A guide to interviewing for a job in a world that's gone cray-cray
Gen X, you’ve survived two digital revolutions already. You’ve got this.
The CEO of Shopify just announced he’s not hiring anyone unless there’s proof AI can’t do the job. The stock jumped 33% on the news. So yes, it’s one of those unworkable ideas that sounds great to investors. But the trendline is real: Where CEOs once boasted about headcount, now they brag about who they’re getting rid of.
Which makes it a strange time to be looking for work, especially in marketing. The rules are shifting. Team structures keep morphing. In some places, the marketing function is being quietly hollowed out altogether.
For Gen X-ers, it’s the vibe that’s changed the most. With two or three decades of experience, you likely came up in a world where your work was big budget, visible and personal. The office was like hanging out with friends. Where you laughed, supported each other, maybe even met your life partner. Interviews were coffee chats. Great companies were collectors of talent. And good talent had options.
Today? It’s an employer’s market. Post-AI. Post-loyalty.
If it’s been a while since your last interview, prepare yourself for a process that is longer, stranger, and weirder. More rounds. More stakeholders. More “surprise final boss” moments. And yes, you’ll be asked to present a full strategic roadmap for a business you don’t work for yet.
And after all that, you may still get ghosted.
So we brought in help. A human.
Anna Papalia is a former Director of Talent Acquisition turned career coach turned unlikely TikTok oracle. Her book, Interviewology, has become gospel for execs navigating the messy middle of a career pivot. Her feed is equal parts truth and tough love. Three million followers and counting.
Anna doesn’t do hacks. She doesn’t believe in algorithms for human chemistry.
Her take is simple, sharp, and slightly uncomfortable: The biggest problem with interviewing isn’t the format. It’s that you haven’t looked in the mirror long enough to know who’s showing up.
We’re All Just Interviewing Ourselves
"A job interview,” Anna says, "is just a series of questions about you.” Not about the company. Not about their annual report. About you. The more you know yourself, the better you’ll do.
Simple. Not easy.
Anna starts by acknowledging that interviews are subjective. They’re not science. They’re not fair. Often, they’re not even logical.
That’s where people get thrown. We think interviews are about right answers. We’ve been trained to play to the room. To calibrate. To read what they want.
But there’s no perfect script. The only thing you can control? How well you know yourself. What you’re good at. What you’re still working on. And how you carry that in the room.
And if it doesn’t click? That might not be a reflection of your worth but a sign their culture wasn’t yours to begin with.
Which is hard to accept when you need the job. But essential to remember when your self-worth is at stake.
Your Style’s Showing and So Is Theirs
If you’ve ever walked out of an interview feeling like you blew it even though you were wildly qualified, you’re not alone. According to Anna, that disconnect often comes down to interview style. Not job title. Not experience. Just how people show up in the moment.
Drawing from her work with thousands of candidates and hiring managers, Anna developed a framework of four styles. They apply to both sides of the table, and they shape everything from tone to interpretation to who gets hired.
What follows is not exactly how it goes. To get the proper rundown down you'll need to pick up Anna's book Interviewology (also, get in touch if you want a promo code to try out some of her online tools here.) This version is what we got out of the session we did together:
Charmers want to be liked.
As interviewers, they keep it warm, breezy, and friendly, sometimes too friendly, leaving expectations unclear. As candidates, they bring energy and connection, but may skim the surface or dodge depth.
Challengers want to be respected.
As interviewers, they’re direct, even confrontational. As candidates, they’re bold and articulate, but risk sounding combative if not balanced.
Examiners want to get it right.
As interviewers, they stick to structure. Scorecards. No small talk. As candidates, they freeze on vague questions, prefer logic to stories, and sometimes leave their personality at the door.
Harmonisers want to adapt.
As interviewers, they’re gentle, culture-focused, and collaborative. As candidates, they’re thoughtful and humble but often undersell themselves, defaulting to “we” instead of “I.”
The goal isn’t to shapeshift. It’s to know your style and play it with awareness. Let’s say you’re a Harmoniser. Great. But you may need to practice taking up more space. If you’re a Charmer, you may need to tighten your story. And no matter your style, you need to own your impact.
