Hey everyone,
It’s that time of year. Companies have finalized their budgets for the second half of the year, new roles are popping up, and a fresh wave of talent is hitting the job market as summer winds down. Before you dive headfirst into updating your resume and practicing your interview answers, let’s talk about something more important: learning to spot the red flags. Because here’s the thing—the job search is a two-way street. You aren’t just trying to impress them; you are interviewing them just as thoroughly.
When a Passion Project Turns Into a Red Flag Parade
I learned this lesson the hard way.
A few years ago, I turned a personal passion for fitness into a part-time job as a group fitness coach at local independent gym I had been a member at for two years. I was so excited about the opportunity that I ignored every single warning sign.
I was so focused on being that star example and helping others achieve what I had during my own fitness transformation that I didn’t stop to ask the important questions:
- Why was there such a high turnover rate for coaches?
- Why was the path from internship to a paid offer so ambiguous?
- Why was there a complete lack of transparency around compensation?
- And the biggest red flag of all…why was I being asked to solo teach a week’s worth of classes unpaid as part of the “interview process”?
I was so thrilled by the idea of turning a passion into a side hustle that I let my excitement overpower my rationality. I ignored my gut, and it was a mistake. That high turnover, I later learned, was a classic symptom of a much larger issue, something to be keenly aware of especially in the startup world: instability at the top.
One of the biggest lessons I learned is this: if there is a history of unresolved conflict between founders, proceed with extreme caution. A few months before I joined, the founding partners dissolved their partnership.
While there are two sides to every story, a leadership split is a major indicator of instability. It often signals underlying issues in communication or conflict resolution. Furthermore, when one partner buys the other out, it can put immense financial stress on the business as capital is expended or debt is often leveraged to facilitate that transaction, impacting everything from budgets to team morale. Instability at the top always trickles down.
That situation taught me a crucial lesson, and it’s one that goes far beyond startups. Every job search requires you to look past the promises and spot the potential problems before they become your problems. To help you do just that, I’ve put together a checklist based on my own career wins and face-plants.
Your 10-Point Red Flag Detection System
Based on my own career wins and face-plants, here are the things you should be investigating before you even think about signing an offer letter.
1. 🗣️Talk to Current AND Former Employees.
This is non-negotiable. Current employees might sugarcoat things, but former employees have nothing to lose by telling you the truth. Early in my career, I took a job in D.C. that paid $25k more than my last one. I was thrilled. A 15-minute chat with a past employee would have revealed it was still below market rate for the area and the company was a side-hustle for the two founders.
2. 📉 Investigate the Company’s Financial Health.
A recruiter once gave me some of the best advice I’ve ever received: look at the number of open roles. Is it a sign of healthy growth or desperation? I learned this firsthand when my role was created to backfill two recent departures—a data point I overlooked. Just eight weeks after I started, the company announced it was laying off 30% of its employees. Always do your homework on a company’s hiring velocity versus its attrition rate.
3. 👻 Beware of ‘Ghost Jobs’.
These are fake job postings companies use to project growth or, more often, to gather free market data on compensation without committing to a hire. I watched this happen over six months as a “Director of Lifecycle” role morphed into a “Sr. Lifecycle Campaign Manager,” and finally into a generic “Braze Specialist.” Months after I first applied, contract recruiters were still reaching out about it.
If the job description and seniority keep changing, it means they don’t know what they want. Don’t waste your time helping them figure it out—you’ll just burn out while they burn bridges in a talent community that’s much smaller than they realize.
4. 🚪High Turnover is the Ultimate Red Flag.
This is the best barometer for company health. Period. While there isn’t one magic number, experts suggest that what’s considered “high” turnover depends heavily on the industry. The key is to investigate the context. If the role you’re applying for has been a revolving door, you need to understand exactly why. Use LinkedIn to check the average tenure for that role at the company versus its competitors. Don’t accept vague answers like “it wasn’t a good fit” in an interview—dig deeper.
5. 🪜 Look for Promotions (or Lack Thereof).
Are people growing within the company, or do they have to leave to get ahead? This isn’t just a nice-to-have; it’s a critical retention issue. According to LinkedIn data, employees stay 41% longer at companies with high rates of internal hiring compared to those with low rates. Before you even interview, scan the LinkedIn profiles of team members. Do you see a pattern of promotions, or does everyone seem stuck in the same role for years? A stagnant team means there’s a ceiling, and you’ll likely hit it too.
