Holding Up The Mirror: Time To Reflect On Your Leadership Journey

Every six months, I take my clients through a retrospective to give them time to reflect on the progression and leadership they've built.

But I think it’s important to name upfront that I don't do things like everyone else does. If you’ve ever been part of a standard/traditional retrospective, you know exactly what that looks like. It’s a template someone pulled off the internet with a checklist of concrete tasks and a standardized form. It can really only lead to a sterile "start, stop, continue" exercise. Not that doing that type of exercise can’t be useful, but it’s not a retrospective in my view. 

It’s a framework built for HR that does not bring real insights. 

When you are in the trenches doing the day-to-day work, time moves differently. The demands and the fires rush by so fast that your baseline shifts without you having time to notice. Yesterday’s massive growth edge quietly becomes today’s new normal because you’re focused on the next thing that needs your attention. You miss the opportunity to actually see your progression, because your memory is naturally clouded by whatever challenge you are currently facing. 

So, in my retros, we don't go over a literal checklist. And my job is not to ask a leader to try and figure out what they’ve done over the past twenty-six weeks. 

Instead, we hold up a mirror that is fully backed by data.

Ahead of a retro, I take all of our session transcripts from the last six months and analyze them. I want to show my clients, with actual evidence, what their progression has been. And I want to do it from a neutral lens. Because of that, no two retrospectives look alike. 

For one client, that meant bringing a TL;DR one-pager and a literal seven-page synthesis mapping the progression from session one to the final session in that six-month span. For another, it was split into leadership progression, organizational progression, and emerging themes—the things they are finally ready to sit with only because of the groundwork they’ve already laid. And importantly, their next retros won't just copy the past format because that's what we did before. Each one is catered to the actual data. The insights I can pull from looking at the progression from session to session dictate what the framework will be. 

I do it this way because, when a leader pauses and says "Wait, am I really doing that though?", I am not just a cheerleader. I can say, "Absolutely. Here are the exact examples of it from our sessions." In my opinion, that’s how the shift really lands.

Data without context is just an unanchored story. 

True growth for a leader isn't an arbitrary metric. It looks like the messy, human work of building leadership capacity and intentional organizational design. It’s watching the data show how you moved from hesitant delegation to concrete examples of your team carrying meaningful responsibility without you directing them.

It’s seeing the evidence of you building the capacity to distinguish between capability and responsibility. Recognizing that just because you can do something doesn’t mean you have to (or “should”). 

It’s tracking the timeline of how you stopped automatically softening corrections or silently fixing things, and instead started giving direct feedback, naming mistakes neutrally, and explaining the downstream impact so your team can learn from a misstep. It’s the data of you setting and holding difficult boundaries, ending client relationships that don't serve the company, and refusing to feel obligated when old dynamics resurface. It's getting more honest about your own capacity and recognizing when the missing resource is actual space rather than another productivity mechanism.

Stepping out of the daily grind to reflect on what all of your hard work and commitment has brought to you and to your company… there’s nothing else quite like it. The energy that a data-driven retro brings is a complete shift from daily demands and problem solving. It shows the things you’ve accomplished, the ways you’ve grown over time, and most importantly that you have choice over where you head next. 

When we make time to slow down and sit face-to-face with the reality of your specific progression, the experience is pretty glorious. The emotions move from "really, I am doing that?!" to "wow, I didn't realize that!" to "omg yeah, I do see that! It actually showed up the other day when I..."

You’ll leave the session feeling incredibly seen and profoundly proud of the hard work you’ve put in. It helps you realize that you aren't just surviving the day-to-day… you are actively building something that holds.