Jerry Colonna, the Founder and CEO of Reboot has one of the best podcasts for Entrepreneurs, Founders and VCs. I would highly recommend you all listen to the podcast if you really want to accelerate your life learning. I am trying to get Jerry to come to Iceland and be a speaker for Startup Iceland 2017.

I have written before that I feel that Entrepreneurship and Startup Founding is a truth game and how it is a good proxy for the struggles of life. Learning to become an effective founder or an entrepreneur or an investor is nothing more than becoming an effective leader. Once again, #Leadership is something that I have written about before. Leadership is the X-factor, being a leader is about building a great team, having a clear strategy and the will to pull through all the struggles that comes with building something.

Great leaders and founders figure out a way to infuse a leadership culture at every level of the organization. It is easier said than done. I wanted to write about one of the most important jobs of a leader, giving feedback. Giving feedback is a skill like everything else in life. It cannot be taught but it can be learnt. First time founders struggle with this skill, understandably. When you are starting to build a business it is lonely and you are working in a small team usually 2 or 3 team members. Communication is easy, but as the team grows to over 20 people thats when you start seeing cracks. In addition to this, the strength of scaling the team is the ability to get a lot done, but it also means everyone brings their own way of doing things to the table.

The founders and leaders in the organization need to grow with the team, the founders and leaders need to learn how to inspire, encourage, guide, coach and lead the team from one milestone to the next. This is again easier said than done. Founders come in all shapes, size and background. They are idiosyncratic, eccentric and downright anal at times, that is what makes them unique. The strength of the founders that comes from the above traits also become one of the biggest weakness when the team grows. Many founders struggle with communicating their vision and giving encouraging feedback to really unleash the power of their teams.

One of my favourite podcast by Jerry had Brad Feld and Fred Wilson, 2 of my mentors. I really enjoyed listening to the elders in this podcast. If you have not listened to it, go and listen. I will wait right here. Did you listen? I particularly liked the part when Brad was talking about how his partners at Founder Group have figured out a way to deal with conflict and giving feedback, I really like the way he puts it Brutal honesty, delivered kindly. If you are a leader learn the skill of giving brutally honest feedback, but do it kindly. In order to grow as a leader, you need to learn empathy. Believe me early on in my career, I got the part of brutal honest very easily, but delivering it kindly part took almost 20 years to even be part of my vocabulary. I struggle with it as much as anyone else, but I have realised one thing. People matter more than anything, if you treat someone harshly because they did not do something right or not according to your wish. You would have given them feedback but at the same time you would have crushed their soul. You see we are all fragile and soft on the inside, we try to put on a brave and hard shield when we go into the world but that is a mask. Being vulnerable and showing your soft side is a true strength of a leader.

Jerry, through the Reboot podcast continually brings the Founders he talks to about being vulnerable. Being vulnerable, showing your soft side but also being hard on the goals of the company is a delicate balancing act. You need to make hard march towards the milestones of the company but also do it without stomping on everyone on the way. When you are the founder and leader of an organisation, you have the mandate and power to do the stomping, but that does not build the team. It only kills the moral, dispirits everyone around you and sets you up for failure. When things are going well, it is not obvious that is what is happening but believe me as a leader you are setting the tone of how everyone in your organization operates. If you don’t have the temperament to lead, then the organization will not have the temperament to lead in the marketplace. I strongly believe that a startup is like an organism, the founders and leaders are the heart and soul, they are the role models and everyone looks up to them to learn to act within the startup and outside. Building a winning team culture is always done by example at the top. Create a positive team culture by subordinating your own whims and fancies, put the company first. Every single team member in your organization matter. I see it all the time, when startups are successful, the founders can get away with bad behaviour they think they can do no wrong but life has a way of showing us that we are not invincible. You will face challenges, that is part of the process, when you do, you need everyone to help you. If you crush them on your way up believe me nobody is going to catch you when you fall.