Tips for having Difficult Conversations…Remotely

Leanne Lazarus • August 5, 2020

With the world of business always evolving it is inevitable that there will be times or situations that arise where a difficult conversation will be required; whether it be covering off productivity (or lack of), results, behaviour or constructive feedback.

Prior to the pandemic, it was easier to raise these issues with an employee as most people were all in the office together. Now with a lot of people working from home, it can become more challenging. If you are planning to have a sensitive conversation with a member of staff, consider a video call rather than a phone call.

Here are a few tips for having remote discussions with your employees:

PRIORITISE THE RIGHT ENVIRONMENT AND TIMING

Consider their environment! Some people are working in a shared space at home with their family or flat mate, or they may be based at a coffee shop, as they just don’t have the space at home to work efficiently. So, before engaging your employee in a difficult conversation remotely, alert them in advance that you need to have a confidential meeting with them and ask them to ensure they are able to have a discussion. And, if you have employees working from a different time zone, consider the time that works best for both parties when scheduling the remote meeting.

ENCOURAGE TWO-WAY COMMUNICATION

Start the meeting by letting the employee know that this is a discussion and encourage them to engage, ask questions, share concerns and thoughts both during the meeting or afterwards. Some people need a little time to process the information before the are ready to discuss; but leaving this door open, you foster a strong working relationship.

FOCUS ON THE HUMAN ELEMENT

Technology is an essential resource, but it can also create a disconnection between you and your workers if you are not careful. When having difficult virtual discussions with your employees, you cannot afford to ignore the human element of the person or individuals behind the screen. Remember that your workers may have a hard time coming to terms with the news, especially if it is not what they expect. As such, you should remain professional and empathetic as you engage your employees in serious discussions during a virtual meeting.

SET CLEAR EXPECTATIONS

You cannot conclude a remote discussion on sensitive matters with your employees without explaining what you need from them. The recommendations you give after difficult virtual discussions with your workers will dictate the actions they take going forward. That means that you should set clear expectations, mutually agreed goals / objectives and give them a defined deadline to work towards. And again, let them know that you are available should they have questions or concerns!

Conclusion: Having difficult discussions with your remote workers is tough, but also inevitable to some extent. Note that the way you approach such conversations will have a direct impact on your company operations. For that reason, ensure you listen attentively, be honest, and offer solutions as you engage your remote employees in sensitive discussions.

Find the job you love I Find the right talent
Get in touch with people2people

Australia   I   United Kingdom

In business since 2002 in Australia, NZ, and the United Kingdom, people2people is an award-winning recruitment agency with people at our heart. With over 12 offices, we specialise in accounting and finance, business support, education, executive, government, HR, legal, marketing and digital, property, sales, supply chain, and technology sectors. As the proud recipients of the 2024 Outstanding Large Agency and Excellence in Candidate Care Awards, we are dedicated to helping businesses achieve success through a people-first approach.



Share insights

Recent articles

By Liz Punshon September 11, 2025
Brooke Lord and Guy Davy join Liz Punshon to explore how Australia’s job market is recalibrating in 2025. They discuss internal mobility, AI integration, and the critical importance of adaptability in a market moving from volume to value.
By Kalinda Campbell September 9, 2025
Kalinda Campbell leads a deep dive into the legal landscape with Damian Gordon and Emma Elliott. They unpack how law firms are using flexibility, leadership development, and tech adoption to retain talent and future-proof their practices across Australia and New Zealand.
By Bianca Luck September 4, 2025
Leanne Allen and Chris Yam join Bianca Luck to explore the future of finance in 2025. They examine how teams are balancing stability with innovation, why upskilling beats offshoring, and how finance professionals are being asked to become both analysts and storytellers.
By Aiden Boast September 2, 2025
Nicole Clarke and Karl Sullivan join Aiden Boast to explore the future of marketing in 2025. From AI and predictive analytics to immersive tech and human storytelling, they unpack what it takes to build a modern, high-performing marketing team across Australia and New Zealand.
By Leanne Lazarus August 28, 2025
Leanne Lazarus is joined by Adeline Rooney and Samantha McCall to explore how HR teams across Australia and New Zealand are embracing personalisation, AI, and employee-centred strategies. From microlearning to remote workforce tools, they unpack what’s redefining success in 2025.

Latest Media Features


Get in touch

Find out more by contacting one of our specialisat recruitment consultants across Australia, New Zealand, and the United Kingdom.

Contact us