Managing a career conversation remotely

As we are all home, this should be freeing up more time as we are away from distractions that we would normally get sitting in an office, such as chatting with colleagues and being in back to back meetings. We should use this time to action the tasks that are sadly often put to the bottom of the to do list, such as 1-2-1’s with our direct reports and having career conversations with them.

Your direct reports will really appreciate and value that you are taking time to talk about them, especially as there is currently so much uncertainty within businesses. Software such as Microsoft Teams, or Zoom, enable us to have meaningful conversations and engagement as much as a face to face conversation, especially as we are now all using such tech, it is making it the new ‘normal’.

Here are some of our top tips on how to run a career conversation, both the virtual considerations and how to manage the conversation itself:

  1. Ask your direct report when a good time to have a development conversation would be and book time in both your diaries accordingly with the link to Teams or Zoom etc. You will need at least 90 minutes for a quality conversation. Be clear as to the purpose of the conversation and the outcomes. Outline the agenda in the invite. Allow time for both you and your direct report to prepare for the session and reflect on their development areas.
  2. When it comes to holding the meeting using video software, ensure you won’t be disturbed. This is a private conversation, so don’t hold it in a communal area in the house. Most video software enables you to blur out your background, so do this if you don’t want your direct reports to see your house. You can test your microphone and camera in advance. Make sure your head and shoulders are in view and the sound is working. Turn lights on if you need to, your direct report needs to be able to see you properly as this will aid in having an engaging conversation.
  3. Use the first 30 minutes to get to know your employee. Understand their background, (if you haven’t already done so), where they have lived, qualifications, family life, previous roles, current challenges and how they are responding in the current environment. Ask open questions and probe a little deeper when they talk about key pivots in their lives. Doing this enables us to identify what makes people tick. For example, in the discussion, you may discover that your team member used to be a runner, but then took up Netball, because they preferred being part of a team. This therefore gives us insight into how they might want to work.

  4. Ask what their goals are in their career. This should not just be focused on the business you both currently work for; they may have aspirations to work for a large organisation in a different industry to broaden their skills. Ask to what level of seniority they want to get to; do they want to manage people?
  5. Ask what they like and dislike about their current role. What frustrates them, or gets them up in the morning?

  6. Map it out – Based on the areas you have discussed and the longer-term goal, identify possible skill gaps. For example, if they want to be a Senior Department Head, but have had no experience or training in how to be a line manager, then consider suitable training courses, or future roles that will give them the opportunity to manage people.
  7. End with action. There should be a clear focus on the “So what?” Discuss what career development strategies they can use to make progress and the actions to take. Agree how often you are going to check in with them and review progress.
  8. End with a smile and a wave! – It goes a long way on camera especially in current circumstances and ends on a positive note!
  At Pure Blue Ocean, we understand the importance of career conversations. We can support Line Managers virtually on how to run a career conversation, or we can hold one directly with an employee in a coach or mentor capacity, so please get in touch at
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