The One Thing You Need to Know: Beyond the Check-In

“I’m doing weekly check-ins with my team, but is there a bigger picture conversation we should be having?” – Gavin from Maryland.

Being a leader means bothering to listen. Click To Tweet

Hopefully you are having weekly check-ins with your team members – frequent conversations about near-term future work. But is that all you should be doing? What does the larger, yearly or biannual conversation look like?

If you want to show your employees that you care about them and their future careers, having a “Super Check-In” is imperative. This is the longer, more robust conversation that should happen at least once a year, or more if that’s what your employee needs. There are two types of questions you should ask:

  1. Ask them about them. What do they love about their current job? What do they get a kick out of? What are their aspirations? Their perfect job? What do they love about what they do, and where could that lead them?
  2. Ask them about their performance. What are their skills? What are their certifications? How do they feel about their present and past performance?

Once you’ve covered those two subjects, you can pull what you’ve learned into a conversation about where this team member is headed.

You’ll quickly realize that just by asking these questions and listening to the answers, your team member will appreciate your awareness and concern for them. You’ll also be able to help your employee see their own possibilities in new light. You’re helping them see what they could take with them, what they’ve picked up along the way, and what skills they should build on to achieve their best outcomes.


What about you?

Do you have bigger career conversations with your team? Leave a comment below.


  1. Darren April 10, 2018 at 6:24 AM - Reply

    “Most careers are built out of serendipitous adjacencies.” I’m going to be quoting that one.

  2. Marty Pantoja October 27, 2020 at 10:00 AM - Reply

    Convicting to be reminded of just how often as a leader I am making time to have career discussions with my staff members! Asking the right questions is important and quite frankly easy when you are being intentional about it.

  3. Amit January 18, 2021 at 9:30 PM - Reply

    This truly is an amazing way to get exactly the information needed to have a great conversation about one’s career interest and guide them

  4. Paul Nelson January 27, 2021 at 2:36 AM - Reply

    Truth! Thanks for sharing.

  5. Melanie Sage March 26, 2021 at 3:47 PM - Reply

    I was a sales manager at my previous company and I had weekly one on ones as well as bi-weekly team meetings. Most meetings were face to face, but I did have one sales rep that was 6-hours away, so that prevented the face to face interaction. This article is spot on. You can’t lead a person that you know nothing about and I believe that when you don’t get to know someone, your own assumptions about who he or she is, or what motivates he or she could be completely wrong and prevent a leader from getting the most out of that employee, or from retaining that employee altogether.

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