Care and Swear

Highly empathetic, highly demanding leaders

Robert G. Cole was the son of Colonel Clarence F. Cole, an Army doctor. He followed his father’s footsteps into the military and eventually graduated from West Point in 1939. He then married his longtime teenage sweetheart Allie Mae Wilson and began his military career by volunteering for the new and experimental parachute infantry (airborne). By June 6, 1944, he was a lieutenant colonel, promoted four times in five years, and in command of the 3rd Battalion of the 502nd Parachute Infantry Regiment. Cole parachuted into Normandy with his unit as part of the American airborne landings in Normandy. On June 11, 1944, LTC Robert G. Cole fixed bayonets and led a do-or-die charge down the causeway to Carentan, an act of raw resolve that earned him the Medal of Honor and, more importantly, the trust of every paratrooper who followed him.

As told by Robert Edsel in the book Remember Us, at one point in his career, Cole, found a soldier asleep on guard duty. He berated and cursed him so much that when he was done the soldier was crying. Cole then proceeded to take off his poncho and give it to the soldier so that he could stay warm throughout the remainder of the night while on guard duty. This was the type of leader that Cole was and is the epitome of what is referred to as “caring and swearing leadership”.

Robert G. Cole’s story captures the paradox of a certain kind of leadership. On the one hand, he was relentless, the sort of officer who would berate a soldier so fiercely for falling asleep on guard duty that the man was left in tears. On the other hand, he was the same officer who, just minutes later, took off his own poncho and handed it to that same soldier so he wouldn’t freeze during the rest of his shift. That duality, uncompromising and compassionate in equal measure, is what I call “care and swear” leadership.

It sounds contradictory at first. How can a leader both curse someone out and comfort them in the same breath? But the answer is that Cole understood something most leaders never do: that people need both demand and devotion. They will rise to impossible expectations if they believe the person setting those expectations genuinely cares about them.

“Care and swear” leadership isn’t about being a tyrant who occasionally shows softness, nor about being a pushover who occasionally gets stern. It is about embodying both sides at once. The “swear” is not gratuitous anger or intimidation. It’s the insistence on standards, the refusal to compromise when the mission matters. The “care” is not coddling or lowering the bar. It’s the act of seeing your people as human beings, of ensuring they know you won’t leave them behind.

When the two are held together, the result is powerful. People don’t just follow orders, they follow the leader. They aren’t motivated by fear of punishment or the lure of reward, but by trust. Cole was not unique in this. History is full of leaders who embodied this paradox.

General George Patton was infamous for his harsh discipline. He demanded perfection in the details, uniforms pressed, boots shined, tanks maintained with immaculate care. His soldiers cursed him for it. But he also wrote to his troops with almost poetic fervor, telling them that history would remember their courage, that their sacrifice would echo for centuries. His men knew he was hard on them because he believed in them.

In business, Herb Kelleher, the eccentric co-founder of Southwest Airlines, was the same. He once arm-wrestled another airline executive over a contested slogan, chain-smoked through board meetings, and was known to bark expectations with intensity. Yet he also showed up to employees’ weddings, funerals, and parties. He laughed with them, cried with them, and stood up for them when times were tough. Kelleher proved that you could be both demanding and deeply caring, and that, in fact, one gave the other credibility.

Colleen Barrett, who started as Herb’s secretary and later became president of Southwest Airlines, often told stories that reveal how he could be both demanding and deeply caring. She described how Herb would push his team relentlessly on performance — he obsessed over cost control and punctuality, famously telling employees that “we’re in the customer service business, we just happen to fly airplanes.” He expected every single employee to live that philosophy, and he was blunt when they didn’t.

But here’s the other side: Barrett recalled that when her mother died, Herb called her every day for weeks, just to check on her. He was her boss, yes, but also her fiercest supporter. Employees knew that if they gave their all to Southwest, Herb would give his all to them. He was known to write thousands of handwritten notes to employees and to show up for their life events, even when he had no time. One pilot once said, “Herb could chew you out for a mistake, and then the next day you’d get a note from him saying, ‘You’re still the best damn pilot I know.’” That’s care and swear.

Even Steve Jobs, a man remembered for his searing critiques, embodied this. He could eviscerate a designer with a single sentence, but those who stayed with him also recall the fierce pride he took in their work and the deep admiration he showed when something truly brilliant emerged. To work for Jobs was to walk a razor’s edge: terrifying at times, but also intoxicating, because you knew you were building something that mattered.

