What to check for before accepting that newly created role

A checklist to go through when making the leap to that new dream job.

Man in gray suit holding hands up in frustration
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"Risk comes from not knowing what you’re doing." – Warren Buffett

They want me?!?

When the recruiter first contacted you about her client’s search, you might have been feeling a bit dubious: “It’s a newly created job running the IT organization for a rapidly expanding services company!” You said to yourself, “Hmmm. Sounds risky but they’re looking for their very first CIO and this is my big chance for a seat at the table.”

The interview process went exceedingly well and moved very quickly. Except for a few bumps in the road during compensation discussions, you felt like this was the job and the company you were meant for. The team was on the small side and the capex budget seemed underwhelming, but the leadership team was staffed by a nice group of people and the new CEO was a seasoned executive who successfully ran another business and was tempted out of retirement by the opportunity to build another empire.

But things aren't what they first seemed

Except, you’re 18 months into your new gig and your worst fears are about to come true because at any moment you’re expecting to hear from your new boss (the company’s third CEO within the last three years) about your last day with the company. When you look into your rear view mirror, you’re able to identify all of the accretive little steps that led to your departure from your "dream job."

What could you have done differently? How could you have avoided what appears to be the biggest mistake in your career? What steps do you need to take to redirect your career in an upward trajectory?

Properly assessing that "dream job"

Here’s a checklist to keep in case you get "the call" again from an external recruiter or within your current organization:

  1. History: Do your homework regarding the company and its executive leadership team. I’m not just referring to 10Ks and LinkedIn profiles — although they have their value. What does the recruiter or HR know about the people with whom you’ll be spending the lion’s share of your time for the next number of years? If it’s a small- to mid-sized company, have they had success when an internal function was elevated to a new level of corporate responsibility? If it’s another department or division within your current organization, then you should be able to discreetly make your own inquiries and assessments.

  2. Executive buy in: During the interview process you’ll meet your prospective boss and his direct reports. But what about the key members of the revenue side of the business? Who is on board with this newly created executive role and who isn’t? The quality of your questions will help you determine which side of the fence everyone’s sitting on. Are there pockets (or entire suits) of shadow IT lurking in marketing or finance and will the heads of those departments ready to relinquish C - O - N - T - R - O - L of their IT fiefdoms or will you have to pry their cold, dead fingers from their data facilities?

  3. Budget, title, staffing: The saying goes that, “They’ll never love you as much as when they’re trying to hire you.” Every successful executives knows that goodwill isn’t a zero sum game. You don’t draw from it like a bank account until you’ve emptied it. You can and will grow it if you’re meet and then exceed expectations. However, you need to honestly appraise the CEO’s commitment to this new role because money talks and (you know how this ends). Everyone likes to say that "title isn’t everything," but if the new CIO’s corporate title is a step below the CEO’s direct reports, then that’s telling you something about his embrace of technology for his company. Bottom line: don’t let wishful thinking interfere with cold, deliberate reasoning. No matter how tempting this "once in a lifetime opportunity" may seem, it won’t be your last rodeo.

  4. Your resources: My executive coaching clients know they’re the "CEOs of their careers." That means they assemble a virtual Board of Directors from their network ecosystem. Those are the people — e.g., colleagues, ex-colleagues, family, friends, vendors, recruiters, etc. — who not only know them well but who can coach them and tell them things they don’t necessarily want to hear. If you don’t have a virtual Board of Directors, then what are you waiting for?

I’m not arguing for or against this big decision in your career. My job is to help people navigate decisions outside of their normal experience and comfort zones. You use a variety of decision tools in your job; when you’re considering a new one, you need to repurpose some of those tools to properly calibrate the factors in this next step of your career.

"There is the risk you cannot afford to take, and there is the risk you cannot afford not to take." – Peter Drucker

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