Leaders! How to have difficult conversations at work

 | News

Most leaders don’t enjoy having difficult conversations with their team.

They can be awkward, uncomfortable and often lead to anxiety and stress, even for the most experienced professionals.

In some situations, leaders avoid them for these reasons. In others, they might be unaware they need to happen or don’t know how to have difficult conversations at work in the best way.

Unfortunately, avoiding tough talks, or tackling them poorly, can lead to misunderstandings, conflicts, and missed opportunities. It can also impact your collective ability to get the work done—and done well.

Here we unpack this common leadership roadblock and show you how to put on your brave pants and handle them with confidence.


A difficult conversation scenario

Picture this: your direct report fails to deliver a project to a deadline.

If a conversation doesn’t happen to share your concerns, the potential impact could be increased (and unfair) pressure on the wider team as they’re forced to pick up the pieces and do the additional work.

This inevitably shortens deadlines to complete their original tasks further, potentially causing stakeholders to lose trust in the quality of the project.

You can see from this familiar example the negative consequences of difficult conversations not happening. Lack of calling-out behaviour puts the wider team and business in a compromised position.

On the flip side, there can also be negative repercussions if leaders do speak up but don’t do it effectively.


Common difficult conversation mistakes

 So what are those (brave) leaders who do speak up not doing well? Some of the common mistakes we see include the following:

  • Being too aggressive – They’re being overly aggressive in their communication style, which can come across as intimidating or confrontational. This can make it difficult for the other person to feel comfortable sharing their perspective.
  • Failing to listen – They’re so focused on getting their point across that they forget to actively listen to the other person’s perspective. This can lead to misunderstandings and an inability to find common ground.
  • Making assumptions – They assume they know what the other person is thinking or feeling without taking the time to gather all the facts or listen to the other person’s point of view.
  • Not making sense – They don’t get their message across well, leaving the other person confused about what they’re trying to say or what’s expected of them.


Three steps to difficult conversation success

To avoid these common mistakes and become confident in having those difficult conversations at work, here are three steps we recommend you follow:

 Step 1: Prepare before you speak

 Most of the mistakes out-of-their-depth leaders make in difficult conversations stem from one clear issue: they simply weren’t prepared.

To successfully tackle those difficult conversations with team members, it’s important that leaders do these three key things in advance:

  • Get clear on their concerns by understanding the facts of the situation, not emotions, interpretations or assumptions.
  • Find examples and facts to support their concerns, as this provides crucial context.
  • Think about the best time or place to have the conversation. We suggest  allowing some space and time to let things settle.

Step 2: Be clear in what you say

 As the wise Brené Brown once said, ”Being unclear is unkind”.

Therefore, during any difficult conversation, clarity is crucial.

Often, leaders try to water down their message to make it easier to communicate and not upset the person they’re giving feedback to.

What they may not know is this actually does the opposite of what they’re trying to achieve. It can actually have a negative impact on the discussion.

Instead, it’s important that leaders are clear in their feedback by detailing the scenario or situation with facts, discussing unacceptable behaviour and explaining the impacts of that behaviour.

However, they should also listen to the other person’s side of the story to try and establish some common ground.

Step 3: Document the outcomes

It’s easy to focus on the conversation and overlook the follow-up required afterwards (because, by golly, that was hard, and you don’t want to revisit it!).

But, after the difficult conversation, it’s vital that leaders document the outcomes, provide ongoing support to the team member and follow up with any agreed-upon, accountable actions.

Agreeing on how things will shift or change and ensuring both parties are accountable for that agreed outcome helps ensure long-term improvement.


Start tackling those difficult conversations

Having difficult conversations at work is an essential skill for leaders. It’s not always easy, and it can be uncomfortable, but avoiding tough talks, or executing them badly, can lead to even bigger problems down the line.

By being proactive and clear, listening and ensuring you follow up, you can confidently navigate those tricky conversations, become a more effective leader, and build a stronger team and healthier workplace culture.


Get in touch today to arrange a tailored and in-depth workshop co-designed to develop your leadership team skills and create a confident leadership team.

Meet the author: Stacey Kelly

Stacey brings extensive industry experience and knowledge, as well as the energy, passion and inspiration of a great leader. She previously held senior people/cultures roles in private and public organisations, including Hunter TAFE and Insurance Australia Group (IAG).

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