Things To Watch Out For When Interviewing at a Company

I was inspired to talk a little bit about this question on HackerNews: https://news.ycombinator.com/item?id=40649536 - about red flags to look for when interviewing.

Other People’s Red Flags

I had some thoughts about some of the points that were mentioned in the conversation. Some of them are good things to look out for while others may not be indicative of much.

Unorganized or disjointed interview process.
Lack of responsiveness or clear communication.
Excessive number of interview rounds.

Disorganized interview process is definitely a huge concern. This is often an indication that there are some foundational issues that very likely are endemic to the org as a whole and not just HR. I feel like lack of responsiveness and clear communication is related to this one as well - as is, excessive number of interview rounds.

Overuse of business jargon and buzzwords.

Overuse of business jargon is not something I’ve experienced myself except in the job description. Often times the company is looking to fill a generalist role which is difficult to describe in great detail and so writers of the description tend to fall back on commonly used (and vague) references to business process and culture. If you are asking directed questions and still getting vague answers, that should be considered a red flag.

Misleading benefits like "unlimited PTO" with restrictive policies.

The unlimited PTO thing is not really an issue for me though it can be misleading to people who are not aware that there are significant benefits to the company that institute this plan.

Rigid compensation structures.

On the rigid compensation structure front, I don’t think this is actually an issue that is indicative of a larger problem. As companies are required to share compensation more broadly, there has to be some level of structure to the way that people are compensated otherwise you get into areas of fairness and subjectivity that are difficult to navigate. That said, the rigid part can be excessive and it’s worth figuring out just how far the org goes with their structure.

Asking Questions

In the end, though, the best way to learn is to ask question. Here are some questions that I like to ask when interviewing at a tech company:

What collaboration software to do you use?

This is helpful to understand how much importance they put on cross-team collaboration. If there are vague answers or they refer to tools that are known to be difficult to use or completely unknown to you, it might be worth asking some deeper questions about teams communicate with each other. Especially important for remote roles.

How are decisions made about what to work on and how do know if it was the right thing?

Depending on the environment you like to work in you might want a place where they depend heavily on user research vs. trusting their gut. Do they try a bunch of things and work quickly or do they plan out their work way ahead of time and spend a bunch of time implementing a full solution before rolling it out.

How do you handle tech debt?

This is an open-ended question but it’s interesting to hear how the interviewer responds. Listening for things like frustration are indication that this is a sore spot and the org may not make time for this sort of thing which can make the developer experience tough. A well thought answer might mean that this is something that taken seriously. Understanding that tech debt cannot (and maybe should not) always be addressed, it’s good to understand where the line is drawn.


It’s important to look for red flags during the interview process. A messy and unorganized interview experience, poor communication, and endless rounds of interviews can hint at bigger problems within the company. Similarly, if a company is throwing around too much business jargon, giving vague answers, or offering misleading benefits like “unlimited PTO,” it might be a sign to dig deeper. Likewise, while a rigid pay structure isn’t always a bad thing, it’s good to know how strict they are about it. Ultimately, the interview process should help you figure out if the company is a good fit for you, so ask some good questions when you are seeing some gaps or red flags.