How to Have Difficult Conversations

Navigating difficult conversations is a critical skill in both personal and professional settings. Whether it's addressing a sensitive issue with a colleague or providing constructive feedback, the ability to communicate effectively can make a significant impact.

 

A few weeks ago, I posted a poll on LinkedIn asking for opinions on how the community would handle a specific situation: A young man working as a retail store manager came in to relieve the current manager, but as he walked in, the small store was filled with a strong, unpleasant odor. His colleague, a middle-aged woman, noticed and recoiled as well but felt it wasn’t her place to speak to him about it. I, as the customer, couldn’t just ignore it. For a few reasons: 1) it was an absolutely horrible smell, in a very small store, making it a terrible shopping experience, and 2) I felt this was a coachable situation, and a young career professional such as this one deserved to have that feedback provided to him in a constructive way.

 

Here's how the poll results came back:

Even though only 14 people responded to this poll, I couldn’t help but wonder if this is truly a representation of what the professional population would do in this case. In any case, it was good to see that more than half, in fact 78%, felt compelled to do something, and 57% would do something directly. The 21% that felt it wasn’t their problem was a bit disturbing to me for many reasons. Pretending that problems go away on their own is delusional. Feeling that someone else will do something and it isn’t your concern is also similar to assuming that after witnessing a car accident, someone in the bystanders must’ve called 911 for help, and in fact, no one does, until the situation becomes dire and leads to a more critical health condition for those impacted.

 

In this situation, as I shared in the post, I chose to tackle this “difficult conversation” directly, in a kind and constructive way. I felt strongly that someone had to be gentle but direct with this young man, framing the situation in a way that he would understand, learn, course correct, and not recoil. Thankfully, I had some experience giving constructive feedback in tough situations, and so I did.

 

Unfortunately, this young man was left in the store alone, and I doubt he was able to execute his plan until the end of the day, for fear of closing the store and getting in trouble. I don’t know if other customers walked in and then right out in reaction to the strong smell. However, I think the strong lesson here was that putting this young man’s career and well-being trumped having a negative reaction and voting with my wallet by exiting the store and then writing a poor review about it online.

 

I think back to other situations as a manager when I was faced with having an “uncomfortable” conversation with a staff member. It was not easy. I didn’t look forward to it. It was beyond uncomfortable for me personally, and I could only imagine how the other person felt. But it was necessary. Delivering with grace required a few elements, so here are the tips that have worked for me:

 

1. Find the Right Place and Time: Choose a private setting and an appropriate moment to have the conversation.

2. Build Trust: Ensure that the individual knows you have their best interests at heart.

3. Explain the Why: Clearly articulate why the conversation is necessary.

4. Be Factual: Present the issue without emotional bias.

5. Seek Understanding: Confirm that the person understands the situation and has a chance to respond.

6. Request Commitment: Ask for a commitment to change the behavior.

 

Depending on the person and how much trust and history you have with them, you may get different responses. Sometimes it’s relief that you pointed out something they needed to know, other times it’s awkwardness, and sometimes, sadly, it’s disbelief or anger. The latter happens when the individual is clearly not self-aware enough or has some accountability issue. It could also be that you haven’t built enough trust with them, so they are questioning your intentions.

 

In any case, it’s not the most comfortable thing to do, but when you get past your own anxiety, you usually feel better after doing it than if you dismissed it altogether. I recall a time when a very high-performing young woman on my team fell into a rut and began a trend of coming in with very sloppy attire; clothing with stains, fraying in obvious areas, and the last straw was a gaping hole in her pants where her undergarments could be seen. I didn’t want to have the conversation, that was for sure, but I also didn’t want to make it an HR matter unless she refused to remediate the situation.

 

Another case was an individual who was very pleasant with customers but was extremely abrasive with internal people, peers, and his manager. He could come off sweet as honey with customers, execute conversations perfectly, and on the other hand deliver snide and underhanded remarks that thwarted his peers and created tension in the room. That too was a very uncomfortable conversation. Having to point out how the behavior impacts others and give examples to substantiate the claim can be exhausting. Doing it in a way where they understand how it impacts them negatively, and their career trajectory, takes skill (and patience).

 

Finally, I remember this one expression that resonates with me: “Bad news never gets better with time.” How true is that! The longer we wait to give feedback, to correct behavior, to point out an issue, the harder it is to avoid damage or change habits. It takes courage to have hard conversations, and embracing the discomfort is painful but not deadly. With time, you recognize the benefits outweigh the costs, and you learn to find graceful ways of sharing truth to help people and not hurt them.

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