7 Mistakes You Make As a Leader When You Have Difficult Conversations

7 Mistakes You Make As a Leader When You Have Difficult Conversations

Having difficult conversations at work – with your team members or colleagues – is one of the hardest and least enjoyable aspects of being a leader. But not shying away from these discussions is so VERY important… for yourself, your team, and your business as a whole. Because leaning in and talking about hard-hitting topics and challenging issues fosters growth, helps resolve conflicts, and promotes a healthy work environment. It’s truly culture changing stuff.

Although difficult conversations are never going to be easy or fun, there are things you can do to make these discussions better for everyone involved. Here are some of the most common mistakes I see leaders in organisations make and some tips and considerations on how to resolve them.

Mistake number 1: Avoiding the difficult conversation altogether

One of the biggest mistakes I see when it comes to leaders having difficult conversations in their business is actually not having them at all! No matter how tough or uncomfortable they might seem, these challenging conversations promote transparency and trust within the team. Over time, they help you create a culture where everyone feels comfortable sharing their ideas, concerns, and feedback.

By openly discussing difficult topics, as a leader, you can address any simmering conflicts or misunderstandings that might be hindering collaboration or productivity in your team. And this, in turn, enables colleagues to navigate challenges more effectively and find mutually agreeable solutions. In short, it helps clear the decks and nip issues in the bud before they get too problematic.

Honest conversations also facilitate the growth and development of individuals and the company as a whole. Constructive feedback, even when difficult to deliver, helps employees identify areas for improvement and provides valuable insights for their professional development. In a nutshell, by learning how to have difficult conversations, you can play a crucial role in:

  • Promoting a culture of continuous improvement.
  • Building stronger relationships.
  • Enhancing team dynamics.
  • And fostering an environment of trust and growth.

What’s not to like?!

Related topics:

How to Have Difficult Conversations with Your Employees (with Examples).

How To Find The Right ‘Difficult Conversations’ Training For Leaders And Managers.

Mistake number 2: Not preparing for the difficult conversation

Another mistake I often see leaders make is not preparing in advance for the difficult conversations that you, inevitably, are going to have. So take the time to gather your thoughts and collect any relevant information before going into the meeting. For example, ask yourself:

  • What points do you want to cover?
  • What outcome do you want?
  • And what suggestions do you have for improvement?

Here are a few more steps you can take to ensure a productive outcome:

  • Clarify your understanding, thoughts, and expectations. Take some time to reflect on the situation, gather relevant facts, and identify key points to discuss.
  • Be prepared to approach the conversation with empathy and understanding. Before you go into the meeting, consider your employee’s perspectives and their potential concerns. Be ready to lead with kindness and without judgement. Always.
  • List expected questions and responses. This will help you anticipate possible reactions or pushback and prepare for potential objections or difficult emotions.
  • Make notes and set goals to stay on track. This will help you organise your thoughts, ensure key points are addressed, and maintain focus during the conversation, so you can achieve a constructive outcome. Be clear what the meeting is about, and if necessary – what it isn’t about. Make yourself available for the other stuff if it seems it’s important to your team member, but it’s absolutely ok to keep the boundaries around this conversation clear.
  • Pick the right place for the meeting. Where will this conversation take place? It’s important you strive to establish a safe and private space for this meeting. So book somewhere where both parties feel comfortable expressing their thoughts.
  • Prepare to communicate effectively. Do you know if this person has a preferred way to communicate? If you do, you can tailor your approach to effectively convey your message, minimise misunderstandings, and ensure that the conversation is productive and constructive. In short, be proactive in driving the conversation, but meet them where they’re at. No bulldozing here.

Two business people at a desk having a conversation

Mistake number 3: Choosing the wrong time to speak

Timing is important, so don’t pick a time to talk when you know you won’t have the right amount of time or the concentration to speak openly. Ten minutes before home time or before you have to walk into the next meeting might not be the perfect choice. And neither might the day before a large deadline or the only 30-minute slot you could find in someone’s diary when their day is otherwise filled with meetings.

Picking the right time can greatly impact the outcome of any discussion, especially important ones. Choosing the wrong time to speak to someone about an important issue can mean they’re not in the right frame of mind to have that conversation in the first place.

They might be feeling overwhelmed or distracted by other pressing work matters. And as a result, you may have less of their focus, attention, and receptiveness. Plus, addressing sensitive issues at inappropriate moments can create unnecessary tension and negative emotions. And that’s a guaranteed recipe for hindering a productive dialogue!

So before you schedule a difficult conversation meeting (and scheduling it in advance and with plenty of warning where possible is key here), consider the overall circumstances that surround this situation.

Look at the bigger picture and ask yourself:

  • Is this a good time for the person on your team you need to speak to?
  • Are they available in terms of time?
  • How will they be feeling at that point?
  • What’s their mindset going to be?
  • And will they be mentally present and ready to engage in a constructive discussion with a view to finding a solution?

