All Agile Journeys start with a’s my “story”


Time is a fickle mistress.

There are days where I look back, and the time that has passed feels like decades.  At other moments, I remember certain events like they happened yesterday.

In this case, it feels like both.

I was an eager Product Owner.  Newly anointed, fresh from a story writing workshop, and ready to conquer the world.  Story writing was nothing more than a ‘mad lib ‘to me.  All I had to do was fill in the spaces with the appropriate entries.

As a       USER       , I want         THIS FUNCTIONALITY    , so that      I CAN HAVE THIS BENEFIT.

I set off with my new script, and fondly remembered the nouns, adjectives, and verbs, little kids used back in the age of innocence.

I cranked out about 30 stories that evening.  I was no Roman Pichler, Mike Cohn, or Jeff Patton – but I was certainly on my way to being a resident expert.  Unbridled enthusiasm will do that to you.  So will the Dunning-Kruger effect.  But in that moment, I was proud.

I could barely sleep that evening.  I was so excited to show my new team what I had accomplished for them.  I was the “runway creator”, the “accelerator”, and probably some other stupid superhero I had invented that night.  Time, the fickle mistress, opted to take the scenic route that evening, converting seconds into minutes, and certainly delaying my day of glory.

Upon walking into grooming, I confidently took the chair at the head of the table, and paced around the room as we discussed each story.  However, instead of glory, my team was disenchanted.  They wanted stories broken up a certain way, with certain details I had neglected to provide.

“What – no mockups?”

“What does that acceptance criteria even mean?”

“That one isn’t even testable.”

“You really worked on this all night? “

I went from superhero to court jester in less than an hour.  And to add insult to injury, we had only gone through about 4 stories in 40 minutes.  We ended early to preserve any modicum of hope I had to be productive for the remainder of the day.  Time, the fickle mistress, was adamant about making that 40 min feel like hours.

Defeated, I went to my Coach.  He was the guy who built me up.  He instilled confidence leading up to that session.  He had reviewed these stories.  Was he paying attention?  Did he set me up?

Si – who I still remain in close contact with as a friend, colleague, and mentor – simply smiled.  He seemed amused with the adversity I had encountered.  That made one of us.

In a stroke of incredible timing, Si pulled out a gift he had purchased for me.  He was from Chicago, and had (actually still has) an unhealthy obsession with Starbucks coffee.  It was a 20 oz Chicago Starbucks mug.  He smiled, and said “There are going to be days like this.  What I suggest is, go get a cup of coffee.  Decompress.  Accept the feedback the team presented to you, and try again tonight, my friend.”

I am positive Si does not recall this moment.  But it was career altering for me.  At that moment, it wasn’t.  The gesture was very nice.  I think Si saw potential in me.  I pretend like he did not get everyone Starbucks mugs to secretly get free coffee from all the Starbucks he visited.

It did not occur to me until many years later how profound that moment was in shaping my career.

The Chicago mug became representative of my Agile Journey.  It was a reminder of humble beginnings.  It was a reminder to exude patience with people just beginning their own personal journey.  We were all students once.  We have all had moments where we fought to transcend frustration.  There will always be moments where we don’t have all the answers.  More importantly, those moments are what make Agile practitioners into Agile Coaches – and Agile Coaches into Agile Leaders.

The desire to crave chaos, to be comfortable “being uncomfortable”, and to possess the humility to always look for innovations, are what defines ‘Coaching’ to me.  Coaching is making the impossible, possible.  Its finding hope, in hopelessness.  Its bringing calm to the chaos.  Its leading by example, and showing people how its done – not telling them how to do it.

Share your story with others.  Be an inspiration.  Encourage people to challenge the “why” behind the institutional DNA we call “process”.  Be an advocate for change.  Be a teacher, but also be a student.  The second we think we have it all figured out, is the moment we do not.

I learned a lot that week writing stories.  What felt insurmountable in that single moment, became the cornerstone for how I approach my engagements many years later.  The Chicago mug will forever be a symbol of my Agile journey.  Ironically, the mug is also inscribed with the “windy city” beneath the picture, which inspired a conversation that led me to this quote:

While the ledge may be windy, you never get to see the good views by staying inside.


As the years pass, Im grateful for the privilege to continue this profession.  I know a decade from now, I’ll look back at the experiences I’ll have a few months from today and think “wow, that seemed like yesterday”, because Time – will forever be – a fickle mistress.