For me personally, in no particular order: PTO/Other leave I very much prefer the "unlimited" policy in terms of vacation, from my experience with it it's a no brainer. As for things like personal days or sick leave, it's very important for me that these things aren't strictly tracked. At my current job I overlooked this aspect due to excitement about other areas and I've come to realize how important this is. Things like timesheets or otherwise managing (and spending) rollover days and such are a pain and frankly counterproductive. Particularly given that I can work from anywhere, I have a very low bar for taking a sick day. Even if I'm just feeling a little under the weather I can either stay home, work a full-ish day and be comfortable, or go to the office, work a full day and be miserable. Of course the former makes for a more productive day (generally speaking) and I respect an employer who's willing to think beyond traditional convention on the subject. Flexibility of Hours A question I like to ask when being interviewed is this, If I wanted to work from 11am to 1am, can I do that in your organization? Reading between the lines, I'm asking whether your org values office face-time over actual productivity. I have a lot of respect for companies that trust their employees to know when they're going to be most productive, and that they will be. Additionally work from home days are a must, either set days (a previous employer liked to do Tuesdays and Thursdays) or whenever a person feels necessary. Though I somewhat prefer the former. Again, given that as an engineer I can work from anywhere, if I want to power through a problem or something at home I want to be able to have the freedom to do so. Stability of Company This is highly subjective, I personally prefer startups because of the environment but I've known plenty of great people who dislike these environments and find them frustratingly chaotic. What I do not like though, is large companies "operating like a startup". To me this says that the company has likely chosen not to deal with growing pains and may be seriously lacking in things large orgs need like process, documentation, etc... But I'll freely admit that this preference is biased from some past experiences. Employee Impact It's important for me to know where I stand within an organization that I'm entering and what I stand to influence within it. Knowing that I can help make tech or process decisions helps me set expectations around culture or org hierarchy and is helpful for me to determine how fair a compensation package might be. The Work It's an absolute requirement for me that the work I'm doing be interesting to me personally. While of course from time to time an engineer might need to put in some tedious or otherwise boring work, generally the work given to me should be challenging and growth oriented. If I'm working on something I find boring for a long period of time with no light at the end of the tunnel, I simply can't stay. Something that helps immensely with this problem are organizations that encourage engineers to move to projects or even teams that they find most interesting given that they're otherwise a good fit for it. Tech stack also plays a big role here, and I particularly appreciate it when an employer gives me room to fail in order to learn a new technology.