Eat the Frog and other strategies for handing tough conversations by William Carozza


Tough conversations


A teacher who has known me for many years, knows that I appreciate my job because of the energy I receive every day from teachers and students. Yes, Sunday night is not always easy on the soul but once I’m in the building on Monday morning, all is well. I avoid my office as much as possible during school time and work the job in classrooms and hallways. 

It doesn’t hurt my allegiance to the job that many members of our staff have been together for years and those that have been recently hired have melded in nicely with the family.Truly, it is all about relationships. 

Yet, in our job as building administrators, there are times when we can’t avoid the tough conversations. Good people make mistakes. Conflict can happen when perspective and personalities collide. That’s the time the Principal needs to step in and take the conflict head on. Rick Dufour has stated that Principals should confront those individuals who are not committed to the values of their team or professional learning community:

They are willing to use their authority to break down the walls of educator isolation and create new norms of collaboration and collective responsibility for student learning.

But when you’re in the midst of the conflict with people you care about, having tough conversations is one of the hardest parts of the job. I have not always done it well, but here are some things I’ve learned:

1. Eat the frog

Productivity expert Brian Tracy says that we should tackle our most difficult and important task first thing every morning. The concept is that if we can “eat the frog”, everything else will seem easy. Don’t wait for the day to go by. Procrastinating may result in your “deciding” not to tackle the issue at all. And, the conflict may fester if you wait too long to intervene. 

2. Prepare for results

I prepare bullet points for every tough conversation I have in person or on the phone. There is a natural tendency to lighten the exchange with your colleague so if you don’t plan for the result you want, you simply won’t get there.

3. Lead with the punchline 

The tendency is to begin a difficult chat with small talk to lighten the load. Writing in theHarvard Business ReviewPeter Bregman suggests that leading with the tough news will ensure that the recipient will hear the constructive criticism with clarity. 

4. Listen as much as you can

If you want the colleague to change a habit or behavior and be personally reflective, they need to know that you care about their improvement. Validate whatever response they may have…if it’s valid of course. But listen either way. 

5. Take good notes. 

A tough conversation might take unexpected twists and turns. Be sure that the meeting is documented accurately.

6. Follow up (both right after and set date for next meeting)

Long term success is based on at least a second follow-up meeting to reinforce your message. Set a date for that meeting before the first meeting is complete.  

7. Assume good intentions

Most people want to do well at their job and truly care about professionalism. Let good intentions be the default unless you know otherwise.


There is great satisfaction in caring boldness and seeing progress as the result of these tough conversations. 

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