Clarity Break™ Thoughts for Entrepreneurial Leaders

The Quarterly Conversation – What’s Stopping You?

One of the highest impact disciplines you can practice as a leader/manager is the quarterly conversation. 

After teaching it to our clients for more than 15 years, the feedback and results are undeniable. It’s high-impact, due to the limited time it requires (one hour per quarter, per direct report) and the outcomes it produces. The outcomes are issues getting solved, improved communication, faster growth, and a stronger and healthier bond between you and your direct report, just to name a few. The math is a no-brainer. 

 The quarterly conversation is simply a one-hour, one-on-one meeting with each of your direct reports every 90 days. It’s an opportunity for each of you to share what’s working and what’s not. It’s not a performance review; it’s just a conversation. 

So, what’s stopping you? 

It might be that you don’t want to hear about any more issues or give people a chance to complain. Hopefully the following context will help, as it usually does. 

First of all, as a leader/manager, if you want to be great, you must be aware of everything your direct reports believe are issues (real or not). 

Here’s the context. Any issues that come up in the quarterly conversation will fall into one of three categories: 

  1. Ones they must solve
  2. Ones that can’t be solved
  3. Ones that you must solve

1. Ones they must solve: Ideally you want to push as many issues as possible back to your direct report to solve themselves. This is where you must coach, mentor, help, and direct them on how to solve them. This is your opportunity to create independence, not dependence on you.

2. Ones that can’t be solved: This is frankly the key point that motivated me to write this Clarity Break. These types of issues typically frustrate most bosses because they view them as whining. They can’t be solved to your direct report’s satisfaction, or it’s something that they don’t like but isn’t going to change, which leads you to feel guilty or anxious. Many of the issues on the list during a Quarterly Conversation fall in this category. Here’s what’s critical for you to understand about issues that can’t be solved or won’t change:

  • They just need a response, answer, or acknowledgment!

I know this might be hard to believe, but as a great leader/manager, you have to get good at saying something along the lines of “I hear you, and I know it’s an issue that’s driving you crazy. What I need you to understand is that the issue that you are describing exists for the following reasons [state the reasons] and it’s not going to change. I just hope you can live with it even though I know you don’t agree with it.”

As a great leader/manager, you’re going to disappoint people from time to time and you must learn how to take some grief every now and then. Knowing that will make you stronger. The truth is, most of the time the Right People in the Right Seats will say, “I understand and can live with it. Thanks for listening.”

Sometimes they will stew for a while and you have to live with some discomfort for a week or so, but they usually come around and accept it. Most not-so-good leader/managers don’t give an answer or say, “I’ll get back to you on that,” and they procrastinate—because the problem can’t be solved—and therefore they let the frustration build. This leads to a murky cloud of unresolved issues that weigh your relationship down. And it’s all because, in most cases, you are being a people pleaser and don’t want to deliver the unfortunate news.

Again, they just need an answer.

3. Ones that you must solve: Once the first two types of issues are clear and addressed, that will leave very few issues in this third type. Unfortunately, you will have to take on and solve some issues. The bottom line here, though, is to make sure you solve these issues and quickly. It’s the best thing you can do to build trust and respect with your direct report.

The quarterly conversation is one of the most impactful leadership/management disciplines we teach our clients, and I urge you to schedule your quarterly conversations with your direct reports now. Grab your calendar and schedule one hour for each direct report in the next 30 days and then every 90 days after that. You will begin to make wonderful course corrections and improvements in your relationships. It will keep getting better and better.

For a deeper dive into the quarterly conversation and to learn and master all 10 Leadership and Management Practices, order How to Be a Great Boss here.


I’d like to express my sincere gratitude and appreciation for all of your support for the EOS cause. Our growth has been exponential due to your word of mouth and passing the content along to your peers.


Stay focused,
– Gino

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