Three Envelopes - A Short Leadership Fable

This is my version of a leadership fable that I've used in presentations over the years to describe what is unfortunately the reality in many organizations.

For me, it summarizes the approach many new leaders take in bringing change into an organization.


Once upon a time, a CIO showed up for her first day at ACME company.  She was excited and couldn't wait to get started.  After the usual HR forms and routines, she was shown her new office.
As she sat in the high backed chair, she did what most people usually do... she opened the drawers to see what had been forgotten. 
In the upper right drawer, she found three envelopes. The envelopes were numbered and they came with a note attached.  It was from her predecessor. 
"Welcome to ACME", the note read. "You have a very challenging position, and if you ever find yourself overwhelmed and unsure of what to do next, open an envelope." 
"Curious" she thought as she closed the drawer and dove into her new role.  
As with most IT organizations, the honeymoon period was short lived for our new CIO.  Budgets, delayed projects, and personnel issues soon dominated her calendar.  She could sense the frustration from her boss, her colleagues and her team who were waiting for results from the new person.\ 
At the end of one particularly frustrating day, she remembered the note and the envelopes. 
She opened the drawer and picked up the first envelope.   
The note inside simply read; "Blame your predecessor". 
So she did... and the energy level picked up as people started talking about everything that was frustrating working for her predecessor. They had a common enemy who wasn't there to defend himself. 
But our new CIO found that changing things wasn't all that easy, and many of the things that frustrated people didn't go away, and the frustrations soon returned. 
It was time for the second envelope. 
Inside envelope number two was one word; "Reorganize" 
So she did, and the murmuring stopped as people were busy with the shuffle, the office move, and learning their new roles. But like many reorganizations, it didn't solve the original issues, and the frustrations returned. 
Our CIO was no longer new in the role.  She couldn't claim that she was learning the business. There hadn't been any significant change in results, or team morale since she started two years previously. 
She was frustrated, overwhelmed, and unsure of what to do next.  Which led her to opening the next envelope. 
On the card inside were three words.... 
"Prepare Three Envelopes"

Fortunately, this doesn't have to be your story. Today's IT leader is faced with significant challenges, and must understand how the role has transformed over the last few years.  My purpose with this blog is to share some of the things I've learned about this transformation, and point you to resources from others who can help you in your role.

So let's transform our fable a bit.  If you were to leave three envelopes in a drawer for your successor, what would you put in them?

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