Jony Ive, Apple’s former Chief Design Officer, has shared some striking memories of working with Jobs. Ive said Jobs could be devastatingly critical: if he thought a design was wrong, he would say so in terms that left no doubt. “This is shit” was a phrase designers at Apple heard more than once.

But Ive also said that Jobs had an unparalleled way of making you feel that your work mattered profoundly. He had the ability to make you believe you were part of something world-changing. Ive recalled that Jobs once told him, after ripping apart a prototype, “You can do better than this. I know you can. Don’t settle.” That wasn’t an insult, it was an expression of belief. Jobs cared enough to be brutally honest, and he cared enough to invest in pushing people to their full potential.

Ken Kocienda, a longtime Apple engineer who helped design the iPhone and Safari, in his memoir Creative Selection: Inside Apple’s Design Process During the Golden Age of Steve Jobs (2018), describes how Jobs could be brutally harsh in one moment, then later make you feel like your work was indispensable. “Working with Steve was sometimes terrifying, sometimes incredibly rewarding. He could make you feel like the most important person in the world, or like you had no business being in the room, sometimes in the same week.”

The reason “care and swear” works is simple: human beings crave both belonging and achievement. We want to know that we matter and that what we are doing matters.

The “care” addresses the first need. It creates trust and psychological safety. It tells people, you are valued not just for your output but for who you are. It builds loyalty that can’t be bought with bonuses or perks.

The “swear” addresses the second. It sets the bar high, refuses excuses, and demands excellence. It says, what we are doing here is too important to accept anything less than your best. It creates pride in the work and in the standards of the team.

When these two forces combine, the effect is explosive. People will endure hardship, overcome setbacks, and go further than they thought possible. They will run through walls for a leader who they believe cares about them enough to push them to greatness.

But like any paradox, it is easy to get wrong. A leader who only swears, who demands without caring, builds a culture of fear. People may perform for a time, but eventually they burn out. They stop taking risks. They hide mistakes. They leave.

A leader who only cares, who empathizes without demanding, builds a culture of comfort. People may feel good, but they coast. Standards slip. Respect wanes. The team stops stretching. Both extremes fail. The art of leadership lies in maintaining the tension between them, firmness without cruelty, compassion without indulgence.

So what does this look like in practice? In today’s workplaces, it means creating environments where people feel both protected and challenged.

The “care” side is about more than pizza parties or wellness budgets. It’s about protecting your team from unnecessary politics. It’s about standing up for them when things go wrong. It’s about recognizing the lives they lead outside of work, and showing them that they are seen.

The “swear” side is about more than barking orders. It’s about setting clear expectations and holding to them. It’s about giving unvarnished feedback when someone falls short, even if it stings. It’s about making the hard calls, the ones that no one wants to make, because the mission requires it.

I often tell people: be kind, not nice. Niceness avoids conflict. It smooths things over. But kindness tells the truth, even when the truth is uncomfortable. It says, I respect you enough to hold you to the standard I know you can reach. That is caring. And that is swearing.

This balance is especially critical in environments where the stakes are high and the pace is relentless, startups chasing scale, hospitals under pressure, or engineering teams building mission-critical systems. In these places, “care and swear” leadership isn’t just effective, it’s essential.

Think of the best leaders you’ve worked for. Chances are, they were the ones who made you both sweat and smile. They pushed you harder than you thought possible, but you knew they would fight for you when it mattered. They were the ones whose stories you tell years later, not because they were easy, but because they were unforgettable.

Storytelling itself is part of this leadership style. Cole’s poncho story still resonates today not because it was dramatic, but because it revealed his humanity. Teams remember those moments. They retell them. They build culture around them. Leaders who care and swear don’t just manage, they create legends.

“Care and swear” is not about being perfect. It is about being fully human as a leader. To demand without demeaning. To care without coddling. To hold people to the highest standards because you care too much not to.

LTC Robert Cole’s poncho moment wasn’t a break in his toughness, it was the completion of it. His men followed him not just because he ordered them forward, but because he carried them through the night. That is the paradox: the leaders who care the most can also swear the loudest. And their people wouldn’t have it any other way.