Breaking down difficult conversations: giving constructive feedback

One of the toughest things that I’ve personally seen leaders (myself included) struggle with at the start of their leadership journey, is having difficult conversations with the people they work with. It’s uncomfortable, often times getting pushed aside or avoided as much as possible, because it’s built up as being an overall unpleasant experience.

I get it. However, it’s unavoidable. So here are my thoughts and strategies on tackling this.

Throughout my career as a leader, and now as a Business Coach & Mentor, one of the toughest things that I’ve personally seen leaders (myself included) struggle with at the start of their leadership journey, is having difficult conversations with the people they work with – and more specifically, the people who report into them.

Difficult conversations require you having to deliver constructive feedback which is often perceived as negative by the recipient. It’s uncomfortable, often times getting pushed aside or avoided as much as possible, because it’s built up as being an overall unpleasant experience. I get it. However, it’s unavoidable. It’s a very important leadership skill, one that requires practice and preparation. And personally … I recommend being more intentional about working on this skill because it’s an unavoidable aspect of not only your career – but your life.

Let’s break down the discomfort we feel at the mere thought of having a difficult conversation. It’s usually rooted in a few things:

  • Worry about how the feedback is received
    • That it won’t be received well
    • That it will hurt the other person’s feelings
    • That the feedback does more harm than good
  • Worry that our good intentions are questioned
  • Worry that our “likeability quotient” will dip by a few points
  • These worries are understandable – but there is a silver lining to them. They indicate that you care – about the other person, their feelings, and making sure that they walk away from that conversation in the right direction. Between caring too much and not caring at all – I can tell you the latter has the worst impact; on leaders, their employees, and their organizations overall (more on that in another post).

As a mentor, here’s what I recommend to long serving leaders, along with new and emerging leaders, when asked how to tackle having hard feedback conversations:

  • Lead with positive feedback! Let the other person know what they have done well. (This is an important and commonly applied starting point).
  • Make sure that the quantity of “positive feedback” and “negative (or constructive) feedback” are more or less in proportion to one another. (This is what most leaders don’t do well).
  • Don’t gloss over the positives and go gang busters on the constructive. Spend roughly the same amount of time articulating feedback from both sides. (Balance is important – you don’t want them feeling horrible by piling on the negative, but also can’t have them confused with so much positive they don’t see the constructive comments).

One last tip: take the time to organize your thoughts prior to the meeting. 

Taking the time to break down your thoughts also helps you stay clear and on track – having something to reference if the conversation get’s derailed, or ensuring you’ve covered what is the most important aspect of your talk.

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