6. 🧐 Scrutinize the Leadership Team’s Diversity.
Take a hard look at the leadership page. If it’s a sea of the same faces, proceed with caution. A lack of diversity at the top isn’t just an indicator of a culture that may not value different perspectives; it’s also a potential sign of weaker business performance. According to a major study by McKinsey, companies with the most ethnic and cultural diversity on their executive teams were 36% more likely to outperform their less diverse peers on profitability. A homogenous leadership team is a significant red flag.
7. 🎠 Watch for Leadership Turnover.
If the C-suite is a revolving door and VPs are swapped out every 6-12 months, it signals deep instability. This isn’t just a feeling; it’s a major business risk that drains the company’s bottom line and disrupts its culture. According to Gallup, the cost of replacing a single leader can be as high as 200% of their annual salary. A company that is constantly spending money to replace its executives is a company that isn’t investing in its people, products, or your career growth. You can’t build anything meaningful on a foundation that’s constantly shifting.
8. ⭐ Watch How They Treat Customers.
How a company treats its customers is a direct window into its culture. Don’t just look at the star rating on Google or TrustPilot. Look for patterns in complaints and, more importantly, how the company responds to them. Defensive, robotic replies are a major red flag—a company that blames its customers will have no problem blaming its employees.
9. 🕵️ Use Your Backchannels.
Go where employees talk candidly. Use sites like Glassdoor for reviews and the anonymous network Blind for verified employee discussions. Dive into niche subreddits (like r/marketing) and professional LinkedIn Groups to see how current employees talk about their work and industry. Perform your due diligence to see the culture that exists behind the curated career page.
10. ☕ Ask for a Virtual Coffee.
Find someone at the company who isn’t on your interview panel and ask for 15 minutes of their time. The key is to be respectful and specific in your request—make it clear why you’re reaching out to them and what you’re hoping to learn. Most people are happy to share their experience, and it’s an invaluable way to get an unvarnished view of the culture. For a complete guide on how to approach these conversations effectively, this article offers excellent, practical tips.
11. Bonus: 😵💫 Turn it Up to 11 – The Endless Interview Gauntlet.
Of course, I couldn’t just stop at 10. As a lifelong overachiever, I have to give you this extra credit point, because it might be the second most important red flag outside of high turnover.
A lengthy interview process isn’t a sign of diligence; it’s a symptom of dysfunction and indecisive leadership. I once went through six rounds of interviews over six weeks for a single contract role. If a company can’t make a timely decision on a hire, imagine the bureaucracy you’ll face on the job. In stark contrast, the best roles I’ve landed, like my first “real full-time job” in marketing with Erni Hernandez Armstrong, came from decisive leaders with a clear need. The process was quick and respectful. As Erni wrote, “Hiring should be a path, not an obstacle course.“
A bad job can break you. I know because it happened to me, as I’ve written about before. Your career is too important to leave to chance. Trust your gut, do the research, and remember that you hold the power. You are the asset. Choose a company that deserves you.
See you next month, Seth
P.S. What’s the biggest red flag you’ve ever seen (or ignored) during a job search? Let’s talk about it in the comments.
On Transparency, Tools, and Trust
If you’ve ever worked with me, you know I’m an open book. The stories and lessons in this article are all mine—drawn from years of my own missteps and face-plants. To bring it all together, I used Google’s Gemini 2.5 Pro as a thought partner to help refine the structure and flow, ensuring my voice remained front and center. For the hero image, the concept and Photoshop work are mine; I used Adobe Firefly to extend the background (inspired by The Hitchhiker’s Guide to the Galaxy) and render the image of the two professionals. My philosophy is simple: Don’t just talk about AI—use it. You have to get your hands dirty to truly understand how it works 🤓.
And Finally, A Note on Em Dashes
Yes, I use em dashes—a lot. This isn’t a new habit. A brilliant copywriter taught me how to use them properly back in 2007, and I’ve been using them in my web and email work ever since. I knew what an em dash was long before it became a hot topic (got — anyone?). So to the em dash haters: bring it. This Aries always comes prepared for an argument with charts, facts, and data 😉.
