A CIO and Three Envelopes

Josh Upton

by Josh Upton

An incoming CIO replaces a recently fired CIO. On his way out, the former CIO hands the new CIO three envelopes and tells him, “When you reach a crisis point, open these envelopes, one per crisis.”

Things go well for a while, but then along comes the first real crisis. The manager goes to the drawer where he keeps the three envelopes, and opens #1. It reads: “Blame your predecessor.” He does this and the crisis is resolved.

More time passes and a crisis looms again. The manager dutifully opens envelope #2. It reads: “Reorganize.” Again, following his predecessor’s advice works like magic, and things settle down.

But sure enough, a few months later, troubles are mounting once again, more than ever. This time, though, the manager knows for sure that help is just an envelope away. So he turns to the drawer one last time and opens #3. It reads: “Prepare three envelopes.” - Peter Kretzman

Why the joke?

The story of the three envelopes is ironic. In times of crisis many leaders revert to a “save yourself” mentality. This joke lays out three steps in a way we’ve all probably seen before and some of us have even done.

  1. Blame the guy before you if your ideas don’t take off
  2. Get rid of the old guard and bring in your own folks
  3. Quit or be asked to leave when/if it doesn’t work

Recently we helped put together a CIO Roundtable in Birmingham, Alabama.  What these IT execs spoke about did not lend itself towards a “three envelopes” situation taking place.  The conversations that took place focused on how best to create transformation in today’s landscape. These individuals felt like the business is successful when IT is successful, and it is on the CIO to drive that message home.

Key Takeaways

CIO Roundtable: A Process Problem

One executive said, “You can put the best technology in the world with bad process and you will see terrible results.” But why so much bad process to begin with?

Quite simply we don’t like change. We want what we want, but we don’t want to change. It’s the, "I want it now," instant gratification world we live in, “If we don’t provide what our employees want they’ll just go get it themselves, so maybe we should focus on being more interactive with them to bridge that gap?”

There are, however, organizations that have started to figure this out. These organizations have taken proactive steps to remove barriers that historically have kept IT from truly driving change.Things like:

  • Focus on positions like business relationship managers who help create better communication and alignment between IT and the business.
  • Joint committees designed to find common ground between users who want to work how they want, and IT who needs to focus on security, compliance and corporate governance
  • Business process reviews before adopting any new technology initiative that include both the business and IT

In short, proactive organizations bite the proverbial change bullet and suck it up. As a result, they are plowing ahead collaboratively as one organization with a common set of goals.

CIO Roundtable: Innovating While Keeping The Lights On

Every executive in the room felt the need to drive change, but was dealing with the reality of keeping the lights on. How could they stop the baby-sitting reality and move toward a model designed to change the way IT provided services to the business?

Every executive in the room agreed that undergoing a transformation was necessary to stay competitive. In fact, many already implemented strategies to help more their organization in a positive direction.

  • Financial transparency and metrics for the business – Getting them to understand 90% of their budget being spent on legacy infrastructure won’t equate to driving change
  • CIOs working with their C-level counterparts (CEO, CFO, CMO, COO, CTO) to breed a culture of joint ownership and “we’re in this together” mentality
  • Executives evangelizing and spending more time with their customers - less time behind the desk
  • Examining existing processes jointly with the business – cutting out the old and focusing on getting leaner, faster and smarter
  • Leaning on mentors and apprenticeships to strengthen culture and fill in skills gaps

To summarize, communication is key to organizational success in today’s age. Out of sight is out of mind. Worse, you’re leaving others to create their own opinions because of your lack of action. Never a good thing.

A Final Note

I mentioned it above but didn’t pay the statement enough credit:

Business success means IT success.

We’re at the point where one shouldn’t exist without the other. The executives who attended the roundtable session clearly understood it was on them to move the ball forward. They understood that change started and stopped at their level and collaboration with the business was the only way to gain buy in for true change.

We live in a digital world and while software defined everything, public cloud, IoT and the like dominate conversation it still all breaks down to people. We’re the ones that created the problems, and as such we’re the only ones that can fix them.

Business Success Means IT Success… there is no way around this moving forward, and it’s on us to drive that message home.