Charles Day is an accidental consultant. After building a successful, creative film editing company others started asking for his input on developing their company to be more creative. In this episode, he shares his insights and what he’s learned about organizational creativity.

What You’ll Learn

  • Common practices of the most creative businesses
  • Three elements leaders need to do a lead a creative organization
  • Four weapons every leader needs – and they don’t cost anything

About Charles Day

In addition to running The Lookinglass, Charles is a Principal of the Boswell Group which provides psychodynamic management consulting to CEOs, corporate directors, and senior leaders. He is also an Adjunct Professor at New York’s Columbia University, where he has taught the art and science of building companies that unlock ‘Profitable Creativity’, and he coaches at The Harvard Business School in their Executive Education Program. Charles writes frequently for Fast Company and speaks regularly on Creative Leadership.


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Feel like reading instead of listening? Download the free transcript or read it below. Enjoy!

Transcript for Episode #096: Leading Creative Organizations with Charles Day

Amy Climer: Welcome to The Deliberate Creative podcast Episode 96. In today’s episode I am talking with Charles Day and we are talking about leading creative organizations.

Before I introduce Charles, I want to share with you two announcements. The first is a gift for you, really, and that is updated brand new resources page on my website. If you go to, head on over there you will find, basically, I just talk about my favorite books on creativity, leadership and teams. The page has been there for a while, but quite honestly, it was pretty sad. It is much better now. Head on over there if you are looking for some new resources and books on creativity.

The other thing I want to talk about is Episode 100. Oh my gosh! It is only four episodes away. I am so excited about this. I cannot believe that I actually made it to Episode 100. And honestly, I would not have done this without you. If I did not see the stats and get the emails from you all and the notes on LinkedIn and Twitter and Facebook saying, “Hey, I’m listening, and this is awesome! Yay, thank you,” it says to me that you are trying to help make the world a more creative place, which is exciting.

For Episode 100 I wanted to do something a bit different and a bit special. I want to highlight your stories. I want to highlight stories from listeners about something you have learned on the podcast. Here is how this will work. In a moment, I am going to give you a phone number. Call the phone number and leave a three-minute message telling me your story of what you learned from this podcast and how that has impacted your life. I will either replay that message on the podcast or I may reach out to you for a more in-depth interview. I would love to hear your stories.

The thing with stories is that they really inspire and motivate us. When we hear other people’s stories, it helps us understand like, “Oh, wow, I could do that or wow, I had that same problem. I loved how they solved it.” It gives us insights, it gives us motivation and that is what this podcast is all about. So I want to share your stories.

Here is the phone number; 828-571-0884. Call that phone number. If you want more information, if you are like, “I don’t want to write that down right now,” that is cool. Go to and there are more details there. The phone number is on that page. Check it out. I would love to hear from you. If you can give me a call or call that phone number in June or July of 2018, that is ideal. The podcast episode will go up I believe in August so leave a message soon.

Today’s episode I am talking with Charles Day. Charles, for eleven years, owned a film editing company. He built this company up to be incredibly successful and incredibly creative, which I think, particularly for film, those two things go hand-in-hand. But in this episode, he shares his insights and the learnings that he gained from that experience and he talks about how to create a creative organization. He now is a consultant and he works with all sorts of companies, helping them be more creative.

Our conversation specifically focuses on the C-Suite level; CEOs, executives, but even if you are not at that level right now, you may be in the future. And either way, I still think you will find value in our conversation. I found it particularly fun to have this conversation with Charles because we got to do it in person, even though he lives in New York and I live in North Carolina. Fun coincidence that I happened to be visiting my brother who lives in New York right around the same time we wanted to do this interview. And I was able to borrow my brother’s car and drive over to Charles’s house and we got to do the interview there in person, which was super cool. For me, that was just an added bonus, instead of having to do it on Zoom or another tool like that.

By the way, speaking of my brother, he is also an amazing artist and you can listen to his episode which is Episode 69 with Greg Climer. Check that out if you are curious about that.

Charles and I are going to talk about leading creative organizations. Here is Charles.

Charles, welcome to The Deliberate Creative podcast. Thanks for being on the show.

Charles Day: Thanks so much for having me.

Amy Climer: Can you start off and share with us a little bit about who you are and what you do?

Charles Day: That is a harder question, isn’t it, than we would ever like to admit. Yes, I am a leadership adviser and confidant to leaders of what I would describe as creative businesses. Anybody, any company for whom creativity is an important or essential fuel source for their business, I work with their senior leaders and their leadership teams.

Amy Climer: How did you get into doing that?

Charles Day: By accident, and against my instincts, actually. We, as in my wife and I, we had built a film editing company and we sold that business. We built it with real intention and with very clear ambitions and goals. When we sold it, we were approached by a number of people to give them advice. People would say, “That business was very thoughtfully put together, can you give me advice?” Then they started paying us for the advice and I finally turned to Chris and said, “I think this is called consulting.”

We realized how much we learned about running and building a business. Because it was a film editing company, we were not film editors, we were focused on, actually, building the business. And so we had absorbed all the information from lawyers and accountants and experts of various kinds about what were best practices and followed our own instincts as well. And so we had real clarity.

