Have caring hard conversations with coworkers on Slack

When you do not have that hard conversation at work


Have hard conversations with coworkers on Slack


Life presents us with ample situations to have difficult conversations. That is one of the certainties of life. The workplace is no exception.


3 types of ‘hard’ conversations:


  1. Conversations that are hard and are not productive

  2. Conversations that are hard and are productive and aim to strengthen the relationship between people.

  3. Conversation that should happen, but we do not have them.


Whenever we feel frustrated or upset, there is a ‘hard’ or ‘difficult’ conversation that has not yet happened.


7 examples of hard conversations:


  1. Your boss does not listen to what you say

  2. Your boss talks for 25 mins of your 30 min 1-1

  3. You need to tell your direct report they did not deliver on their work as they promised

  4. Your coworker is late to the meeting you set up.

  5. You want to ask for a raise.

  6. You need to put someone on a performance improvement plan

  7. You need to fire someone



What happens when we do not have hard conversations?


  1. We feel resentful.

  2. We get bitter.

  3. Things start to fall apart.

  4. The situation gets worse between the coworkers.

  5. Problems get buried.

  6. We stress about going to work.

  7. We do not sleep well.


Just as Michael Seibel, CEO of YCombinator says, having direct hard conversations in crucial to helping founders succeed (see his tweetstorm):



What if you could have hard conversations easily and productively in a way that strengthens relationships? You can!


We heard from lots of people that they suffer because they do not have hard conversations, or that they have hard conversations in a way which is not productive. There are certain frameworks that have been used over several years which helps people have authentic & hard conversations in a way that strengthens the relationship between the people. One such framework is used in the Stanford Graduate School of Business highly popular ‘Interpersonal Dynamics’ course (nicknamed ‘Touchy Feely’). There are a few concepts that are useful:


  1. Be authentic.

  2. Be vulnerable - share your feelings. (feelings are magnets for deep connection)

  3. Stay on your side of the net (meaning when you talk about what happened - talk about facts only (and not about things you are speculating about (for example, you know what you are feeling, but you do not know that the person was angry (you can only say that ‘you told me you were not happy with this proposal’)


Introducing Caring Candor in GoodRipple


GoodRipple is a Slack bot/app that helps you send fun positive messages to your coworkers on Slack. Caring Candor is a feature of GoodRipple, which uses some of the principles of how to have effective conversations. Caring Candor is a Slack Action that works like this:


  1. You see a conversation in a channel. You can hover over the message and start a Caring Candor Action.

  2. approach the hard conversation with a caring mindset;

  3. lets you be authentic about how you feel and help them address what is on your mind;

  4. Oh, yes you can have the conversation in person or we make it super easy for you to start the conversation on Slack with Caring Candor.


When to have a hard conversation in real life (IRL) v/s on Slack?

We think there are certain conversations people generally would like to have in person and we are all for that. You can use Caring Candor to prepare you (getting into the zone and having a script) to have this conversation IRL. For other things, you can use Caring Candor on Slack - we set the right context so the person receiving it knows it is coming from a place of caring, and you can jump to an IRL conversation to continue the conversation.


We are excited to see how GoodRipple can help you have hard conversations with your coworkers so you are fully self-expressed, happy and so important work can get done.