Productivity Coach’s Corner: 3 Challenging Conversations for 2022

There undoubtedly will be more than a single topic or theme for each conversation, but take them one at a time.

It is easy to feel overwhelmed. I am right there with some of you. Though this column is titled “The Productivity Coach’s Corner,” I am here to humbly report that making it through the last couple of years has been challenging. Sure, I want to sit up straight, open my journal, and make a to-do list. The thing is, when I did this earlier today, I stared at a blank piece of paper for what seemed like minutes. I then sat back and asked, “What could I write for now?”

The next thing I knew, my pen moved across the page, left to right, top to bottom. Some sentences, fragments. Other sentences just went on and on. It seemed that the edge of my mind and the beginning of the paper merged; I let myself see what I was saying to myself. And that is when I identified three challenging questions:

  1. What do I want?
  2. What do you want?
  3. What do we want?

It is important to note that there undoubtedly will be more than a single topic or theme for each conversation, but take them one at a time. It’s easy to get overwhelmed—aka stressed—if you try to think, write, and talk about all the things at once. Instead, decide to use the “for now” approach on a single topic at a time. By allowing yourself to focus on writing things that are on your mind “for now,” you might feel a reduction in the pressure or stress of wanting to write the best or the right things. Here are some ideas to get you started.

Question #1: What do I want?

Start by giving yourself a time range. Are you a big-picture, future-casting kind of thinker? Maybe you go out a full 12 months, at least six. Start by making an “out-of-order, write-it-as-you-think-it” inventory of whatever comes to mind. If you tend to think more short-term, make it OK to write anything you think of. Personal or professional; big or little; possible or probable. This is not a to-do list or a commitment to do anything. Instead, it’s you giving yourself the gift of your attention, letting yourself be vulnerable with the most important person on your team: you.

Question #2: What do you want?

Before you ask someone that question, you need to have gone through the process yourself. And when I say “go through the process,” I mean mindfully asking yourself the question you’re going to ask someone else. When you sit across from someone—or meet with them via phone or video—and ask them the question, “What do you want?” you want to feel empathy for how challenging a question that can be. How do you build that empathy? Notice what comes forward FOR yourself when you ask that question OF yourself.

Note: When you do talk with someone, and they are sharing their hopes, dreams, fears, and goals, challenge yourself to resist the urge during that conversation to fix, educate, or even mentor. Use that discussion as a reason to follow up with them in the weeks and months to come. When you practice listening, and they practice being heard, it opens the door for further conversations to continue building on possibility and opportunity.

Question #3: What do we want?

How many of these conversations will you need to initiate? Certainly, some at home and several at work. There will be people who hesitate to engage in this conversation and others who will tell you they’ve been hoping you’d bring it up. Again, remember how challenging it can be to focus on a topic at a time. Together, share what you see and feel as you look out over the weeks and months to come. Then, at the end of that conversation, make a pact with one another to check in on, and help, one another.

As you embark on yet another trip around the sun, make it easier on yourself and others by sharing honestly, vulnerably, and completely. Future you will be thankful you did!

Dr. Jason Womack
Dr. Jason W. Womack ( is an author, TEDx speaker, and leadership coach working with organizations as they re-imagine not just how people work together, but the way colleagues both take care of AND challenge each other. His programs help people stress less, focus more, and achieve greater levels of success…as defined by each individual who contributes to the organizational mission. His books can be found at Amazon: