5 Questions Every Creative Pro Should Be Asking

Todd Henry [00:00:02]:

Well, hey, everyone. Welcome to Daily Creative. So this episode is going to be a little bit different. I have spent a lot of time in conversation with leaders, both at speaking events, training events all over the world, and also just in one on one conversations over the last few months. And I don't know if you sense it, but something is shifting. I think that there has been a tremendous amount of uncertainty introduced into many of our organizations and certainly into the marketplace to the extent that it's creating a different kind of conversation on the leadership level, one that I don't know that I've seen in all of my time doing this work. So today I wanted to do an episode that's a little different. Normally we feature an interview and then maybe some thoughts from me, some contextualizing thoughts, and we're certainly going to get back to that format.

Todd Henry [00:00:54]:

But today I wanted to share something that's been on my mind of late, which is five questions that I think all of us who are in creative leadership, and by the way, if you have influence on everyone around you, you are a leader. So I don't want you to dismiss this and think, well, this is for my boss. No, this is for you. If you influence clients, if you influence your peers, if you have a voice in the decisions that are being made in your organization, this episode is for you. So this episode is going to be a little different. I want to introduce five questions I think that we all should be asking right now during this time, and maybe some context for why I think that they're important. This quiet tension I've sensed, it's not burnout exactly. It's a kind of drift, it's almost a numbness to some of the general uncertainty that we're experiencing.

Todd Henry [00:01:47]:

And the most talented, driven people that I'm encountering are they're hitting goals, we're achieving our objectives. But we're kind of wondering, why doesn't it feel right right now? What is it that doesn't feel right? And I think some of it is a technological shift that we're experiencing and some of the uncertainty around that, Some of this just the economic shift, just the general turmoil right now, I think that's, that's going on in the world. So today we're going to slow down and I'm going to offer you these five questions. And they're not comfortable questions. And by the way, these are not designed for you to be able to just, you know, okay, I've got the answer to that and move on. These are questions that I think we need to wrestle with. But I think they're going to help us all gain some clarity about where we are, where we're going, and maybe how we're going to get there as we move toward our objectives over the coming year. Okay, so here is question number one.

Todd Henry [00:02:44]:

Am I succeeding my way into failure? Okay, let me put some context around this one. It's possible to be doing everything right and to still end up in the wrong place. You can hit all of your goals, your objectives. By every metric everyone has given you, you are succeeding. And in the process, you're actually failing because you have failed to understand the true problem that you're trying to solve. A couple of years ago, I was working with the leader. The company had grown really, really fast. They were doing really well.

Todd Henry [00:03:16]:

They were very well known for what they were doing. Revenue was up. There were lots of awards, lots of buzz. But when I asked what he was most proud of, he paused and he said, honestly, I'm not even sure what we're doing anymore. I'm not even sure what we're making. And the reason was that at some point, it became more about hitting those metrics. It became more about getting the awards, getting the buzz, than it was about the work they set out to do. They became so focused on chasing success, on hitting the targets, scaling the team, or making their boss's boss's boss, you know, happy with what they were doing that they'd lost touch with why they started doing the work in the first place.

Todd Henry [00:03:54]:

So success can be a form of failure. If it moves you further from the core purpose that you set out to accomplish, you can win all the wrong games. So here's a question I encourage you to ask yourself right now. Regardless of how successful what you're doing may seem to be to everyone around you, regardless of what metrics you're hitting, what are you optimizing for right now? Is it the metrics that matter to others, or is it the meaning that matters the most? Are you solving the right problems, or are you just checking off boxes? Okay, it's not an easy question to answer, but you definitely don't want to wake up one day and realize that you and your team have checked all the right boxes, at least according to what you think you're supposed to be checking. And you realize that you actually have succeeded your way into failure because you've not made headway on the important work that you're really trying to do. You don't want to build a machine that's running perfectly in the wrong direction. So that's question number one, are you succeeding your way into failure? Question number two, who is telling me the truth right now? So leadership of any kind creates distance. Even if you don't intend it to, it creates distance.

Todd Henry [00:05:15]:

But I believe, and this is the foundation for a new community I'm building called Creative Leader Roundtable, that leaders leadership is only lonely if you're doing it wrong. When you're the person in charge, people edit themselves around you. They tell you what they think you want to hear, not what you need to hear. But here's the thing. Nobody's going to just step up and say what you need to hear if you don't give them a clear invitation to do so. Over time, the echo chamber grows uncomfortable. And here's part of the problem. Part of the problem is that many leaders get very defensive because of their own insecurity, because they don't want to hear things that are uncomfortable for them.

