How to have a Challenging Conversation at Work

By Shamsa LeaPropel Her
Reading Time: 5 minutes

By Shamsa Lea and edited by Lyndsay Freeman. This article is part of the Propel Her Australia – Defence Women’s Leadership Series.

The difference between an ordinary conversation and a challenging one is a bit like the difference between kayaking on smooth open water or down raging rapids. Both involve a degree of balance, but the stakes are much higher and the skills are more demanding on the rapids. 

Many of us don’t like to have challenging conversations with members of our team, and giving constructive feedback can be awkward and stressful. Leaders may feel anxious that they will make the situation worse, that their positive intent will not be portrayed correctly, or that the feedback will make the receiver upset or combative. These are all valid fears as it is human nature to respond emotionally when confronted about your work or behaviour in the workplace. It seems easier to avoid discussing the issue or let the problem disappear with the next posting cycle – but avoidance will only foster more conflict. 

Constructive and direct feedback, if done right, has the potential to bring out the best in the people that you work with, helping them grow and reach their own potential. Clearing the air will also be a welcomed relief for other members of the team. While conflict can be positive – a marker of progressive, stimulating work environments – when things get personal, it can be tricky to address. As a leadership coach, I have seen the instant weight off a person’s shoulders once that conversation has occurred and a resolution has been reached.  How can you do it in a way that is helpful, tactful and with positive intention?

1. Ask yourself WHY you are having this conversation

The compounding situation is likely to be one challenging conversation away from resolving the issue that is holding a person or team back from accomplishing what they need to accomplish. Think about what you are trying to achieve by having the conversation, and why it is important that YOU are the one that needs to have it (instead of someone else). Remind yourself of your positive intention and reflect on any of your pre-existing biases. 

2. Prepare, prepare, prepare

Jotting down a soft ‘script’ may seem unnecessary, but as any military tactician well knows: “the planning is more important than the plan”. The process of drafting your thoughts will ensure you speak with openness and honesty while directly solving the issue at hand. There are many models available for you to tailor, depending on the conversation you need to have. Try this one out:

  • I’d like to talk to you about < insert topic> / I’d like to share with you that < information>.
  • I’ve noticed that <be very specific>.
  • I feel <state the emotion clearly>.
  • The impact is/ what is at stake is <highlight current risk if the matter is not dealt with>.
  • I may have contributed by <time for self-reflection here>.
  • What I would like is <explicitly detail your preferred outcome>.
  • What do you suggest/ How can we move forward on this? (This puts the responsibility back on the other person to address their behaviour). 

Knowing your most effective communication style and being emotionally aware of your own limitations and strengths is important when preparing for a challenging conversation. The conversation may go off-script due to the other person’s unplanned response, but have an idea of how you will respond to any potential rabbit holes. You may also consider running through the script with a trusted mentor.

In spite of our preparation and best intentions, we all blow it from time to time. In the heat of the moment, a statement or reaction might get the best of us and you will need to press the reset button. Start by acknowledging where the conversation went wrong, restate your intention for the conversation and make a simple request like: “That didn’t come out quite right. Can I try that again?” or “I’m concerned some of the things I said aren’t helping. Can we start over?”

3. Know when to stop the conversation

Sometimes, despite good intentions and a well planned and respectful dialogue, communication will break down. To protect yourself, it’s important to acknowledge when it is time to stop the conversation and pass the issue onto a third party to resolve through formal methods. The ADF has robust tools and structures in place to support you and the chain of command through any conflict resolution or unacceptable behaviour concerns. 

ADF leaders can refer to the Complaints and Alternative Resolutions Manual (CARM) on the DPN which outlines the process for managing and resolving unacceptable behaviour, complaints, and workplace conflicts. The CARM details options for Alternative Dispute Resolution Services, which is an additional tool for leaders and individuals to manage workplace conflict.

Receiving feedback

What if it’s you that is on the receiving end of constructive criticism or feedback ? Accepting constructive criticism and using it as a source of growth is an important skill that demonstrates humility and maturity. Here are my top tips:

  • Think about the positive intention of the person speaking to you (even if the delivery is poor or the feedback has missed the mark).
  • Listen fully, be open to the feedback and avoid getting defensive, interrupting or making assumptions.
  • Verbally acknowledge the feedback, because it would have been difficult for them to deliver it to you. Thank them for their honesty. Without it, you would not have been offered the chance to view your work output or behaviour from their point of view.
  • Remember that seeking out, considering and actioning feedback is a sign of leadership, and it is power to improve, grow and learn.

Left unresolved, a minor issue may grow into something that depletes morale, saps your energy and reduces productivity in the team. If you have had a specific person or issue in mind while reading this article, don’t delay. Plan your challenging conversation, firm up your support network, confidently address the issue and propel forward  towards the higher purpose of your team. 

Handy Resources

About the authors:

Shamsa Lea is an Air Force Logistics Officer, leadership coach and Board Director of a veteran support organisation. She has been engaged in female recruitment, retention and progression activities in Defence for a number of years, with a specific interest in helping ADF women achieve their leadership potential.  Twitter: @ShamsaLea.

Lyndsay Freeman is a mother of two and a Transport Officer in the Australian Army. A former Chief of Army Scholar, she is currently the Senior Instructor for the ADF’s Gender, Peace & Security Courses at the Peace Operations Training Centre. Lyndsay is passionate about the ADF’s pivotal role in advocating for women’s empowerment across the globe. Twitter: @LyndsayFreeman8.