I've been getting this question quite a bit lately. The economy is starting to pick up a little and more people are hiring, so I thought it might be helpful to share the brief email advice I gave him. It's pretty basic stuff, but sometimes you need to hear what you already know from someone other than yourself. :)
You can also check out My Top 10 Job Search Tips--they were featured in US World News Report Online!
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Here was my verbatim email response. Hope it helps those of you considering a job switch right now.
Personal
* What do you gain by making the switch -- what more do you learn, how does it progress your skillset or get you closer to your career goals, does it improve your home/work balance, etc -- regardless of whether or not the company succeeds (meaning these are things you would be able to take with you or at least enjoy if it fails).
* Are you well-prepared (financially, emotionally) for if it fails or you get laid off soon after you are hired?
* If it succeeds, what is enough upside for you that would balance the risk you are taking in making the move?
* What is really attracting you to this opportunity--is it the opportunity itself or is it just that it is different and you are bored where you are? If the latter, is there something you could do where you are that would make it worth sticking around? And if the answer is no, is this the right opp or just the one you happen to know about? Because if you are really ready to go, it may be in your best interest to look at all available options, not just this one.
* Setting aside the fact that you know some people there and have worked with them, does the company *feel* right to you otherwise in terms of a fit? Would you be working with people you respect and can learn from or just people you happen to like and know?
Business
* Who is funding the business, for how long, and do the investors have a record of funding successful businesses?
* How old is the business, how often has the business needed funding (ie what is their burn rate) and does their growth rate in head count and in other overhead areas make sense with the revenue and profit increase they are expecting?
* Do you understand why the business isn't profitable and how they plan to get to profitability?
* Does their business strategy make sense to you and do you believe in it?
* Do they have a history of making good choices and of making the numbers and/or goals they have set? When they haven't, do you understand why not?
* How big a market is it and how crowded? What is the competitive space for their offerings and how are they differentiating? Are they gaining customers or losing them? Etc.
Two of the most important things I can recommend overall in making this choice is to:
a) Know yourself and what you are really good at and match that against what you think you are really looking for in your next move. How does this match up? Make sure you are making the switch for the right reasons.
b) Play out the most likely scenarios and at least a few of the least likely ones so that you feel confident you are making a well-informed choice. You can't predict the future, but you can imagine the different ways things might play out and how you might respond in those situations, and then decide how much of a risk you are willing to take.
You know me--I am always up for taking a (smart) risk--but it is a big decision to switch jobs, especially in this economy, and now you have a family to take care of. At the end of the day, you've got to do what I call the smell test, meaning does it smell right to you--another way of saying you need to gut-test it. My own personal smell test involves gauging how excited my brain gets about a business. This means does the business challenge inspire me and trigger my brain to come up with lots of new and different ideas that I want to go and get done? If not, I know that no matter how much someone pays me or how sexy the business is, I will not be at my best. I might still do a great job relatively speaking, but I won't be really engaged like I could...and should be. You've got to find your own equivalent of a smell test and check this against that. Hope this helps. xo SYP