The Retro

I used to work as a Product Manager building software.

In the Agile software development process (what I was trained in), there are standard operating procedures to ensure you successfully collaborate to build and deliver software that is useful to customers —things like the daily standup, requirements gathering, user interviews, writing user stories, sprint planning, grooming your backlog, and the retrospective. If this sounds like corporate mumble-jumble, I mean, to some extent it is, but go with me on this, I have a point, and I think you will find it useful.

For Agile software development teams, Sprint Planning is essentially planning your next two weeks of work in collaboration with your engineering team. As a Product Manager, you negotiate which User Stories (chunks of software functionality described by what a user will be enabled to do once the chunk of software is in production-level code) the engineers think they can complete before the end of the sprint, how many stories are reasonable for completion during the two week work period (The Sprint), and then teams go off and get shit done. Each day, you check-in via a 15 min meeting whereby you literally Stand Up and discuss what you did the day prior, what your goals are for the current day, and any dependencies you have on others to accomplish that work.

At the end of The Sprint, the team comes together and they do a Retrospective. The focus of the Retrospective is to collectively discuss 1) What worked well during the two week sprint, 2) What didn’t work well during the two week sprint, and 3) What should the team do different/better during the next sprint to take the learnings with them?

For those of you who are naturally retrospective, perhaps. you’ve always found time to retrospect your business and your personal life, and don’t need the Software Engineering process as an analogy to inspire you to do this.

For me, I had never really been retrospective in either work, nor in life until this style of working was introduced to me through becoming a Software Product Manager. I found The Retro to be an incredibly useful format for identifying areas of opportunity and unnecessary energy drains across my team. Over the course of time, I realized that I could apply this format of retrospecting to virtually any area of life or business where I, or me + others were working towards accomplishing something… and the results were always better relationships, more ease, and better results.


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These days, I am far removed from my career in Product Management, yet I still force myself to set aside an hour or two to look back on the prior month, and ask myself a few key questions:

  • What went well?

  • What didn’t go well?

  • What are you most proud of having accomplished?

  • What did you struggle with most?

  • What tasks/clients/business challenges/activities drained you the most?

  • What tasks/clients/business challenges/activities/collaborations gave you the most energy?

  • When did you feel most confident?

  • When did you feel least confident / most anxious?

  • What processes / systems felt most supportive in your day to day/week to week?

  • What processes / systems were ineffective/otherwise not useful?

  • What deals (or customer types) did you feel the most momentum with?

  • What deals (or customer types) did you feel had a lot of drag/resistance?

The thing I add onto this exercise at the end is “What’s this telling you to change, accelerate, or continue evaluating?” so that the buck doesn’t stop with just the reactions to these questions, but actually drives me to “Oh okay, I see how I can make a change and things will go better next time.”

Listen up, it’s easy to shortcut this process and not answer all of these questions. I have been known to do so. That said, when I do go through all of the questions, I find they always lead me to some new insight… oftentimes an energy drain, an area where I need to optimize, or even a conversation I need to have that I’ve been putting off.

While the fruitfulness of this exercise will change from month to month, the process of doing this is like a steady drum beat that ensures I will always find new ways to improve personally, professionally, and in my relationships both in life and business.

With it being the end of April as I publish and share this, I thought maybe just maybe The Retro might help one of you identify an area of opportunity and improvement in your own work and life!

Hope you enjoy! If you do it, and love it, I’d love to hear from. you!

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