We understood about all the steps of building a business from, literally, white paper start-up to expansion, merger and acquisition. We dealt with the post 9/11 trauma of the advertising industry. It was more than a recession in the advertising industry post 9/11. It was a real depression for about a year. And so we had to manage the business through all of that and then further expansion and adding other officers, and then ultimately, to sale. And so we had gone through the entire lifecycle which we had not realized in the moment, but we did when we started being asked questions and so we built a consultancy around advising creative businesses.

Over a couple of years as we formalize that, we started working with production companies and advertising agencies and then big brands would approaches us as well and we started working with them. At various points, the leaders of some of those companies would come to us individually and say, “I found working with you really helpful. I feel more focused, I feel more clear-headed, I feel more confident, more aware. Can we continue this relationship on a one-to-one basis?” Both Chris and I would say “no” because we did not see ourselves through that lens. We had not been trained as “coaches” or “advisors” and so we kept saying “no.”

At one point, I was asked again by somebody and Chris said to me, “What is the worst that could happen? How badly could you screw this person up? Have you heard the advice they’re getting? It’s not that great. Why don’t you just say ‘yes’ and see?” I took her advice and said “yes” and realized very quickly that I was helping.

Over the last, I guess, four-five years my practice has evolved a lot towards that. Probably, 75 or 80 percent of what I do now is working specifically with leaders and leadership teams, more often, individually. And then the other 20 to 25 percent is spend doing some kind of consultancy work with creative organizations; how do they unlock creativity, how do they scale it. Various strategies around organizational dynamics.

I think the balance of the two is really helpful because you need to understand when you are working with a leader what is the impact of this decision on the organization. And I think working with the organization helps me understand the things that get in organization’s ways that really only leaders can unlock for them.

Amy Climer: What do you mean when you say a creative organization or a creative business?

Charles Day: Any organization for whom creativity is a fundamental fuel source. There are obvious ones like advertising agencies and marketing companies and production companies and content companies, but also a lot of big brands these day. I do quite a lot of work in the fashion industry which is, obviously, a fundamentally creatively driven business. Anywhere where creativity and commerce have to intersect in order to create value at the backend for stakeholders and shareholders.

Luckily for me, increasingly these days many businesses require innovation and original thinking to be brought into problem solving to be successful. We started getting calls from tech companies. We started getting calls from software companies, obviously. We started getting calls from creative service companies or service companies who are bringing innovation into what creative service looks like. Increasingly, it is a broader and broader spectrum which I think is, obviously, great for our business, but it is also just the fundamental indicator of where society is moving.

Amy Climer: In the flipside, are there businesses that you see that do not need to be creative or should not be creative?

Charles Day: No. I think it is hard to define a business that does not benefit from innovation. I think part of the challenge for businesses is the world is moving so fast and changing in so many different fundamental ways that the problems that they are facing are problems they have never seen before. You see the food chain breaking down. We used to all have a very clear understanding of where we sat in the food chain in any particular industry and where that industry sat in relationship to other industries and those rules do not apply anymore. Part of that is scary because we do not understand the hierarchy, but part of that is great. And if you have the right mentality, you suddenly realize there is opportunity everywhere because I can define myself on almost any basis that I want.

I think what you see is from a consumer standpoint, you see expectations changing. There is a fascinating evolution in terms of consumer analysis which is called Post Demographic Consumption where demographics used to be the guide and the reference point for every interaction with a consumer if you are on the brand or marketing side or even the product development side. You would focus on this is designed for or this is intended for a woman who is between 25 and 34 from this kind of income stream. What we are seeing these days is that you cannot group people through those lenses. They are too specific and they miss too many aspects of what makes that consumer connected or interested in your product or service.

There is a great piece of research that brings this to life. If you ask a 13-year-old and a 70-year-old for their top 100 favorite music artists, there is a 40 percent overlap. You will have grandparents taking their grandchildren to the same concert because they both love that artist. You cannot begin to access that relationship through demographics. When those kinds of realities start to emerge, the problems and opportunities that they provide for companies are literally problems they have never seen before. And so you cannot access the solutions to those problems unless you are able to unlock innovation or creative thinking within your organization.

Amy Climer: Absolutely. Let’s talk about unlocking creativity within the organization. In the work that you have done with leaders, you talked about helping them be more creative and lead the organization. What are some of the ways that you are helping them? What are you teaching them or what are they doing differently when they work with you?

Three Elements Leaders Need to Lead a Creative Organization [13:17]

Charles Day: It is a great question. I think there are a number of things. First of all is reminding them, in some cases, that the leader is the most important member of the organization because they have access to levers that only leaders get control of. And so encouraging them to pull those levers and do something significant in certain situations is really important.

A lot of people, I find, who move into positions of authority in creative companies bring a real humanity with them as part of what allows them to access creativity. I was going to say the drawback, which is probably not fair, but I think the flipside of that is it makes them hesitant to make decisions about moving people out of the organization which is really damaging to the organization.

