The Halfway Reset: Maximizing Mid-Year Check-ins (Issue #39)
Strategic conversations for second-half success plus the reset all leaders need
📌 Tip of the Week
Here are some important June reminders:
All Month Long - Celebrating Pride Month & Diversity
June 6th - National Donut Day
June 15th - Fathers Day
June 19th - Juneteenth
June 21st - Summer Solstice (longest day of the year)
Want to keep up on key dates throughout the year, get your hands on the free leadership calendar template!
Quote of the month:
“Success is not final, failure is not fatal: It is the courage to continue that counts” —Winston Churchill
It’s that time (again) for a mid-year check-in!
How to make the most of your halfway point conversations
We've officially hit the halfway mark of 2025. The fresh energy of January has faded, December feels distant, and your team is deep in the everyday rhythm of execution.
This is precisely why mid-year is the perfect moment to pause, realign, and reset.
Mid-year check-ins aren't just another calendar obligation, they're a strategic opportunity to ensure everyone is moving in the right direction with clarity and purpose.
When done thoughtfully, these conversations can reignite motivation, course-correct challenges, and set the stage for a successful second half.
Here's how to transform your mid-year check-ins from obligatory meetings into meaningful catalysts for growth:
1. Preparation is non-negotiable
The quality of your mid-year conversations directly reflects the quality of your preparation. Both you and your team members should come ready with substance, not just sentiment.
Leader prep work: Review your notes from previous one-on-ones, revisit Q1 goals, and identify patterns in performance. Look through your calendar for the past six months—what projects consumed most of your team's energy? What unexpected challenges emerged? What wins deserve recognition?
Also, ask team members to prepare by reviewing their own calendars, completed tasks, and project milestones. This creates shared ownership of the conversation and prevents that dreaded "put on the spot" feeling.
2. Balance the rearview mirror with the windshield
Effective mid-year check-ins strike the perfect balance between reflection and projection. Start by acknowledging progress. The goals achieved, obstacles overcome, and growth demonstrated. This isn't just feel good fluff; it's establishing a foundation of accomplishment before pivoting to what's next.
The magic formula: For every look back, include a look forward. "I've noticed your project management skills have significantly improved since January. How might you apply those same organizational approaches to the cross-functional initiative coming in August?"
3. Make it a dialogue, not a monologue
The most impactful mid-year check-ins feel like a collaborative exploration rather than a performance evaluation. Research from Betterworks shows that companies adopting continuous performance feedback outperform competition by 24%. This isn't surprising—humans crave regular, meaningful feedback.
Conversation starters that work:
•"What's been most energizing about your work these past six months?"
•"Where do you feel you've had the biggest impact?"
•"What obstacles keep coming up that we should address together?"
•"How aligned do you feel your daily work is with your bigger career aspirations?"
4. Create clarity through specificity
Vague feedback leads to vague improvements.
Instead of "you're doing great with clients," try "the way you handled the pricing objection with the customer account showed remarkable emotional intelligence and negotiation skills."
Remember, the goal isn't just to make people feel good, it's to help them understand exactly what's working so they can intentionally replicate those behaviors.
5. End with actionable next steps
The true test of an effective mid-year check-in isn't how it feels in the moment—it's what happens afterward.
Before wrapping up, both you and your team member should articulate your top two takeaways and specific actions you'll take as a result.
And, don’t forget to document these commitments and revisit them in your regular one-on-ones. This creates continuity between your mid-year conversation and day-to-day work.
When approached with intention and care, the mid-year conversations can be the reset button your team needs to make the second half of the year even stronger than the first.
Wellness Corner
The reset is just as important as the start
June marks the halfway point of our year—a perfect moment to check in not just with your team, but with yourself.
While January gets all the attention for fresh starts, this mid-year moment offers something even more valuable: the wisdom of experience combined with plenty of runway ahead.
This month, we're embracing the theme: "The reset is just as important as the start."
The middle of the year often brings a unique form of fatigue. The initial enthusiasm has settled, routines may have become ruts, and the finish line still feels distant. That's precisely why this moment matters most for your wellbeing.
A reset doesn't mean radical change. Instead, think of it as a gentle recalibration, a chance to ask yourself some important questions:
•Are you getting enough restorative sleep, or just enough to get by?
•Have your movement practices become negotiable when the calendar gets crowded?
•Are you protecting your boundaries around work, or have they slowly eroded?
•When was the last time you did something purely because it brought you joy?
Research consistently shows that leader wellbeing directly impacts team performance. When you're operating from a place of depletion, everyone feels it. Conversely, when you're grounded, present, and taking care of yourself, your team benefits too.
Until next time, stay well
~Colleen