How To Tackle Difficult Conversations At Work

Tackling difficult work conversations

From delivering performance reviews to saying no to extra projects, difficult conversations are a regular part of work life. The ability to tackle tough issues with tact and respect is an important skill for any professional. By cultivating a culture of trust and openness and fostering strong communication practices, you can successfully navigate tricky topics and help your team thrive. 

But while that’s easy to say, it’s not always easy to do. Fortunately, there are some steps we can all take to make these difficult conversations not only possible but productive. Let’s take a look at some of them.

Create an environment of psychological safety

An important characteristic of successful teams is psychological safety: when members and leaders trust one another to speak up, ask for help and voice concerns without fear of reprisal. In psychologically safe environments, mistakes both big and small are viewed as learning opportunities, not as failures. Everyone feels comfortable and supported to do their best.

And this isn’t just a feel-good approach. Research shows that psychologically safe environments lead to better performance while encouraging employee curiosity, confidence and motivation

Of course, good communication between managers and employees is a two-way street. It involves ongoing effort, and there is often room for improvement on both sides. In fact, only half of managers report handling tough conversations well — and, even more alarmingly, a majority say they’re uncomfortable directly communicating with employees in any way. These feelings are similar for employees: half report handling toxic situations by ignoring them

Avoiding potentially challenging conversations can make them even more loaded and intense; to create a safe and trusting workplace, address issues head-on — and with a healthy degree of empathy. Try to understand the other person’s perspective, concerns and limitations.

Build openness, equanimity and trust

How can you tell if your team needs to amplify its trust levels? One way is to give members a short, anonymous survey addressing the following questions:

  • Do employees feel comfortable speaking up about what is and isn’t working, both for themselves and for the team?
  • How do they handle disagreements with managers and teammates?
  • Are they comfortable providing feedback and asking questions in meetings?
  • Do they believe that mistakes, whether big or small, will be held against them?

If the answers reflect a need for improvement, there are a variety of strategies you can use to build trust and openness. Managers with an open-door policy are seen as more available and responsive, and this can encourage your team to reach out. You can also facilitate discussions and prompt question-and-answer sessions in team meetings and group chats. 

In all communications, stress that workers are in a safe, judgement-free space. Remain objective; focus on actions and policies, not individuals. And always stick to the facts rather than taking things personally or making them personal. 

The best managers don’t just support their teams; they also lead by example. Model positive behaviours and avoid negativity, such as gossiping or playing favourites. Help employees learn from their mistakes by sharing stories of your own professional challenges and how you overcame them. 

And when an individual or team doesn’t hit their goals, use the opportunity to focus on how to prevent it in the future and correct what went wrong. Remain open, confident and clear about expectations and limitations going forward.

Communicate frequently

Teams with effective communication systems are better equipped to tackle any topic, from everyday tasks to big challenges — and practice makes perfect. Build in time for regular conversations through team meetings, weekly one-on-ones and internal chats or email updates. By making open communication part of your team’s culture, you can prepare them to tackle difficult topics when they arise.  

Communication isn’t just about quantity, so take steps to make every conversation count. Plan ahead and set clear goals for conversations to ensure you cover pressing topics. Make a list of specific questions and issues to serve as your roadmap. And remember, when dialogue is ongoing, there’s no need to cram everything into a single conversation. Only cover what you have time to address.

Transform trust and dialogue into success

Difficult conversations can seem intimidating, but they don’t have to be. Create an environment of psychological safety; make frequent, open communication a priority; and remember that this is an ongoing process that takes empathy, effort and dedication. 

By actively encouraging a culture of trust and not sweating the small stuff, managers can help teams tackle difficult conversations head-on — and set everyone up for success.

Paul Wolfe is SVP of Human Resources at Indeed.

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