Carment Guillen

Dare to Lead: Seven Leadership Lessons to Remind Us All

By: Carment Guillen | June 21, 2021 | 
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Dare to Lead: Seven Leadership Lessons to Remind Us AllBrene Brown’s Dare to Lead is one of those books that will have you clutching your face in recognition.

You’ll smile at the things you’ve done right, gasp the things you’ve done wrong, and applaud the leaders in your life who were quietly knocking it out of the park.

I read an extract to my partner one night:

Don’t do that thing where you nod faster and faster—not because you’re truly listening—but because you’re signaling to the other person that you want them to wrap up

I buried my face in the book.

 “Oh,” I said. “I do that sometimes, don’t I?” 

“Yes!” he said. “But only sometimes.”

Luckily, the book was more than a long cringe.

Here are seven lessons that stuck with me.

To Be Courageous, You Must Be Vulnerable

Have you ever witnessed a moment of courage that didn’t involve vulnerability?

Neither have I.

Thinking back; every moment I was brave, I was also scared witless. 

A few years back I did something crazy: I got a boat license and, a week later, crossed the English channel on my houseboat.

The day before I mapped the tides perfectly, checked and triple-checked the radio, and taped down all movable objects.

I packed licorice for seasickness, energy drinks for drowsiness, and aspirin for a headache.

I even made a sea-themed playlist.

But no matter how well I prepared, being on the open sea is vulnerable.

I was living out a vulnerability metaphor.

There was nowhere to hide, and if things went wrong, no one to save me. 

And yet, I made it. I docked up on the Belgian coast the following night and got a fist bump from a drunk sailor.

Thinking back on my catalog of uncomfortable memories—moments where I felt afraid, exposed, and vulnerable— I realized they were invariably followed by acts of courage.

We’re all far braver than we think. 

Clear Is Kind, Unclear Is Unkind

I grew up in England, a place where strangers mumble “sorry” at you in the street, for the mere inconvenience of their presence.

It’s taken me years to undo this cultural conditioning.

In the UK, politeness means telling white lies to spare another person’s feelings. 

I nearly fell off my chair the first time a Dutch colleague looked at my work and said “I don’t like this—do it again.”

The infamous Dutch directness can be brutal, but my work has improved.

This is one of Brene’s core teachings: Clear is Kind. Unclear is Unkind.

As an editor, I have to turn down writers every day.

When I started, I would be vague, so as not to hurt applicants’ feelings. I soon learned that saying, “Your English is not yet strong enough for this position, here are some books you can read to improve” is much kinder than “due to the large volume of applications, you have not been accepted for an interview.”

Robospeak. 

In the first response, I’ve given them actionable feedback.

It’s difficult to hear at first, but they can now go off and improve. This is kind.

In the second response, I’ve chosen my own comfort over respect for the applicant. This is unkind. 

It’s worth saying that being clear and honest is not code for being obnoxious.

A lot of cruelty can be masked behind the phrase “I’m just being honest.”

You can be clear while also being respectful, courteous, and generous.

Clear is kind.

Shutting Off Vulnerability Creates Toxic Cultures

Dare to Lead points out one of the biggest ironies of our time: while we complain about AI replacing our jobs, we are simultaneously removing humans’ unique gifts from the workplace.

Namely: emotional literacy, vulnerability, and empathy. 

By removing vulnerability from the workplace, we create more work for ourselves.

Because managing the problematic behaviors that come up in armored cultures takes a lot more time than embracing the necessary, tough, and awkward conversations that invariably come up at work. 

I can’t help but think of Basecamp’s recent decision to ban political conversations—leading to a mass exodus of a third of their staff.

While the political climate in the U.S. is particularly polarized, and no one can know what happened behind the scenes, it’s hard to imagine the culture will recover from this. 

Brene explains that many organizational cultures subscribe to the myth that by severing vulnerability and emotions, we’ll be more productive, efficient, and easier to manage.

So they build cultures that require and reward armor.

But by killing the heart we also kill courage, trust, creativity, and accountability —and instead invite shame, fear, and cynicism. 

The Antidote to the “Dress Rehearsal of Doom”

We’ve all done it.

We get a promotion and think, “Well, they’ll probably fire me soon anyway,”

We fall in love and think, “Well, they’ll probably leave me for someone else.” 