One of the things that I encourage leaders towards is a mindset that says you are responsible for the entity that is the organization. If you look at the organization as a living-breathing entity which has its own needs, if you are not taking care of it, nobody else is because everybody else is self-invested and self-interested. Even if they are collaborative by nature, there is still a fundamental ego attached to each individual. And so you have to be responsible for the whole.

It is your job to act and if people do not fit, then it is your job to move them on. And it all serves in their best interest because when I was running my own business, whenever I got to the point of realizing it was time for somebody to move on and they needed to go, there was actually a relief on their part because they were miscast. And there was a relief for the people within the organization, almost all of whom recognized this person did not fit. The number of times they would come up to us and say, “Thank God.” And you say, “Why didn’t you say something?” Because the leader is often the last to know because people manage-up and you are removed from kind of the day-to-day dynamics. Part of it is pulling the levers of power.

Part of it is also helping them to understand their own strengths. We have a saying which is do the things that only you can do. If you focus on using the strengths that you have to do the things that only you as the leader has access to — in many cases, the leader is the only person with real access to the client, if you are in a service business. The leader is the person who has access to levers of power like financial spending decisions.

If you focus on understanding the things that only you are able to do, that nobody else in the organization is allowed to do or can do, and you move as much of the rest of the stuff down to people below you, two things happen; one is you spend more of your time doing things that are really important and not junking up your calendar with extraneous stuff that somebody else could be doing. The other thing is you actually develop other people much more quickly because now they have responsibilities that used to be yours and so when you empower them to make decisions, they grow, you also find out what they are capable of, and the organization starts to move up.

If you take that philosophy and push it all the way down through the organization, keep pushing it down through layers, what you end up doing at the end is flushing out of the bottom of the organization the 30 percent of stuff that the organization should not be doing at all and just wasting their time on some bureaucratic process that somebody decided ten years ago in a different industry at a different time that we should do that. It is amazing, I am sure you see this yourself. You go in and say, “Why did you do that?” “It’s just the way we do it.” “But why?” I think that is powerful.

I think the third aspect of it is helping leaders to understand the things that they are naturally brilliant at. Most of us suffer from the impostor syndrome in some fashion or another and so we are desperate to prove to everybody that we are not imposters. And so we fixate on our weaknesses and then we worry about becoming better at our weaknesses. We might be able to take our weaknesses from real weaknesses into just mediocrities and we invest all this time, and again, because you are the leader, the most valuable asset in the company’s arsenal, your time, and you are spending it doing things to make yourself just slightly less poor. Something that there are probably fifty other people in the organization who can do way better than you will ever be able to do it.

Amy Climer: And probably love doing it.

Charles Day: Probably love doing it and validated and rewarded for doing it. One of our priorities is let’s help you understand the things that you are naturally brilliant at. Let’s help you understand that not everybody can do that. The fact that it is easy to you does not make it easy to anybody else. Let’s encourage you to use it much, much more. And let’s encourage you to let go of all these things around you that you worry make you seem inadequate in some way or inferior in some way and get other people to do that stuff and have you be confident about that decision and that process.

Amy Climer: I just want to summarize. Pulling the levers and basically making those tough decisions, particularly, maybe moving people out, if needed, understanding your own strengths and understanding your own abilities.

Charles Day: And doing the things that only you can do. Prioritizing properly. One of the things that we see a lot is leaders giving over control of their calendar to their assistants. The assistants that I have encountered working with my clients are extraordinarily talented, extraordinarily committed so this is not in any way a statement about their lack of ability. They cannot know what is really important to the organization in the same way that the leader can.

When you find leaders abdicating responsibility for deciding what they are going to spend time on and just showing up in meetings that somebody else has scheduled, it is an incredible waste of leadership authority and judgment. They do not really learn very much from that process because they have not made a decision about whether they should be there or not. They just show up and then they are playing catch-up in terms of what is this about and what is the issue and what is the dynamic and why are we here. It creates all kinds of different tension dynamics in the organization. It also makes people dependent upon getting the leader in the room to make a decision.

I think that conscious leadership, mindful leadership really starts from – and it is a very practical step and it is hard for people, but take responsibility for your calendar. Be more decisive about saying, “No, I am not going to be in that, I do not need to be in that. Why are you asking me to be in that?” This is your authority. This is your responsibility. And again, I think you empower the organization through that willingness to be much more discerning about the things you should be showing up in. And again, I have never seen an example where an assistant does that better than the leader themselves do. And the leaders sort of absence themselves from the responsibility of deciding and I think that is not healthy either.

Amy Climer: There is so much there. I feel like that goes back to developing the people below us. And as leader, if you are always showing up in a meeting, you are not developing those people below you their skills in decision-making and their skills in helping you decide what is important for you to be there. It is all connected.

Charles Day: It is three-dimensional, and some cases, probably four-dimensional. I think a lot of people try and take on a leadership role through a sort of a two-dimensional view of the business, but you have a third dimension of self-awareness and being conscious of what the impact is on other people. Not just what is the business we’re in and how do we improve that, but this third dimension of how do we actually connect to who we are and how we impact other people and what we can help other people to become is actually, at the end of the day, fundamental to effective and successful leaders.

