Eight Things I Learned About Leadership

When I became a boss at age 30 I was not a leader

Annalisa Monfreda
11 min readFeb 23, 2017

Alas, my case is not an isolated one. In fact, I would say that there is a pathological lack of synchronism between the time a person takes on a role of responsibility and when he becomes a leader.

If you look about, you will find that there are many more bosses than leaders around.

Of course, it is never too late to become a leader. I believed that, I worked at it and I was able to achieve some results.

But if there’s one thing I’ve realized over the years, it’s that the opposite — it’s never too early — is especially true.


It’s never too soon to become a leader.

You don’t have to wait until you have a responsible role, resources to manage, interns to assign tasks to. You can and you must be a leader from the very first day on the job, regardless of the role you have.

And not because you want to get ahead or please the boss or the company.

But because working as a leader is much easier. And definitely more enjoyable.

What does it mean to be a leader nowaday? Everything I know about the subject I’ve learned from my mistakes and from a series of encounters that took place in a variety of places and situations. That I will now share with you.


Serena, 25 years old, worked as a waitress. A high school graduate with a major in science, she’d been waiting tables forever. At 13 in a café, at 17 in a restaurant and by 22 in a pub, with unsatisfied customers snapping their fingers at her, a boss whose only concern was money and indolent barmen.

Unable to change the situation beyond her control, Serena tried to change something within herself: her attitude.

She stepped out from the stereotype of the submissive, frustrated waitress and embraced the role of caring employee, showing respect to everyone she came across, regardless of their gender, nationality or social status. While her colleagues displayed disdain toward customers who snapped their fingers to call them over, she treated them with greater kindness, offering more smiles, more attention.

This attitude brought her unexpected results: she no longer felt angry, she earned more tips, customers came back and little by little treated her better. The finger snapping lessened and her personal victories increased. In a very short time, the boss gave her more responsibility.

Serena, while she was still a waitress, did a number of things characteristic of a leader. The first was critical: she practiced kindness.

In my professional life I have never had clients who snapped their fingers at me. As editor-in-chief, however, I have had staff who responded to my proposals for change with:

“What you’re asking is impossible. I’ve been doing this job for 20 years, trust me.”

“We already tried that eight years ago, if you want to go back to it, no problem.”

“We’ve always done it this way, what’s wrong with doing it now?”

To deal with these attitudes, I initially saw only two avenues and I tried them both. I was authoritarian, appealing to “I’m the boss, you’re not.” I was challenging: “I’ll show you I was right, I’ll do it myself.” Nothing changed.

Then one day I glimpsed a circuitous, curving by-road, not knowing where it might take me. When I decided to follow it, I discovered that it was a fast shortcut to being recognized as a leader.

It is the path of kindness, the greatest show of force there is. In my case it consists of responding to “it can’t be done” with a smile (a sincere one!) and an equally sincere: “Let’s try it, if it doesn’t work, we’ll go back to the old way.” Kindness is the primary trait of a leader because it shows that he is clear about his goal, which is not to be respected or to prove he’s capable, but to enable the team to achieve the best result (not necessarily in the way he had planned).

By the time I arrived as editor of Donna Moderna, I was sure that kindness was effective. Yet I was surprised to see that a kind leader was viewed with suspicion, even by those who should have benefitted from that kindness. Some thought the result would be anarchy. And others conjectured that I would appoint someone else to maintain order in my place.

But no, it was kindness that caused me to be recognized as a leader even though I was not the most brilliant or the most experienced.


A third thing about leadership I learned from the results of a study commissioned by Google, aimed at discovering the magic formula that made workgroups function.

The researchers analyzed both the composition of the groups and their operating rules. But to no avail: no results. Among the effective groups there were some that were totally anarchical as well as others that were rigidly moderate and organized.

To break out of it, they formed their own groups, observing them at work, and at last the magic formula was revealed. In the most effective teams, there was one constant: each member of the group felt free to voice his own ideas or concerns without fear of humiliation.

So I understood that a good leader affords everyone the same opportunity to express himself. He lets each person know that his ideas are fundamental. And he takes each and every contribution under consideration, without snickering, making faces or offering remarks. In short, a leader makes every member of the group feel safe.


A fourth thing about leadership I came to learn during these years of the “digital revolution.” Which essentially means: doing more things than before, at the same time, for the same salary, while maintaining high quality. A seemingly impossible equation.

The digital revolution overwhelmed me. One day I found myself editing two newspapers instead of one. And seeing to a TV broadcast, the contents of a website, the planning of the social pages, a daily newsletter, the classes for our digital school …

At first this is how I dealt with it: more things to do, more hours at my desk. But the method quickly proved to be ruinous. When I realized that the quality of my work (and my life) were in serious danger, I knew that I had to reconsider everything I did and how I did it. I had to completely rethink the way I worked to fit more things in the same amount of time.

In brief, I stopped thinking in terms of adding and I began resetting.

In the last three years I have reset the way I work countless times and I try to encourage my colleagues to do the same. To that end, I adopted the practice of not restructuring procedures from the top down, but merely indicating the new objective to be achieved. Those who are already leaders grumble and frown, but after a few days they have already completed the reset and come to my office with a new organization in mind, a new method, a new procedure.

Those who are still studying to be leaders, however, usually appeal to the sacred totem of quality: “But doing all these things, it’s not possible to maintain the same quality as before.” To which I reply: “Maybe you should also reconsider your concept of quality.”


