InsideOut Development

A Summer Vacation Check-In Conversation

by Michael Rutkowski


This post is a follow up to A Summer Vacation GROW Conversation.

As summer came to a close the time arrived to chat with my son about the progress we made on our special father-son “creative project.” We had decided at the beginning of summer that his goal was for us to create our own family board game. I loved the idea because it seemed like a great way to keep his mind active while school was out, and was curious to get his input on the summer because we hadn’t quite succeeded at creating our own unique board game.

Using three quick questions, I was able to have an effective conversation with him about his perspective on our progress toward his goal. At InsideOut Development, we call this type of coaching conversation a “Check-In” conversation. Asking questions gave me the opportunity to provide my son with a helpful prompt, while giving him the room to describe what was happening in his own words.

What’s working?

The first thing I asked my son was what was working as we tried to achieve his goal. He mentioned that among the two Options we chose for our Way Forward that he thought we did well playing a variety of different games to learn how other games work and what kinds of rules and conditions they use to make the game fun. Not only did he enjoy that time together, he also mentioned that we felt free to think of our own rule changes to the games we were already playing to make new versions of existing games for ourselves.

Where are we getting stuck?

We next discussed where we had gotten stuck on the way to creating our own board game. The second Option we had selected for our Way Forward was to create a chart outlining each of the steps needed to create our own game. That chart would give us the chance to think through everything we needed to do to build our plan step by step.

It is my shame and #parentinggfail to report that when I asked my son where we got stuck, he mentioned that we talked a few times about creating that chart…but never actually made the chart. Suddenly it was very clear why we hadn’t completed our game.

What could we do differently?

Lastly, we talked about what we can do differently moving forward to meet our goal. The obvious first answer was to create the chart as we had planned. His second answer was similarly insightful; my son recognized that we did a great job of finding time to play other people’s games, but didn’t schedule enough time for ourselves to work on our own game. He felt confident that with those lessons learned we could continue working on our special creative project, and that we could be even more successful working towards future goals.


In the same way that I found the guiding principles behind Breakthroughs conversations to be applicable to family life and not just work life, the principles behind Check-In conversations could also be applied in any aspect of life. Becoming more adapt at using these tools means I won’t just be a better leader at work, but can be a better husband and father to my family.

Category: GROW Model Check-Ins and Feedback

Picture of Michael Rutkowski

Michael Rutkowski is all about growth. Over his career he intentionally joined companies that make a difference in helping people and organizations grow, and has been blessed to play a driving role in three different education and coaching companies as they scaled from being startups to global leaders in the power of learning. It is no coincidence that he now serves as InsideOut Development’s VP of Marketing. He lives in Lehi, Utah with his wife, 2 children, and 2 dogs. He believes in the healing power of cooking good food, and is a competitive axe thrower on the side.

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