5 Strategies for Handling Difficult Work Conversations

During your career as a manager, you may encounter sensitive situations with colleagues and employees. Often these problems don’t resolve themselves on their own and employees may be upset, confused and the list of potential situations you may face is endless.

When difficult situations arise it often falls to the manager to have the hard conversation with their direct report. No one told me this when I became a manager and I have had to teach myself this skill, apply knowledge gleaned from others, and consolidate what I have learnt on the job. It’s my hope that with this post I’ll leave you with tips you can use the next time you find yourself in a “what the heck do I do with this?” type of dilemma.

My top five strategies for having tough work conversations:

1. Ask someone you trust for their suggestions and approach.

Ask them what they would say given the scenario. You can ask your HR department, your supervisor, a mentor or a colleague in another department. Sometimes, though, your workplace resources aren’t enough. After consulting my colleagues, my go-to person for management advice is my mother who held a high-ranking position at a chemical company for decades before she retired last year. Over the years she managed several unique personalities and encountered every situation under the sun. Whenever I have an issue with a direct report, I change the details and don’t reveal any personal information, but I ask her how she would handle the situation. Usually, the advice from people around you is spot-on, but needs to be tweaked for the specific matter at hand.

2. Consult free literature that exists on the topic.

Harvard Business Review has a lot of articles that cover this very subject. HBR has a great Management Tip of the Day newsletter that covers a myriad of sticky issues that can be reviewed when needed. I also love Alison Green’s Ask a Manager web site which is my personal favourite. She has tons of archived content about every personnel issue you can think of; it’s easy to search by topic. Forbes and LinkedIn are also good resources.

3. Schedule a time to chat with your employee and write up your talking points a few days in advance.

This isn’t a conversation you want to wing. You need to have a plan and make sure you hit on your key points. Are they showing up to work late and not completing their assignments? You better decide which is the larger issue you need to tackle. Are they being offensive to colleagues or harassing their own direct reports? Again, you want to come armed with specific examples and provide strategies or suggestions for them on how to handle themselves according to your standards and/or company guidelines. You want to be perfectly clear about what the problem is, why it’s a problem, and provide your employee with ideas on how to fix the problem. You can also ask them how they would address the issue.

4. Practice the conversation out loud.

It can be to the wall or to your dog, but saying the words as if you are having the conversation will help you identify what parts of your script need work and what should be eliminated or added. Are you focusing on the wrong things? Wasting time with small talk? Stumbling over clunky wording? Is your message getting lost? Make sure to do a run-through a couple of times to find weak spots and smooth them out.

5. Have your notes handy, but don’t recite them word-for-word.

Employees want to know that you’re being sincere and not just giving them the party line during these types of discussions. If they think you’re phoning it in they won’t understand the magnitude of the situation and what performance issues need to be corrected. Remember, no matter how difficult this conversation is for you, it’s undoubtedly hard on your employee, too. Let your employee ask questions and if needed, promise to schedule a follow-up meeting in two weeks to revisit the discussion and review what steps the employee has taken (or not) to address the issue you discussed.

In the end, if you take adequate time to prepare yourself for difficult conversations it will make them that much smoother and hopefully create an environment that fosters open communication. Do you have your own tips for tackling difficult conversations at work? If so, I’d love to hear from you.

About the Author
Deanna Cabinian is the director of consumer marketing for a global media company. She has six years of management experience and twelve years of experience working in the corporate world. When she isn’t working, she loves to write. She’s the author of a series of novels for young adult readers and is represented by Aevitas Creative Management. Find her online at https://deannacabinian.com/