When Is Crossing the Line Actually a Good Thing?

Dec 11, 2021 | Executive Coaching, Political Agility


“That’s it. You’re done,” he said, unplugging the karaoke machine.

“What do you mean?” she challenged.

Pulling her aside to get out of view of the many cellphone cameras in the room, he said, “You’re going to thank me in the morning. Give me your keys. I’m calling you a cab, and we’ll take care of your car tomorrow.”

She was always buttoned-down and under control in the office, but she had decided to let her hair down at the company holiday party.  Drinks were flowing.  Everyone was taking turns at the mic.  By the time her name was called to sing, she was slurring words, tripping over her feet, and dropping f-bombs into the song lyrics.

This was a side of her no one had seen before. So, multiple partygoers pulled out their phones to capture the moment someone made a fool of herself.

“You represent the company and our brand at this function.  People have you recorded, and they’re probably going to share it on social media. I’ve got your back. I had to turn it off.”

“I’m never, ever drinking at a public event again,” she confided to him, “I’m so embarrassed.”

He could have capitalized on her very public faux pas.  Hugh* was next in line on the org chart if Kay* had lost her job (names changed to protect their identities).

So, what made him step in to protect his senior executive, rather than leave her twisting in the wind?

It was Kay’s leadership style every day prior to this.



Armored vs Daring Leadership

In her New York Times best selling book, Dare to Lead (Random House, 2018), author Brené Brown explores two leadership styles she sees among people, Armored vs. Daring.  These qualities lie on either end of a continuous scale that ranks how a leader might respond to a challenging situation or specific trigger.

In the case of uncertainty or problem-solving, the armored leader “knows” the answer and will defend his viewpoint as “being right.” Conversely, a daring leader will frame the scenario as a learning opportunity to ensure “getting it right.”

Kay, like all mortals, had her moments of weakness. Rather than build walls to protect her ego when insecurities arose, Kay would lean into the moment and enlist her team for their strengths that complemented where she was lacking. Everyone in her department shared in the victories because they were almost always a collaborative effort.

Hugh had often described Kay as the most daring manager he’d ever met.

She’d risk being open and vulnerable in hard conversations, and she would not let her direct reports “tap out” in awkward moments, either.  The culture in Kay’s department demanded peers hash out differences over complex issues as a standard operating procedure for achieving team goals.

So, when the time came for Kay to be held accountable on the spot, it was already ingrained in Hugh to act upon it.



Connection is Key

Hugh had a choice. He could throw gas on the fire that Kay had lit with her karaoke act, or he could be a lifesaver and extinguish the flaming shit-show.

If Kay were an armored leader, this could potentially be devastating to her personally and professionally.

“Ah-hah! You’re wrong for doing this!” they’d all say while pointing fingers at her heroic failure.

After all, what better time to be in the spotlight than while you upbraid and embarrass the person standing between you and a coveted title with stock options?  He would have something to gain by bringing her down a peg or two. However, the relationship cultivated in their three years of working together stayed his hand from taking advantage of the circumstances.

Brené Brown describes Daring leadership as “wholeheartedness” and leading with an unarmored heart. It’s operating from the worldview of having compassion for and desiring connection with your fellow man. It opens the doors to developing affection for your teammates, and it guides your decision making when your choices impact others. Caring and connection are prerequisites for Daring leadership.

But what about that old saying that claims you must maintain a professional distance from subordinates, no fraternizing or crossing lines? The very best leaders that I know are actually masterful about blurring lines between professionalism and chumminess. They take time to develop a bond of friendship with their direct reports. They may confide personal matters with each other or celebrate personal victories together.

In the end, there’s a sentiment of “I’d take a bullet for her/him,” and that’s what Hugh did.

Yes, Kay crossed too far over the line with her drunken chanteuse act. Had she not led with her heart the other 364 days of the year, Hugh would not have felt constrained to run damage control for her. Nor would he have had the liberty to speak to her bluntly about her actions being out of place for someone with her gravitas in the workplace.


“Culture eats strategy for breakfast.” ~ Peter Drucker


Building a company culture that encourages vulnerability and daring leadership takes time, reflection, and investment in your leaders. The process requires hard conversations, exactly the types of conversations we love to have at inclineHR.

Building Exceptional Leaders