It is interesting because as you know, I have a podcast called Fearless Creative Leadership. I wrote an article four or five years ago for Fast Company where I talked about the four weapons of exceptional creative leaders. And I had been saying to people for a long time when I give presentations, “Here are the four weapons. I am open to the possibility there is a fifth. I haven’t yet seen one, I haven’t heard one, no one has ever convinced me there is a fifth, but I am happy to change the title of this to the five weapons if somebody can convince me.” In interviewing lots and lots of really extraordinary leaders over the last year, one of the themes that has come up, which I think might be the fifth, is the ability to listen and really listen.

Four Weapons of Exceptional Creative Leaders

Providing Context [22:06]

The four weapons that I identified are providing context. Only the leader can provide context. Why are we doing this? Nobody else can articulate that and define that in the way that the leader can.

Defining the Values of the Organization [22:22]

Every organization that I work with wants to talk about its culture. All of them do. And I understand that because culture is powerful, but you cannot manage culture. Culture is an outcome. Culture is an outcome of values and behavior. Those are the two things that determine culture.

If you are working with an entrepreneurial business that has grown from say 20 or 50 people as a starting point and is now a couple of thousand and they are clinging to the culture that they established when they were 50 people and they cannot figure out why it is not working when they are 2,000, because culture does not scale like that. Culture has to evolve as an organization evolves. And so the leader is responsible for defining values. They do not have to define them just by themselves, they can bring other people into the conversation, but they have to be the people who lead that process and build that requirement in.

It is not enough to define them, you have to live by them. There are some companies that I have worked with who are so committed to their values that they actually compensate their senior leadership team for whether they actually are living to them and helping their people to live to them. And they will run workshops internally about when we say transparency, for instance, what do we mean by that? Here is an example of when it works and here is an example of what we do not mean by it. They will, actually, survey the group and say where do you feel we are in terms of transparency? And if the needle has not moved by the end of the year, that leader does not get their full compensation. I think that is real commitment.

So actionable values. I think that those values also apply to themselves. Are you clear about your own values? Because it is easier to say I do this, except, when the chips are down you do not. So it is not really a value, it is just a wish.

Amy Climer: Like it is easier to act good when there is no pressure.

Charles Day: Right. If you say to somebody what are your values? Seven or eight times out of ten somebody will say honesty. And I will say, “Really? Honesty under all circumstances?” “Absolutely.” “Okay, great.” You have got this really difficult employee who everybody has been telling you for a year is awful and you finally come to realize how destructive that person is. And you and the head of HR are really worried that you are going to get sued by this person and you have decided that Friday is the day you are going to let them go. The HR director has built this whole process and consulted the lawyers and has got the script down and you and the HR director have to have this conversation.

That person walks into your office on Wednesday and says, “So am I getting fired?” You are going to tell them the truth at that particular moment when you do not have the HR director with you and you do not have the script with you and you do not have the protection of the legal process that you have gone through? You are going to tell them the truth in that particular moment? I do not think you are because I think you will be responsible if you did. When you say I am going to be honest, I think you have to really be careful about what you mean by that. I think part of our role is to kind of challenge that kind of thinking.

Building Trust [25:30]

Building trust is the third thing that I think the leader has enormous responsibility for. Part of that means being consistent. What we say is what we do and vice versa, and what I say is what I do and vice versa.

I worked with somebody early in my career, a man called Grant Hill who is the head of production at DDB in Chicago. One of the things Grant told me very early on, he said, “I will never tell you something I cannot deliver.” He said, “It will be easier to say I’m going to get you this big raise next year, but I do not know that I can so I’m not going to tell you that.” We learned a lot from that kind of philosophy from him. So I think the ability to build trust fundamentally sits with the leader.

Ability to Create Momentum [26:11]

The fourth weapon is the ability to create momentum within an organization, which is fundamentally just making a decision. I think a lot of leaders get hung up on we need more evidence, we need more research, we need to have another conversation about this, we need to make sure that we are meeting our standards. Fine, except that the inability to move anything forwards kills momentum. In any business for whom creativity is a fundamental fuel source momentum is everything. The ability to learn, the ability for people to feel like we are making progress. I have this saying which is that creative people want to make one thing more than anything else. They want to make a difference. And if you do not give them the ability to make them feel like things are moving forward, even in small ways, that is an absolute organizational killer. Again, you as the leader can say we are going to change the standards so that we can just make progress. We can decide what the metrics are by which we do make decisions. You can do all that in a moment. You walk into a room with the leader, the leader says X, you walk out. Okay, we are doing that.

One of the things that I have found incredibly rewarding about working with leaders is if you give them a piece of insight, you offer them an observation, something they had not thought of before and you see that there is this magical moment where their face changes. And then you realize now you trust me, now you understand I am only here to help you, this is my only agenda. Everybody else surround you, benevolent or otherwise, has an agenda. Most everybody around a leader means well, but there is an agenda. I do not have one, except, helping them be great. Helping them unlock their potential. When you get that moment where you realize you have made a difference, what you know is that you can come back tomorrow and the organization will be different to a result of that.

