Having Difficult Conversations with People
You Can Use Tough Conversations to Strengthen Trust
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Having Difficult Conversations with People
You Can Use Tough Conversations to Strengthen Trust
If you manage people, work in HR, or care about your colleagues and family members, you'll eventually face a situation that requires having difficult conversations.
Whether the conversation concerns performance, behavior, or personal habits, avoiding these talks creates frustration and disconnection, blocking growth.
Having these conversations isn't easy, but how you handle them reflects your values and directly impacts relationships.
Let's explore when these difficult conversations become necessary and how to handle them with kindness, clarity, and integrity.
When a Difficult Conversation is Necessary
You'll know a conversation is unavoidable when minor frustrations pile up, and complaints begin rolling in.
Whether the problem is performance issues, personal hygiene, or inappropriate behavior, you'll want to have the tough conversation sooner rather than later.
Even simple issues like replacing a toilet paper roll or failing to clean lunch items in the shared kitchen can cause hard feelings.
Examples you face may include:
Performance issues: Missed deadlines, repeated mistakes, or skipped meetings.
Behavior concerns: Vulgar language, gossiping, or flirtatious behavior at work.
Cleanliness or hygiene: Leaving dirty dishes or food that attracts pests or not meeting basic hygiene standards.
The goal isn't to shame or punish but to help the individual grow and preserve workplace harmony and cohesion. Avoiding these conversations only lets the issues fester, creating frustration for others.
Their frustration can lead to disharmonious behavior, such as once occurred in a client's workplace. Exasperated coworkers left a bar of soap and deodorant in a coworker's cubicle with a mean note.
For those of you in helping professions like HR, your first reaction to having a difficult question might be, "Why me? Isn't their manager responsible for holding tough conversations?"
In a perfect world, the answer is yes. However, few managers are trained, skilled, or comfortable having difficult conversations. Without the capability, they may make matters worse.
Steps to Hold an Effective and Compassionate Conversation
Ask Permission to Start the Conversation
You don't want to address the issue without warning. This approach almost guarantees an adverse reaction.
So, you might say, "I want to share some feedback with you, and it's not the easiest thing to talk about." Is now a good time, or would you prefer another time and place? (Within reason, of course.)
Even if you're their manager, this small gesture gives the person some control. It makes the feedback feel less confrontational and ensures they're mentally ready to listen.
Start Softly: Ease into the Conversation
Begin by giving the other person a moment to prepare for potentially problematic feedback. Instead of jumping straight into the issue, frame the conversation empathetically.
For example, "John, I have feedback to share with you that may upset you, but if you can hear me out, your helpfulness to your team could double."
Most people are as uncomfortable providing feedback about personal issues, such as an individual's dress or habits, as the person receiving the feedback. This is normal and human. No one wants to make another person sad or feel bad.
This approach sets the right tone, allowing the other person to feel respected and ready to engage.
Be Clear and Direct: Don’t Beat Around the Bush
"We need to discuss how your missed deadlines create a ripple effect, increasing workload for others."
Don't sugarcoat the issue or hide behind vague language. Be straightforward and specific about what needs to change.
Avoid Grouping Feedback as "From Others"
Saying things like: "Several coworkers have complained" might make your job easier, but it also heightens the individual's embarrassment and destroys trust.
Take ownership of the feedback by saying, "I've noticed this behavior, and we need to address it."
Explain the Impact of the Actions
"When deadlines are missed, teammates are left scrambling to pick up the slack."
Help the person understand the broader impact of their behavior. Frame the change positively by showing how improving can benefit their growth and success in the future. "Improving this area will show leadership you're ready for more responsibility."
Agree on the Next Steps and Follow Up
Following your initial conversation set a clear plan: "Let's revisit this in two weeks to check on progress."
Make sure you and the person agree on the steps to improve. Summarize the steps and ask for agreement.
Make sure you schedule a follow-up conversation to hold them accountable.
Follow Through with Support
Say, "Let’s set a follow-up in two weeks to check progress so I can offer support." Reinforce any progress you see in the meantime with small encouragements, and if needed, clarify further.
If the problem does not improve, you may need to escalate the situation to disciplinary action. But always approach this fairly and transparently with warnings and documentation.
Consistent follow-up is essential for fostering accountability. Without it, employees may assume that feedback and warnings are just words without consequence.
In a client’s company, an employee in an on-site role repeatedly arrived late. After several warnings, the manager terminated their employment. On their way out, the surprised employee said, “Geez, I’ve had so many warnings, I never thought you’d actually do it.”
This example highlights how unclear follow-through can confuse expectations and undermine trust and accountability.
Care Enough to Have the Conversation
Difficult conversations aren't just a managerial task—they demonstrate that you care. Whether you address performance, behavior, or personal habits, these moments offer growth and ways to build and maintain trust.
When handled with empathy and fairness, these conversations reflect your commitment to doing what's right, not easy.
Every difficult conversation you avoid adds to frustration and an eroding workplace culture. But when you engage openly and thoughtfully, you help individuals grow and reinforce the values that build a thriving environment at work and beyond.
Wrap-Up
The key to mastering difficult conversations is practice and consistency. As uncomfortable as they are, these conversations can make the difference between failure and success for the individual, the team, and the organization.
Caring enough to have these difficult conversations benefits everyone.
Expand Your ValuesCrafting Toolkit
Discover curated resources that deepen your understanding of having difficult conversations.
“Strategies to Make Tough Conversations More Effective” by Amy Morin in VeryWell Health highlights empathy as a key element in managing difficult conversations. The article offers practical advice on validating emotions, showing support, and being transparent. While especially helpful for personal interactions, it also provides insights applicable to professional settings.
“4 Tips for Making Difficult Conversations Easier” by Helene Brenner, Ph.D., and Larry Letich, LCSW-C, in Psychology Today, emphasize the importance of preparation when discussing sensitive issues with a partner. They describe these conversations as "emotionally risky and challenging." Their tips help set the stage for productive dialogue, increasing the likelihood of achieving positive outcomes without harming the relationship.
“Make Your Meetings a Safe Space for Honest Conversation” by Paul Axtell in the Harvard Business Review (unlocked article) outlines two key conditions for fostering honest discussions in meetings: permission to say or ask anything and creating a sense of safety for participants to express their thoughts freely. I found Josh's example of running meetings particularly insightful.
“How to Have Difficult Conversations Virtually by Art Markman provides valuable insights for managing tough discussions online. As hybrid workplaces grow and families remain connected across distances, these practical tips are more relevant than ever.