How to Take a Difficult Teammate Out… to Lunch

sopranos paulie take out teammateEveryone has that person at their office or work location.

The difficult teammate.

The person who, if you were living in an episode of The Sopranos, you would just tell Paulie to “take out.”

Sadly, we don’t live in that world.

But you do still have options.  You can take them out… to lunch. (and if you feel the urge, make it an Italian restaurant). 


The truth is that in many cases, difficult people are just different.

And in our culture, that becomes an issue – because we are used to seeing and being validated by what we find familiar

We like what we like online in social media to ensure that we get more of the content and opinions and ideas that we like.

They make us comfortable.  They validate our perspective and have similar insights. 

They confirm us.

But difficult teammates stretch us.


I wrote in an earlier blog, about how to deal with the sandpaper person on your team, that “…often the most annoying and uncomfortable relationships we have are the ones that we most need to become better ourselves.”

It is important to challenge your ideas. 

It is important to consider other perspectives and beliefs.

And it is important to know how to take a difficult teammate out… to lunch.


So, first remember your WHY!     

Because you will benefit tremendously from better understanding that someone in your life with whom you may often disagree.

At the least it will likely soften your level of dislike toward a person you are in conflict with… and it will certainly help you to get to know a teammate from a group or background that you may have negatively stereotyped.


Okay, then next decide on WHO!

Well, that depends.  Who is it in your office or organization that you often find yourself judging harshly or disliking because of beliefs or values that are not the same as yours?

Identify that person – the difficult person you are unacquainted with beyond nodding a hello in the hallway that you need to know more about – and put their name on your list…

But be careful to NOT invite people who are clearly aggressive, rude, hateful, violent, etc.  Life is too short for suffering through a meal with someone like that! 


Good, now you are ready for the HOW!

Begin by approaching the person and saying simply that you’d like to get to know them better.

Ask if they would be interested in having lunch – and then ask if they have a place that they would like to go already in mind (as long as it’s not fast food – you want time and opportunity to talk in a nice environment)

Once you agree on the place and the day of your lunch date, send a confirmation email that lets them know you are excited at the chance to spend a bit of time together.

When you arrive (a few minutes early, of course), remind yourself before going in that it is your job to adhere to the following personal guidelines during the meal:

  1. Turn off your phone and be intentional about listening more than you talk
  2. Go in with an open mind, and remain curious, not judgmental
  3. Be honest and relatable and vulnerable so they feel safe enough to share
  4. Ask thoughtful questions about their family and background
  5. Mention any problems or assumptions you’ve had, and ask for clarification
  6. Ask if there are any questions they have about you…


Alright, so what comes NEXT?

I honestly can’t say for sure… 

What I can promise, without hesitation, is that the heavens will not open up for a host of angels to sing “hallelujah” – and no white doves will fly as you exit the restaurant.

Your discomfort will likely not disappear completely over one lunch.

Building rapport and strengthening relationships is a process that takes time.


Taking a person out to lunch is just an important first step…

It will have been a successful lunch if you are even slightly more able to relate, compromise, and collaborate with them. 

And then you can do it again… 

And after you become a bit more aware of their heroes, their highlights, and their hardships, you can even include a few of these 25 fun questions to ask.

Of course, your initial time together with this person should be used to create more understanding.  Usually, we dislike what we don’t understand because in the absence of information, we often assume the worst about people.

By taking your difficult teammate out to lunch, you will have a chance to create a valuable connection and improve communication with someone that you are depending on for your success.  


Don’t just smile mysteriously as you imagine the Soprano’s scenario.

If you truly want to be a winning teammate – take a difficult person out to lunch!


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