Context, values, trust and momentum are the four weapons that every leader has access to. They cost nothing. There is no investment required. It just requires a change of mindset and behavior in terms of your willingness to use them. New awareness that they actually exist here. I am still debating whether this is actually a fifth weapon or just an attribute that every leader has, but I think the willingness and the capacity to listen not just audibly but actually listen kind of through that third sense that I think the best leaders have to know where ideas are coming from and where is the company headed.

I realized pretty early on when we were building our business — we ended up with four offices — and I realized that some were out of instinct, I guess. I had the ability to walk into any one of those offices and within about two minutes have a really clear sense about how that office was doing, what its mood was like, I could see the data in terms of business performance, but I had a different awareness of that office. Often, I found that it was different and sometimes more acute than the people who work there every day. I think that that ability to listen, as I would describe it, is a very, very powerful asset for the best leader. Maybe it is not a weapon because you have to develop it as a skill. It is not available to you if you do not have it. Actually, this is helpful just saying it out loud, but I do think it is a really, really important attribute of the best leaders.

Amy Climer: It is interesting that you say maybe it is not a weapon, maybe it is a skill, and I am looking at this list and I am thinking aren’t all of these skills?

Charles Day: I think that these are things that you can decide to do. I think you can decide to apply context, to provide context. You can decide to define the values. You can decide to build trust by behaving consistently. You can decide to build momentum by making different decisions. I think the ability to listen is something you can improve as a personal skill, but I do not think it is necessarily available to you just by deciding I am going to do this.

Maybe I will correct myself as I think this through, but I think that to me, instinctively, there is a different kind of ability that goes with listening really well. These things are almost things you could put on a piece of paper and say I will do this, I will do this, I will do this, and you can actually see tangibly at the end of it. Have I done that? Have I done that? Have I done that? I think the ability to listen is one of those things where you are not actually sure whether you heard, even if you think you are listening. You could say to somebody at the end of that, “I heard this,” and they can say, “Yeah, but I also said this and this and this and this and this.”

Even if you think you are listening, it is difficult to empirically figure out whether, in fact, you are. I think with these four weapons there is empirical data at the end of the process to make you say I have done this, I have done this, I have done this, I have done this. Check the boxes. I do not think you can do that with listening in the same way.

Amy Climer: I would be curious to hear how this thought evolves for you and just grappling with this. I think it is awesome. If a leader is listening to this today and is like, “I need to work on these four things,” where do they start? What is the beginning?

Charles Day: I think they start with that classic question of “why?” I think it comes from two perspectives; one is why does this business exist? What difference are we trying to make in the world? I think, equally with that is why am I here? What difference do I want to make in this business and in the world beyond? I think it is important that a company is clear about the difference it wants to make. It does not have to want to change the whole world. You do not have to be Tesla or SpaceX or Amazon, but I do think you have to want to make a difference in your corner of the world. I think you have to do something that makes you valuable to the people who are buying your services or buying your products. I think there are not enough companies, still, who are clear about that.

One of the exercises that we run with some clients is a brand or business obituary, where you get a leadership team together and you take people through a process where you ask them to articulate through a number of steps what would happen, what would the outcome be if this business died today? If you shut the doors, what would the obituary looked like? Where would it be published? Who would show up at the funeral? What would people do instead of being able to access this company?

It is pretty startling, in most cases, how easily the clients or the customers would move to something else to replace that in their lives. It is not always true. Apple is a good example for those of us who have a whole suite of Apple products. If that company went out of business tomorrow — I do not think they are as compelling a company today as they were under Steve Jobs. They are probably more reliable in terms of product manufacturing, but I do not think that is interesting.

Nevertheless, if you took that away that would hurt because you would be sitting here having to figure out how to use Windows, which is pretty dreadful. I am sorry for those of you that do not agree, but that is my view. They have built through a number of different lenses a real sense, for me, anyway, and obviously, millions of people like me, if that company did not exist we would be lost for a while. We would feel the loss for probably some significant time. But there are lots of companies where you are like, “Okay, I can’t buy Eveready batteries, I’m going to buy Duracell.” Who cares? Literally, who cares?

Amy Climer: Yeah, I could not even tell the difference.

Charles Day: Could not tell you the difference. It does not matter to me if either one of those companies does not exist. It makes no difference to me. I think you see lots and lots of businesses like that for whom there is no real “why.” I think figuring out why this company exists, whatever it is that you are there to do.

For instance, when we built our film editing company, I probably could not have articulated this as well at the time. I have become better able to articulate it now with clarity, but I was always instinctively clear about what we were trying to do. We were trying to connect talent with opportunity regardless of geography. In the business that we built that company, post production, especially, film editing was a very localized, pretty parochial industry. You almost always worked with an editor who sat in the same city that you were working in. That did not necessarily mean you were always getting the right editor for the job based on talent and the needs of the project.

