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Lessons learned series: Get comfortable with uncomfortable conversations

This is the second in a four-part series chronicling the four most memorable leadership lessons I learned in my career – the hard way. And by “the hard way” I mean – boy did I get it wrong sometimes when I first started out, at times painfully wrong, but over the years I’ve learned by trial and error.
I originally meant for this to be one “listicle” post, but it turned out to be a long one, so I’ve broken it into a series. We’re at lesson #2, stay tuned for the others:
1. Criticism doesn’t work
2. Get comfortable with uncomfortable conversations
3. People make their own choices
4. Great leaders are servants

(I have a mild cuss word in this post. You’re warned; I do swear sometimes.)

Focusing on what works (see post 1 in this series) doesn’t mean it’s all sunshine and roses, and it doesn’t mean shying away from difficult conversations about performance. Very few leaders are given the chance to practice this deliberately, in a safe space. Most of us had to learn by trial and error, in real world situations.

The TL;DR on this is: formal performance reviews generally do NOT work. What works is to intentionally build a culture of trust that leaves space for frank, compassionate conversations that can include performance issues.

Preferably over a cup of tea. Tea solves everything.

Learning how to give feedback is a skill, and like any other skill it takes practice to master. Learning to have those candid, forthright conversations, especially when they’re about the most difficult subjects, can mean deeper and more trusting relationships with team members.

Every time I must have a tough conversation, I re-read the book Thanks for the Feedback by Stone and Teen. When I’m in the moment, I try to remember four things:

  1. be specific,
  2. be non-judgmental,
  3. focus on the impact, and
  4. be curious.

A sample script might be: “I’ve observed (specific example of behaviour) a couple of times, and it has affected me/the team in the following ways. Can we talk about it? Where’s that coming from?”

Ironically, being empathetic by nature does not serve well in situations where you need to give specific feedback and outline expectations of better performance. The danger of an overdeveloped sense of empathy is twofold:

  1. knowing you might hurt someone’s feelings can make you hold back and not get specific enough. Your message won’t get through. You’ll step back from saying what needs to be heard.
    And that “shit sandwich” thing where you couch “bad” feedback between two “good” pieces of feedback? Well, shit is shit. It doesn’t taste any better when you slap it between two slices of bread; you’re just confused as to what you were supposed to be eating.
    I have had supervisors do this to me, and it always leaves me guessing: do I need to do something better? What WAS that conversation was all about? Why couldn’t he just get to the point?
  2. on the other hand, turning off that highly-tuned empathy button to get through your prepared list of grievances can make you come across as a wooden, unfeeling automaton. In turn, that amplifies any hurt feelings that may arise, provoking a negative, panicked reaction from an employee or co-worker.

Both (1) and (2) are over-corrections, and I have been guilty of both in the past.

I knew I nailed the balance between trust, compassion and candidness when I had to have a frank conversation with an employee who was starting to drop the ball on several projects.

I had set up a meeting and, as usual, couldn’t sleep the night before. However, I had already established a good relationship with the employee. At the end of our hour-long meeting, we had an action plan for improvement, including ways I would help her through it, and she said “I’m so glad we had this talk. It was hard but – I trust you.”

Instead of leaving my direct report confused or upset, the conversation deepened our relationship and added to a high-performing team atmosphere. And her performance did improve.

Candid, compassionate feedback is a skill, but it’s also a gift that will return itself many times over.

Image: Tea for Two by Naama ym used under CC-BY-SA-2.0

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