Grab coffee with your potential boss

Vibe-check them before signing the contract

I had just wrapped up one of my first interviews, where I found myself in a room with four men who, the moment they realized the reporter sitting in front of them was a young woman, decided to dumb down their business model for me.

Was this just part of being a female reporter? How was I supposed to write an article based on watered-down, condescending quotes?

I trudged back into the newsroom defeated. My editor clocked it immediately.

“How did the interview go?” he asked.

“I don’t know if it’s me, but they sounded pretty patronizing,” I admitted.

He looked at me and said, “If they’re being dicks to you, they don’t get coverage. Do you want me to have a word with them? Or you’d rather I don’t get involved?”

I was surprised at his protective response. Maybe not every female reporter had to tolerate condescending men after all.

A good boss makes or breaks the workplace, no matter how good or bad the work or the company is. Your boss is your first line of defense against company bureaucracy, politics, and wellbeing initiatives. Unlimited paid time off means nothing if your manager never approves your requests. Reversely, your boss might also grant you time off and winkwinknudgenudge you to keep it off of the company’s HR system.

Whenever I am looking for a new job, I keep the manager factor an important part of my search. While companies assess whether I’m the right fit for them, I’m also evaluating whether they—and more specifically, my future boss—are the right fit for me.

At a bare minimum, I always meet my potential manager for coffee before signing a contract.

Some of my friends find this intimidating. “What if they don’t like you?”

“What if I don’t like them?” That, to me, is far more important.

This approach is not at all scalable, such as when mass-applying to internships in college. But I haven’t had much luck applying through the job portals (I prefer to third-door my way in), so I prefer to approach my job (and manager) searches much more slowly and deliberately.

So how do I vibe-check my future boss?

These are some of the things I’ve done to see if I will be compatible with my manager:

1. Talk to people I know who know this manager

If I know someone at the company I’m applying to, I reach out with two questions:

• Who is the hiring manager for this role? Knowing the name of my future boss allows me to personalize my cover letter and look them up.

• What are they like? If I trust the person, I trust their judgment. A close contact will be more candid than a total stranger.

When I applied to my second job, my former colleague Grace was already working there. She not only introduced me to the hiring manager but also vouched for me. It was a win-win. If I got hired and passed probation, she’d receive a referral bonus. She ended up buying me a nice lunch with that sweet referral money.

I have also walked away from roles. A content agency once approached me, and I happened to know someone who worked there. His advice: “Knowing you, you won’t like this place.” I still did my own research, but his warning was part of the factors I weighed before I ultimately passed on the job.

2. Reference check your future boss

I only started doing this for more recent roles, but it’s been helpful: Reference-check your boss the way they reference-check you.

I reach out to both current and former team members and ask:

• What’s their communication style?

• How strict are they with KPIs?

• Do they micromanage?

This is especially crucial when switching industries. When I moved from journalism to banking, I had no idea what to expect, no “industry gossip” to lean on, so I asked around. I met former classmates for lunch and had drinks with future teammates. Even my then-editor spoke highly of the manager at the bank I was eyeing. Everyone had good things to say, so I took the job.

3. Grab coffee with your future boss

If you do nothing else, do this. This is where you vibe check your future manager.

This meeting is a preview of your future one-on-one check-ins. It’s like speed dating for your professional life. Do they seem engaged? Do they communicate clearly? Do they respect your time?

When Grace introduced me to an editor for coffee, it was invaluable. We nerded out over newsletters and the evolving business models of journalism. It was clear we’d get along.

I’ve also met future managers over beer. Some prefer a more casual setting. As long as you’re comfortable, these informal conversations can tell you far more than a structured interview ever will. In fact, many future managers I met would then skip the “interview-in-the-office” step of the hiring process because they also found the casual chat to be sufficient.

But what if I don’t have connections?

Early in my career, I didn’t have a built-in network. Job hunting discreetly while employed can also be tricky. But the internet is a powerful place.

When I was interested in working for The Wall Street Journal, I didn’t have any direct contacts, so I asked around on LinkedIn. Eventually, a distant contact put me in touch with one of their editors. We met for coffee, and while it didn’t lead to a job, she shared tips for the hiring process.

A good boss is worth the effort

Thankfully, my diligence has paid off. I’ve never had a nightmare boss. Part luck, part careful vetting. And as a result, I never hated any of my jobs.

A great boss will have your back, push you to grow, and provide honest, constructive feedback. They really have a hand in shaping your career. Some of the many skills I learned from my managers over the years: sounding confident over the phone, making evidence-based arguments, and diffusing conflicts amicably.

So the next time you’re job hunting, remember: you’re not just looking for a job. You’re looking for the right person to work for.

Thank you to friends who gave this essay their casual coffee-chat pass:

Rik

,

Josh Ponelat

, and

clare chai

.

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Update log:

• 🚮 Decided to not proceed with the email sequence I wrote last week

  Nat Lee
  ’s note made me realized I hate being at the receiving end of email sequences.

• 📺 Caught up with Severance, all the way from the beginning. Wow. I get the hype. I’m now binging the official accompanying podcast to ride out the wait for the finale.

• 🕳️ Went down an overthinking rabbit hole for writing my book. Thankfully

  Camilo Moreno-Salamanca
  dragged me out of it real quick.

• 🦠 The Hwangwara household is down with a horrible stomach bug. Never knew these things were infectious. It’s the worst stomachache I’ve ever had.

• 📖 Listening to The Seven Husbands of Evelyn Hugo (25% completed).

• 📹 On my YouTube channel: The 2-Notebook System: Planner vs Journal

Book a call: Have a bite-sized creative project you want to start? Let’s figure out the systems to get that going. I promise to be your earliest fan - https://calendly.com/beckyisj/

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