And so we believed that if we built a network in which you could move talent and the media that went with it and the ability to service clients between offices and make that completely effortless and seamless, if you could do that, it would change the dynamics by which companies worked with you and the value proposition that you provided. And the value proposition you provided, your talent. Because you would suddenly be opening doors to them that they would not have access to and so you get better people to work for you, which was true. And clients would see you as a solution to whatever their business problem was because they might want to shoot in LA and do part of the post in New York, but their office was in Chicago or London or whatever.

We made it so that we did not care. We literally did not care what their geographic needs were. We could provide support for all of that and make it effortless for them and so it gave us an enormous competitive advantage. And we were very clear about that. Everything we did was designed to satisfy the needs of that business model. And I was clear, again, through instinct as opposed to sort of analysis back then about what role I wanted to play and the difference that I wanted to make. And so it allowed me to make, in many cases, more confident and more risk-oriented decisions. Because they did not seem risky to me, they just seemed like the things we needed to do in order to become that business.

I remember I had a group of partners who were film editors and they had a different view of the world. I would make decisions in investing in technology that would give us this ability to connect offices and talent and clients and so on. They got very upset with me very early on about this $17,000 piece of technology that I ended up buying because it gave us the ability to move media through our network much faster and they were indignant about the fact that I would just spend $17,000 in this piece of technology because they had never worked like this. They had never really worked across geographic boundaries like this with this kind of freedom.

I think having that kind of consciousness is really important. I do not think I did a great job of providing them with a context for this because they still moaned about it for months afterwards, but if you are clear about the change you are making, it starts to be able to give you the ability to tell that story and so you can make those kinds of decisions. I think you have to start there.

And then I think the notion of developing values is important because they have to match up with the business objective and your own personal view of yourself and the role that you want to play. And then trust becomes the ability to kind of accelerate the process and allow people to keep moving forward. It also allows you to retain the talent you need to be that business. If they do not trust you, they are not sticking around.

By the way, trust is a fundamental component to collaboration. If you do not have trust, you are never going to get people to collaborate. If you do not get people to collaborate, you are not changing anybody’s world these days. Not on a scale, anyway. Then with all of those pieces, it allows you to make better decisions about where you are going to make decisions. And so momentum becomes an output of that. If you know where you are trying to get to and you know how you want to behave on the process, then the ability to define these are the decisions we have to make, and I can make them as simple as this, allows you to start building momentum towards them.

Amy Climer: Awesome. I love how you just basically walked through the process of those four weapons.

Charles Day: Yeah. It is why I have realized that they are all so important and so interconnected. Because once you establish momentum and you start making progress, then you need to go back to the beginning of the circle again and say is the context still relevant? Are we still interested in doing that? And is the other things that we are doing taking us closer to that or not? That becomes very powerful. Because we were given an opportunity at one point during the development of that business to open an office in Detroit. Detroit was a very lucrative market in the post production business. Probably still is because you have those car manufacturing and the car advertising that comes out of it.

The reality was the goal was to become one of the best film editing companies in the world. I personally did not think that certainly back then — this was 15, 20 years ago — a lot of the car advertising back then was not very inspiring. It was not very creative. It was not very interesting. It was highly lucrative, but I think at the end of the day my realization was we were not going to become the best film editing company in the world by opening an office in Detroit and taking a lot of time and energy and resources away from doing New York better and LA better and London better and Chicago better. And making that really work and being able to attract better talent by offering them better opportunities.

I thought we probably would have made more money faster, but that was not the only definition of best as it matters to us. And so we turned down that opportunity and another company went in and built a very financially successful company there because the demand was there. I never looked back and thought that we did anything other than exactly the right thing for what we were trying to achieve.

Amy Climer: That is a great example of knowing what your goals are and sticking to them because that could have been a bright shiny object. You are just chasing this like oh, that looks cool. And it would have probably been fine, but…

Charles Day: Yeah, it was very bright and very shiny and a lot of partners saying, “Why are we not doing that?” “Because that’s not the company we’re trying to build. It’s not what you said you wanted to sign up for.”

Amy Climer: It is about looking further ahead than a year or two.

Charles Day: Absolutely.

Amy Climer: You have talked a little bit about these elements that leaders need and I am wondering if we can expand a little bit further into like the organizational creativity. Are there some things you found in your work that if organizations want to be creative, let’s assume like the leaders are doing these things well, what does the organization as a whole need to be doing?

Common Practices of the Most Creative Businesses [40:44]

Charles Day: It is a really fascinating area. Four, five, six years ago, one of the things about the work I do that I feel — and I do not say this lightly and I do not say this superficially — I feel incredibly privileged by is the fact that I get access to some of the most creative businesses in the world at an incredibly intimate level. Whether I am working with the leader of those businesses or whether I am working inside the organization, I see them for who they are and as they show up. And often, with greater clarity than they are experiencing themselves because I do not sit inside it every day. I have a different perspective.

At some point, five or six years ago, I started to recognize certain characteristics and practices that were consistent among the best creative businesses in any industry. It did not matter what the industry was. What I saw was they started showing up in the same way. One of the underlying or the overarching theme that I recognized was that they were not intimidated by creativity. They were not worried about it. They did not see it as a sort of magical thing. They valued it. But they were not sitting there just so enamored with it that they thought, “Oh my God, there are creative people and non-creative people.” They did not think that way. They think everybody contributes to the creative process, whatever your title.