Mistake number 4: Talking over the other person/people

A surefire way to anger people during a difficult conversation is to not fully and properly listen or talk over them. If you find that active listening doesn’t come naturally to you, take some time to perhaps remind yourself of some key principles. For example:

  • Pay full attention. Focus on the speaker without distractions and show genuine interest in what they are saying. Don’t just pretend to listen, but actually listen carefully and intently, and try to put yourself in their shoes. If you haven’t done so before the meeting, try to think about things from their point of view.
  • Maintain non-verbal cues. Use eye contact, nodding, and facial expressions to convey attentiveness and understanding.
  • Avoid interrupting. This is key! Let the speaker finish before providing any input or asking questions. If you talk over them, you won’t only interrupt their train of thought but also risk accidentally communicating the message that what they are saying isn’t important. And this may cause them to become defensive and closed off. As a leader, you’re probably a natural problem solver, which makes you great at wanting to give advice. But try to refrain from doing so until the time is right.
  • Paraphrase and summarise. To make sure you’re fully understanding what the other person is saying, repeat and reflect back the key points to double-check your take is correct and to show that you are actively listening.
  • Ask open-ended questions. Encourage the other person to share more by asking questions that require thoughtful responses and that promote further dialogue. Sometimes (and depending on the topic or circumstances) you can even do this by stretching the silence a little further. You’ll find that if you don’t say anything straight away, the other person might volunteer more information.

A man in a business suit having a conversation with a colleague.

Mistake number 5: Not being assertive in decisions

If the difficult conversation is necessary, and you’ve decided you need to go ahead and have it, the best thing you can do at this point is to go into it being assertive and confident in your position. As a leader, you need to be able to make active decisions, so don’t avoid coming to a resolution.

Having said that, it’s important to point out that speaking assertively and taking a strong stance on an issue doesn’t mean being aggressive or accusatory. You’ll still want to be respectful and kind, so you can create a safe space for open communication and, where possible, facilitate a mutually beneficial outcome. However, you want to come across as confident and decisive.

You can do this by:

  • Setting clear expectations. Make sure the person you’re talking to fully understands the purpose of the conversation and what needs to be addressed. This way, you’ll both be aware of any objectives you want to achieve and create a solid framework for the conversation that will allow you to stay on track and maintain focus.
  • Use empathetic communication. Difficult conversations are labelled as difficult for a reason! If you need to speak to a team member about their consistent lateness to work and know they might be having health or family issues at home, for example, you’ll need to be assertive and firm in your position but still empathetic to their situation. So make sure you acknowledge the person’s emotions and perspective and show that you understand where they’re coming from.
  • Provide constructive feedback. If you’re tasked with telling a team member that their request for a pay rise has been rejected by your director, try and offer specific examples that support the company’s point of view. If you need to talk about the person’s performance, focus on behaviours rather than personal traits and always be direct but courteous. And, of course, remember to balance criticism with recognition of their strengths to maintain a positive tone.

Mistake number 6: Lashing out and getting emotional

Despite all your preparation, while you’re in that ‘difficult conversation’ meeting, emotions might come to the surface – for you and/or the other person. Instead of reacting quickly or letting feelings get the best of you, take a moment to consider a calmer response.

Here are a few tips to help you keep your emotions under control and avoid reacting impulsively:

  • Try not to take the conversation personally. Even if you feel the other person is trying to get a reaction out of you, it’s important that, as a leader, you stay in control and try not to rise to it. This is where emotional awareness comes into play, and if you’ve done any work on your emotional intelligence and learning to recognise your own triggers, it will pay dividends in these situations.
  • Refer back to the notes you prepared in advance. Listing your objectives and goals to avoid going off-track and down a rabbit hole of words and sentiments that cannot be taken back.
  • Practise active listening. Even if you feel you’re starting to become defensive, remember why interrupting or talking over the other person is a mistake. Now more than ever, especially if you feel your emotions are rising towards the surface, it’s important you try and show patience and understanding.
  • Emphasise problem-solving. Probably one of the easiest things you can do as a leader and problem-solver when you feel your emotions are threatening to take over is to focus on finding a solution instead. And if one cannot be found, perhaps this is the time to re-assert your/your company’s position in this matter. Wherever possible, try and shift the conversation from an emotional exchange to a constructive dialogue aimed at addressing the issue at hand. This will help you maintain a more productive discussion.

Related topics:

How Can Leaders Improve Their Emotional Intelligence?

Mistake number 7: Not following up or delivering on promises

And last but not least, a mistake I see leaders make is not following up on delivering on their promises. When you do come to a resolution and create action plans, always follow through. This is particularly important if the other person has given you feedback on something you should act upon or improve as their leader (in your team or the wider business).

So after the meeting, make sure that you:

  • Recap and clarify. Perhaps you could send a follow-up email summarising the key points discussed during the conversation. This ensures everyone is on the same page and has a clear understanding of the expectations and any agreed-upon action steps.
  • Offer support. Follow up with the team member individually to check in and offer any support or resources they may need to address the situation. This shows that you are committed to their success and willing to help them navigate any challenges that may have arisen.
  • Monitor progress. Keep an eye on the situation to check for any progress. If improvements have been made, acknowledge and appreciate the efforts made by the other person. And if not, what can you do to help? What guidance or further assistance can you provide to make sure the outcome is positive? Regularly checking in demonstrates your ongoing commitment to their success and adds a sense of accountability, so keep discussing the topic until you’re both happy the issue has been resolved.

Learn how to master difficult conversations

Difficult conversations in the workplace cannot and should not be avoided. It can be particularly challenging for leaders to navigate sensitive topics, but it’s important to approach these discussions carefully and avoid these common mistakes in order to foster understanding and maintain a productive work environment.

If you or your company need some training, coaching, or accountability, I offer Difficult Conversation Training and Leadership and Communication Training. If you’d like to find out more, drop me a line and let’s chat!

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