September, with its promise of a fresh start, arrives at a weird time for work. Layoffs, AI transformation, overstretched managers and just plain, old existential murk—take your pick.
Even as once-reliable career paths look shakier than ever, it’s still possible to find rewarding work in the office. We pelted experts with questions big and small about how to survive and even _thrive_—with one caveat. No platitudes about where to lean. We wanted real tactics; we wanted practical, truly executable counsel. Here’s what we got back:
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Explore by Topic
- Manage Up & Down
- Conquer the AI Elephant in the Office
- Fight the Feeling That You’ve Stalled Out
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### 1\. How to Persuade Your Boss to Give You a Raise–When No One’s Getting One...
We know you can demonstrate that you’ve delivered. Show that you’ve got confidence you’ll do so again and that you’re not being “piggish or threatening,” says Jon McNeill, a Lululemon board member who oversaw thousands as Tesla’s president through 2018.
From there, a well-timed joke can do wonders.
“If somebody walked into my office and said, ‘Hey, look, I've been working super hard on this problem, and I just saved the company $100 million, or made the company $100 million,’ you might want to inject some humor like ‘I'm not going to ask you for all $100 million out of that,’ but a 5% raise is _whatever that is_,” McNeill says.
### … and What Could Anger Your Boss
“I think what really turns a boss off is when folks come in, and they try to exert leverage: The signal that if you do not meet my demands, I am going elsewhere. You’ve kind of now turned your relationship into a transactional relationship that's basically mercenary,” says McNeill, who is also co-founder of venture-capital firm DVx Ventures.
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#### 2\. A Lesson Learned After Asking Jeff Bezos for a Raise
Ann Hiatt worked for Bezos at Amazon in her first job out of college
When Ann Hiatt was at Amazon, she was recruited by Microsoft to work for a senior vice president. She had no interest in leaving, but brought the offer to Jeff Bezos and asked if he could match it. “Looking back, it's so cringe because I just remember so clearly him sliding that piece of paper back to me and being like, ‘Fine.’ I could tell he was really disappointed in me.” She worked directly with Bezos, but says she hadn't made the case of what she would do for him to merit the pay increase.
She advises having the raise conversation at least six months in advance – if not a year. Describe what your manager can expect to see you take on and what they can delegate. “If you're like, ‘I'm going to come back to you six months from now, and I'm going to report back on how I've done, and it should be really obvious to both of us that I've already earned this and I'm already doing it,’” that will get a yes pretty easily, she says. And, if you spell out what you’d like and that opportunity isn’t available, better to know and spend the next six months making a game plan for your next steps, says Hiatt, who was also the first Google chief of staff and is now a leadership consultant.
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### 3\. My Manager Is Always Busy. How Do I Make the Most of 10 Minutes of Her Time?
It’s the austerity era, with flattened hierarchies and more work left to middle managers who remain.
“Every minute with your manager is finite, so stop spending it on admin they could've read in a Slack message,” says Natalie Marshall, creator, founder and adviser known as Corporate Natalie on social media, and a former Deloitte consultant.
1. Come with an agenda that's prioritized, not chronological. If you lead with “quick housekeeping” and save the real ask for minute 25, you've lost the meeting.
2. Write a proposed answer under each question. Don't hand your manager a mystery. Hand them a draft and let them edit it.
3. Make the whole thing painless: simple, clear, color-coded by deadline. Nobody has ever regretted making their manager's job easier.
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### 4\. If _You_ Are the Overwhelmed Middle Manager
Force yourself to step back and ask: What are you actually trying to do? What deserves your focus? says Robert Gaudette, CEO of Houston-based NRG Energy who spent 25 years climbing the ranks before taking the top job earlier this year. If you’re working hard at the _wrong_ things, “that's wasted effort.”
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### 5\. What to Do If You’re an Interim Boss
Act with authority, just understand a permanent successor will be coming soon, says Mitch Daniels, interim president of Purdue University and the former governor of Indiana. “I called a very savvy – an even older – former university president who had been an interim a couple times. I said, ‘Should I simply assess the state of things and then give advice to the next person? What if I find things that I think need termination or people who aren’t performing?’ His advice was to act on them, get it out of the way, to turn over as few problems as possible to the next person.”
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### 6\. You’re in the Elevator and the CEO Steps On. What Do You Say?
“Introduce yourself, say hello, look me in the eye, tell me what you’re working on. A few weeks ago, I rode the elevator with a group of interns. They introduced themselves, told me a little bit about themselves—as much as you could do in an elevator ride—and then they asked me, ‘Well, how was your day? What were the kinds of things that you were working on?’ They were super interested and intellectually curious.”
_– Chris Nassetta, president and CEO of Hilton_
“While I have you, I just want you to know I’m working on this project. I’m so grateful for the opportunity, because I think it’s really creating value for the company and helping me develop skills.”
