and objects in motion stay in motion. We choose to be in motion… even if it means a wrong turn.”

See? That actually does give you some insight into how we think about daily work; we value progress more than we fear mistakes. That might color your assessment of how much you’d like working with us. If you’re very nervous about breaking stuff, you might be happier somewhere else.

4. Reach out to current (or former) employees and ask smart questions.

Here’s somewhere you have an advantage with job hunting over dating; it’s not like you can reach out to exes to ask for a reference. But you absolutely can do that when it comes to shopping jobs.

Current or former employees can be a great resource and are generally pretty willing to give you honest feedback. Just poke around on LinkedIn and see if you can find someone you’re comfortable reaching out to. 

A couple caveats on this one: Be cognizant of how long someone’s been gone if you choose a former employee (the company may have changed a lot). And remember that experiences can differ greatly from team to team, so your mileage may vary. 

Just use those critical thinking skills you’ve got listed on your resume.

I have two offers and they both look pretty good. How do I choose between them?


First off, good for you! Ultimately, if they’re both competitive, your decision should come down to people. Did you connect with the folks you talked to more at one organization than another? Those instincts are worth trusting. It’s also a big factor in retention. I’ve heard this time and time again in engagement and exit interviews — people stay for the people.

“Clicking” with people matters. And that’s true whether it’s over a conference table or a glass of Pinot Noir.

Kayla Duperreault is Head of People at on-demand delivery provider Roadie. She leads efforts to help the company find, grow, engage and retain team members.