They do not group them separately. They do not silo them. They do not put them over in one particular part of the company and then turn their back, cross their fingers and hope that something magic comes out of that. Let’s not interrupt them, let’s not disturb them, let’s not ask too much of them, let’s just hope that something great comes out of that. They do not do that. They put real intention, real ambition behind it. They put real rigor, real process, real expectations.

One of the things that I always thought was really important as we were building our business was to build systems and have process and have structure around it. Because I think creative people benefit from understanding what are the rules and where are the guardrails. Because then they can unleash themselves on solving the problem that matters most to that business. If you give them really well designed tools and systems, every business needs to collect data. Fundamental. Most creative businesses are terrible at it.

But when you build systems that are intuitive, that are instinctive to use, that make people not just feel like, but actually help people do their jobs more easily when they are designed through that mindset, creative people thrive in that environment. And it also allows you to get better information about what to task them with. There are consistent practices and elements that I think exist in the best businesses and most creative businesses.

I wrote an article for Fast Company, actually, that articulated these pieces. I said there are four foundations — maybe there is something in my head that works in fours, I don’t know, but it just struck me that I thought there were four, what I would describe as domains, that were foundational to every business. And that inside each of those there were both emotional characteristics and practical characteristics.

For instance, one of the things that I think is fundamental to every creative organization is this ability to conceive the future in a different way. That they have a really clear sense of vision for what the future should look like or what they would like the future to look like, again, in their corner of the world. There is an emotional component to that and a practical one in the best businesses. The emotional one is they articulate that in a way that is compelling, and they draw people to it. The practical one is that they are making that happen. Because if you cannot make it happen, if all it is, is this hope and this dream, but it never gets closer to becoming a reality, the people that were drawn to it start losing interest after a while.

I think you see that in a lot of businesses, and particularly, in creative businesses, the way people get excited by it earlier and then a year, 18 months in they start to realize, yeah, it’s not that, is it? They did not really mean that. They are not built to do that. They are not acting that way. As you get into millennials and Gen Y and Gen Z who have got much less interest in career paths — I read some research the other day that said 30 or 40 jobs is not going to be unusual, which is basically a job a year or more.

Amy Climer: I could see that.

Charles Day: In some cases, they like doing two things at once. I read somewhere that 50% of Google’s employees do not work at Google full time, which Google thinks is a massive asset. They are not threatened by that. They like the fact that those people are out in the world experiencing other things and bringing all of that knowledge back into the company.

I think the best companies are built on these four foundations; the ability to conceive the future is one. What I also saw is they then build their organization around delivering that. So they did not have this sort of antiquated hierarchical top-down organizational structure, they were built to create teams, they were built to move quickly, they were built around collaboration. The third domain is that they develop the resources to satisfy the needs of that organization, both in terms of how they attract them, how they unlock them, how they keep them, how they develop them. Then the fourth is that they evaluate the progress they are making. They put all that together and say let’s figure out whether all of this is turning into something that is valuable. Part of that evaluation is financial. Of course, it is a business. It has to be. But there are other things that they look at to determine success. One of which actually is are we living by our values? To go back to the leadership parts.

These four domains of conceive the future, optimize the organization, develop the resources and then evaluate the progress, and then to complete the circle, go back and reconceive the future, is what we are doing. Bringing us back, it becomes the organizational version to some extent of what I had seen from a leadership level. But it is remarkably consistent among the best businesses.

A couple of years ago, somebody said to me what you built is a foundation for an organizational evaluation tool. And I said, “Okay, how do you take this and turn it into that?” They said, “You have to go and work with an organizational psychologist,” which I did not know about. I did some research and got a recommendation and brought a woman in who is genius at building these kinds of tools. There is enormous science behind this stuff, which I find fascinating. It is not just ask a bunch of random questions. There is incredible science about how human beings respond to this kind of probing and how to build a tool so that is scientifically valid.

We built this tool and have now taken a number of companies through the beta program and have now actually just started working with clients to deliver this analysis. This tool measures a company’s creativity, and no one has ever tried to do that before. People have always been scared about it. It is this amorphous thing and you cannot measure it. It is just this magical force. It is not. It is a measurable asset and you can tell where companies are wasting it or blocking it or losing it. And you can see consistencies and patterns in terms of data of the companies that do this best.

We have started to bring that into the marketplace. We call it UCX for Unlock Creativity Exponentially. It is a dynamic ongoing process in all the great businesses. We are bringing real rigor and real science, and I think, real empathy and real experience and insight into helping organizations be able to systematically increase the amount of creativity that they can bring to their business.

What I think has been extraordinarily rewarding and validating is that as I bring this out to people that I know and trust and say this is a proposition and we can do this, people are blown away by this notion. What is fascinating is as I take them through the process, nobody has said anything to me other than this will do that, and I believe that, and why has no one ever tried to do this before, and thank God that this is now going to happen. My goal is to create an industry standard so that you know, with absolute certainty, where we sit and what the ambition is inside this company to be creative.

