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Rotman Insights Hub | University of Toronto - Rotman School of Management

How to set yourself up for success for difficult conversations

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Beatrix Dart

Most people dread having difficult conversations – especially if it’s with their boss.

But what if a co-worker’s culturally insensitive comment left you stinging? Or you discover your male counterpart is paid more than you?

Dr. Beatrix Dart, a professor of strategy and executive director of the Initiative for Women in Business at the Rotman School of Management, says these situations are common conflicts that arise for workers across all different sectors and positions – from administrative assistants to management-level employees.

But whether you have a close, neutral or even a tense relationship with your boss, Dart says there are effective ways to approach these conversations so they aren’t painful experiences.

And while every situation will be unique, with some prep work, having these tough discussions may even provide employees with skills that will help them further their career, she says.

Before the conversation

Dart says once you recognize a problem, it’s important to bring it up to your boss sooner rather than later.

“You build up your own anxiety the longer you wait, which makes the problem worse,” she says. “When we teach women in our leadership in administration program, we point out that it is important that you keep your emotions as much at bay as you can.”

To help keep your discussion factual, Dart says it’s a good idea to write down exactly what the problem is, and the points you would like to make during the discussion.

No matter the type of relationship with your boss, she adds it’s important to gather your facts and be well-prepared beforehand.

While you can likely expect a much easier conversation when you have a great relationship built on trust, it’s still important to stay fact-based and remain clear about the objectives of the conversation – particularly if it’s a subject that can be harder to broach than other topics, like pay inequality, Dart says.

Timing is also important. Avoid having the difficult discussion when your boss is busy and on deadline, and instead, schedule a meeting at a convenient time for both of you, Dart says.

She adds that it’s important to prepare your boss ahead of time that this discussion will include a difficult topic so they can go into the meeting with the right mindset.

“You can say, ‘Do you have a few minutes? I have a difficult situation I would like to run by you,’” says Dart.

During the conversation

Dart stresses that it’s important to approach the situation with empathy.

For instance, if there is a conflict between you and a co-worker, don’t go into the conversation with a black-and-white view of the issue. Perhaps there is more going on in your co-worker’s personal life causing stress at work that you’re not aware of, or perhaps there’s no issue at all, and it’s only your perception.

Recognizing you may not have the full picture, Dart encourages the use of words and phrases such as “this could be what’s going on” or “may be what’s going on” when describing the workplace issue.

Overall, it’s important that your boss knows you’re only delivering this information because you care – and even offer suggestions that could help with the issue, she says.

For example, if you think a co-worker isn’t pulling their own weight, you can suggest brainstorming together to help your co-worker feel more productive.

“Don’t just come in to complain. Have a suggestion on what the path forward might look like,” Dart says.

After the conversation

Dart acknowledges that every situation is different, and if it might lead to a future grievance, it’s important to send an email to your boss thanking them and recapping the conversation so there is a paper trail.

She adds that it’s usually not a good idea to escalate the situation after the discussion happens – unless for example there’s an issue around diversity and inclusion or personal safety and harassment and your boss takes no action or is conflict-shy themselves.

Once you’ve had the difficult conversation, you can walk away knowing that it was a learning experience that provided critical skills for future success.

Dart adds that it’s particularly important for women to learn these skills.

“Women do worry more about speaking out forcefully, and that it might result in them being labelled and stereotyped,” she says. “It’s important that they are prepared so they can shine in their careers and get the advancements they hopefully deserve.”

Want to learn more ways to enhance productivity and grow your management skills? Explore Initiative for Women in Business’ wide variety of leadership development programs to level up your career.

Beatrix Dart is a professor of strategy, academic director of experiential & global learning and the executive director of the Initiative for Women in Business.