Managing Difficult Conversations with Employees - A Comprehensive Guide for Managers

Photograph of Jenefer Livings, Founder of Silk Helix Ltd
17 October 2023
LinkedIn TikTok Facebook

Effective communication is the cornerstone of a harmonious workplace and one of your most critical responsibilities is managing difficult conversations with employees. These discussions, though challenging, are essential for resolving issues, creating a positive work environment, and ensuring the well-being of both employees and the organisation.

These conversations are called difficult for a reason, they challenge us as the person who needs to start the conversation. We’re often dealing with our own thoughts and fears like wanting to avoid conflict, wanting to be liked, not wanting to upset people or we simply don’t know how to start. In this comprehensive guide, we’ll explore the intricacies of managing difficult conversations with employees, providing you with strategies to navigate these conversations successfully.

The Importance of Addressing Issues:

Ignoring workplace issues can have far-reaching consequences, including decreased employee morale, productivity, and even potential legal implications. When issues are not addressed they grow, in my experience - they never simply go away on their own. Whilst not addressing issues feels like avoiding conflict, in reality it’s creating conflict and building an environment where no one really knows where they stand or what the boundaries are.

We need rules and boundaries within which to operate, just like playing a game without rules it’ll end up in chaos. Addressing issues as and when they arise helps to form those expectations and understanding. Having a clear culture, values and expectations as a foundation is also essential to reducing the need for these challenging conversations and makes the conversation less challenging to have.

1. Preparation

Before initiating a difficult conversation, it’s vital to prepare thoroughly. Ensure you’re really clear on what the issue is, where relevant have the evidence and be specific, maybe this is dates and times or something documented. Avoid going into a discussion with a general feeling, for example if you feel they’re not pulling their weight be specific about what you expected them to have done that they haven’t.

Know what you’re aiming to achieve from the conversation. Do you want them to show an understanding of the issue or find a way to rectify it? Are you working with them to create an action plan including support so they can improve? Do you never want to see an incident like this again? Have a clear idea what will be achieved in order for you to feel the conversation went well.

Adequate preparation ensures you stay focused and maintain a constructive atmosphere during the discussion.

2. Choosing the Right Setting

The physical setting for your conversation matters. Find a private, neutral space that allows for open and honest communication. Ensure you have enough time for the conversation, and notify the employee in advance, so they are mentally prepared.

Regular conversations with your team are really helpful to enabling the challenging ones. When you regularly sit down one to one with someone, it’s natural to do it again and they’re more likely to enter the conversation positively. If the only time you ask them to talk to you is when you have an issue to raise they’ll feel anxious or defensive as soon as you ask for a chat.

3. Communication Tips

Effective communication is the linchpin of a successful conversation:

  • Begin by being really clear about the concern
  • Express your concern and empathy for the employee’s perspective
  • Be curious, seek to understand what’s going on for the employee (it may not be what you think)
  • Actively listen to their viewpoint and ask open-ended questions to encourage dialogue
  • Avoid assigning blame or passing judgement, instead use specific and objective examples
  • Use “I” statements to express your feelings and observations, fostering a less confrontational atmosphere
  • Seek to reach agreement on the outcome, gaining their suggestions and buy in will improve the likelihood of positive change

4. Staying Solution-Oriented

The primary goal of your conversation should be finding a solution collaboratively. Work with the individual to identify underlying issues and brainstorm potential solutions. Encourage them to take ownership of the problem, and establish clear expectations for improvement.

5. Documentation

After the conversation, document what was discussed, any agreements made, and any action items. This documentation is crucial for tracking progress and serves as a reference if the issue escalates.

6. Follow-Up

Don’t let the conversation be the end of the matter. Regularly check in with the employee to assess progress and provide support. Positive reinforcement for improvement is just as important as addressing the issue initially.


Managing difficult conversations with employees may never be easy, but with the right approach, it becomes more manageable and can lead to positive outcomes for both the employee and the organisation. Remember that as a people manager, you play a pivotal role in maintaining a healthy workplace environment.

Keep up to date with our weekly hints, tips and news.
Sign up to the
Silk Helix
Your email address will only ever be used to send you HR hints, tips and news from Silk Helix Ltd. Don't worry, you can unsubscribe at any time.
Silk Helix

Products and Services

Unlimited advice and support, when you need it
Employment Contracts and Employee Handbook
On-site and digital courses
Our fully outsourced HR department for small business

Experts in HR for Small Business

Silk Helix take the stress out of managing your people. Contact us for a free consultation today.

Not found the answer you need?
Don’t waste any more time Googling. Book a call with a qualified advisor. We’ll answer your question, no obligation.
Book a Free Advice Call