C-Suite Advisory

How to have tough conversations with staff working remotely

Darren Hill

Tough conversations, while uncomfortable, are part and parcel with managing a team. Up until recently, leaders have had the benefit of being able to sit down face-to-face to address issues and discuss behaviour change in a personal and familiar setting.

But as we continue down the rabbit warren of working remotely, it’s key for great leaders to adapt their approach to tough conversations to suit the medium. Let’s dig into the principles that sit behind having tough conversations with staff working remotely.

Don’t put it off

For any tough conversation to result in behaviour change and an ideal outcome, the issue needs to be addressed as soon as possible. Reducing latency between behaviour and feedback is a critical factor for success. This is particularly important in a remote working context where there are plenty of day-to-day distractions that could lead to a tough conversation being drawn out for days, or even weeks on end.

Leaving too much time between the initial tough conversation trigger and your 1:1 dialogue can result in misinterpretation, assumptions being made, and ultimately, a defensive reaction from your team member. Make the conversation a priority.

Set a time and context

While you’ll want to get to your tough conversation quickly, we’d recommend setting a dedicated time for your 1:1 rather than picking up the phone and getting straight to the tough stuff. But don’t confuse this as an excuse to procrastinate or delay. Setting time and context for a discussion can happen in half an hour.

In a remote work environment there are distractions aplenty, and without clear context around the tough conversation your team member could be interrupted, off-topic, and even leave the meeting more confused than anything.

Setting a dedicated time for your conversation and communicating the main topic of conversation (i.e. a project) as well as anything you’ll need the team member to bring will ensure that both you and your colleague are able to be present for the conversation at hand, leading to it being more focused and effective.

Opt for video 

The closer that you can get to a face-to-face experience, the better. In a remote working context this means opting for video conferencing over audio-only calls when teeing up tough conversations.

Being able to see each other’s body language and pair that with tone of voice are critical in ensuring that you’re both on the same page and that you’re able to pick up on non-verbal cues to direct the conversation further.

Use a third point

A useful tool to depersonalise your tough conversations is to make use of a shared visual medium or what we’d refer to as a ‘third point’. You’re point one, they’re point two, and the visual is point three.

During a video conference call this could mean sharing your screen to the specific piece of work or to a document that you’ll be using to direct the conversation. Another method is to have them use pen and paper and draw a model or write out a continuum as an anchor point for your conversation. This will direct your focus to talking about the object or behaviour, rather than the person, which allows people to separate themselves and the behaviour; a critical method for depersonalisation.

Clarify your request

If your tough conversation is leaning towards behaviour change, it’s important to make use of behaviour based language rather than general traits.

With behaviour based language you’ll be offering clarity to the situation, providing the individual with specific areas they can work on rather than leaving them guessing.

Behaviour based language assists in creating clarity and primes people to move towards the desired outcomes while also helping minimise assumptions and varying interpretations.

For example, punctuality is a vague trait that has many different meanings for many people, especially in a rapidly changing remote working context. Asking the team member to join the morning meeting 3 minutes before start as a best practice is a much clearer request.

Close the loop

Before signing off from your remote tough conversation, make sure that you’ve addressed your key points and come to a resolution or action plan for the way forward.

Two powerful questions that are useful to close a conversation, but are rarely asked are:

  1. “Can you talk me through what your actions are after this meeting?”
    This serves to clarify understanding and do some error correction if there is still ambiguity.
  2. “Can you tell me what you think my actions are after this meeting?”

This is your chance to check in on any expectations your team member has of you. Imagine the scenario where they are expecting actions from you, and you haven’t delivered on them – not a great place to be.

Another way to ‘close the loop’ on a tough conversation is to commit to another time to check in on progress made. It could be in a few days or a week’s time depending on the action items.

So there you have it, six guiding principles to help you tackle tough conversations while working remotely.

With time and practice you’ll strengthen your virtual leadership skills and role model how to achieve results from these tough conversations across your team.


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Darren Hill
As a behavioural scientist and best-selling author of Dealing with the Tough Stuff, Darren Hill knows first hand what’s required to build high-performance workplace cultures. With a client book of Fortune 500 and ASX 200 companies, Darren is the co-founder of Australia’s premier Behaviour and Motivation Strategy company, Pragmatic Thinking — a company that has made the Australian Financial Review's Fast 100 list for the last 3 years running. Darren Hill is an opinion columnist for the CEOWORLD magazine. Follow him on LinkedIn.