Handling difficult conversations

There may be times when you have to handle difficult conversations relating to flexible working, and that’s okay.

Leading discussions that enable multiple, contrasting perspectives is how problems are solved, and performance improves.

Below are some examples of possible conversations around flexible work, and some suggested responses.



“I’m sick, but I can work from home.”

Remind employees that they should use sick leave when they are sick as a general rule. However, there are times when an employee may be well enough to do some work at home, and this is when to exercise judgment.

“I want to work from home on Wednesdays, like Kevin does. It’s not fair he gets to and I don’t.”

Remind employees that context does matter. Applying a policy fairly doesn’t mean everyone has the same outcome. Instead, offer to talk to them about their needs and desires and how best you and the team can accommodate them.

“I work from home on Wednesdays, but there is a team meeting scheduled Wednesday afternoon.”

Remind the employee that flexible working is about give and take. Making inflexible arrangements around flexible work does not work. Sometimes team events on flexible working days is unavoidable. Discuss whether remotely dialling is an option and the possibility of scheduling the next team meeting on another day.


“I want to work from home but will need another computer to do this.”

Response to requests for infrastructure will depend on the context of your business. Have a conversation about why they think they need another computer. When you understand the reason for the request, you will be more equipped to help them find a meaningful solution.

“I’d like to work a compressed week. I could easily fit five days work into four.”

Talk to the employee about the reality of compressed work. Ask if they think they can do the job effectively in four days without impacting on their colleagues and the businesses and discuss whether they will be willing to flex and adapt as required.

“I know I received a poor performance rating, however I want to work from home 1 day a week”

Remember that poor performance should not preclude flexible working. Have a discussion about their performance and how they plan to address it. Consider trialling a flexible working arrangement with clear goals that they need to achieve.

Handling difficult conversations


This resource provides examples of possible conversations around flexible work and some suggested responses.

Handling difficult conversations.pdf