How to Start the New Decade in Deeper Conversations

How to Start the New Decade in Deeper Conversations

As we start a new decade, what if you took a minute to have some deeper conversations with your team? In addition to your kick-off meetings and goal setting sessions, what if you also paused to have a deeper conversation to build trust and connection, and inspire one another to something bigger?

I’ve designed this conversation starter to help you go a level deeper with your team.

Ways to Use This Tool

  • Ask each team member to complete one section of their choice to start your deeper conversations. Note: Giving them a choice enables them to pick the conversation they are most inspired (and feel confident) to have.
  • Complete one of the sections yourself as well and be prepared to discuss (your team needs to know you’re willing to be vulnerable too).
  • Have a mutual exchange of sharing your responses in your one-on-one developmental discussions or as part of a teambuilder or staff meeting.

Deeper Conversations to Help Your Team B.E.C.O.M.E. More in the New Decade

Have each person pick one section (e.g. Boldness, Openness, or More) and answer the questions before coming to your one-on-one or team session. This will work best if people have had a chance to think through rather than feeling put on the spot. Of course, now that you get the gist, feel free to modify and make up your own questions. If you do, I’d love to hear them.

B- Boldness: Moving Courageously
  • What could you accomplish this year if you had unlimited resources? How can you accomplish something similar under your current constraints?
  • Where (and with whom) are you playing it safe? What is that costing you?
  • What dreams are you saving for later? Why?
E- Energy: Igniting Passion
  • When, where, and with whom do you feel most alive?
  • Which aspects of your work exhaust you?
  • What will you do to renew your energy this year?
C- Callings: Connecting to Bigger
  • What work would you pursue, even if you weren’t paid?
  • Who most inspires your professional life? How can you attract more people with those qualities?
  • Which of your gifts lie dormant in your current role?
O-Openness: Staying Open to Possibilities
  • What possibilities are you ignoring?
  • How and where will you find creative inspiration?
  • How will you invite input and feedback?
M-More: Seeing Bigger, Broader, and Giving More
  • How will 2020 be categorically different from last year?
  • For what do you most want to be known?
  • What new contribution are you meant to offer?
E-Execution:  Envisioning Breakthrough Success
  • What could you do to make this the best year of your career?
  • Who else can engage to support you?
  • What could get in the way of success?

Other Resources to Have Deeper Conversations With Your Team

4 U.G.L.Y. Conversations to Have With Your Team Before Year End

7 Icebreaker Questions to Melt Frustration and Build Trust

4 Workplace Resolutions Your Team Can Make

Posted in Communication and tagged , , , .

Karin Hurt

Karin Hurt, Founder of Let’s Grow Leaders, helps leaders around the world achieve breakthrough results, without losing their soul. A former Verizon Wireless executive, she has over two decades of experience in sales, customer service, and HR. She was named on Inc's list of 100 Great Leadership Speakers and American Management Association's 50 Leaders to Watch. She’s the author of several books: Courageous Cultures: How to Build Teams of Micro-Innovators, Problem Solvers, and Customer Advocates (Harper Collins Summer 2020), Winning Well: A Manager's Guide to Getting Results-Without Losing Your Soul, Overcoming an Imperfect Boss, and Glowstone Peak.


  1. Great tool! Thank you!
    Do you know of any schools or school districts using this tool with principals, teachers, even students? and If so, how are they using it?
    Again, thank you!

    • Kelly, Thanks so very much. I just developed this tool for some of our clients to use as they start the new year so it’s hot off the press. We have used our Own the U.G.L.Y. tool with educators (link at the bottom of the post) and they have found it very useful.

  2. I have saved this one for reflection. Karin, this is excellent. I can already tell that, when I go over this, your questions will get right to the heart of things. Self-evaluation can be confusing, because it is so open-ended. Thank you for questions that will help me focus!

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