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Not everyone loves a leader

How do you avoid the pitfalls of being a strong leader?

I’m obsessed with trying to find the best ways to lead creative teams because I realized early on in my career that only being a good designer wasn’t going to take me where I wanted to go in my career. To become a creative director or a leader meant that I was going to need to develop a whole new set of skills I didn’t possess. It has been a road riddled with ups, downs, insights and hard realizations that were all necessary to help me get to where I wanted to go.

One of the biggest realizations that came to me out of that process has been that not everyone loves a leader. It is a hard thing to accept because so much of what we read and see leads us to believe that if you stand up, try to do something new and try to lead a team that we will be celebrated for your effort. It’s not all gloom and doom by any means as there are times when you will find that happy ending for stepping up into a leadership role but it isn’t always the case for a number of reasons. I don’t see people talking about this problem or coaching their teams on it and as a result, a lot of great potential leaders get discouraged and shrink back to smaller roles because it wasn’t what they thought it was going to be. So I wanted to talk about some of the challenges I have found and some of the ways I have been about to overcome them in the hopes that more people will get a complete understanding of the challenges that you may find trying to change things.

Having a vision means you can be judged on it

I have written and spoken at length in articles like ‘Are you a creative leader or manager?‘ about how some people are leaders who make a difference and some people are just managers who just maintain the status quo. I have found that the same themes of that discussion continue to be true here as well.

Managers are people who will just go with the flow and won’t make waves. It is easier for them to go about things that way because it means you have fewer problems from not challenging bad decisions and not standing out from the crowd.  It also means though that you won’t ever change anything, make anything better or have a team that really does great work.

Leaders will take a stand and put forth a vision of how things need to be to bring about change, a stronger team and better work. The challenge is that you are taking a well-defined position and you stop floating around in the status quo like a manager. That defined position means that everyone can have a variety of reactions to your vision like judgment, support, criticism and even being downright mean by taking shots at what you are trying to do. The positive end of the spectrum is the start of bringing your team together and starting to bring about change as it clearly defines your standards, hope and what you want everyone to aspire to. The negative end of that spectrum is hard to deal with because you are putting a vision out that is deeply personal and it is rooted in a passion that you want to change things for the better which is then met with negativity.

“If you are not willing to be the champion, cheerleader, leader and protector of the change you are trying to bring about at every single step in the process then no one will is going to believe in it and it won’t happen”

If you find yourself in that position of having your vision land on the negative end of the spectrum then remember that everyone will always talk about how they want innovation or better work right up until the moment when they realize it means things are going to have to do things differently. Change is uncomfortable because it means people are going into the unknown and stretching beyond what is familiar. So if you are going to try to bring about change then you have to know and expect that people will react this way because it is just human nature. It will be up to you be the person who can help them see how your vision will make things better, how you have thought through the details but want everyone to go on the journey together and most importantly how you will be with them through the entire process. All of this is critical because if you are not willing to be the champion, cheerleader, leader and protector of the change you are trying to bring about at every single step in the process then no one will is going to believe in it and it won’t happen. People have to see and feel your faith in the what is about to happen to bring about change to believe it in themselves. I will talk more about how to keep that fire of faith alive in a minute.

Become a leader, not a dictator

One of the other reasons why people don’t always love a leader is because not all people turn out to be leaders as they pervert their authority into becoming dictators. Dictators make it even harder for you to become a leader because you will have team members who have been subjected to a dictator in the past and have a hard time trusting you and bring about change.

Leaders are people who have a vision but also understand that the best work comes from a team of talented people working together to solve the interpersonal, business and political problems presented by trying to bring that vision to life. Dictators are people who have a vision and are blinded by their ego or ambition to the point where all they want it, everyone, to do what they say without question. There is a profound difference between these two types of people but if you don’t take the time to understand the difference you can write off a leader as a dictator and even worse you can think that a dictator is a leader.

What dictators don’t understand is that they weaken the work and they weaken the team very quickly because no one wants to just be told what to do all the time – especially if you are creative. Creative want to express themselves, grow their skills and create things that get them excited. If they are just executing on someone else’s vision all the time then none of that is happening and as a result, you will see these teams have extremely high turnover or extremely unmotivated team members.

So your challenge will be not to let this happen and to create an environment where you have the confidence to get ideas from your whole team. It’s then up to you work with the people who had the strongest ideas to refine their process to make them stronger and work even harder with the people who had the weakest ideas to teach them how to understand their creative process to become better. If you do this then you will also have a team that is MUCH more likely to buy into what I laid out in the last section and helped bring about the change you want to make with your vision.

Embrace your crazy

I wrote earlier about the importance of a team having faith in you to bring about the change you are proposing. I think it is just as important to understand how critical it is for you to have faith in yourself. This is something that is easy to say but it’s hard to make happen because when you are creative you are also wired with self-doubt. That doubt is born out of the fact that creating something is a deeply personal process where you are risking part of yourself in every design. It is again human nature because everyone wants people to like them, believe in them and support them when they risk something.

This is something I struggled with for a long time because I have a certain way of working, a certain level of thinking I want in everything and not everyone works at that same level. As a result, for a long time, I felt like I was crazy and different and didn’t think that was a good thing. It was only when I was lucky enough to start working with Apple that I saw that they worked the same way that I did and that gave me the confidence to embrace my ‘crazy’. I wish it didn’t have to take that external validation for me to believe in myself but it was a valuable lesson I try to teach everyone on my team which is to be successful you have to embrace and own your flavor of crazy. It is the only way you will be confident enough as a leader to bring about change and it is the only way you will be able to author a vision people will want to rally behind.

It was also a lesson I never wanted to forget so I went so far as to get the phrase ‘Here’s to the crazy ones’ tattooed on my right arm. It is something that I know most people write off the tattoo as an expression of an Apple fanboy but I didn’t do it for that reason at all.  I did it because there are days when I am weak when I am down and when I doubt myself and I wanted a reminder of what it is that I need to aspire to and what the standard I need to keep. On other days, it is a validation that I need to keep embracing my crazy to do the type of work I love. I will encourage you to embrace your crazy and think about if there are physical things you can keep in your office to motivate and remind you of what it is you want to aspire to.

Final thoughts

As I said before, the intention of this article isn’t to make leadership out to be all gloom and doom. It is to hopefully start a conversation and some realizations that great leadership is a lot of work. It is a struggle to make things better and that struggle will happen to you on a personal, team and corporate level. But the struggle is worth it. It is worth it because when you can change a team, when you can make the work better or when you can help someone discover their inner talent then it is one of the most magical experiences of your career. For me, the things I am most proud at this point in my career will never appear in my portfolio because they are the people on my teams over the years who have grown into leaders and changing things with their visions. That makes all the struggle worth it a hundred times over and I will keep fighting in the hopes of being able to keep making that magic for more people in the future.

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Creative Director, Designer, Brand Builder, Speaker, Podcaster, Crazy One. As a designer, I have 20+ years experience creating the strategy, concepts, and designs for award-winning integrated global advertising campaigns, building multiple global Fortune 500 brands and creating innovative digital experiences. As a leader, I have 15+ years transforming agency and client-side teams using a mix of creativity, business strategy, process and political skill to create innovative, world-class work and cultures that change industries and companies. My clients have included American Airlines, W Hotels, Disney, Citi, ExxonMobil, Acura, Old Navy, Nationwide Insurance, Verizon, Subaru and many others. My work has received over 150 international awards, my app designs have been named as one of the World’s 100 Greatest Apps, Apple has featured my work in 9 keynotes, 4 TV commercials and more.

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