How to have difficult conversations at work

Often what makes conversations challenging is the discomfort we feel in anticipation of the interaction.

With end-of-year performance reviews underway, many managers are preparing for conversations with team members. Not all of these will be easy or pleasant. We asked experts for practical tips on how to best approach difficult conversations and use them to effect positive change. Read on.

No matter how much you might want to avoid a potentially tense interaction, difficult conversations are an unavoidable part of working life. 

Delivering bad news – whether a complaint, a performance issue, a rejection or a refusal – is sometimes necessary to resolve conflict, improve productivity or meet strategic goals or compliance requirements.

The good news is that a challenging conversation, handled with forethought and sensitivity, can have a positive effect on team dynamics and culture. 

Karen Dillon, former editor of the Harvard Business Review and author of the HBR Guide to Office Politics, offers this advice: “If you find ways to navigate difficult conversations, your colleagues will come to respect your candour and your ability to work through a problem without making it personal.

“And when you conduct difficult conversations, you’re contributing to an environment where having hard talks, offering different points of view and giving honest feedback are accepted – and that is better for everyone and your organisation as a whole.”

Before the conversation 

Often what makes conversations challenging is the discomfort we feel in anticipation of the interaction. Fortunately, your mindset going into the exchange is under your control.

Leadership expert and founder of BoldHR, Rebecca Houghton, coaches her clients to reflect on three key points before they launch into a difficult conversation – first, that “this person is a good person” who has been trying their best; second, that I also have a role to play in whatever has gone wrong; and third that “all is not what it appears – whatever information I have, it is inconclusive until I have heard from them”.

Houghton says that keeping these points front of mind ensures you approach the discussion with “appreciative enquiry” and an open mind rather than judgement. 

“You’re taking joint accountability, so it’s a conversation about what ‘we’ could do rather than what ‘you’ should do, which is a lot more accusatory.” 

During the conversation

Many people assume they can be either honest or kind when delivering unwelcome news, but not both at the same time. This is not the case, says Dr Ruchi Sinha, organisational psychologist and senior lecturer at the University of South Australia’s School of Management.

“They decide to be straightforward and blunt,” she says. “They think that’s being genuine and authentic, because they are being honest.” 

However, “there is no reason why truth can’t be delivered with kindness and compassion,” Sinha says. Set a neutral tone and acknowledge the challenging nature of the forthcoming discussion.

“It’s important to start with empathy.” 

When offering feedback, keep it concise and focused. 

“Don’t use broad generic terms like ‘good’ or ‘bad’ and ‘effective’ or ‘ineffective’, because they don’t tell you ‘what’ and ‘why’,” says Sinha, who recommends zeroing in on two or three issues rather than enumerating a long “laundry list” of criticism. 

“When you give feedback, and you want someone to learn and improve, you have to keep it focused. Keep it to [the] most relevant and salient points.”

Sinha also advises following up perceived concerns or problems with potential solutions. 

“Providing resources and avenues to improve is what makes feedback constructive,” she says.  

Dillon cautions against engaging in a difficult conversation when tensions are running high. “If you are so angry that you can’t control your emotions, you are not in a good frame of mind for a discussion,” she says. 

“You’ll say the wrong thing, embarrass yourself or your colleague, or create awkward scenes for others.”

If either party loses their cool during the discussion, Sinha advises taking a break and rescheduling the meeting for a later time, when everyone is calm and has had time to reflect on the issues. 

Adopt a peer-to-peer approach

Seniority is not licence to talk down to a team member. In today’s workplace, there is much less tolerance for the “master-commander relationship”, says Houghton, who has observed a shift in the collective psyche in recent years, particularly during the pandemic, that has come to reject traditional hierarchy. 

Employees are “not interested in being told what to do or treated like a naughty child,” she says. Instead, people want autonomy in the workplace and for their voices to be heard. This affects how you should frame your message. 

“Instead of saying, ‘This is what you must do’, you are saying, ‘I’ve seen this, and I’m wondering if there’s something wrong.” 

Follow up with a question about what you can do to help, and what a good outcome might look like, offers Houghton. 

“You are engaging that person in a peer-to-peer style conversation,” she says. “You are asking for their opinion, you are asking for their input, you are giving them the autonomy they crave, you are showing them respect, you are not judging them. Ultimately, you are not telling them what to do – you’re coaching them to come up with their own solution.” 


December/January 2022
December/January 2022

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