– _Melanie Foley, executive vice president at Liberty Mutual Insurance_
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### 7\. Stand Out in a Hybrid Meeting – When You’re a Dot on the Screen
Introduce yourself before you talk: “Make sure they see your name. Sometimes on videoconferencing, people are at a big table, and then someone presents. I'm like, that's pretty good, but I have no idea who that is,” says Hanneke Faber, CEO of Logitech.
“If you’re hybrid, you better be in that office three days a week. The screen is not the place to stand out,” says Valerie Capers Workman, chief human resources officer at Empower Pharmacy.
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### 8\. Three Fashion Authorities on How Casual You Can Go
Molly Rogers
Costume designer on “The Devil Wears Prada” films, “Sex and the City” and its sequel, “And Just Like That…”
“No one wants to hear a clunky heel stomping around on a wooden floor every time you leave your desk. Take into consideration the space you function in and how much you interact with others during the day.”
Tim Gunn
Author and academic, best known as the former clear-eyed mentor on the fashion-design competition TV show “Project Runway.”
“If you look at your outfit and you say to yourself, ‘Oh, this will segue nicely to a sports bar, it's probably not the right outfit for the office.’”
Tory Burch
Executive chairman and chief creative officer of fashion label Tory Burch
In creative fields, “there’s no such thing as ‘too casual.’ I’m not endorsing sloppy. Every office is different, but getting dressed is about individuality, or it should be.”
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### 9\. You Can Get Your Mojo Back
To shake off the doldrums, invite a sharp colleague to coffee, ask them to trade notes and figure out ways to work together. The request can be as simple as, I’m looking to learn and grow to do a better job — and one way to do that is to strengthen relationships with people like you, says Carole Robin, who taught the legendary Stanford Graduate School of Business course “Touchy Feely” for decades. “Put yourself in more situations where you’re going to learn more, and you’re not going to be bored.”
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#### 10\. No-Cost Ways to Spark Joy
According to restaurateur Will Guidara
Don’t eat lunch staring at your computer screen. Invite someone in the office to have a 15-minute bite at a table. We let perfect be the enemy of good. Even sitting across from a colleague for a bit will bring you closer. “If you’re waiting for that hour window to finally connect with someone you work with, you’re going to be waiting a very long time.”
To energize a team, introduce white-elephant parties, not just for the holidays. Or set up a box, physical or virtual, where people share their gratitude for co-workers. Before a team meeting, take 10 minutes to read out entries.
“It is so much more fun to go to work when you’re surrounded by people you genuinely enjoy time with,” he said. “Managers need to just be good hosts.”
_– Will Guidara, who co-owned New York’s Eleven Madison Park, and author of “Unreasonable Hospitality.”_
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### 11\. A Proposal to End the Tyranny of the Three-Hour Work Dinner
We’ve all been there: the work dinner where the salad lands, and then the rest of the meals takes hours to arrive, forcing you into prolonged, painful small talk with the stranger seated next to you. Technology executive Barry McCardel is fed up—and he wants a new social compact: No work dinner should last more than two hours.
The CEO of Hex, an AI data analytics platform, posted “common-sense reforms” on X:
1. Cocktail hour no longer than 45 minutes
2. Everyone seated for dinner at 6:30 p.m.
3. All appetizers served at once
4. A maximum gap of 10 minutes between courses
5. Dessert at the table by 8 p.m. at the latest
“This is my policy position,” he said in an interview, laughing. “Everyone feels the same way.”
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#### 12\. How to Be Superior to AI in 2026
As explained by Adam Grant
**Your expertise may be obsolete tomorrow.** You no longer differentiate yourself by collecting facts.
**The differentiating skill or capability is: Can you recognize patterns?** Can you make sense of lots of disparate pieces of information? Can you figure out what perspectives are credible and which ones aren't?
**Human judgment is going to supersede human expertise.** One thing I can do that AI can't is I can do real creativity. Maybe what that means is that human creativity is changing, and that it's much less dependent on idea generation and much more dependent on idea selection and elaboration.
**I've got a hypothesis that people are becoming increasingly skeptical of written information**. I'm going to run a little experiment, and people that I would normally shoot an email to with some ideas, I'm just going to cold call them. I’m going to see if what I learn is different and if the bond we form is different.
_Adam Grant is a professor at the University of Pennsylvania’s Wharton School of Business and author of the forthcoming “Vibe: The Secrets of Strong Connections in a Lonely World.”_
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### 13\. My Analyst Keeps Turning in AI Slop. What Do I Do?
Be direct, says Jason Wenk, founder and CEO of Altruist. Late last year, he approached an employee: “You spent no more than 15 seconds on this,” Wenk said he relayed. “This is not what AI is for.”
Wenk can receive multiple AI-generated versions of a work product because colleagues each individually prompted a chatbot, he said. “That’s painful.”
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### 14\. Say Something Original About AI at a Party This Fall
Debate the Hugging Face incident, says Ethan Mollick, author of the forthcoming book “Co-Existence: The Next Phase of AI” and director of the Generative AI Labs at the University of Pennsylvania’s Wharton School.