Todd Henry [00:05:52]:

They get very defensive when someone offers them feedback. And frankly, sometimes that feedback is incorrect. It's not right. It doesn't have the same context that you have. So they don't understand why you're making decisions you're making or why you're doing things you're doing. So sometimes the feedback is wrong, but that doesn't make it invalid. All feedback is valid whether or not it's true. And the reason is because feedback is given from somebody's perspective.

Todd Henry [00:06:22]:

So even if it's not true, it's still valid. It's still their perspective and needs to be accounted for because there's something that's causing them to see things in a way that's inconsistent with reality. So when we get defensive, we push away that kind of feedback. We push away the things we need in order to succeed. I was once working with a design leader who was blindsided when the team revolted against a major initiative. She was convinced that everyone had been on board, but the truth was they had been quietly disagreeing for months, but nobody felt comfortable saying so. And this is the problem, is that sometimes we confuse compliance with alignment. We confuse silence with agreement.

Todd Henry [00:07:06]:

If we're not inviting disconfirming information, if we're not having those conversations and making it a safe environment to offer feedback about in ways that maybe we disagree, then it's very common for us to just. We're all moving in the same direction, so we assume everyone is along with us. So who is telling you the truth right now? Who is the mirror in your life? Who is speaking things to you that maybe you don't want to hear. And are you creating the environment where your team can do that for you? You need that person, but you need to create the environment where anybody on your team can be that person. You need to give them permission. The moment that you punish someone for speaking their perception of truth to you is the moment that your incentives are misaligned from your desired outcomes, which is the death of any organization. Without honest mirrors, even the best leaders end up believing their own press releases. So who is telling you the truth right now? Number three.

Todd Henry [00:08:05]:

What am I avoiding? Because I might look foolish? So fear of embarrassment kills more great ideas than lack of talent ever will. I remember once meeting a creative director who'd been sitting on the bold concept for a really long time. And it was weird, risky, maybe a little bit too far out. So the team kept polishing, kept tweaking, kept waiting for the right moment, and that moment never came. And inevitably somebody else comes along and they pitch something similar. And the thing is, we often sit on ideas because they feel out of left field. They feel like something that's not maybe acceptable in the moment. And so we just don't share them, right? Because we're afraid we're going to look foolish.

Todd Henry [00:08:51]:

And there's some validity to that sense. There's some validity to that fear because often we say we want innovation, but then the moment something innovative comes along, our first response is to reject it. And so that's valid. It's valid to feel that. That concern. But we cannot let that paralysis, that fear of looking foolish prevent us from sharing ideas that could be game changers. This is how brilliance dies. Not from bad ideas, but from a fear of looking foolish.

Todd Henry [00:09:19]:

So what are you holding back because you're worried how it might look? What dream, what project, what conversation have you postponed? Because it just feels risky, too risky to share, right? Find a group of people around you you can share it with. You have people in your life who you can share these ideas with, who can offer you valid perspective. Kind of like what we just talked about, having a mirror. Instead of just jumping off the ledge, right, and hoping you can fly, Find a small, trusted team that you can begin sharing these things with in a. In a low risk way. Remember, and this is what I wrote about the brave habit. Courage isn't the absence of fear. It's choosing to act even when your ego's on the line.

Todd Henry [00:09:59]:

So where are you avoiding something? Or what are you avoiding because you're afraid you might look foolish? All right, when we come back in a minute, I'm going to Share with you questions four and five. And question five, I think, is one that's especially important for anyone leading a team right now. So we'll be right back with questions four and five after this break. Stick around. Okay, question number four. Have I built a system that's serving my ego more than my mission? Now, this one's tricky because it hides behind good intentions. Ego always hides behind good intentions. I wrote about this in my book Die Empty.

Todd Henry [00:10:56]:

Ego causes us to become inflexible. We begin protecting ourselves ahead of our productive passion or the thing that we're really trying to do, the thing that we're willing, if necessary, to suffer on behalf of because it matters more than our temporary comfort. And I think a lot of people start looking to external signals, you know, things like audience size or the accumulated power and influence within an organization instead of the quiet internal ones that really matter. Are you doing work that is true? Are you serving the people you lead? It's sneaky because ego often disguises itself as excellence. It whispers, you're doing this for the mission. You're doing this for your productive passion. This is for the greater good. And sure, you're going to be recognized in the process, but it's for the greater good.

