The Art of Difficult Conversations

As humans, we are wired to connect and cultivate meaningful relationships, both in our personal lives and our work lives. Yet, the last two years of the pandemic have done a number on us, amping up levels of anxiety and feelings of isolation. As leaders, we need to recognize and acknowledge the challenges and struggles our teammates may be facing – as well as our own. So, when it comes to giving feedback that might be a little uncomfortable to deliver, many of us are resistant to entering into a conversation that might be difficult.

I think feedback is one of the most underused tools in any manager/leader’s toolkit.  The issue is that most of us do a lousy job at giving it.  We spend more time sweating over how to give constructive feedback but will toss off a “great job” comment without batting an eye. Here are three strategies for having easier rather than difficult feedback conversations.

Walk the Walk

One of The Roundtable’s strengths is helping organizations to create the leadership behaviours and foundational components needed to foster a culture of psychological safety. Creating space for vulnerable conversations builds connections – whether people are in the office or working remotely. By sharing our own struggles with our teams, it creates the safe space needed for them to do the same and for all of us to strengthen and support each other. When the workplace dynamic is one of mutual respect and encouragement, there is the understanding among team members that we don’t have to go through this alone.


“Feedforward” is a different way to give feedback. In a nutshell, it flips the emphasis from the past to the future. Traditional feedback doesn’t break new ground; it simply confirms what we know about ourselves, and when the feedback about the past is less than positive it can actually reinforce negative behaviours, as the recipient feels helpless to change. Instead, feedforward” is a concept that was originally outlined by management expert, Marshall Goldsmith, and it focuses on the person’s development in the future. As coaches and mentors, we have found that the most effective kind of feed forward helps people see opportunities for growth and expands possibilities.

Make It a Habit

Sure, we give feedback to our colleagues, although in most cases, these exchanges don’t happen as often or as freely as they probably should. When feedback is relegated to a few times a year during performance reviews or other major manager-employee check-ins, it can easily become something that is dreaded by both the feedback giver and the feedback receiver. Leaders should set a goal to say a meaningful (read specific and clear) piece of feedback to each member of your team on a regular basis throughout the year.

Peer group coaching may be just what your organization has been looking to help build psychological safety and communication skills in order to take its employee development efforts to the next level. If you’d like to know more about our group coaching programs, contact us to start a conversation.



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