Leadership Lessons: End of Year Planning, OKRs, and What’s Next

As a CEO, one of my favorite times of the year is End-of-Year (EOY) and departmental planning. Honestly, it’s like my Super Bowl—but with spreadsheets instead of touchdowns.

All year long, we’re tweaking things, solving problems, and chasing opportunities while keeping an eye on the big picture. EOY reviews are where it all comes together. Did we crush it? Did our decisions pay off, or do we need to rethink some strategies? This is when we pause to look back, celebrate the wins, and learn from the detours (and, let’s be honest, some of those detours were… creative).

The best part? The alignment that just happens during this process. No arm-twisting needed—everyone gets on the same page naturally. It’s a magical moment when the team’s energy and focus align, and you can practically see the growth we’ve achieved together.

OKRs are the backbone to a strong strategy

A big player in all this is our OKRs (Objectives and Key Results). These little gems are the backbone of our strategy. They help us aim high and track what really matters. During EOY, we get to dissect them: Were our goals bold enough? Did we measure the right things? And most importantly, did we move the needle? This review sets us up to do even better next year.

Speaking of next year, setting new OKRs is where the fun really begins. We take everything we’ve learned—the good, the bad, and the “what were we thinking?”—and use it to map out our next big moves. This part is all about teamwork, making sure every department’s goals align with the company’s mission and fit together like pieces of a puzzle. When everyone sees how their role contributes to the big picture, it’s like lighting a motivational fire.

Participate, Don’t Facilitate

One of the most important things that makes departmental planning successful for me is the ability to participate rather than facilitate. Stepping into the room as an active contributor allows me to focus on collaboration and engagement, rather than trying to steer the conversation. It’s a refreshing change of pace that leads to some of the most insightful and productive discussions of the year.

Another key recommendation? Never miss these meetings throughout the year. Seriously. They’re invaluable opportunities to reflect, adjust, and grow as a team. And always get a facilitator. We use Crews and Co., and let me tell you, “excellent” doesn’t even begin to describe them. Their expertise ensures the conversations stay focused, productive, and impactful.

Problems Are Opportunities in Disguise

Problems, issues, and changes? They’re not just challenges—they’re opportunities. Each one carries valuable lessons, and when approached with the right mindset, they’re stepping stones to innovation and growth.

Another part of my role during annual planning is crafting the right message—one that captures who we are, where we’ve been, and where we’re going. It’s a bit of a balancing act because the message has to be real and honest, but also inspiring enough to keep the momentum going. Acknowledging our hard work while giving us the push to aim higher? That’s the sweet spot.

We’re not just planning once a year, either. Quarterly planning plays a key role in keeping us agile and aligned throughout the year. It’s like the halftime huddle that ensures we stay on track, adjust our plays, and move forward with confidence. But we don’t stop there. We check-in weekly to ensure we’re continuously making progress, staying focused on the right priorities, and pivoting in real-time based on the value delivered. These quarterly  and weekly check-ins make the annual planning process even more effective because we’re already in a rhythm of reflection and realignment.

Celebrate, Reflect, Repeat

EOY planning isn’t just about data and goals. It’s about people. It’s about celebrating the grit and determination that carried us through the year. Whether it was smooth sailing or a rollercoaster of challenges, this team stuck together. And now, we’re gearing up to do it all over again—but this time, we’re coming in stronger.

And let’s not forget to celebrate the milestones! Sure, it’s easy to get caught up in what’s next, but taking a moment to recognize what we’ve accomplished is huge. It’s a reminder of what we’re capable of when we focus, collaborate, and give it our all.

EOY planning is also a peek into the future. It’s exciting to imagine the growth ahead—not just in numbers, but in how we’ll evolve as a team and as a company. We’re not just setting goals; we’re setting the tone for how we want to show up and make an impact.

So here’s to looking back, learning, and gearing up for what’s next. Let’s make this next chapter the best one yet!