Todd Henry [00:11:45]:

What it really wants is applause. It wants the recognition. You know, culture can look great on the outside, but you can build a culture that's really centered around you and your ego more than it is about accomplishing the mission and helping other people be empowered and equipped to do the thing that you're trying to do. So here's a simple test that you can ask when you're wondering if maybe you're doing things because of ego instead of because of the mission or the purpose or the objective you're trying to serve. The question is this. If nobody ever saw this, would I still do it? Would I still do it even if no one saw it? And if the answer is yes, you're probably aligned right with your mission. If no, then you may have built a system that's purely designed to serve your image instead of your impact. Leaders who succeed over time are those who make echoes in the lives of the people they lead.

Todd Henry [00:12:41]:

They're ones who recognize that your job as a leader is not to do the work, but it's to unleash great work in other people. That's what brilliant leadership is. So question number four. Have you built a system that's serving your ego more than your mission? And finally, question number five. And this is, I think, one that's really important right now. For all of us to be asking, am I giving my team stability, or am I just keeping them safe? So in Herding Tigers, I wrote about the two things that all talented, ambitious people need. The first is challenge. Talented people want to be pushed.

Todd Henry [00:13:21]:

They want to try new things. They want to experiment. They want to risk. They want to do work that matters. But they also need stability. Stability means clarity of process, clarity of expectations, clarity of relationship. They need to know they have a stable playing field on which to do their most important work. And most of the book, Herding Tigers is about the tension that exists between stability and challenge because we want stability.

Todd Henry [00:13:44]:

But often when we're doing difficult work, it destabilizes the environment. It creates challenge in the environment. And that challenge is healthy and natural and normal if we're doing difficult things. So how do we balance stability and challenge? Well, sometimes leaders overreact, and they're not just providing stability, they're keeping them safe. There's a fine line between protecting your team and smothering them. Over time, it's really easy for teams to become complacent, to just settle in. Right. Teams become dependent on you to protect them instead of venturing out and doing the things they need to do in order to succeed.

Todd Henry [00:14:24]:

To take risks, your team doesn't need you to keep them comfortable. The great poet Kahlil Gibran wrote, verily, the lust for comfort murders the passion of the soul and then walks grinning in the funeral. The lust for comfort murders the passion of the soul and then walks grinning in the funeral. If you want more passion in your work, if you want more passion in your team, then you need to avoid the lull of comfort. Your team needs you to create a stable enough foundation that they can take smart risks. Stability says you're secure here. Safety says, don't move. Right? These are very different things.

Todd Henry [00:15:07]:

So ask yourself, am I creating conditions where my people can stretch, where they can grow, where they feel challenged? Or am I unintentionally keeping them small? So those are the five questions. Question number one, am I succeeding my way into failure? Question number two, who is telling me the truth right now? Question number three, what am I avoiding because I might look foolish? Question number four, have I built a system that's serving my ego more than my mission? And question number five, am I giving my team stability, or am I keeping them safe? Now, these questions are not meant to diagnose or to shame. These are simply frameworks to provoke reflection. Okay. I believe that frameworks are forcing functions. They force us to have to ask questions or to look in areas where we may not otherwise look. The hardest part of leadership isn't managing others. It's staying awake to your own drift, to how you're moving off center in your own leadership, your own perspective.

Todd Henry [00:16:05]:

So these questions are, I think of them, kind of like buoys in the water. They only tell you exactly where to go, but they help you know when you've wandered off course. So I encourage you to take some time this week, write down these five questions, spend some time thinking about them, journal about them, talk about them with your team. Use these questions to spark conversation that maybe hasn't been happening. Because listen, leadership isn't about having all the answers. It's about creating the conditions where the right questions can live and thrive and can be asked in a non threatening way. Okay? And if you want to have more of these kinds of conversations, we've just created a community called Creative Leader Roundtable at Creative Leader. So I encourage you to check that out and apply if it's something you think would be interesting to you.

Todd Henry [00:16:53]:

Hey, thanks so much for listening to Daily Creative. My name is Todd Henry. You can find my books, my speaking events and more@todhenry.com until next time. May you be brave, focused and brilliant. We'll see you then. Sam.