One of the things that we have learned is that not every company has the same ambition for creativity, nor should they. If you go and talk to Wieden+Kennedy, creativity is everything to them. If you go and talk to the underwear group at PVH, creativity is a very important part of their business. They cannot succeed without it, but there are other things that are equally important to them.

Helping a company to be clear about its own creative ambition and then helping them to understand where they are delivering that and where they are missing opportunities to expand on that and to unlock it further has proven already to be very powerful and very insightful. I think we are bringing real science to this amorphous extraordinary power source.

Amy Climer: Absolutely. I love that you are talking about the science behind it because there actually is a fair bit of research around creativity. And that is one of things I learned in my PhD is that you can measure creativity. Actually, we have been measuring it for a long time. A couple of decades, at least, but it is not out in the world yet. The general public, I guess you could say, does not know about that. It is not like an IQ test. And so this idea of measuring organizational creativity makes perfect sense.

Charles Day: It is, on one hand, surprising that it has not been tried before, but on the other hand, not really because I do think there is such an emotional connection to creativity. People bring so much emotion to it. I think for people for whom their sense of their own creativity was driven out of them pretty early on through the education system, the notion that there are some magical people who are creative and there are some people who just are not, I just do not think that is true.

I was very fortunate a number of years ago to do some work with Sir Ken Robinson for 18 months to a couple of years. He speaks extraordinarily powerfully. He has given three TED talks. His first one, especially, really still resonates with me on this notion that everybody is creative. His perspective, which I would not argue with at all, is that the education system does a pretty great job of driving creativity out of kids and, therefore, out of many people’s lives. And it takes a long time for some of us to recover from that and to recognize we are.

My film editing partners would tell me routinely that they were creative and I was not. I gained confidence enough for myself to say, “I’m pretty confident that I’m creative, I just express it in different ways. There is a lot of original thinking that is coming to this company.” There are lots of institutional societal norms that we battle against it to define it, but I think that if we are willing, in part, through this lens of saying we believe it is measurable, we believe that every organization is capable of it because we believe every person is capable of it, and that there are practices and behaviors that unlock it systematically. I think not only will we build much better organizations, but we will help people to live much more fulfilling lives.

This starts to sound sort of grandiose and esoteric if you are not careful, but I fundamentally believe that. I think businesses that are more creative make for a better planet and I think businesses that are more creative unlock creativity in people which makes for a better society. And so I would like to change the world through that lens. I would like to leave a legacy behind that said creativity is a more accessible, more available, more ubiquitous force, more powerful, and as a result, it is more powerful than we realize and the world is better as a result of that.

Amy Climer: Absolutely. I love it. I totally agree with you. Charles, you have shared a ton of stuff. If someone is listening and they want to take what they have learned from you today and they want to start by applying one thing this week, what would that one thing be?

Weekly Challenge [53:38]

Charles Day: It is easy to say, but it is hard to do. You have to figure out what difference you want to make in the world. It is a scary proposition, and maybe on some level it comes to the meaning of life and why we are here and so people kind of put it aside because it is too hard. But I think the people that I have seen who are most successful at any level in any walk of life are the ones who have the clearer sense about the difference that they want to make.

It is a lifelong journey and the thing that you think today might not be the thing you think 10 or 20 years from now. I am clearer today than I was 20 years ago, for sure, but I think you have to start that process and then give yourself something to measure what you are doing by and to challenge yourself with. And to put a stake in the ground and define it and live with it and test it. Over time, as I say, it will probably evolve, which is fine. You do not have to have a perfect answer, but having an answer today is really powerful.

Amy Climer: That evolution is really powerful and helpful. I think if we all had the same ideas we had 10 years ago or 20 years ago, that is not good. Evolution is valuable.

Charles Day: Essential, actually, for the survival of the species.

Amy Climer: Yeah. Charles, if people want to learn more about you and your work where can they go?

Charles Day: They can go to a couple of different places. I have a podcast. You can go to and you will find the podcast, you will find the transcripts and the conversations with lots of different leaders. If you go there, you will also find a link to our leadership practice which is called The Lookinglass, which has one G. I do not know why Lynne named it with one G. It would have been easier with two, but it has one G. You can also go to and you will discover there what we do and how we do it, and a bit more about us.

Amy Climer: Awesome! Thank you so much for being on the show.

Charles Day: Thank you for having me. I love this.

Amy Climer: Wow! Thank you, Charles. So much there about how to unlock and scale creativity, about organizational creativity. Lots of information. I hope you found that valuable, those of you listening.

Thank you for listening to The Deliberate Creative podcast. If you have not yet, please head over to iTunes and write a review for the podcast. Please share this episode or other episodes with your friends and colleagues. Help spread the creative good word around the world. You could find me at If you want the show notes for this episode, where we have a number of resources and links that Charles mentioned, you can go to

You all, thank you so much for listening. Have a wonderful creative week. I will talk to you next time. Bye.

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