Stop Winging It: 3 Steps to Transform Your Check-Ins
Your manager/employee check-ins are an essential leadership tool you should be using to build a foundation of trust and communication with your team. Stop winging it, and bring a leadership mindset to your check-ins—whether you’re the manager or the employee.
Step 1: Define Success
A meeting without clear desired outcomes is a meeting without purpose. Before your one-on-ones, identify your success metrics. What are you hoping to achieve in the meeting? It’s only once you have that clarity that you’ll be able to structure the meeting in a way that gets you there.
If you’re the manager, you can also experiment with having your team members define success for the meeting. Encourage them to take ownership, but make sure that they don’t just take ownership of “winging it.” Give them a simple framework. Our favorite is to get clear on what you want the other person to know, feel, and do by the end of the meeting.
Experiment with different ideas and get feedback from your employees; every employee has different needs. Consider which topics make sense on a weekly basis and which set you up for longer term conversations. Depending on the frequency of your check-ins, you will likely find that even if you want to, you won’t be able to cover every single topic at each meeting. The more you can step outside of what has likely become a default for both you, the better served everyone will be.
Most check-ins drift into the same tired patterns and scripts:
- Light chatter: “What’s going on?”
- Project updates: “How’s project X?”
- A half-hearted attempt to help: “Anything you need help on?”
- A vague attempt to connect: “Is there anything else on your mind that we should talk about?”
- Rushed, pushed or cancelled meetings
Check-ins fall into these predictable habits because both parties show up and wing them. Clarity is non-existent. People don’t have a clear sense of why they’re there, what they should get out of the meeting, and how best to use the time. How often do you walk into these meetings with no agenda or sense of purpose? This is a wasted opportunity.
Step 2: Ask Powerful Open-Ended Questions
Too much time is spent in most check-ins updating or directing. Powerful questions demonstrate curiosity and encourage productive conversation. Use open-ended questions (questions that begin with where, when, how, and what) that help the conversation move forward. For example, instead of asking, “Any hurdles with project X?,” try, “How will you build momentum with project X?” or “What worked particularly well on Project Y that you think you can try again on Project Z?”
Here are a few great powerful questions to try:
- What would be a great outcome to achieve during this conversation?
- What makes you feel valued at work?
- What can/should/will we celebrate?
- What workstreams do you wish you could stop doing? Why?
- What would you like feedback on?
- Where would you like me to let you experiment and learn?
- What’s left unsaid?
Consider the purpose of your next check-ins and what powerful questions you might ask to help you get there. For more ideas our
Inspired Check-Ins card deck
contains over 90 questions like these that can help you transform your Manager/Employee check-ins into truly meaningful touchpoints.
Step 3: Make Your Employees Feel Seen, Heard and Understood with Deep Listenin
Listening is one of the most underrated skills of managers, especially first-time managers. Many first-time managers think they should have all the answers, so they talk a lot and offer advice or solutions. But often, employees don’t want a solution, they just want to be seen and heard.
No matter what, you need to show a willingness to listen, ask follow up questions, and acknowledge what you hear. Create a space where your employee knows you won’t judge, jump to conclusions, or tell them what they “should do.” This will make them comfortable coming to you, asking directly when they want your advice, and growing with you.
What’s Next?
If you want to provide support and clarity to your team, stop winging it and start having one-on-one check-ins with purpose. Whether you take the reins or you empower your team members with tools and ideas, your meetings have the potential to be meaningful opportunities to connect.
On March 19, 2026 we’re hosting a free webinar, Lead With Clarity: Check-In on Your Check-Ins, join to bring more intentionality and structure to these critical conversations..
On March 26, 2026, we’re hosting a hands-on workshop to explore the same concepts in even more depth.
Missed the events? Join the
Wolf & Heron Influence Library to access webinar recordings as well as many practical tools that’ll empower you with clearer communication, better meetings, and stronger leadership.
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