conversations to have with your team

4 UGLY Conversations to Have With Your Team Before Year End

The second half of December is a great time for recognition, celebration, white elephant gifts and other fun. Yes, yes, please do all that, but don’t stop there. The best holiday gift you can give your team is to “own the ugly.” To help your team have the tough conversations they’re longing to have; to stare squarely in the face of what’s not working and clear the decks for a remarkable 2017. Here are four conversations to help your team think more strategically.

Own the Ugly: 4 Conversations to Have With Your Team

The other day I was facilitating a 2-day offsite strategic planning retreat for one of my start-up clients. We’d designed a “speed-generation” problem-solving session where groups rotated through stations to identify the ugly issues that needed to be addressed and worked on real solutions.

Within 60 seconds of the first rotation, one group listed every “efficiency” tool their company was using to make “work easier” and then created two columns on their easel sheet–a  “should it stay or should it go” vote.  Everyone who rotated through their station got a vote and indicated what workgroup they were in. By the end of the session over half of the tools were “voted off the island.” The chairman raised his eyebrows, but took the lead in initiating a curious conversation.

What they found was that the tools they had selected one at a time for good reasons all made sense, but the requirements to keep everything up to date were driving people crazy.

I’m convinced that 40-minute conversation (which everyone gladly stayed beyond our promised closing time to continue– even though the beer was being poured in their next agenda item…a holiday happy hour right outside the door) will save them thousands of hours of frustration next year.

“Why didn’t you raise this before?” Well, “No one asked.”

Own the Ugly. Make it safe to talk about what’s not working. It’s getting talked about somewhere. Best to lift it up, stare at it, vent if needed and then figure out what must happen next.

4 Ways to Own the U.G.L.Y.

Here are four ugly conversations to have with your team. Ask, and then really listen.

U– What are we Underestimating?

Competitive pressures? New technology? Risk?  The destruction that new manager is doing to our culture? The opportunity that we “don’t have time for?

G– What’s Gotta Go?

What are we doing now that doesn’t make sense anymore? What processes are more habit than value? What meetings are wasting our time? What’s gotta go for us to be remarkable?

L– Where are we Losing?

Where are we still under-performing despite our best efforts? Why? Who’s doing it better? How?

Y– Where are we missing the Yes?

What must we say “Yes” to in 2017? What new opportunities are yearning for our attention? Where must we invest more deeply?

Teams admire managers who “own the ugly.” Winning Well managers have the confidence and humility to go there– to start the conversation, and then listen deeply to the solutions.

Posted in Winning Well 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. How great that the start up you ran the offsite for was willing to not only have the meeting but actually made decions based on the feedback from the people who were present. Tools not working? Gone. I’ve worked for my fair share of leaders who were so afraid of any critical feedback that they’d either avoid or defend but never really embrace the employee’s ideas, input and perspectives.

    Hope organizations everywhere are having those UGLY conversations thanks to you!


    • Thanks so much, Alli! I love it when teams can move quickly to make changes to make their work easier and more impactful.

  2. I love the idea of an UGLY conversation! I think the way you set up the process for leaders to think and then own their decisions is fantastic. It sounds like your offsite was so successful due to a great deal of trust on the team and respect for each other’s suggestions and opinions.

    Well done Karin!

    • Terri, Thank you! Yes, the team has built a lot of trust… and done a good bit work around eliminating “diaper genie” feedback and telling one another the truth.

  3. Great post Karin. I’m a big fan of the “G” – what’s gotta go. So many times I hear, “we’ve always done it like that.” Just because a process has stuck around doesn’t mean it needs to stay.

  4. SUCH an important process! It is important to clear the air and make sure all team members have the same line of sight about what the challenges are and what can be done better. I would even see this as a best practice for a quarterly process as it makes more sense to create strong open dialogue around this rather than traditional operational reviews. This really gets to the core of what a team should be working towards! Love this post! Happy Holiday Karin!!

    • Thanks so much, Jonathan! I agree this would be great as a quarterly cadence. Happy holidays to you as well.

  5. Love this article Karin!

    “Own the Ugly. Make it safe to talk about what’s not working. It’s getting talked about somewhere. Best to lift it up, stare at it, vent if needed and then figure out what must happen next.” As you point out, it’s getting talked about anyway so why not be a constructive part of the conversation? One of the biggest problems I see is that no one wants to call the baby ugly…this is especially true if leadership has ownership in the project…it’s vitally important for leaders to set the tone and bring it up before it ends up as water cooler chatter…

    • LaRae, Thanks as always. You raise a good point… it IS getting talked about somewhere. So much better to have a healthy conversation about it.

  6. Great post Karin – We have been raving fans of a company for 12 years. Investing heavily in their products, merchandise and recruiting others to do the same. We recently had an experience that caused us to communicate with every level of Customer Service in the organization and finally with the CEO. They refused to own the ugly. Our investments and communication to others about them have been completely altered.

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