Kevin Pashuk

5 years ago · 2 min. reading time · visibility ~10 ·

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Three Envelopes - A Short Leadership Fable

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 for all of these posts 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?


Image: MS Office Imagebank

A version of this post has previously appeared on LinkedIn

About the Author:

Three Envelopes - A Short Leadership Fable

I'm the Chief Information Officer for Appleby College, in Oakville, Ontario Canada, where my team is transforming the delivery of education through innovative application of technology.

I'm convinced that IT leadership needs to dramatically change how IT is delivered rather than being relegated to a costly overhead department.

In addition to transforming IT in my role as CIO, I look for every opportunity to talk about this... writing, speaking and now blogging on BeBee, LinkedIn (, ITWorld Canada, or at

I'm also an avid amateur musician and photographer (but not at the same time).  Check out my photostream on Flickr  or on beBee hive: serious-amateur-photographers

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Kevin Pashuk

4 years ago #13

Envelopes have so much better dramatic effect. I would agree that we rarely get beyond the band aid. As the old proverb goes.. "The person who does not learn from their mistakes is destined to repeat them forever."

Ken Boddie

4 years ago #12

We have a great system (in theory) called the Fix-it, Kev. It comprises four parts as follows: 1. Recognise and define the problem. 2. Undertake an immediate/short term fix. 3. Analyse what caused the problem (most management systems would call this a 'root cause analysis'). 4. Put a suitable long term fix in place and monitor its effectiveness prior to signing off. Unfortunately, in practice, most Fix-its only look at 1 and 2 above and, without properly addressing 3 and 4, we often end up, after a while, on a merry-go-round of putting the same or similar Band Aids on the same festering wound. Sounds to me that your letters story represents the same series of Band Aids and that, without the root cause analysis, there is no possibility of a long term fix. Incidentally I would have thought, in your chosen field, the drawer would contain a USB stick with three separate pdfs? 🤔

Sarah Elkins

5 years ago #11

Completely agree with Kevin Pashuk. You are all over the place! Except for Montana. When you get here, let me know and I'll treat you to pizza and beer in my garden.

Mohammed Abdul Jawad

5 years ago #10

Every role has its own ups and downs and scared of any challenging situations you cannot simply quit the job. Try to read the pulse of the organization and work culture, then begin to correct people and systems with guts and patience. As the work wagon moves and picks up pace, deal justly with your people for bettering work atmosphere and staff well-being.

Sarah Elkins

5 years ago #9

Envelope #1: Ask Questions. Ask a lot of questions with the intention to listen. "What is the process for this? Who usually handles...? How did my predecessor handle this? Did that strategy work?" Envelope #2: Prioritize & Communicate. Figure out the biggest problem you have and take steps to fix it. If that means confronting staff, do it. Make sure everyone knows your intention and make sure the problem you've identified really is a problem in the larger context of the business. Envelope #3: Tell your employees when they do good work. Celebrate small wins. Good post, Kevin Pashuk for tagging me.

Javier 🐝 CR

5 years ago #8

LOL I am multi tasking !!! This is me not a robot !! :) probably I will need several "Javier" :)

Kevin Pashuk

5 years ago #7

Thanks for sharing this post Javier C\u00e1mara Rica?

Kevin Pashuk

5 years ago #6

Thanks for sharing this Laura Mikolaitis!

Kevin Pashuk

5 years ago #5

Great content for envelope number 1 @Gert Scholtz. When I started my last role, i interviewed every member of the team (over 70 people) with the same 3 questions: 1. What is going well around here? 2. What would you change if you were in my position? and 3. What do you do when you are not at work? Not only didbI get a feel for the outstanding issues,I got to know my team on a much more personal level.

Kevin Pashuk

5 years ago #4

Great content for envelope number 1 Gert Scholtz. When I started my last role, i interviewed every member of the team (over 70 people) with the same 3 questions: q.

Gert Scholtz

5 years ago #3

Kevin Pashuk Wonderful post. What would I put in the envelopes? 1. For the first 30 days in your new job - listen, listen and listen more. 2. Ask all what changes they would like to make and implement. You decide, take responsibility and implement 3. If the changes work well you give credit to others. If they don't, you take the blame and start again with envelope 1.

Kevin Pashuk

5 years ago #2

#3 Thanks for reading and commenting Jason Attar!

Kevin Pashuk

5 years ago #1

I could have titled this post "Never confuse motion with progress". I'm gobsmacked at the unproductive dynamics that are so prevalent in our business culture today.

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