Mid-Year Mirror: 5 Mid-Year Reflection Questions for Leaders

Mid-Year Mirror: 5 Mid-Year Reflection Questions for Leaders

pexels-luis-ruiz-348343-954539

Somewhere between the sparkle of New Year’s resolutions and the year-end rush of deadlines, June rolls in —full of potential, but quiet and not making a fuss. It’s not quite the beginning, and it’s not the end. It’s halftime.

And if you’ve ever watched a good halftime talk — whether in sports, business, or life — you know that’s where momentum shifts, strategies realign, and second-half victories begin.

So here’s your invitation: take a breath, take a beat, and take stock. This is your moment to reset your leadership — not because something’s wrong, but because great leaders reflect before they redirect.

Why Mid-Year Reflection Matters

Let’s be honest: January gets all the attention. I must admit, I love me some New Year vibes. The goals, the planners, the fresh-start energy. But mid-year? That’s the real MVP. It gives you space to course-correct, recalibrate, and recommit — with the wisdom of the first half of the year’s experiences under your belt.

This isn’t about scrapping everything and starting over. It’s about checking in. Are you living and leading by choice… or by chance? Are your actions aligned with the kind of leader — and human — you want to be?

Your team may be looking for direction, but they also benefit when you model reflection. Leadership isn’t just about setting the pace — it’s about knowing when to pause.

Five Mid-Year Reflection Questions for Leaders

You don’t need a retreat or a long weekend to reflect. Just 15 quiet minutes, a cup of coffee, and the willingness to be honest with yourself. Try starting with these:

  1. What’s working — and how can I do more of that?
    What’s felt energizing, effective, or aligned this year? What got you the best results? Double down on that.
  2. What’s not working — and what needs to change?
    Where are you stuck, drained, or off-course? Consider what you might need to release, rethink, or delegate.
  3. Where have I grown so far this year? Please, for the love of all that’s holy, give yourself some credit. Growth doesn’t always look like fireworks — sometimes it’s subtle, gritty, and hard-won.
  4. Where am I showing up as my best self — and where am I just going through the motions?
    Leadership is more than what you do — it’s how you show up. Check your presence. It’s much easier to do with my brief self-assessment.
  5. What do I want the second half of the year to feel like?
    Not just what you want to achieve, but how you want to feel — focused, connected, light, bold, grounded? Not to sound like Captain Obvious, but status and achievement are no replacement for physical health, mental well-being, or relationships.

Ready to Reboot? Choose One Thing.

Resetting doesn’t require a grand reinvention. Sometimes it’s as simple as returning to something you’ve let slide — a healthy boundary (Yikes I’m raising my hand), a morning ritual, a leadership intention.

As you reflect, try this: choose one thing to recommit to. Something that brings clarity. Energy. Purpose. Let that be your anchor for the months ahead. If you’ve read my book Live and Lead by Choice, Not by Chance, you know that I talk about choosing three words for the year (AND if you haven’t picked up my book yet, what exactly are you waiting for?). If you’ve done this, go back to your three words – or heck, add a new one based on your reflection. Communicate it to your team if it’s relevant. When you lead with intention, it gives others permission to do the same.

Your Next Right Step

You don’t have to figure everything out right now. But you do get to choose your next right step.

Mid-year isn’t a checkpoint to judge how “on track” you are. It’s a gift — an opportunity to be more present, more intentional, and more aligned with who you’re becoming.

You’ve made it this far. Take a moment. Take a breath. Then lead on — not just with direction, but with reflection.

Photo by Luis Ruiz