As book-end to the advice for just starting out, here are some notes on getting that next job. As we get older, hopefully you’ve picked a great industry (if not, then see Notes on getting (re)started). But assuming you have a good set of expertise, how should you think about your next job. Most of the time it will be another division in your company but sometimes, it will be outside.
When I think about this, I ask myself three questions to make sure I choose well, I sometimes add this up to get a rating for the job, each question is worth 10 points, so ask yourself, if the rating is a 1 (“Iron Man himself couldn’t do this job”) or a 10 (“I could do this by 10AM and garden the rest of the day”):

  1. Is it a job that I can succeed at? Mike Maples was VP of Application at Microsoft when I started there 100M years ago and he said in one of the first presentations I attended, “make your commitments.” Alternatively you can think of this as, “under-promise and over-deliver.” Or as my buddy Reed told me early on, “find a job that is hard, but not too hard.” What all that means is that all to often, I get enamored with the title (I can be VP!) and forget that about seven seconds after you get the title, people start judging you. If you don’t have a 30-, 60- and 90-day plan for how you are going to blow away expectations, then watch out. As an experienced hire, people want to see instant results and you don’t want to get on the wrong end of that expectation. It is sometimes true that it is better to be a director and then earn the VP title than the other way around.
  2. Will my boss love me anyway? Put another way, if the job is super hard, what is the internal dynamics like. Is it a boss who has known me for years and willing to give me say six months. Or it is the kind of matrixes job where all the other VPs hate me, yet I need their help to succeed. Obviously there is a tradeoff between this and . The easier the job for you, the less you need love, you can just deliver.
  3. How long will it take and what’s the downside if I fail? If this job will take 10 years to get right, that means that you have to deliver for 40 quarters (put’s that in perspective doesn’t it) and survive five CEOs (most CEOs survive 1-3 years). On  the other hand, it might be worth it to take a difficult job in a difficult environment if the payout is in six months and it is guaranteed. The bigger question is what does your Linked page look like if the job or the company implodes since that affects the next gig.

While this isn’t foolproof, when I ask people these questions, I normally learn a few things:

  1. Most people spend less time casting a wide net for a job than they do researching the next cell phone they want. When you are heads down working, it is super hard to know what is out there. Being out looking for something is a full time job, so many times it pays to invest in the future when you sense the end of near. You want to get out before everyone else gets out (that’s the topic of another post :-). But one way to look at it is that for every ten years of job experience, you probably need an additional month to find the right position. So please don’t settle for the next job because your buddy told you about it, finding the next gig is going to take time. It is uncomfortable to be sure, you have to ask your personal board of directors, you have to meet investors and new people, but it’s your life and you d0n’t get a second chance!
  2. Be choosy about what you are choosy about. In other words, what are your real criteria for the next gig. So many times, you see and job and try to fit into it, the more senior you are, the more the job needs to fit you. If it fits, then you are going to be better at it. If you need more time with the family, don’t take a job that requires 100 hours a week. If you are exhausted and burned out, don’t become CEO of a turnaround. If you need to make that final nest egg before moving to Tahiti, then don’t take a job that will show results in 10 years.
  3. Finally and to repeat from the first post, ask your personal board. Deciding this stuff for yourself is really hard, you need a set of folks who can be dispassionate and analytic about who you are and have the courage to go against your best judgement.

And finally, good luck! The stakes are much higher as you are more experienced and each step is an opportunity to create a hole in your resume that’s hard to explain or a chance to solidify an amazing career 🙂

I’m Rich & Co.

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