Learnings and Pitfalls of a Sales Leader.

Today, I want to talk to you about something essential and very close to me.

I have been managing people for 5+ years and found it to be the most challenging skill to develop in my career.

Managing people is not easy, and managing salespeople is even more difficult.

There is a constant line to be in, which involves, from one side, driving performance, making changes and, from the other side, the most crucial part.

Take care of your people. Your team. Make them feel part of something, heard and understood, yet challenged to improve.

It’s like a dance; you want to listen to the music, remember your moves, and try not to step onto your partner’s feet.

However, managing people is the only thing that matters in a leadership position.

The processes, the frameworks, the money, the board, the CEO.

Everything is essential, but at the same time, it is not.

If you fail to manage your team, you can forget the rest. Nothing will work.

When I started my leadership career, I struggled a lot with (apparent) aggressiveness.

I’m not a bad person, and the people who know me wouldn’t say I’m aggressive, but I’m passionate, and sometimes the passion can become aggressiveness.

Or at least it can be perceived like that.

And when you fail someone or make somebody feel unsuitable because of something you said or did, there is something you need to do.

That is what happened to me.

During my first leadership role, I struggled a lot. I used to be very emotional.

As this became a straightforward issue to me, I stepped back.

I left my leadership role and went to LinkedIn to restart my career as an individual contributor.

I knew I needed to improve and get better. I had to take my emotions in control.

That was when I stumbled upon compassionate management, which was the moment that completely changed my career.

At Linkedin, during those years, our CEO was Jeff Weiner.

Jeff was the best leader I have encountered in my short - yet long - career.

And Jeff was talking a lot about compassionate management.

He did not only talk, but he walked the talk, and all the interactions I have seen showed an incredible, compassionate leader.

I started becoming obsessed with it, reading all the articles and books and watching all the videos I could find.

One of the best videos is Jeff’s speech at Wharton University; check it out below. 👇

​Among all, 3 critical aspects of compassionate management are the most important.

These are the aspects I try to remember every day.

1. Be the Spectator of Your Thoughts

I used to prioritise winning the argument over constructive collaboration.

During a heated discussion or moment, I would jump on my chair, anxious to answer to whoever I have in front.

However, I have since started to pause and reflect on my emotions.

Whenever my heart rate increases and my face heats up, I stop and ask myself: “What’s going on with you, Matteo?”

My heart slows down, and I centre myself.

This has been my most significant improvement, thanks to compassionate management.

2. Recognise Empathy vs Compassion

I always tried to be empathetic, but whilst it is a great start, it’s not enough.

Empathy means feeling what others feel.

Compassion is a step further: see the world through their lens to alleviate their suffering.

Compassion is empathy + action. It’s more complex but way more effective.

3. Trust to Fast-Track Decision-Making.

I used to think my team had to “earn” my trust.

Most managers don’t trust their teams or, worse, don’t trust them by default.

It’s challenging to make decisions when there is a lack of trust and constant questioning.

Developing a culture of compassion will build indefinite trust, allowing for faster and better decision-making.

Trust your team by default.

Summary

I know I’m not there yet.

I still get some feedback on my way of managing people. Sometimes, I come across as direct and assertive.

It’s not easy to profoundly change your personality, but I strive daily to be more compassionate and see the world through my team’s eyes.

It’s a journey, and I’m in the middle of it.

However, even if sales is harsh sometimes and we have to drive performance, everything you wish can be achieved through compassion.

Today was short but intense. Thank you for reading this far, see you next Saturday.