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My boss told me I needed to have a talk with one of my employees. 

The boss was mad at the employee for not meeting her expectations while I was out on vacation. Honestly still not sure why my boss asked me to talk to her if I wasn’t involved but I was asked so I did it.

I hate having conversations like this.

My top strengths on Gallup’s strengthfinder are harmony and empathy so I naturally ignore conversations like this at all costs.  I knew I had to have this conversation.  So what did I do?  I made it a conversation and not a “we need to talk” moment.  I was not confrontational or accusatory.  There was a miscommunication between what was expected and what was not expected.  The boss was not clear on what was wanted and the employee didn’t ask for clarification when confused.  And I got to be in the middle – using empathy and harmony to solve the situation.

There were some difficult conversations I’ve needed to have that I didn’t know how to approach.  Here is what I’ve done to prepare for conversations I don’t want to have.


1.  Think of the other person’s feelings.  Old but good simple advice…Put yourself in their shoes.  If you were on the receiving end of this talk, how would you want someone to approach you? 

2.  Read up on or google articles that address specific conversations you may need to have.  The advice is out there such as how to tell a coworker they smell.  I recommend the book “100 Tough Conversations To Have With Employees” by Paul Falcone, even if you have no employees.  If you work with people, this book helps.  There are tips on how to deal with someone’s attitude problem or if a coworker is on the phone all day.  The book is geared towards managers, but the tips apply to coworkers as well.  

3.  Be open to and listen clearly to what the other person has to say.  They may have valid points that you need to hear.

4.  Don’t have the conversation when you are feeling emotional.  If you are really angry and think you may yell or if you feel like you could cry, take some time to cool off and ride that emotional wave.  If it needs to be addressed immediately, just tell the person you need a few minutes to collect your thoughts.  I’ve also said, “Hang on I need to run to the bathroom before we continue”.  In those few minutes, do deep breathing and think about the steps above. 

5.  Write a really emotional letter to that person on paper (You won’t be sending it).  You just write without thinking and just get those thoughts out.  If you want to say ‘Jane Doe you are a f*ck)ng B and I hate you and you make me feel like sh&t’, then write that. Keep writing until you start to feel better. Ignore punctuation and spelling. Then tear up the paper and get rid of it.  Trust me, this works wonders.

6.  Ask a friend to practice with you if the conversation doesn’t need to be had immediately. Saying it out loud always helps to make sure you are using the appropriate tone, plus the friend may have tips such as slow down or get to the point.

7.  Get it over with.  You don’t want to spend time worrying about it or wait so long that it’s too awkward to bring up.  Just do it and you’ll be happy you did.

Tell me some of the difficult conversations you’ve had and how you handled them. Share this with any friends who may dread these conversations too.

Written by Lisa

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