New Job Angst

Dear Evil HR Lady:

I am writing to ask your advice about a dilemma I seem about to face.

I have a great job in the high-tech industry. I largely make my own hours, and like my company. I'm probably about 10% underpaid (according to at least two salary surveys), but I'm generally pretty happy.

So what's the rub? The work bores me to freaking tears!

On a lark, I recently applied for my dream job at my dream company. It's a huge, famous company, and getting to work there would be a dream come true for me (it would be like growing up a baseball fan in New York, and getting a meaningful job with the Yankees); in terms of corporate prestige/scale, think Apple or Microsoft. Moreover, the recruiter at HR volunteered the salary range to me: the minimum that she mentioned is what I currently earn.

I first applied a few months ago. I've since been through a very rigorous hiring process (worthy of a whole other e-mail), and we've gotten to the point where they've sent me the job application and the background check is now in progress. In short, it seems quite likely that an offer will come in a matter of days.

If the prospective employer and I can agree on a salary--I've asked for 25% over my newly raised salary at my current job--these are the things that will still make me reluctant to leave my current job: (Yes, even in the face of a major pay increase and a dream job.)

* My freedom with hours. (Also, the commute to the prospective job would be really awful if I have to start doing 9 to 5.)

* On a related note, the almost-complete lack of micromanagement I enjoy, serving as my own department head (though I'm only an individual contributor)

* The better 401k match at my current job

* One more week of PTO at my current job than at the prospective one

* The severance I'd get if I got laid off from my current job, as opposed to nothing at the new job, at least for a few years, 'til I built up seniority again. This is especially important to me because the prospective company has had a hard time of it lately, and just did a RIF. There's good reason to think they'll have a better year this year and, especially, next year. But if not, things could get bloody.

On a closing note: I feel that I'm in a very strong negotiating position with the prospective company. This job requires a certain, highly specialized skill set, and they've had this req open for months; people with this skill set are fairly hard to come by. I also felt that I totally nailed the interviews, work samples, and presentation. They know I'm pretty happy at my current job, although they also know my enthusiasm to work for them. I also really need to stop being underpaid: My wife and I recently had a baby, and my wife just quit her job.

My questions, then, are:

* Would I be out of line trying to negotiate flex time even if the prospective company doesn't currently have it (I don't know if they do or not)? This would cut the commute down to 40 mins. each way, from an unsustainable 90 mins. each way. Or even telecommuting one day a week, say after my initial 90 days?

* Would I be out of line highlighting the risks I'm taking by giving up my severance eligibility, and asking them to guarantee me a severance package? Perhaps I could ask for a starting bonus equal to half of the severance I would have gotten at my old job? (Less money, but guaranteed.) Is there another way to propose that they help me mitigate the risk? I've heard of things like this at the exec level, but not at the lowly individual contributor level that I inhabit.

* How can I feel my prospective boss out to find out how strict he is about time/being at your desk? I'm a very talented worker, and I work very hard, but I kind of march to the beat of my own drum sometimes. Before I sound like a total prima donna, I need to point out that this is not uncommon in my industry, and lots of workplace "conventions" kind of go out the window here. Still, I'm sure it also depends on the company. I've heard one or two things that makes me suspect that this company is stricter than some others...

* I've read that PTO is very hard to negotiate. Do they really just expect a mid-career professional to give up his juicier time-off package, or is this more negotiable than I understand it to be? Between wanting to negotiate some form of severance eligibility and PTO, I seem to be asking to be treated as having x-number of years on the job. Am I just totally off-base?

This is a very long note--thank you for bearing with me. As you can see, I'm totally agonizing, and I'd be grateful for any clear-eyed perspective and insights you could offer.

Two things I want you to think about:
1. When you currently have a job that doesn't drain the life blood out of you don't take a new job you don't want.
2. Everything is negotiable.

Only you can address number 1--do you really want this job or do you think you want it because you've always wanted it? Your current job is boring, but boring pays the bills and allows you time with the family. I'm not saying don't go for the new job, just saying you need to be open with yourself about what you are doing and why.

As for everything else, it's negotiable. Sure, some companies are sticks in the mud and won't do anything out of the ordinary for anybody, but that just tells you right off the bat you don't want to work for them.

Flex time should be fairly easy to negotiate--especially if you lay out what you've said. I used to commute down US 1 in NJ (those who live there know the special nightmare that is). I lived farther away than anyone else in the office. If I left my house at 7:00 I would role into the office around 9:00, exhausted and frazzled from the commute. If I left my house at 9:00, I would role into the office around 9:45, ready to work. My boss didn't have a problem with the latter schedule, even though I was probably the only person in the company afforded such a luxury.

Perfectly all right to highlight the risks in leaving your current job as well. Although don't start highlighting those until after you've received an offer. Nothing turns a hiring manager off more than being told why it would be painful for you to leave your current job to come on over--before the offer has been made. (Well, hiring manager thinks, I'll just spare you the trouble and not hire you.)

Severance is a tricky thing to bring up. (So, if I'm not valuable to you, how much will you pay to get rid of me?) You're right that executive types frequently have "change of control" agreements (if the company is bought out) or "golden parachute" clauses in case it "doesn't work out." From what you've said, it's doubtful you'll be able to negotiate any thing like that. However, asking about the company's stability, especially in your area. In many layoffs, some entire departments escape unscathed while in others, the entire group is shown the door. You want to be in an untouchable group. What projects are you working on?

As for marching to the beat of your own drummer, it is sometimes adored and encouraged and sometimes it is hated and discouraged. Definitely ask your prospective boss about the department culture. This is probably not a question for the HR person because, unless the company is overly centralized in it's policies and procedures, managers generally get to decide how strict they will be about starting times, ending times, lunch breaks, etc.

As for PTO, you are right. This is very difficult to negotiate. But, go ahead and try. Some companies have strange policies that would allow this.

Get whatever perks you have negotiated in writing. I cannot stress how important this is. Otherwise, the boss the promised you the world may quit two weeks after you start and your new boss may be a Delores Umbridge type. You need the document saying you can come in at 10:00 or work from home on Tuesdays.

Good luck making you decision!