Have you ever joined a company that you regretted on the first day of work?
Or perhaps the first day or first week was great, then the toxicity starts to flow in like a river.
Maybe you’d be scratching your head, wondering what you missed when interviewing with them and why you didn’t spot these red flags early on.
Many of us have been there, accepting job offers we shouldn’t have, despite the warning signs shown to us during the interview process.
Having worked with over 100 companies in my line of work as a headhunter, here are the top 6 red flags I’ve learned through working with horrible companies that I no longer work with. I hope this helps you identify real and good opportunities vs. fake and terrible ones.

1. No clear reasons for hiring!
Is this a new or replacement role? Why do you need to hire for this role, and what do you need this person to solve in the first 60-90 days?
If it is a replacement role, ask why the previous person left. The company may not be 100% truthful, so if you’re not convinced, work through your network and do due diligence on the company before joining.
If it’s a newly created role, ask why the role was created. What are the goals or problems that need to be solved in the first 60-90 days? This should give you enough intel on the importance of the role.
If the leader/hiring manager doesn’t know why they need to hire, then they will not know why they need to keep you when the company has a cost-cutting exercise.
Vague roles like Chief of Staff are often the first to go during downturns unless there is a succession plan for you. For Chief of Staff roles, find out what your career path within the organization is, along with the metrics you need to achieve to move on from that role to something with more autonomy and decision-making authority.
A job with no clear responsibilities is a job the company can easily do without.
2. Vague or unclear expectations.
Anyone who has interviewed with a good company knows what is expected of them. Vague or unclear expectations show that the company doesn’t know what they want or need. This is costly for candidates because you will be paying for their mistake.
Example: A hiring manager was given a headcount to expand his team. He wants more sales, so he uses the headcount to hire another sales executive. Let’s say the current team already finds that there are too many salespeople covering the same markets, and adding an additional headcount would mean more internal competitions.
Have you ever asked a company what your portfolio or market coverage would be, and they couldn’t answer? It’s highly likely that it’s a mess internally, and there could be infighting (some firms even encourage internal competition among sales reps).
3. Majority of the leadership team has no relevant experience to justify their role.
A candidate once told me he was looking for a new role because he was reporting to a manager who knew nothing about the function. How did that person get the role? He was a good friend of the founders.
This is the worst setup anyone can join because you will have to deal with office politics just to progress to a more senior position. Companies that don’t know how to structure their leadership teams are often poorly run and may not even exist in a few years.
4. No human resources department in the company or no local employment contract.
It’s common for startups not to have an HR department in the early days, but this comes with significant risks for candidates. Why? There is often a lack of governance, and the company may not adhere to local employment regulations, which could lead to legal trouble.
Structured companies are the preferred choice for many candidates because they have established rules and governance to follow. Even the CEO cannot simply fire employees at will; they must justify their decisions to HR or the board.
Now, imagine a startup where no one is enforcing rules on the founder. They can act however they want without facing consequences. How secure do you think working for such a company would be?
If you sign a remote contract with a company in another country, your local labor laws might not protect you if issues come up. You could lose rights related to pay, working hours, or termination. The laws that apply depend on where the employer is located, and resolving issues might be difficult due to different legal systems. It’s important to read the contract carefully and understand which laws apply, and consider seeking legal advice to ensure you’re protected.
5. Founders are anonymous, and you can’t find any information about them online.
For this type of company—avoid at all costs.
There’s a reason why they prefer to stay under the radar or have no media mentions—they don’t want to be traced!
The last thing you want is to join a company doing shady things and allow that to tarnish your professional reputation.
People don’t care how good you are; they only care who you are associated with, and they won’t be willing to take a chance on you.
6. Unwillingness to share financial information about the company.
If you’ve interviewed with a startup, they are either funded by the founders themselves or backed by venture capital.
If they are the latter, they should be able to tell you how long their runway is.
In business and startups, runway refers to the amount of time a company can operate before it runs out of cash, assuming no new revenue or funding comes in.
For any runway shorter than 1 year (if you plan to stay for a year) or 2 years (if you plan to stay longer), it’s risky.
If the firm you’re considering is pre-revenue and hasn’t secured enough funds to last more than 2 years, there is a high risk they may run out of money before securing the next round of funding—which is highly dependent on the macroeconomic climate.
A safer choice is to join a company with revenue that covers ongoing costs and isn’t reliant on investors to survive.
Conclusion
No matter how much we try to avoid it, sometimes we don’t have enough information or the right information. In such cases, it’s crucial to leverage your network to conduct further due diligence on the company or check Glassdoor to see what past and current employees have to say. Here’s a link on how to reference-check your future employer: https://rockrose.xyz/want-to-avoid-a-bad-boss-reference-check-them-first/
If you fail to prepare, you are preparing to fail.
Don’t leave your future to chance—take control, pay attention to warning signs and red flags, and trust your gut!