Project Practitioners > Retrospectives and Getting Comfortable Being Uncomfortable

Retrospectives and Getting Comfortable Being Uncomfortable

By Brian Irwin

The tension is palpable and suffocating, as if a pillow is being held over my face in anticipation of drawing my last breath.  The last team member enters the room and it’s time to begin.  “Welcome to the sprint retrospective,” I say with conviction.  Perhaps I’m trying to convince myself that I’m emotionally ready.  Or, maybe I’m trying to be an insulator to the electricity of anticipation coursing through the team room.

Welcome to the retrospective.  For me, and many other coaches or ScrumMasters, the sprint review is the most difficult undertakings.  Yet, in my view, it is one of the most crucial events to the agile team.  This is where team improvement takes place—process and team innovation.  Aside from the time spent keeping the team shielded from distractions and removing progress impediments, the exceptional ScrumMaster will spend a considerable amount of time preparing for, and planning, the retrospective. 

However, while this meeting is of essential importance to team improvement it is undeniably difficult and can be emotional.  Because of this I witness teams deny themselves prime opportunities for reflection and improvement due to their unwillingness to engage each other in hard and difficult topics so they can learn and grow as individuals and as a team.  It used to baffle me why teams would choose to allow these opportunities to slip away from them—knowingly!  I believe I now have a very good understanding of why.

Retrospectives done well require us to do what most of us, myself included, are terrified of doing—allow ourselves to be vulnerable.  Increasingly, we live in a culture filled with social media which I sometimes refer to as artificial connectedness.  We are all naturally wired to long for connectedness and belonging.  To be vulnerable is to open ourselves up to the possibility of not connecting and not belonging.  We’re fearful that, should someone see who I really am (or, what I perceive myself to be the true me) they will shun me.  Unfortunately, the only way to foster true connectedness and belonging is through vulnerability.  As a husband for 21 years, to show vulnerability in front of my wife was to show weakness—and we’ll have none of that!  My wife does not want to be married to a weak man.  Does this touch close to home in your own relationships?

So, how exactly is this related to technology projects and retrospectives?  To be succinct and to the point, vulnerability is the birthplace of creativity and innovation.  Companies, teams, and individuals all want to be creative.  They just aren’t willing to allow themselves to be vulnerable.  If that’s true then it’s also true that your innovation and creativity will be limited.  Watch the video below of shame researcher Brené Brown discussing vulnerability and innovation, and then continue reading for some hints about how to help your team through this significant obstacle. 


I cannot tell you that the fear of being vulnerable will ever subside.  But, I will tell you that it is vital that we allow it to happen if we hope to be truly connected, creative, and innovative.  Below are a few exercises you can work through with your team to practice vulnerability in a relatively safe manner to help all of you start to practice leaning into the feeling of vulnerability so retrospectives can be as impactful as possible.  However, remember that vulnerability—even practice—is never entirely safe or it would be called certainty instead of vulnerability.  Each exercise below can be an incredibly powerful perspective-inducing exercise.  You will certainly know your team better after each one; I guarantee it.

  1. Draw a life map – Using a flipchart or large butcher paper, have each team member create a map of their life including whatever information they would like.  Use any creative tool you need to—clip pictures from magazines, draw pictures, and use markers or crayons.  Have each person start the life map from as far back in their lives as they can remember (or want to remember) and record significant events.  Have each person share their life map with the team.  This exercise can be funny and may help to draw insight into how team members became who they are.  This can also be highly emotional.  I have laughed hysterically and cried profusely doing this exercise.
  2. Write a life reflection letter – If you’re like me you’ve probably uttered the words, “If I knew then what I know now.”  I’m going to offer you the opportunity to do just that, only with a twist.  Imagine far into the future.  You are 110 years old (hey, I’m being optimistic) and know you are nearing the end of your life (ok, I’m being really optimistic).  Write a letter to your present self.  Write about all of the things for which you’re grateful.  Think about how you want your life to turn out and talk about the impact you made as a person to the world you’re leaving behind.  Think big and do not limit yourself to work and career.  In fact, doing this exercise you’ll be amazed at how much that never even enters into the picture of what’s really important.
  3. Write a letter about your life’s dreams – Imagine you are 5 years-old.  You’ve just entered Kindergarten.  As the teacher, I’m giving you an assignment to write a letter to yourself as a grownup talking about all of your life’s dreams.  Dig deep for this one and really think back to when you were that young, before the harsh realities of the “real world” stepped all over your hopes and desires (hopefully they haven’t, but not all of us have grown up to be rock stars, models, or astronauts).  To make this one hit home, write with your non-dominant hand using crayon as you would have as a child.  That is, if you are right-handed use your left hand and your right hand if you are left-handed.  This can be very powerful.  If you want, put some of this stuff on your bucket list, but at a minimum share it with the rest of your team.  Your spouse might like it also.

Each of these exercises can be extremely powerful and moving.  By doing one of these periodically with your team, you’ll find that you are becoming closer and authentically connecting through discovering who everyone else on the team is as a person.  You may even find yourself through discovering everyone else’s story.  The rub is that to do so, we must get comfortable being uncomfortable.

Not all comments are posted. Posted comments are subject to editing for clarity and length.

Retrospectives are an essential part of agile, as they help the team to reflect how they work together, and find ways to improve. Establishing a culture where people dare to speak up and give feedback is needed to make retrospectives. Does that make you vulnerable? Yes. But that's the case for all team members, and when you feel safe, vulnerability becomes less of a problem.

What I have seen working is when the scrum master, together with other senior members of a team give the example. If they are open on the things that they have done wrong, their mistakes, that can help other team members to open up.


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