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Have the Difficult Conversation

If you don’t say it… then you haven’t said it.

When I was a director at a technology company, I’d have weekly meetings with my managers. One manager was struggling with a seemingly under-performing employee. We discussed techniques to address the issue, but week after week the problem persisted. So, I asked, “how does <insert name of employee here> react when you have the conversation with her?” The manager’s expression then prompted me to ask: “you ARE having the conversation, right?” Her response was, “I’m not sure how to have the conversation.”

What makes difficult conversations so difficult?

That’s when I smacked myself on the head. Two realizations:

  1. When there are difficult conversations to be had, we avoid them. In fact, I read somewhere we spend 10x the energy avoiding difficult conversations as having them. Why? Because we feel the alternative is to confront, and that feels uncomfortable and scary because it is fraught with uncertainty (am I being fair? Will this conversation be damaging? Will the person react negatively? What if they cry, scream, pitch a fit, or call me out? Or…<insert nightmare scenario here>. But avoiding the problem doesn’t mean it goes away. The problem grows and so does your story. (“Mary” isn’t motivated, she lets down the team, I have to correct her work all the time when I’m busy. Let’s face it, she’s a bad hire…I should just let her go).
  2. We don’t know how to have difficult conversations. So, it goes one of two ways. One, the dump and run. We’re so uncomfortable, we blurt it out and it’s a negative, judge-y, destructive rant. The receiver is hurt or baffled and nothing changes. Or two, it’s fantasy land. We want to have the perfect conversation at the right time so there’s no discomfort and everyone is happy. These conversations can be so painfully tactful and diplomatic that nothing is conveyed.

It’s just all too hard…but it’s what leaders do

Having difficult conversations  isn’t a comfortable or favourite part of leadership, but a necessary one to make continued investments in the growth of individuals, and ultimately, the whole team or department. Not having the difficult conversations or addressing the elephant in the room can undermine your leadership.

Back to the scenario with my manager. I explained that by not having the having the difficult conversation she was robbing the other person of the opportunity to correct their behaviour or do something differently. It was a missed opportunity to understand their perspective and share her own perspective.

Purposely not having a difficult conversation can be indicative of a passive-aggressive leadership style. Believing a conversation isn’t worth having, because an individual is assumed not to be capable or willing to change, isn’t providing leadership to that individual. A leader who writes someone off as a failure without offering the opportunity to succeed, is themselves, their own failure. We all have blind spots, as a leader your role is to develop people, give them feedback and increase their self-awareness.

If you’re putting off the hard talk, consider the damage being caused to the individual and the team in terms of employee morale, team cohesiveness and respect for leadership, not to mention the actual issue which needs to be addressed. Putting off the inevitable makes the dance longer, not better.

By not having the difficult conversation, you  fail to give the opportunity to an individual, and the team, to improve, correct, and grow. In the end, everyone fails – including you. The honesty of the conversation must come from both the content and the intent. If the conversation isn’t taking place because the intent is clouded by assumptions of how it will be received, it’s time to revisit (your) leadership.

Have the conversation. Go in curious. Go in with the intent to develop, improve and enable. Be respectful and compassionate.

Difficult conversations are always challenging and are never comfortable because at the core they are about feelings and emotions (am I hurting this person’s feelings, will they be angry, I feel stressed, I’m frustrated). That’s why they are called difficult conversations!

Effective leadership, great people, good teamwork. Ultimately, healthy organizations are the ones where people know where they stand – they have all the conversations.


Catherine Ducharme is a recruiter and leadership development facilitator and trainer with Smart, Savvy + Associates. We find high-calibre marketing, communications, creative and sales professionals with proven track records and in-demand skills for companies who need them, across the Pacific Northwest and in Toronto. We also provide leadership and training development programs for workplace programs, corporate retreats and individual growth opportunities. Contact Peter Reek or Catherine to discuss your organization’s training needs.

Catherine Ducharme

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