[Editor’s note: A previous version of this was posted to my account on cohost.org. It has been reproduced here with edits and format changes for clarity.]

A thread by Charity Majors, co-founder and CTO of Honeycomb, inspired me to try to put into words how I approach work communication from the IC/report-to-manager side of things. The specific thing about her thread that I’d like to hone in on here is not so much the unanticipated responses to the idea of communication with skips, but this part right at the end of her thread— digging a little bit into some of the layers and factors of difficult conversations, primarily in work contexts:

When you start lifting up rocks and looking underneath them, things will come to light. Hard conversations must be had. This is how we get better.

If it hurts, do it more.
– Charity Majors, @mipsytipsy

I want to be upfront here and say that my intention in writing this is to share my specific experience and my mentality when I approach talking about things that would not paint me in a good light or when I talk about things that reveal gaps or flaws. I actually do not consider my experience to be prescriptive of a broader, default opinion about how I think things need to be done. And that is because people’s risk profiles, privilege, status, perception (and more) widely vary and all factor in the calculus of whether or not we can even talk about these things at work. So, keep that in mind as I talk about my experience.

The post I linked in Charity’s thread touches on what goes through my mind when I’m thinking about why I feel it’s important to be candid and honest about difficult matters. The part about doing that in order to get better and improve.

First, I feel comfortable about how I communicate my narrative when I am open and honest about something that is unflattering about me. It’s not a perfect process, and it is often really messy. But when I decide to talk about a topic like that, I earnestly try to focus on:

• Explicitly and accurately acknowledging the facts (even if they paint me in a bad light)
• The role I played that helped to contribute to what happened
• Saying what needs to improve or what needs to be better
• Marking the steps I’m taking towards helping to improve the situation or to help make whole again

Does this process sound familiar? This looks like the steps of an apology. In that light, that probably opens up all sorts of ambivalence and inner conflict. But my point is not that you should treat difficult conversations like how you would approach an apology. The specific point I’m making here is that in order for me to be able to talk about things that are flawed or things that need to improve, the narrative I communicate 1) needs to be accurate about the reality of what has happened, and 2) it needs to be framed as a demonstration of a commitment to tangibly learn from the experience, improve, and contribute to make that better in the future. Being able to frame what you’re saying to do that takes work and personal investment. For me, it starts with having the courage to talk about it (after I’ve evaluated and weighed the risks), then developing the confidence to frame the conversation in a way that demonstrates growth and maturity.

Secondly, the manner in which I choose to work towards the conditions for psychologically safe work spaces is to try to embody that and apply those principles against myself. I try to create the conditions that make it acceptable and safe to talk about mistakes, flaws, and gaps. To talk about when I’m not at my best. To be candid, forthright, and honest when I fuck something up. But again, in a manner that is true to myself, and a narrative that demonstrates active investment in getting better.

These things are important to me because they are tied to essential things like ensuring a healthy incident response culture and a culture that doesn’t burn engineers out. I feel like I have to do it because places that do that are the kinds of places I want to work. Therefore, it is essential that I embody that to create the space to allow it to be ok to do that.

A lot of companies do not have the culture in place to do this. A lot of places out there are outright hostile and unsafe to do this. And so to Charity’s larger point, having open, candid, honest lines of communication with people across teams, across orgs, and to skips, I think, is a reflection of the level of cultural maturity in place to confront flaws, gaps, and things that aren’t working well. Given that I want to see that kind of maturity where I work, I choose to go about it by stepping out and embodying that. I allow myself to be candid and honest about my strengths and weaknesses. I really hone in on making sure that when I talk about things that are unflattering about myself, I craft the narrative to accurately address the facts, to actively demonstrate that I have a vested interest in my own improvement, and to put in the work to make the space and people around me better.

Will that work for you? Do you need to do these things? You will need to make that determination for yourself independently of the ideal vision I’m talking about here. If it is genuinely unsafe or too much of a risk for you to do this, do not do this. But if you have the privilege and have the capacity to embody this, and if psychologically safe team spaces are important to you, contemplate what the investment looks like to embody these things, then go out and make it happen.