When a new CIO steps into office he is given three envelopes in the event he runs into trouble. Inside the 1st envelope a note reads “play it safe”. If that doesn’t work than he opens the 2nd envelope which reads “blame the business unit”.  If neither works than he opens up the 3rd envelope which reads "prepare 3 envelopes".

We all have certain preconceptions we bring with us into a new company or project.  Maybe it’s that most people are resistant to change, or that there’s only one way to solve a problem, or that it’s impossible to introduce new technology solutions in a large company.  These conclusions shape the mind of many executives in corporations around the world. 

It’s a common argument formula and it looks like this:

Since change is difficult, and new initiatives are change, it follows that new initiatives are difficult to execute.

In larger companies another element is added to the formula and looks like this:

I am being paid a lot of money, do I really want to risk my career on a new initiative?

The premises in the original formula appear to be sound which leads to a logical conclusion that new initiatives are difficult to execute.  The trouble is that this type of short term thinking is causing IT to be less and less relevant.  It’s not proactive, it’s status quo. 

If you can’t get to where you’re going go someplace else

Status quo is safe.  Executives swear by it.  I’ve seen many of them fall into its gravitational pull.  Launching something out of it is difficult.  

That’s why when you’re introducing a new initiative into the organization especially when it involves the terms “social” or “Enterprise 2.0” or even “innovation” you get resistance. 

Like when you first presented your Enterprise 2.0 vision and the CIO gave you a glance like the visual equivalent of the words “are you insane?”

His response to your presentation was, “there’s a fine line between a vision and a hallucination.”

That’s when you decided to go to the VP of Sales to pilot the initiative.  He was a risk taker, a rising star, someone who couldn’t afford to stand still.  Sales velocity was slipping and he was open to trying a new solution. A solution that directly connects customers to his sales team and the rest of the company. 

Strategy is 90% theoretical, while the other half is experience

The VP of Sales argument went something like this:

Companies purchase our solution to solve their problems, a lot of companies have the same problems, therefore finding new companies with similar problems will lead to increased purchases. 

His premises and conclusion are also sound.  Yet he concluded to move forward with your initiative.  Which begs the question, how did the CIO and VP of Sales end up with entirely different conclusions considering they are in the same company?

It’s easy to observe that they are approaching the initiative differently.  While their arguments both make sense, their experiences and circumstances lead to different conclusions. Multiply it across the enterprise, and it leads to conflict, confusion and chaos.  

Hence strategy becomes contextual to an individual’s past and current experience and the tug of war between different departments produces little output. 

Is the squeeze worth the juice?

So it’s up to you to decide whether to work with the VP of Sales or not.  While not acting appears to be safe, it’s not going to advance your career and it’s not going to help the VP of Sales.

On the other hand, acting is fraught with danger.  The CIO may sabotage you, your peers may ostracize you, the project might fail, and your children may starve (ok probably not the last one).

The best approach is to check the premises of all parties involved (including your own).  Can each parties’ arguments being aligned to the corporate strategy?

Can you alleviate the CIO’s concerns by piloting the solution with a receptive business unit?  Can you take sole responsibility for the success or failure of the initiative? Can you create and lead a change management plan? 

Will the VP of Sales give you the proper support to be successful? If it fails, will he provide cover?

If you find alignment of interests with the parties involved then proceed.

If you can’t and still proceed, prepare three envelopes.    

P.S. Thank you Yogi Berra for inspiring the sub-headings