"Knowing your style helps you stop pretending,” Anna says. “And start preparing.”
Stop Selling. Rehearse the Real You.
Most people prepare for interviews like they’re cramming for finals. They write perfect answers. Rehearse in their heads. Try to anticipate what the interviewer wants.
Then the interview starts. And something’s off. You can feel it in your throat. You’re selling.
Anna’s advice? Don’t script.
Say it. Out loud. Into your phone. Watch it back. Yes, it’ll feel cringey at first. But notice where you shrink. Where you hedge. The verbal ticks. The nonverbal ones. The moments where your voice doesn’t sound like someone who loves what they do.
Do that enough times, Anna says, and something strange happens—you stop selling and start sounding like you.
The Question Everyone Dreads: “What’s Your Biggest Weakness?”
First, can we all agree to retire “I’m a perfectionist”? It’s a meme. It’s a dodge. And it’s not helping. Anna’s take? Be honest. Stay professional. Show growth.
“I’m a Type A. I get things done. But I’ve had to learn patience, especially with different work styles. These days, I slow down, ask more, and push less. I still have that edge, but I’ve softened the corners.”
Or say you’re great at building consensus, but hesitant to lead the charge. You might say:
“My ability to create alignment is my strength. But I’ve learned that finding answers everyone likes isn’t the same as leading. I now check in with myself before major decisions: Am I agreeing because it’s right or just to keep the room happy?”
The same goes for failure stories. Don’t wrap it in spin. Just show what changed.
“I pushed through a campaign despite local team concerns. I thought I had the full picture—I didn’t. The results flopped, and it was on me. That moment changed how I lead cross-functional work. Now, I start by listening.”
Perspective, not perfection. That’s what they’re listening for. As Anna says, "Tell me how you became braver, wiser, stronger.”
For These Five Questions, There Are Right Answers
Anna’s the first to say most interview questions don’t have one right answer. But these five? They do. And they still manage to trip people up.
"How are you?” One candidate answered: "Well, I’m hungover and my dog just died, so…”
True story.
"Did you have any trouble finding us?" One guy replied: "Your directions were a mess. I almost turned around."
Also true.
The point isn’t to actually answer the question. They’re rituals. Ice-breakers. A handshake in sentence form. So treat them like it:
1. How are you? — “Great, thank you. How are you?”
2. Did you have trouble finding us? — “It was super easy, thank you.”
3. Are you actively interviewing? — “Yes, I’ve got a few options right now.”
4. Where do you see yourself in five years? — “Right here at this company, doing X, and continuing to grow”
5. Do you have any questions for us? — “Yes.” (Always. Always yes.)
These questions seem small. But they’re early tells. And they matter.
They’re Lucky to Have You
If there’s one thread that runs through everything Anna teaches, it’s this: Confidence doesn’t come from the perfect answer. It comes from knowing yourself.
Sure, if your career flourished in the early years of the millennium, the whole thing can feel surreal right now. You’ve led teams. Shaped brands. Navigated crises. Mentored talent. And now you’re sitting across from someone with a clipboard, asking how you handle conflict.
And there are biases. Age. Energy. Industry. Sometimes the interview doesn’t reward depth. It rewards what’s shiny. But as Anna says—and this is where her voice gets clear, almost protective: "They’re lucky to have you in that room."
And she means it.
You’ve lived through layoffs, dotcom crashes, reinventions, reorgs. You’ve raised kids. Buried parents. Managed people through pandemics and pivots. You’ve done work that outlasted platforms. You’ve seen two digital revolutions before this one.
"Take the risk of being rejected—or accepted—for who you are,” Anna says. "The reward is finding the job that fits.”
In a world tilting toward artificial everything, inevitably, the most valuable thing left will be those who know how to be most human.
Update: Shopify’s share price? Oh, yeah. It was back down a few days after writing this.
So no, you don’t need to be the person with the hot takes.
You need to be the person who keeps it real. Someone who knows how to build trust, navigate the tricky stuff, and come up with answers that last beyond today’s technology.
Let's rise together with every issue. ♡
Thanks for sharing!