Navigating Difficult Workplace Conversations

business dialogue group groups leadership management navigating workplace startup team meeting workplace Oct 04, 2018


We all know that being a leader sometimes means having awkward conversations.

The great news is that with the right tools, they don’t need to leave you stumped.

Here are some tips for navigating 3 of the most difficult discussions you may encounter along the way:


SITUATION #1: Your employee shows great enthusiasm for an idea you know will not work.

Avoid: Shutting down their point of view entirely.

Try: Picking out one or two pieces that could be incorporated.

For example: “You know, I really appreciate your enthusiasm! Corporate may not see the value in this entire program, but they do like ideas on how to improve employee productivity. Let’s brainstorm around this and see what could be done.”

Read: How to Tell Someone Their Idea Sucks Without Hurting Their Feelings.


SITUATION #2: You need to deliver negative feedback.

Avoid: Focusing on the person and remain focused on the problem.  

Try: Complimenting the employee on something they are doing right.

For example: “Your work on the ABC project was exceptional; however, the delivery was late, and we now have an upset client to deal with. I will need to document this. How can I better support you in the future, so this does not happen again?”

Read:7 Tips for Delivering Negative Feedback to Employees Without Being a Jerk.


SITUATION #3: You need to terminate someone.

Avoid: Dragging the situation on for longer than needed.

Try: Leaning on your HR department to ensure you are following all processes correctly.

For example: “Unfortunately, today will be your last day with Company ABC. You have missed your sales targets for the past three months. I am sorry the situation has landed us here. Human Resources has prepared this paperwork for us to sign today.”

Read: The Right Way to Fire Someone.

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