How to handle difficult conversations in the workplace


Last month I had a phone call from a friend wanting my advice as they had just found out their position within the organisation had been made redundant. Termination can be a shock for anyone, even when we are aware that organisations or roles are under review. In this case, it was even more surprising, but not for the reasons you may think.

Through sporadic commentary about the past few months, my friend described what sounded like a busy workday, that had ended with a few hours as part of an online training session, and a walk around the neighbourhood. The usual relaxing walk around the block came to an abrupt and shocking end at the halfway point, as a string of text messages from concerned colleagues started to arrive.

It turns out that the boss had sent an email to advise that the position had been made redundant. A short time later, another email was sent to all colleagues and staff to let them know of the decision. The key issue and concern here – my friend hadn’t seen the email and found out through alarmed colleagues via text messages that they no longer had a job.

This got me thinking, what are the best ways for leaders to deliver difficult and challenging messages. Here are a few things to consider the next time you need to have a hard conversation:

  1. Meet face to face – in this day and age staff are often spread all over the state, nation, world, but that should not preclude us from scheduling time to eyeball someone, especially if we need to deliver a difficult message. If face to face (either in person or via an online platform) is not an option, the next best option is a telephone call.
  2. Prepare your message – when it comes to difficult conversations, it is always better to formulate what you need to say and consider following a template to ensure all material is covered. This is also important to protect yourself, organisations, and other parties.
  3. Enough time – remember sometimes these conversations are a shock to the receiver, we need to give people ample opportunity to seek clarity. This is, not only, at the point of the initial conversation, but also should include options for follow-up, as many times as is necessary. Depending on the nature of the conversations there may be important time frames to adhere to.
  4. Follow up in writing – it is important to follow up on difficult and challenging conversations in writing. This may include a record of what has been discussed, any official letters or correspondence, and next steps or action items. It should also highlight any timeframes that impact the process.
  5. Be available – once you have delivered a difficult message or had a challenging conversation make sure you give ample opportunity for a person to seek clarity and ask questions. This is important for many reasons and depending on the context it helps people to finish well, understand and address any performance issues, plan for the future and be part of any consultation process.
  6. Listen more, talk less – hard conversations can sometimes mean escalated emotions from all parties. Listening to people’s concerns can help us alleviate any concerns and get the best outcomes for all involved.
  7. Support positive future interactions – as hard as difficult conversations are, and as uncomfortable termination and redundancy conversations are, it is important to support a person to move on positively. For some organisations that means working with individuals on the public narrative regarding the change, for others, it is providing external coaches and support structures to look for future opportunities and employment.
  8. Set expectations – For someone moving on this is about finishing well, however, it can also be helpful if we are having difficult conversations about performance and conduct. If people have a clear path forward they are much more likely to flourish.

Remember, having difficult and challenging conversations is often hard for all involved. Having a plan, checklist and reflecting on the above-mentioned considerations can help everyone involved have as positive an experience as possible.