Cristiano Ronaldo is more than just a pretty face. Look beyond his chiseled bone structure and gelled hair and you’ll see a source of wisdom in business and in life.

It’s a bold statement, I know, just like his eyebrow game. Please allow me to explain.

In 2005, during an integral time in the season for his team, Manchester United, Ronaldo’s father fell into a coma in London. It was likely that his father would die, and this created a huge dilemma for the Portuguese forward whose presence on the pitch played a key part in the team’s overall success. His leaving would most likely mean the loss of a title for the team.

What could have been a major source of shame for Ronaldo, was quickly quelled by the excellent leadership skills shown by manager Sir Alex Ferguson. Ronaldo explained their conversation to the Daily Mirror;

“I said, ‘Boss, I don’t feel good.’We are in a key moment in the league and theChampions League, but I say, ‘Boss, I don’t feel good. I want to see my dad.’

“[He said] ‘Cristiano, you want to go one day, two days, one week, you can go. I’m going to miss you here because you know you are important. But your dad [comes] first.’

When he told me that, I thought, ‘This guy’s unbelievable’. He was a football father for me.”

Ferguson’s compassion is the lesson to be learned here. He knew that the core values of the individual (or business) is what determines success. He stuck by his guiding principles and proved that ultimately ‘doing the right thing’ would influence not only how Ronaldo would perform in the short-term, but how he would behave and view himself throughout his career and his life. As a result, Ferguson became ‘like a father’ to Ronaldo and the pair enjoyed many successes throughout their time together. 

Why trust should be given upfront

It’s difficult for me to extend high-levels of compassion to new team members upfront because I believe trust is a core value that’s built over time. I’m quickly finding that withholding trust is not only a detriment to my personal leadership, but it is also just flat out wrong.

“In looking for people to hire, you look for three qualities: integrity, intelligence, and energy. And if they don’t have the first, the other two will kill you,” Warren Buffet, CEO of Berkshire Hathaway.

Our new copywriter, Alex, is a perfect example. She started two months ago and has never once given me reason to not trust her work ethic. She possesses integrity, intelligence and energy, but for some reason I found myself holding back on fully trusting her when she requested to work from home (WFH) over the holidays.

Before starting at AirHelp, she was honest about her availability. She was looking forward to joining the team full-time, but was also transitioning out of being a full-time freelance writer and had to wrap up ongoing projects before fully committing to AirHelp. It meant she’d have 15 days out of the office during her first two months at the company.

I wasn’t happy.

I replied to the HR Director who was still in negotiation with her, “That’s 15 workdays she’s requesting to work from home within the first two months of being employed here. It’s going to be hard to acclimate her to the business without her being in the office. I’m not against working from home, but I want to make it clear that this would not be a regular occurrence.”

Show, don’t tell how to trust

As a manager my concerns were valid, but what I failed to see were the examples Alex was simultaneously showing me that proved her trustworthiness. She was forthright with her initial availability and was insistent that time spent out of the office wouldn’t be a regular occurrence. Later, she proved to be true to her word by never missing a deadline and being consistently available for phone calls or last-minute projects. In fact, I was so assured by her work ethic (trustworthiness) that I began ordering her to sign out of Slack and Skype and go enjoy herself.

Nevertheless, the holidays are coming up and when she asked me for if she could work from home for 15 days over Thanksgiving, my old concerns of trust and reliability were renewed. Her reasoning is valid; her grandmother had fallen ill and she wants to spend a significant amount of time in Montana to be with her.

I told her I would think about it.

AirHelp is a tech start-up that is thriving and hiring aggressively. It’s important that the team bonds and grows up together. I was concerned that continued, lengthy absences would break this bond and also set a false precedent that working from home is the rule and not the exception. What I failed to acknowledge at the time was that 60 percent of my team isn’t even based in New York, anyway. We have offices in 15+ countries across the world, so why was I placing different expectations on her than the other team members? I know it’s because I knew them already. Once again, I failed to trust upfront.

You gotta give, give, give

“I’m not a micromanager,” I tell my team, which is true. I don’t question every decision, invoice or metric that comes across my desk. We don’t work off a scoreboard or use templated to-do lists. We don’t have set working hours.

Naturally, this hands-off approach only works with a mutual level of trust that everyone involved will actually do what they say they’re going to do. I failed on my half of the bargain. I didn’t trust. Alex, I’m sorry I failed you!

Naturally, this hands-off approach only works with a mutual level of trust that everyone involved will actually do what they say they’re going to do. I failed on my half of the bargain.

Two nights ago around 2 a.m., while suffering through a sinus infection that wouldn’t let me to sleep, I came across the quote from Cristiano Ronaldo and it knocked me back into place. I learned that I need to trust from the beginning and evaluate if it can be maintained over time. Sure, it was Ferguson who taught me this, but I’d also like to thank the messenger.

The next morning, I was done thinking about it. I sent her an email, “Regarding vacation and WFH days … it does not matter to me how many vacation days you need for spending time with family. Family is the most important aspect of life and you need to do what you need to do.”