Operator Superpowers: Reflection & Retrospective

Operator Superpowers are the methodically-honed skills that make an outsized difference in my effectiveness as an operator and leader - regardless of industry, role, or company size. As we advance in our careers and gain technical and experiential knowledge, Operator Superpowers are the habits that will continue to give us an edge.


There's something I've come to value deeply, both personally and professionally: reflection.

Full disclosure: I’m a thinker, so reflecting sits in my sweet spot of things I love to do, things I naturally prioritize, AND things that have demonstrably helped me to outperform. These all come together in the habit of prioritizing time to reflect.

Have you ever heard of retrospectives in the corporate world? Chances are someone in your company is doing them - and they are using these strategic reflections to help their team work better, faster and smarter. If you have a product/engineering team in your company, they’re likely using a version of retrospective. It may be called an “After-Action Report” or “Post-Mortem”.

 
 

If your team isn’t using retrospectives, imagine the ripple effect you could create by introducing this practice to your team!

When we take the time to reflect, we open the door to uncovering hidden insights that can help us to make better decisions in the future. 

We can also gain clarity and understanding of what has been working and what hasn’t, enabling us to tweak our strategies going forward.

But reflection is more than just a tool for problem solving or decision making - it’s also a powerful way to lead and inspire your team. Adam Grant once pointed out the power of reflection and it’s impact on wisdom:

When we take the time to step back and reflect, we open up a space for meaningful conversations that can help to create deeper connections and trust between team members.

Are you ready to unlock the Operator Superpower of Reflection?

The Why Behind Reflection and Retrospectives

Remember - before you adopt any new method or mantra always go back to the why behind the practice. Why do we engage in retrospection? Simply put, it's our bridge to growth. 

We reflect to glean lessons from our experiences, and these insights only gain value when we actively implement them in our future actions. Because who wants to keep repeating the same mistakes?

Beware: It’s not just a matter of reflecting–it's a matter of using what comes out of the retrospection.

It’s not enough to look at what we did wrong or right. We have to find ways to improve the process and prevent future errors from cropping up – while simultaneously looking to internalize (and possibly operationalize) the right things move forward.

What Retrospectives Are NOT

From a COO's vantage point, it's just as important to clarify what retrospectives aren't as it is to understand their true purpose. In the hustle of operations and the drive for results, we can sometimes misinterpret or misuse retrospectives. Here's what they are not:

  • Blame Game: A retrospective is not an opportunity to pin failures or setbacks on specific individuals or teams. It's about understanding processes, decision points, and outcomes – not finger-pointing.

  • Complaint Session: While it's essential to acknowledge what went wrong, the primary goal is to move forward. A retrospective is not a venting session; it's a focused effort to identify both good and bad lessons learned.

  • Box-Checking Exercise: The worst thing you can do with a retrospective is to treat it as just another task on a long list. It's not something you 'complete' and forget. The insights gained should guide future actions.

  • One-size-fits-all Formula: What works for one team or individual might not work for another. A retrospective shouldn't be a rigid template but a flexible tool tailored to each situation's unique demands.

  • Dwelling on 'Bad' Outcomes: A common misconception is that retrospectives are reserved for addressing problems or failures. In reality, they're equally valuable after successes. Analyzing what went right can provide as many insights as dissecting what went wrong.

From the leader’s perspective, retrospectives are strategic tools. They guide iterative improvement, foster open communication, and cement a culture of continuous learning. Used wisely, they're among the most potent tools in our operational toolkit.

3 Tools for Launching Your Own Reflection & Retrospective Routine

The Decision Journal

Log your predictions regarding significant decisions and periodically review the outcomes against your initial assumptions.

I track the date, a hypothesis/gut feeling, and the actual outcome. Whenever I find myself in a "disagree and commit" situation, this tool is invaluable to help me fully commit. I channel my competitive energy into making a note of what I anticipate the outcome will be.

The Five-Minute Journal

The Five-Minute Journal app prompts a brief daily reflection, asking:

  • What went right today?

  • What could have been better?

I started with this app, but now use the Notes app so I can expand the prompts. Bonus question: When I'm the CEO, what will I do differently? This perspective shift prompts me to think more holistically, considering a broader range of factors and responsibilities. The five-minute reflection journal takes so little time – but the insights it generates are invaluable.

Handwritten Daily Notes

There's a unique magic to jotting things down by hand. It boosts retention and brings clarity. So I always make an effort to jot down ideas, thought, events - anything - into a notebook that I can review later.

While these aren't necessarily organized or easily searchable, if a thought or idea was truly impactful, I'll recall its essence by day's end. Some things just stick, and those are the gold nuggets of insight. So don’t be afraid to just jot down something that resonates. For me, these are my “Aha! moments” that spark an idea or solve a problem.

Pen and paper aren't the only way to capture these insights here and there – you could also use a voice memo app or digital notebook. No matter how you document it, every insight helps!

Harnessing the Operator Superpower

In the world of operations and leadership, mastery isn't just about what you do – it's about how you reflect, learn, and adapt. 

Retrospectives, in all their different and unique forms, showcase this ethos. They reveal an operator's true superpower: the ability to evolve in real-time, learning from both triumphs and setbacks.

  • What AHA moments will you capture?

  • How will you turn those moments into actionable insights?

  • And who will you impact with those insights?

Get ready to make the most of your superpower. You can do this!

Actionable Next Steps

  • Record a recent decision you or your organization made, and note your hypothesis is about how it will work itself out. 

    • Bonus points if you disagree with the decision your organization made - this is an opportunity for you to hone your thinking should the decision work out for the better. 

  • Prioritize 5 minutes at the end of the day to reflect on what went well and what didn’t.

    • If you’re working from home, this is a nice signal to end your day and relax into personal time. If you take the train (like me), this is an excellent time to slow down your thinking and make the mental shift before arriving home. 

  • Host a retro 

    • It can be small, it can be messy, just start to build the muscle in your organization.

    • Keep it simple and reflect on three areas: 

      • What went well? 

      • What didn’t go well? 

      • Commitments for the next time we do this.

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