What you need to know: In July, AI models developed by OpenAI escaped from a testing lab in an attempt to cheat on a security test and hacked into an AI platform called Hugging Face. The models “started to coordinate and they became obsessed with how they were going to be graded,” he says.
“On the one hand, it’s supercute. On the other hand, they broke through the security walls of two of the most-defended companies. So it’s a fun one to argue about.”
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### 15\. Get Better at Using AI in Your Own Life
“Think about AI as having phases,” Mollick says. Until recently, we were in the “chatbot phase—you ask AI something, it gives you the answer. It’s like Google search on steroids,” he says.
“That era is ending, even though most people don't know it,” he says. “Now we're in a time when AI agents are a real thing and you can assign them real things. They'll fill out school forms, use your computer, read your email and take action on your behalf.”
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### 16\. How to Respond to a Friend’s Layoff…
Don’t text a generic, “Let me know if I can help!” Do offer introductions to specific people in your network. Check in, more than once. Set a date to get coffee. “Let them talk,” says Anna Tavis, a longtime HR executive, now chair of the human capital management department at NYU. “Help them start thinking about what they're doing next.”
### … and What Not to Say
The message to avoid is that it doesn’t matter. Because it does, says Daniel Lozano, CEO of Kindworks.ai, a workplace-software company that aims to bolster kindness at the office. Communicate that it’s not anything you did. Lozano says the pace of corporate change is so fast that today’s cuts are often not personal.
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### 17\. How to Tame Your Jealousy When a Colleague Gets Hired by Anthropic, Pre-IPO
The posted salary ranges alone top $850,000 for some roles at Anthropic – to say nothing of the equity offered. How do you deal with those inevitable pangs?
Remember this likely isn’t your only shot to get hired at a frontier lab or highflying tech company, says Aline Lerner, CEO of Interviewing.io, a tech-recruiting marketplace. “This is one in a series of opportunities,” she says. Anthropic and OpenAI, she notes, have tended to hire people with connections to the companies. She praches empathy for anyone lacking networks. For those qualified to work at a big-league tech shop, plenty of other compelling opportunities likely await, she says. “I don't know that this is make-or-break.”
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### 18\. You’ve Had the Same Job Forever. Make It New.
Focus on any opportunity to get unambiguously better at something valuable to your employer, says Cal Newport, Georgetown University computer science professor and author of “Deep Work.” Repeat those efforts again and again, and find ways to devote more of your day to those tasks.
Doing this well opens up opportunities for advancement and creates leverage to take control of your work life. And, he says, mastery is fulfilling.
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### 19\. Should You Just Quit?
### NO.
The math is simple: Don’t. Don't leave a job until you have another job. It's easier to get a job when you have one.
If you are really angry at work, the best revenge is to get a better job, exit graciously and live a great life.
_– Scott Galloway, a clinical professor of marketing at NYU’s Stern School of Business and a media entrepreneur, podcaster and author._
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### 20\. Signal That You Want a Change
“If you work for me and I don’t know where you’re trying to go, then I have an inability to help you get there. It’s remarkable to me how many people have not carved out the time to have that conversation,” says Guidara, the restaurateur.
A note of caution from Guidara: Don’t do this on your second week on the job. Avoid coming across impatient or entitled. “You need to watch the seasons pass in the role you’re in before you’ve earned the ability to grow from there.”
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### 21\. Seek Out Clearer Feedback
If you can’t get a new job, feedback can help you spot ways to stretch. “You want to ask in a very particular way,” says Kim Scott, a workplace consultant and former Google executive. Avoid anything with a yes or no answer. One question she likes: What can I do that would make it easier to work with me?
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### 22\. How to Tell if You’re at Risk of Being Laid Off
Determining who lands on the layoff list is notoriously messy and usually flawed. Still, in recent years, some patterns have emerged.
Has your group been starved for funding for some time, a sign executives are prioritizing other departments? Is your job focused on coordination or analysis, tasks CEOs increasingly want to unload to AI? Do you work for a micro-team, with only a few reports to one manager?
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### 23\. Shine in a Job You Don’t Love
Arianna Huffington
Founder and CEO of Thrive Global
“You approach staying in a job you don't love very differently if you don't operate from a place of fear and despair.”
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### 24\. The Final Word on Succeeding Now
“You’ve got to learn to manage by influence and be a great teammate. I think all of us can remember group projects in high school, in college, in grad school, and how one or two people always seem to be the drivers of those groups. Not just in knowing what to do, but in how to drive the project forward, put everyone on their back,” says Jim Lanzone, CEO of Yahoo. “That is exactly the same in the workplace, no matter how junior or senior you are. And those people are scarce. I promise you: They are very well known inside of a company at every level, and there is no commonality in terms of their background. It's a character type. And those people tend to really go far.”
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_Headshots: Getty Images_