This ‘dress rehearsal of doom’ that humans play out in their heads during moments of joy is self-protectionism at its finest—and it’s very common.

Joy is the most vulnerable emotion we own precisely because it’s so fragile and fleeting. 

When we can’t tolerate joy’s vulnerability, it turns into foreboding.

We start planning the multitude of ways we can get hurt.

But this is not helpful, says Brene.

You can’t plan for painful moments.

You see this show up at work when people say, “OK, let’s not celebrate this win yet, what if we lose funding?”

This robs people of opportunities to be happy. 

Fortunately, there’s an antidote to this: practicing gratitude.

The next time something goes right at work, instead of indulging the doom-gremlins, take a look around and say, “I’m grateful for this moment, and the joy I’m feeling.”

Numbing Negative AND Positive Feelings 

I have an embarrassing confession to make: during the lockdown, I became obsessed with YouTube videos on skincare.

I watched hundreds of hours of dermatologists breaking down chemical compounds.

My cabinet looks like an apothecary.

I’m not happy unless I go to bed looking like The Oily Maniac

At first, it was fun and educational, but soon I found myself doing nothing else.

I’d reach for skincare videos when I was tired, or anxious, or uneasy. Afterward, I’d feel guilty. This is a numbing behavior. 

We all have numbing behaviors, Brene explains. Some people smoke weed, some play computer games, some binge Netflix, others scroll through Reddit for hours.

But when we numb uncomfortable feelings we also numb good ones. 

As a leader, it’s your job to sit with uncomfortable feelings and unpack them, so they don’t show up at work.

It’s OK to spend some time on Instagram, but before you reach for the doom scroll, think: is there a feeling I’m avoiding? Is there something else that could bring me pleasure right now?

We All Have a SFD

SFD comes from one of my favorite books, Anne Lamont’s Bird by Bird.

“The only way I can get anything written at all is to write a really, really shitty first draft,” says Anne.

Everyone has a shitty first draft—you should have seen this article when I started.

The human mind does the same thing, explains Brene.

We are all conspiracy theorists, telling ourselves fantastical stories all day long.

In fact, we get a dopamine hit when we come to an understanding, even if it’s based on inaccuracies and half-complete information. 

This is the Shitty First Draft of the mind, and we need to watch out for it.

Because the vacuum of missing information is often filled by our fears and insecurities.

As you can imagine, the SFD is dangerous in the workplace. 

In courageous cultures, there is space to share your shitty first draft so you can get a reality check.

But you can also do this yourself.

For example, if a colleague was quiet in a meeting, your SFD may say they’re not speaking to me because they’re annoyed that I still haven’t completed that task, in fact, they probably think I’m incompetent. 

One way to combat this is to ask them directly, “Hey, I noticed you were quiet in there, the story I’m telling myself is that you’re annoyed at me, what was the reason?”

But if you’re not yet comfortable giving a colleague a window into your neurosis, which, trust me, everyone has, there are some questions you can ask yourself:

  • What more do I need to learn to understand the situation?
  • What more do I need to learn to understand the other people in the story?
  • What more do I need to learn to understand myself?

The latter takes courage and emotional literacy.

But by looking for answers you build trust with your colleagues, mend communication issues, and learn to be a little nicer to yourself. 

Asking for Help Is a Power Move

When Brene asked leaders for their top trustworthy behaviors, they all listed one thing: asking for help.

If someone asks for help frequently, it means they’re confident, curious, and if sh*t hits the fan—leaders can jump in to course correct.

That’s the kind of person you want to give responsibility to. 

The fearful mind will tell you that asking for help makes you look incompetent.

But the fearful mind is wrong. (There’s a surprise.)

The more you reach out to your peers for support and clarification, the more they trust you.

And the higher up you’ll go in their estimation. 

Dare to Lead Today

And there you have it—one learning for every day of the week.

This book is ostensibly about leadership, but really, it’s about emotional intelligence.

At the heart of every emotionally intelligent leader is a good listener: someone who can listen to both others, and themselves. 

It made me think about active listening.

Some people listen to fix (why don’t you do this?) as it relieves their own discomfort.

Others listen to respond (think: fanatical nodding)—but that’s not really listening.

The best among us, listen to understand. This means giving space for people to finish, asking questions to get the full picture, and summarizing what you’ve understood.

If you can turn this inwards, and also use these techniques on yourself, then you’re ready to lead.