<<< Back Posted: May 2020

Breaking News: Coachee Writes Thoughtful Guidelines for Difficult Conversations!

About a year ago, I coached a young talent rising quickly in the ranks at her organization. She realized that one of the skills she needed to sharpen was conducting difficult conversations with underperformers. Preferring harmony, she had always found this challenging.

During one of our sessions, I supported her in preparing for an upcoming conversation in which she would need to deliver some harsh feedback. A prolific writer, I asked her if she would summarize her takeaways in an email to me. Below you will see what she came up with, and I find it no less than extremely valuable guidelines that others can use, as well.

With her full permission, I am sharing her words with you, dear Coaching Cube readers:

Preparation is key: I prepared by writing down the objectives of the conversation, the main points I wanted to land, and the specific examples I would provide to help explain my feedback. I also practiced delivering the feedback, even speaking out loud to a photo of the person! Doing these things made me feel much more confident going into the conversation, and it helped to ensure I delivered a clear message and achieved my underlying goal. I will always take time to prepare going forward, as this is a variable I can control.

Start in the right way: I often find it challenging to approach the beginning of a conversation. This time, I started by explaining my intent (to help) and asking if I could provide feedback. I will use this simple formula going forward, as it helped to get that awkward first part out of the way and created a two-way dialogue from the outset.

Understand why I do not want to have the conversation: When I thought about it, I realized I did not want to have this conversation, as I needed to tell someone they were underperforming, and I expected it would be disappointing for this person to hear. Digging deeper, I also felt I could have done more to support this person to perform and that the issue was partly my fault. As someone who likes to keep harmony and aim for perfection, it made sense that I had been avoiding this conversation. By knowing what was holding me back, I was able to use my values to try and explain to myself why this conversation needed to happen, and this increased my comfort level. Specifically, if I did not provide the feedback, this person may not have a real opportunity to improve and could lose their job later. And although I may not have done everything perfectly, the issue was not solely my responsibility.

Importance to the team and the business: Connected to the above, reminding myself that this feedback would improve: (1) the lives of other people on the team; and (2) the performance of the organization — helped me to overcome my feelings of guilt around delivering this feedback.

You can be direct without being rude: Not being direct leaves room for interpretation and can mean the critical message you need to deliver will be lost. For example: "Your performance is not at the same level as your peers" is harder to say, but it is more transparent than "Your performance needs some work", which could be interpreted as everything is probably OK.

Don't race through the feedback with the desire to get it over with: I realized I needed to leave much longer pauses so the person could digest the information and respond. While it creates unpleasant silence, it is pointless having the conversation if they don't have the time and space to process what I am saying. 

Don't delay having the difficult conversation: It doesn't typically resolve itself.

Do not assume the outcome: I thought this person would be devastated by this feedback. Instead, he immediately acknowledged the issues I outlined and was relieved to be having the conversation, as it had been a concern for some time.

While it may not work every time, asking your coachee to summarize their take-aways in writing can encourage further reflection and more lasting learnings. It may also result in another thoughtful set of guidelines!

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