Midyear Gut Check: 5 Questions Every Leader Should Ask Themselves Right Now

For many of us, midyear presents a natural but small break in the chaos. It’s a chance to catch your breath, regroup, and decide how you want to show up for the second half of the year.

If you spent part of the first half of the year in the “overs and unders”—overtired, under-inspired, overwhelmed, under-resourced, etc., then now is a good time to take a few moments to reflect and perhaps redirect. 

As a gift to you, I created a mid-year reset. It is designed to help you clear the noise and take a sharp, honest look at what’s working and what needs to shift for the second half of the year. 

5-Question Mid-Year Leadership Gut Check

1. What’s taking most of my time and energy right now—and is that helping move my team forward?
   This isn’t just about time management, it’s about impact. Where are you most needed—and are you showing up there?
   

2. Can my team move forward without me—or do I still need to be in the middle of everything?
   Are the leaders in your organization actually able to lead, or do all decisions tend to stall and bottleneck at you? It may be time to develop a decision ladder and focus on delegating out more responsibilities.
   

3. What important team issue or conversation have I been putting off? How has that affected the team in the first half of the year? How would facing the issue head-on now impact the rest of the year?
   Avoidance always has a cost. The longer you wait, the heavier it gets.
   

4. Where do I feel most clear and confident as a leader—and where do I feel unsure or stuck?
   Lean into what’s working, and take an honest look at what’s not. Decide if the work you aren’t excellent at should be delegated out or if the right support could help you grow into it. If certain responsibilities feel heavy or unclear, it may be time to seek outside support for insight and clarity.
   

5. If the next six months go the same as the last six, will we be where we want to be?
   Are all members of your leadership team on track together, or are some pieces drifting off course? If the current pattern holds, will your goals be met? If not, consider if you should reset your priorities, and assess if support is needed to course-correct.

Strong teams don’t just happen. They’re built through clear priorities and honest reflection. These questions help you make smart calls that strengthen your team’s direction and capacity.

Don’t go into the second half of the year without the support your leadership team deserves. Let’s set you up for what’s next with The Changemaker. Join the applicant list today.