What’s something that screams “red flag” to you in a job interview? For me a big one is when they say you’ll wear many hats in the role.

I’m interviewing at a Series B startup, and the hiring manager keeps emphasizing how they wear many hats. In my experience, that’s usually code for we have no processes and you’ll be doing the work of three people. The equity package is tempting, but I don’t want to jump from the frying pan of public into the fire of a disorganized tech firm. What are the specific red flag questions I should ask during the next interview to see if their finance department is a disaster?

What's the biggest hiring red flag for you? I have a few but tbh, the biggest one for me is when a candidate trash-talks their previous company. I'm all for honesty, and even just understanding how we can be better for this candidate and give them a better working experience... but shouldn't there be some grace and tact in the way that it's talked about? I think yes. It really puts me off because one day the script could change and be about us.

I just saw a job post looking for “rockstars who live and breathe code” and… no thank you. I’ve done the hustle culture thing before and all it got me was burnout and resentment. These days, I want work-life balance, not 12-hour days disguised as “passion.” How do you spot red flags like this early enough to avoid wasting time on companies that still glorify overwork? What language makes you instantly pass on a posting?

Planning to celebrate birth of my first child with a new Rolex. I’m looking at either the Bruce Wayne GMT or the Pistachio OP 41. AD seems to think it’s possible to get either. Which do I go for??? I currently have a white DJ41 smooth oyster and an omega SMP black. Bruce Wayne seems like obvious choice for most but I like that the pistachio almost feels like a a soft pastel color similar to other “baby” colors

Hi, I’ve been given an opportunity to move from Red Hat to Nvidia. The total compensation package — including base salary, RSUs, and bonuses — would increase by approximately 50%. However, the role is expected to come with significantly longer hours and higher stress levels. I'm trying to evaluate whether the trade-off is truly worth it.

“Red flag” managers can be so difficult to work with… please protect yourself (or save this post in case for the future) ☺️🫶 Several asked me these Qs during my weekly “Sunday Chat Q&As” on @kellycareermode IG — so here are a few major tips! Have a great rest of week & long July 4th weekend for those celebrating!

Is there a way to decline to run redlines for the other side without looking like a jerk in front of clients? I like to be helpful and always send against the prior draft but they’re asking for 3-4 more redlines against earlier drafts (different each time) with each turn of the docs and it’s a waste of my time.

What’s the biggest red flag to look out for in an interview? To me, it’s when they start talking about “the opportunity to wear many hats in this role.” That’s code for “this job really should be split but we only have the budget for one person to do it all.”

Have you ever been interviewing with a research director (or someone else in leadership) and everything about them set off red flags in your mind? I had this type of interview today and I wanted to run, however, I've been without a job for three months. So, red flags or not, I think I'm going to take this job. What would you do?