Getting comfortable with uncomfortable conversations as a leader

Once upon a time, a leader would provide tangible operational tools and resources to their teams and it could be enough. The largest work-from-home experiment is still ongoing, with workers forced to dig deep, learn quickly and be resilient in times of uncertainty and change. Today, in March 2022 we are in the midst of a war and conversations can often be sensitive, emotive and upsetting. Here are some practical ways for you to be a supportive leader:

1/ Acknowledgement is the first step — Even if the current crisis in Ukraine does not directly impact your business from geographical or other perspectives, it may impact your people. A simple statement that you know what is happening and that some of your team members may have been impacted can open up a conversation and clear up any ambiguity. It makes no sense to deny or ignore such a world-changing event is happening!

You may not know what you perceive as the exact “right” thing to say but you should at least recognise the situation and express your support. Melissa Doman, an organisational psychologist, says being open about what is occurring and expressing your support intentionally can help foster a psychologically safe work environment. She continues, with the suggested statement:

“Given the global situation, we’re conscious of the fact that this might be impacting people in different ways throughout our company, and we want you to know that it’s OK to talk about this.”

2/ You don’t have to have all the answers to start a conversation — Staying silent can lead to ambiguity at times like this. Many people look to their leaders for a steer, guidance or permission to acknowledge and then discuss ways they may have been impacted. Like the Covid pandemic, this is something that could impact us all in some ways as with other global crises, being open and initiating the conversation, creates space for further dialogue and can pave the way to action.

Ideally, we want our people to feel comfortable to express any concerns or communicate the ways (which we often may not know now) that the crisis has impacted them. Ultimately, this may pave the way to the positive agency for individuals via action, e.g. fundraising, donations etc.

3/ Having supportive conversations — When we do initiate a conversation, it is worth being prepared and ready to be not only a good listener but also be emotionally supportive. Sarah Noll Wilson, in her article for HBR, “How supportive leaders have emotional conversations” gives some fantastic practical advice on using supportive language and also what not to use, i.e. dismissive language in these exchanges. She outlines a clear approach to how to listen, understand, validate, respond, support and approach the whole conversational exchange.

Take a note of the various tips and strategies, making sure you take these with you into your next chats with your team. Moreover, if you have a peer or colleague that you know well and trust, why not try out some of the advised tactics in a sample exchange or role-play, asking for constructive feedback afterwards on your approach?

4/ More than words! Moving to action by doing what you can to help — Individuals often want to do more than simply talk about a crisis, they want to move to practical action. In an age of social media, campaigning and advocacy can happen via easy online monetary donations and also via structured initiatives like organising and donating supplies, food banks etc. Other initiatives can match refugees with hosts, like the Irish Red Cross pledge site, finding Irish people willing to accommodate refugees in their homes. All of these initiatives can be supported practically via your internal communications. Some other companies, have created practical online resources and published them online, e.g. Safety Wing Ukrainian Resources.

There are many other examples of positive action out there — please share in the comments if you know of any!

Reminder: Support yourself first, when and where you can — With all of the above in mind, many leaders forget to start with themselves and their own needs. The age-old analogy goes: “Put on your own life jacket, before you attend to others”

Yet many leaders are distracted and paying attention to their team’s needs and may not “fill up their own cup”, which is the exact place to start. As you are asked as a leader to support and provide to an extra level, remember that your own mental state, self-compassion and self-care need also to be taken seriously and considered every day. Ask yourself, what is the non-negotiable today, where can I support myself and my own needs so I can then help others?

Palena Neale, wrote an excellent article, encouraging leaders to take Self-Care “seriously”, with the following prompts:

To refocus on the tangible benefits of self-care, ask yourself the following:

  • If instead of focusing on “self-care,” I invite you to focus on diet, sleep, exercise, and emotional regulation, how would you feel differently?
  • What could you stop, start, or continue doing right now to improve your mental and physical health?

A Final Note — Maybe you have had a bad experience of discussing a delicate or sensitive topic previously — that is why we tend to avoid them. But please reconsider: the key is to learn how to handle these situations in a way that enables less discomfort for you, and supports the person you’re talking to.

In the workplace, a difficult conversation is one in which you have to manage emotions (both your own and your team’s) and information in a sensitive way. Whenever a problem arises that may scare or impact your team’s wellbeing, make sure you transparently address it so that your peers and workers can feel safe, in an openly supportive environment. Digest the above, plan, but don’t script: conversations are 2-way interactions where compassion and empathy are the key elements to ensuring healthy communication.

Moreover, the very first step to being a compassionate leader is being self-compassionate, first to yourself and then you will be ready to be supportive to others.

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Originally published at on March 10, 2022.



Remote work advocate, educator, lecturer, keynote speaker and author. Follow me on Linkedin and sign up to the Newsletter “Remote Work Wellbeing Digest”.

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