Brene Brown Dare to Lead

Do This 1 Thing To Transform Your Relationships

The other week I woke up to a frustrated text from my project manager (and yes, I have a project manager aka PM. More on why you might want to hire a PM to help you with your art business).

We have been in the process of adding a full-time virtual assistant (VA) to the team. Our new VA lives in the Philippines and is amazing! But she is a newbie and not yet familiar with the software and apps we use.

Basically, overnight she accidentally “blew up” one of our email app connections. It was an honest mistake (being 15 hours ahead of us means she works while we sleep so we wake to any problems she’s encountered).

Normally when I get a text reeking of frustration like the stink of fresh skunk roadkill, my lizard brain kicks in.

Not gonna’ lie, I get defensive.

The truth is I am often reactionary (it doesn’t matter if it is a personal or business message, my brain doesn’t care).

I tend to make the situation worse by immediately sending a curt reply and things spiral out of control from there.

Fortunately this time, I was in the middle of reading Brené Brown’s Dare to Lead. A book that my PM had recommended no less!

Instead of hitting reply and sending a message that would have escalated this into a potentially relationship-ruining exchange, I decided to take a breath.

Our weekly meeting was later that afternoon and if I leaned into being vulnerable and recognized my part of the problem, the meeting would be a productive exchange that would strengthen our relationship not tank it.

Here’s the thing I learned from Brené Brown’s book…

Miscommunication is often at the root of our relationships troubles, whether it is with a co-worker, boss, employee, student, spouse, child, family member, or friend.

Being willing to be vulnerable, to put down our armor, and own our part of the problem allows and invites the other person to do the same.

Switch the goal from determining who’s right to identifying where things began to go off the rails and ultimately agreeing on what needs to be done to avoid this in the future.

What was the problem?

In this case, we had totally different ideas about what onboarding Kathleen (the new VA) looked like.

Just a week before reading the book, I didn’t have the language to articulate what I knew was the emerging problem–who is responsible for what with onboarding Kathleen.

As Brown would call it, what does “done” look like? And not just done but “paint done” look like to each of us.

What Brown means by this is “paint” the complete picture about what this task when completed will look like, who executes what, what the final product looks like, and most importantly how does “done” feel?

I knew this was the root of our miscommunication and the reason my cell phone was waiting with a big 💩 grumpy text at 7 am PT.

If you are lucky when you have miscommunication, the two of you can laugh it off and move on…
The truth is that most of us feel and react more like this…

While this might be our default reaction, we have the power to respond differently and should.

So how did the meeting go?

I wish I could say that we worked through it then. It was clear that my PM was still very aggravated. Our meeting agenda was packed and she channeled her frustration to quickly cover everything.

I was tired (my headaches are worse in the afternoon so I can’t always think quickly) and decided that I would send her a screencast later to address the elephant in the room.

The next day I sent her a screencast walking through some of the items discussed during our meeting regarding tracking projects.

More importantly, I chose to be vulnerable. To open up and acknowledge what was at the root of our miscommunication.

I took the opportunity to acknowledge that she was clearly frustrated.

I thanked her for sharing Brené’s book with me and helping me grow as the owner/ leader. Because of the book, I now had words for feelings I had about what was not working with helping Kathleen be successful in her first weeks. We weren’t in alignment with what needed to be done.

The problem? We never agreed on what “done” let alone “paint done” would look like.

I was concerned about the “soft” onboarding issues:

  • How to make her feel part of the team while working halfway around the world.
  • To have her feel comfortable enough with me to answer my questions truthfully (for example, when I initially asked what hours she planned to work, she said, “During your time zone workday.” I kept explaining that it wasn’t necessary. Why on earth she’d agree to work at night 5 days a week 🤷🏽‍♀️. Perhaps it was fear of losing the job. I knew I made headway when she finally said 1 pm to 9 pm her time.).
  • Does she feel supported?
  • Does she understand we don’t expect perfection or that she knows how to do everything right away?
  • That part of her job is to be paid to learn.
  • Are we encouraging her and praising her accomplishments?

The owner of the site I used to find her (it connects Filipino workers with employers), cautioned that not being attentive to this side of onboarding could result in your new employee ghosting you or unnecessarily struggling and ultimately failing.

After going through 683 applications, (yes!! that is how many replied to our posting and I DID read them all) I didn’t want to lose a great VA because I left her hanging on the other side of the world.


My PM was focused on tech onboarding issues:

  • Does she know how to access her new company email?
  • Did she get screencasts explaining how to do various tasks?
  • Can she access and use Notion, the app we use for project management?
  • Who is responsible for assigning her tasks in Notion?
  • What is the best way to use Notion to break down projects into individual tasks? (Ahh, guess who was the weak link on this?? $1000 if you guessed me 🥳 the gal who took a task format and put a project level item in with many steps buried inside. Completely not efficient for working with our team, I agree *now*.)

I am sure you can see by comparing these two lists that we had totally different ideas about what was most important in onboarding Kathleen. Both approaches were important but we hadn’t clearly identified who would do what and what “paint done” would be for us.

It also didn’t help that my part-time PM was deep in projects for other clients so I was creating most of the screencasts for Kathleen (and maybe not for the most important tasks first).

Fortunately, things worked out and our personal and working relationship is better for it.
I highly recommend you add Dare to Lead to your reading list. It is NOT your average leadership business book.

It is ideal for teachers and parents too. Why? Because it is a guide for how to transition from parenting to mentoring your teen. For teachers, it will transform how you see your role in the classroom and the impact you can have with your students (of any age).

It has transformed the way I look at communicating with EVERYONE.

I just wish it had come out 15 years earlier. I really could’ve used this when my kids were in their teen years.

The good news…it is never too late to improve our relationships by changing ourselves and especially the way we communicate.

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