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  • Writer's pictureDaniel Jimenez

Learn to have difficult conversations in HR

Updated: Feb 21

Confrontation. I have learned it is a cultural thing. Some cultures naturally are more comfortable with confrontation than others. Those who are more comfortable typically do not see it as confrontation at all. Those who are less comfortable avoid it like the plague.

For those individuals, having any conversation that has the potential to get tense is delayed, filled with anxiety before it even occurs and often is less productive than it could be.


Having difficult conversations is an art form. It’s a learned behavior. Something that some are just naturally more comfortable with than others, but even those people need a little help sometimes.

Providing that help is what I’m working on this week.



difficult conversations HR

Learn to have difficult conversations in HR

In every workplace there are a myriad of difficult conversations that may need to happen on a regular basis. Examples of conversations that could be difficult include:

  • Performance conversations

  • Priority shift that renders months of work useless

  • Layoffs/Furloughs

  • Employee relations issues

  • Managing up

  • Personality conflicts


The thing is communication is the most important function in a business, especially a small business. Regardless of how uncomfortable the conversation is, it has to be had.

What I find interesting about these conversations is that, when done right, both parties typically leave feeling much better. Even when the content of the conversation is negative (layoff for example) if communicated properly, both parties can feel disappointed yet happy with the way the information was shared.

By nature, I am a very direct talker who is not conflict avoidant. I have no issue saying what needs to be said. If there is an elephant in the room, I will call it out. Over the years I have learned that being direct, but saying it in a way that the other person can hear it is crucial.






Size/Type of Business

Every week I share the size type of business I am doing this particular work in, but this topic is one that I am facilitating weekly for many clients. There are no shortage of difficult conversations that need guidance and planning.

The particular story I’m thinking about today is around a performance conversation that a leader has to have with an employee. This is a very small organization, 27 employees. The employee has been a top performer for years. They have stuck with the business through hard times, including this past year. In the last 4 months however, performance has declined drastically. In addition to the decline in performance, their behavior towards others has become aggressive if they engage at all. Emails are going unanswered, deadlines are being missed and efforts to correct the behavior to this point have failed.

Exacerbating the issue is that while the business went remote in March, they have since opened back up. They allowed employees to continue working remote if they felt more comfortable doing so. This employee has chosen to do so. When asked if they could come into the office for a meeting so these issues could be discussed in person, they have refused stating safety concerns. This is in their right to do so considering everything on, but has made having these conversations a bit more difficult. I’m a big fan of in-person for difficult conversations whenever possible and it just hasn’t been possible this time.





workplace difficult conversations





Why This Work Matters

My specific involvement in this process is to talk the leader through what needs to be said and, maybe more importantly, how to say it. We have spent a bit of time thinking about the employee’s personality and ways we can frame information to ensure he hears it. We have to say what needs to be said, but in a way that he can hear the words and digest them.

I always say that what you are saying can be absolutely right. You can have every right to be saying what you are saying. But if you do it in a way that make the other person stop listening or shuts them down, your conversation will not be effective.

Having difficult conversations has become taboo in so many workplaces. I think our clients find it comforting to have someone they can call and talk this through with before having the conversation. I always encourage pre-planning these things to avoid the “bad news drive by” feeling where the leader just dumps a bunch of bad news on an employee and then keeps going on to the next thing. This is a process and when followed, the conversation and it’s effectiveness are much greater.



Difficult Conversation Training

I have a entry level leadership training course designed around having difficult conversations. It takes leaders through the exact process I use and has them practice having a difficult conversation with an employee.

The training is 90 minutes long, conducted live via Zoom. It is designed as a Management 101 course, but I have had more senior leaders say they have picked up helful tips from it as wel.

After all, having difficult conversations is not something we ever get completely comfortable with or stop learning about.



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