For busy leaders, June seems to appear out of nowhere. Is it mid-year already?! Your calendar is full of performance reviews and checklists, but are your mid-year check-ins setting you up for success?
To be sure, take time to reflect on your check-in process in 5 key focus areas. If your mid-year check-ins encourage mindful reflection and improved communication, your process is serving you well. If you’re getting blank stares and blank spaces, it’s a good time to make adjustments.
Check In with Yourself
There’s a good chance your schedule is stacked this season: priority updates, briefings, and check-ins are due across teams and departments. It’s tempting to put yourself on the back burner “in service to” your team or organization. But that puts you at a much higher risk of burnout and reactivity.
Make time during the mid-year push to check in with yourself. Here are some of our favorite check-in questions leaders can use for self-reflection and introspection.
- Have I been leading with principles I committed to in January?
- How are my actions (and my communication) shaping the workplace culture?
- What issue, challenge, question, or conflict have I avoided addressing—either within myself or on my team(s)?
- What’s one leadership habit I meant to shift that I’ve ignored or let slide?
- Am I more or less motivated than I was at the start of the year?
It only takes a few minutes to think through one or more of these questions and come up with actionable ideas.
Pro Tip: Want your mid-year commitments to stick? Reflect on paper. Handwritten notes are a practical way to unplug, and help retain information more readily than you do when you type
Check In with Your Team
Checking in with your team is an essential responsibility of effective senior leaders. To keep people engaged and at ease, make check-ins as collaborative as possible. Check-ins are an exchange of ideas, information, and updates, not a top-down way for leaders to keep tabs on their direct reports. Questions you ask should reflect this open mindset. For example:
- Which results are you most proud of this year? Where could you use more support?
- Do you feel our communication has improved, stayed the same, or declined in the last six months?
- What should leadership stop doing, start doing, and continue doing to bolster your success?
- What adjustments should we make to your SMART goals as we head into next quarter?
- Have any of your professional development goals changed or evolved?
Pro Tip: Teams who feel listened to are more engaged and productive, and their morale is consistently higher than people who feel ignored. When planning one-on-ones and check-ins with your direct reports, allow time to pause and pivot as needed.
Check in with Your Peers
Keeping cross-functional collaboration on track through the mid-year rush isn’t as impossible as it feels. It can be done with a framework for clear communication, streamlined information, and regular follow-up. You don’t have to reinvent the wheel. Try using the Role-Actions-Results (RAR) framework. Have each member of the cross-functional team answer the following questions:
- What’s my role on this project?
- What actions am I taking as part of my role, in order to reach our goal?
- What results have I gotten so far?
Pro Tip: Agree on a tool or platform from which to share this information Don’t forget to build follow up into the process (i.e. “Let’s share our feedback in the project Slack channel and follow up in two weeks). If possible, automate whatever parts of the follow up you can.
Check in with Your Leaders
“Communicating Up” is easier when you’re well-prepared. Before meeting with your boss or manager, block out some time to get ready. Think through the questions they’re likely to ask. Review performance data for yourself and your team so your questions/feedback are specific. Asking your manager thoughtful questions can ensure they’ll be ready to support you and your team the rest of the year. One or more of these may enhance your conversation:
- What new resources or tools are available for professional development?
- Would you consider shifting more resources to this area in the next [time frame]? [If goals weren’t met on a project.]
- Do I need to make any shifts in my leadership or communication to better support organizational success?
Pro Tip: If something feels difficult to discuss, practice talking through it. You can do this on your own, with a coach or therapist, or with a trusted friend.
Check in with Your Clients
Touching base with clients/customers during mid-year check-ins could give you valuable sales or customer service insights. The medium you use will vary based on your customer base. They can differ from typical customer satisfaction questions, focusing more on maintaining client relationships and building trust. Questions like these might prove useful:
- How have your business goals shifted since the beginning of the year?
- If you could remove one roadblock or solve one problem for your team, what would it be?
- What would you take off your plate this quarter, if you knew it would still get done?
Pro Tip: Automation tools are helpful, but make sure any check-ins you send are personalized enough to get answered, opened, and/or engaged with. Dedicate a person/people on your team to reviewing and following up with customers as needed.
Let’s Do This More Often
If you make it a practice throughout the year, checking in won’t feel so overwhelming at the mid-point. Your needs may vary according to project scope, team availability, or department structure. But having a system for quarterly or monthly check-ins helps alleviate mid- and end-of-year stress. Improved communication and collaboration can start right now.
Start the Conversation
Stronger teams start with better conversations.
If this article sparked a new perspective, don’t let it stop here. Use one of these questions in your next check-in and see where the conversation leads.
Better communication creates better teams, and better teams create better work-life.

