Difficult conversations for me generally happen when there is something that I want to change in someone else’s behavior. It causes a lot of anxiety because I don’t like the current situation, I might have strong feelings, they might have strong feelings, I don’t know how they will respond and I don’t know how I will respond to their response, etc.

Magic formula

This is what I use to make sure I’m being assertive about needing things to change while giving the other person the benefit of the doubt / assumption of best intent so that they don’t have to be on the defensive. Always try to keep in mind that the goal is to establish how things will be going forwards- it doesn’t matter as much to figure out who was right/wrong, what should/shouldn’t have been done, the real intentions behind certain actions, etc. This formula has worked for me in many other contexts outside of work as well, but I’ll stick with work-related examples.

  1. Objective observation of what is happening

  2. Explain negative impact for you/others

  3. Extend an olive branch / try to see things from their perspective

  4. Give them a chance to respond / be honest / correct any misunderstandings

  5. Assert that you still need something to change, commit to being open to working together on a solution

Example:

"Hi X, I've noticed that we've been having a lot more check-in meetings recently than in the past (x times a week where before it was y times a week). I want to talk to you about it because it's starting to cause me a lot of stress and I feel like I'm having less time to actually get work done. I know you care about my work and want to make sure I'm doing a good job- I appreciate that a lot but I was wondering if we could brainstorm other ways to make sure you get what you need from me without needing so many syncs? I personally haven't seen the quality of my work change recently but please let me know if there's something I missed or something that happened that may have changed your level of trust in me. I am worried that this current system will cause me to be less productive and happy in my role - I'd be happy to work through any concerns with you and try to find a solution that works well for both of us. Let's talk about it in our next 1/1?"

<aside> 🧨 Steps 3 and 4 are extremely important to make sure things don’t escalate. In order to have discussions where people don’t get defensive, you have to give them a way to still feel like a good person even if you are calling out bad behavior.

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Delivery

In person I worry about glossing over things that are more serious or having a hard time asserting myself, in writing I worry about things being misunderstood or feeling like a robot. So what I usually do now is:

  1. Write my thoughts and send it using the formula - be assertive but also very empathetic.
  2. Minimize back-and-forth immediately after the initial message. This is probably the time when both sides are most defensive and most easily misinterpreted. If it happens, make sure to take extra time to formulate responses, still staying assertive and empathetic. You can cut off conversation by saying “I am worried things might be getting misinterpreted over slack, let’s save this for our meeting / do you want to hop on a call now?”
  3. In-person conversation is important to make sure the other person feels heard, smooth over feelings, brainstorm solutions
  4. [optional] Follow up with a written meeting summary, to make sure key points and action items are accepted by both sides. More necessary if I had a hard time being assertive in the in-person conversation and want to re-emphasize some things.

Exceptions: Sometimes for smaller things, I write it out and realize that I can easily improvise what I want to say and I don’t need to send them a written thing first. Sometimes I think things will be better received initially in-person, so then I will have the conversation first and maybe send a summary afterwards to make sure things are framed in the way that I want them to be. This whole write-talk-write delivery process works well for me, but it seems like other people have used the formula just as effectively in delivering real-time feedback. These are just tools you can use and customize as needed.

More Examples

Cheat sheet of phrases