My husband is 45 years old and is a manager in a large multinational. One Saturday morning he was feeling particularly down: the project he was working on, he said, was not proceeding as it should. He felt responsible for the difficulties and couldn’t manage to pull it all together.

We talked about it, we put the elements in order and to me, as an outside observer, it soon seemed clear that the solution was to ask for help. From his colleagues, from his boss, from someone. But for him, asking for help was tantamount to admitting failure.

Hearing him talk, I remembered all the times when I too mistook responsibility for omnipotence. And thought that asking for help meant trading a little piece of my leadership.

Instead, the opposite is true.

When I became an editor-in-chief, I was put in charge of colleagues more talented than me, with greater competence and more experience. It wasn’t quite clear to me why I was their boss. So at first I pretended to know, to have everything under control, and meanwhile I was losing sleep to close the gap that separated me from the others, to catch up to them.

Instead, asking for their help would have been enough.

This finally happened when I arrived at Donna Moderna. I began by telling my colleagues: I have never managed a weekly, my background is not current events, help me. And I discovered that only someone who has the courage to ask for help stops being solitary and is able to draw on the strength of the group, channeling the best energies around him.

The point is that one is a leader not because he is the best, the most effective or even the most competent. One is a leader because he is able to bring out the best in everyone.

Humility is not a lack of self-confidence, or a lack of self-esteem. It is acknowledging that you don’t know everything, but that you can equably continue to learn. From everyone.


A few days ago I went to hear one of the greatest living pianists. The technical perfection of his concerts goes without saying. The variable is how attuned he will be to his audience, how deeply he will be able to move them.

And yet … surprise!

After an hour and a half of flawless execution, the pianist missed one of the notes of the final chord, producing a horrible sound.

Any one of us would have stood up pretending it hadn’t happened, would have smiled, would have accepted the applause, and then spent the rest of the evening beating himself up over the damn note that had eclipsed everything that had preceded it.

He, on the other hand, once he recovered from the disbelief of having produced that terrible sound, burst out laughing, and as a gesture of mock reproach to the missed note, pressed the right key. “Where were you hiding?” he seemed to be telling it.

The applause brought the house down and he’d had to make three encores.

The artist publicly said: I made a mistake. Sure, it was obvious, but admitting it wasn’t a given.

Being able to say “I made a mistake” is one of the most important qualities of a leader. Among the commandments of Kathy Viner, editor-in-chief of The Guardian, there is this one:

Admit your mistakes. Don’t hope that no one will notice them. Rather, explain why you made a mistake and correct yourself publicly. We live in a glass house. Honesty and transparency always triumph.

But this pianist did something more: he smiled at his mistake. He was indulgent towards himself. He publicly forgave himself. And that’s what makes a genuine leader.

Perfectionism and precision are important qualities. But a leader must not lose sight of his true goal by chasing after the chimera of his own perfection. The pianist knew he had hit the mark: thrilling us for an hour and a half. And he didn’t lose his head over a missed note.


As I mentioned above, when I became editor at age 30, “why me” wasn’t clear to me. As a result I took pains at first to fill the gap of experience and knowledge, so that my employers wouldn’t realize they’d made a mistake by giving me the job.

As the months (okay, let’s say years) passed, it became evident that they wanted me there in part because of my lack of experience. They wanted me there so that I would put my inexperience to good use. I was a tabula rasa, since I had spent most of my professional life outside of editorial offices and had been a newly appointed editor for little over a year. Therefore I was able to think outside the box. To stop doing things the way they had always been done. Innovate.

And so, armed with the two lessons I’d learned earlier — asking for help with what I couldn’t do and not being afraid to make mistakes — I started to change the way things had always been done.

When I was editor-in-chief of Top Girl I dared to address issues that had never been covered in a teen magazine. At GEO I tried out cover stories of places that were not very typical for a geographic magazine. At Cosmopolitan I attempted my first integrated editorial division. And since I’ve been at Donna Moderna and Starbene I’ve changed the way we work, the layout of the editorial unit and so on. The result?

  • Not everything worked. But even the least effective choices taught me something.
  • I have learned not to get too attached to my ideas, not to dig in my heels about following them when they were a mistake.
  • And nobody, I mean nobody, has ever criticized me for my mistakes.

If there is one thing they would not have forgiven me for, however, it is not having taken a risk. Because what you expect from a leader is the courage to dare. Even at the cost of making mistakes.


The final thing I learned is that a true leader surrounds himself with leaders. Better yet, he helps his team members become leaders. How?

This is how I tried to do it. One day I resolved that I would no longer read the issue before it was printed, but afterwards. This made each member of the editorial staff responsible for his own article from start to finish. And it led to an improvement in the process and consequently in the product. Within a few months, my colleagues increased their leadership.

This innovation caused quite a stir. Some accused me of the sin of omission by not checking. And that, by turning others into leaders, I was failing in my duties as a leader.

I’m not so sure about that. My goal is to put out the best publication possible and there is no doubt that having several people check the galleys is more effective than having one person check.

That’s not all. My other goal is to continue to improve and innovate the product. Reading the finished product and working on feedback (instead of on revision) allows me to come up with more insightful reflections, which lead to real evolution.

All in all, by helping others become leaders, I think I myself have become a better leader.

The original article was published in Italian here.
English translation ©2017 by Anne Milano Appel



Annalisa Monfreda

Co-founder di Diagonal. Qui parlo di giornalismo, leadership e innovazione