What to do after a courageous conversation
- mayadolgin
- Nov 6
- 4 min read
(November 5, 2025 Newsletter)
I love having moments of clarity as a result of conversations with clients. The one we’re talking about today comes from an accumulation of conversations, which is ironic since that’s the topic itself. I’ll explain.
When I teach about courageous conversations, I tend to treat them as discrete units.
Your boss said something you found upsetting, and it’s a pattern that needs to be addressed? Have a courageous conversation!
A team member stepped out of line and it had big implications in ways they don’t realize? Have a courageous conversation!
A colleague consistently assures you they will prioritize your projects but misses most deadlines? Have a courageous conversation!
What I’ve learned from my clients, though, is that when those initial conversations end, there is almost always follow up.
They report back that it was an important step in clearing the air and getting aligned, and the now conversation needs to continue.
Moving forward, we will treat them as launching points, not stand-alone interactions.
Instead of courageous conversations, let’s start to view them as courageous invitations.
Why it matters
Our relationships aren’t an accumulation of stand-alone interactions, but rather a product of them. The interactions impact each other – they make the next one better or worse in response to previous moments.
If we feel that someone leaned in and met us where we are, even if we disagreed, then we are more likely to believe it is safe to circle back and keep going.
On the other hand, if a conversation left a bad taste in someone’s mouth, they would come into the next one more hesitant or reserved, or avoid it altogether.
If we mistake courageous conversations as independent of our interactions before and after, we risk planning for them inaccurately.
Instead, if we see them as courageous invitations, we set ourselves up for sustained learning, rather than expecting to reach all conclusions in one go.
Naming relationship context
One of the steps in my BRIDGE Prep Guide to Courageous Conversations is to articulate the most concise and elegant summary of the facts as they stand.
This can be harder than it seems, as oftentimes by the time you’re working up the courage to have a tough conversation, there’s a lot to summarize, and it can also take effort to separate fact from interpretation.
One thing I’ve left out of this step, though, is referencing your ongoing dynamic with the person. For example, times when the issue has already been raised, progress made (or not) up until now, or naming a pattern that the two of you fall into together.
This step can be helpful in making sure that we’re not treating this conversation as if it’s in a vacuum. This can sound like “We’ve always gotten along so well” or “I know that when you and I are stressed we get into this loop.”
Being explicit about follow up
My BRIDGE Prep Guide ends with setting practical follow up steps about the actions being discussed. I now see there are two holes here:
Sometimes, the conversation will end with open questions for both parties to consider and continue discussing. In this case, I would recommend deciding together when and how the conversation will continue, not leaving it open ended.
Other times, the follow up needs to be about your working relationship, not the next steps at hand. In those cases, decide whether it will be more effective to be explicit or not about your desire to check in about how this conversation is impacting your dynamic, when the time is right.
Final thought
Relating to courageous conversations as courageous invitations allows you to deepen your partnership with the other side.
It adds extra humility and respect to say, “I want to open this conversation but don’t expect we will finish it in one sitting.”
It takes the pressure off and acknowledges that better ideas are yet to come, and you are committed to finding the best answers to your toughest challenges together.
The Coaching Corner
Feed back what you heard and make sure you're alignedWhen a team member launches into an explanation with a lot of details or moving parts, pause to make sure you got it. Summarizing it back in a sentence or two indicates that you're listening closely, models speaking more concisely, and confirms whether you understood correctly.Don't forget to end with something like "Did I get that right?" to get their confirmation or allow them the opportunity to edit the summary in their own (few!) words.
Recommendations
I haven’t finished reading Brené Brown’s new book, Strong Ground, yet but I have been binging her podcast episodes and appearances in the meantime. Here’s my favorite episode so far from her series with Adam Grant.
If anyone wants to do an informal book club with me as we read it, just reply to this email and we’ll figure out what that could look like! Seems better to read it in community than alone.
“Don’t Cling to your Old Job After Being Promoted” – a new and helpful HBR article on making the sort of transition I spend much time with my clients exploring.
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