Why You Don’t Want to Rely on AI for Hard Conversations

An executive I know asked AI to prep the talking points for an exit conversation.

The employee was leaving because they did not feel appreciated, by that executive, their boss.

(Are you smirking? I’m smirking.)

AI gave back what you would expect, reasonable advice without real context. Thank them for their service. Wish them well. Ask for closing feedback.

The exec walked into that exit interview with the list and began checking of the tasks.

Then the employee let loose. Years of feeling unappreciated came blasting out towards the exec.

The exec was blindsided, and it was avoidable

The exec was blindsided. They stuck to their own point of view, never considering the exiting employee's POV. They walked in expecting to run through a list, check some boxes, wish them well and move on to the next item on their to-do list.

They delegated their thinking to AI not realizing AI can’t do humanity skills. It doesn’t have full context. And it can never replace the uniquely human connections that we need in our relationships, whether they’re on solid foundation or so bad that people are leaving the team.

They had outsourced the thinking, not just the wording. They treated a hard human moment like a task on a to do list, and a person who had served the company well for years handed them the bill.

Yes, use AI to prepare but don't stop there

 Use AI. Use books, coaches, whatever helps you prepare. Then walk in knowing you are dealing with a human being who has a perspective and a memory.

AI can provide insights and polished scripts but it will still be hollow without your human context.

And the person across from you feels it immediately. AI isn’t the one who sees their face fall, their jaw drop, their eyes tear and their fists clinch. That’s you. It cannot sit across from someone and build understanding in real time. That is your job, and no tool is coming for it. (And, isn't that cool?!)

Honor that interaction by preparing thoughtfully and authentically.

Ask yourself some honest questions before your next hard conversation.

• Are you using AI to prepare, or to escape? 
• How would you want to be treated in this situation? 
• What do you know that AI won’t ever understand?
• What are thing POVs that you’re blind to at the moment?

A flawless script is a hollow one

You have a performance conversation on the calendar and you dread it, so you have AI write the words for you. Professional. Correct. Nothing you can get in trouble for. It comes back polished and hollow, and if you read it as written, the person across from you feels your disinterest before you finish the first paragraph. 

We are all getting good at spotting sloppy AI, and it gets worse when the message is carrying feeling. Studies of workplace communication have found that when managers lean on AI for personal messages, employees rate them as less sincere.

 In 2023, an office at Vanderbilt sent students a message of comfort after a campus tragedy elsewhere, and the message carried a line noting it had been written with Chat GPT. Students were furious. A message about community and care, generated by a machine. Even reviewed and edited, it felt wrong, because it was. 

You can't prompt for the unexpected convo

Then there is the conversation you never scheduled. The conversation that starts in a hallway, or the meeting that turns tense. No time to prompt anything. If you have not built the muscle, you freeze, or you overcorrect and say the thing you cannot take back.

Have the conversation only you can have

AI can draft a flawless script. It cannot deliver it. It will not look someone in the eye and watch their face fall, and it will not keep the conversation going with kindness and candor when the plan falls apart. You prepare. You breathe. You lead the conversation.

 Go deeper in the episode

Watch this week's Mini but Mighty℠ Leadership Lesson on YouTube: How to Prepare for a Hard Conversation

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Start with yourself. Have the conversation only you can have. Lead yourself. Then lead others. Be a Boss.

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Hard conversations are a skill and they can be taught. Our courses go deep on the tools:

Navigating Conflict in the Workplace

The Ultimate Guide to Leading your 1x1s

Communication & Candor Across the Org

And Boss at the Helm builds the skill across entire manager populations through live workshops and the Helm Leadership Essentials℠ cohort program. Start a conversation at bossatthehelm.com/contact.