Why Confident Leaders Build Stronger Organizations

Confidence: it’s one of the most critical traits for effective leadership, but also one of the trickiest to master. 

In this episode of Designing Tomorrow, Eric and Jonathan dive into what it truly means to embody confidence as a social impact leader. From personal struggles with self-doubt to lessons on humility, resilience, and overconfidence, this conversation pulls back the curtain on the realities of leadership in nonprofit and social enterprise sectors.

How can confidence breed success? When does it go too far? And most importantly, how can you build confidence in yourself, your team, and your organization? 

Tune in for actionable insights, relatable stories, and a fresh take on leadership growth.

Episode Highlights:

• [00:00] Introduction:
  Eric introduces the theme of confidence and why it’s essential for social impact leaders.
• [00:08] The Struggle with Self-Doubt:
  Jonathan shares how he’s often questioned his ability to lead major projects.
• [00:17] Why Confidence Matters:
  Eric explains how indecision and lack of confidence can undermine effective leadership.
• [00:33] Confidence ≠ Arrogance:
  Jonathan emphasizes that confidence and humility can coexist, and being confident doesn’t mean being an "asshole."
• [00:40] The Paradox of Expertise:
  Eric reflects on how experience reveals how much there is still to learn.
• [05:43] Embracing Growth Zones:
  Eric’s story of “faking it until making it” and how leaders can thrive outside their comfort zones.
• [09:13] When Confidence Goes Too Far:
  Exploring the pitfalls of overconfidence, from cockiness to overreliance on charismatic leaders.
• [21:17] Building Organizational Confidence:
  The role of strong branding, strategy, and structure in creating sustainable success.
• [24:02] Closing Thoughts:
  Why confidence, when cultivated authentically, is a leadership superpower—and how it can benefit your entire organization.

Notable Quotes:

• "If you're always in your comfort zone, you're not growing by definition." - Eric Ressler  [05:43]
• "Confidence begs the question: What are we confident in? Is it my skillset, my inherent value as a person, or that the destination is the right one?" - Jonathan Hicken [07:03]
• "I realized I had set the bar way too low for what I could achieve because of some limiting beliefs I had built during challenges and failures." - Eric Ressler [15:50]
• "It’s not about me. When I can see our mission as divorced from my own contributions, that washes away some of the fear and helps me show up as a more confident leader." - Jonathan Hicken [17:35]

Resources:

• David C. Baker
• Podcast - Designing a Purpose and Strategy with Eric Ressler
• Article - In Defense of Moonshots: True Social Innovation Requires Taking Risks
• Article - 3 Signs That It's Time to Hire a Creative Agency
• Article - How to Defeat the 3 Toughest Challenges All Nonprofits Face
• Article - Define Your Social Impact Niche to Build a Brand That Matters

Transcript:
 

Eric Ressler [00:00]:

Today we're talking confidence and specifically how to embody confidence. As a leader in a social impact organization, I

Jonathan Hicken [00:08]:

Felt completely unequipped to lead this particular project. I often question, am I the right guy to do this?

Eric Ressler [00:17]:

If you're not confident and you come across as being wishy-washy or indecisive or whatever flavor of non-confidence that you have, my sense and my experience frankly, has been that that is a not constructive way to be as a leader.

Jonathan Hicken [00:33]:

Being a confident leader does not necessarily mean being an asshole. You can be confident and humble.

Eric Ressler [00:40]:

The longer that you do something in any given niche or field, the more you realize how little you actually know about that work. 

Jonathan, today we're talking confidence and specifically how to embody confidence as a leader in a social impact organization. I think there's a lot to unpack here actually, but let me tell you about how this topic came to be. So I'm a big fan of David C. Baker. He is a consultant for agency leaders like myself. And he, over his years of working with different agency owners, noticed that agency owners who were more confident significantly overperformed their peers. And then he went on to actually break down how to create competence and confidence as an agency owner through an equation. And his equation is confidence equals opportunities divided by a capacity, which basically means that if you have more work than you can handle, it's going to give you confidence.

[01:51]:

And if you have less work than you need, it is going to erode your confidence, which I can absolutely confirm. So that's maybe an equation that we could try and figure out how to size for the social impact sector if we think about maybe fundraising opportunities compared to your capacity to the impact, whatever. But that's not actually where I want to go today. I want to go a little bit more abstract and obscure and just talk about confidence in general and how that plays into leadership in the social impact space and why confidence is important, my own struggles and journey with confidence over the years. And then also a little bit about when being overconfident can actually become a problem. Are you game?

Jonathan Hicken [02:36]:

Let's go.

Eric Ressler [02:37]:

Alright. So let me start with some personal reflections on confidence. I've actually had huge struggles with confidence, not even just in the professional setting, but actually even more so kind of in the personal setting around even things like social situations and anxiety. The very common one that I most people struggle with is confidence in any kind of public speaking situation. As a creative director and as a founder of cosmic, I've had to present really high stakes presentations to really high stakes people many, many, many times. And over the last 15 years, I've built a good amount of confidence as a leader and as a creative director for cosmic, I feel generally pretty comfortable, but I got to be honest, this is something I still struggle with as I'm growing, especially as when we're in a situation where we're doing something new, we have a new approach for how we do a part of our process, or we're starting to sell a new service or new offering. This is where I see it come into play the most, which is logical. If it's something that I don't have as much experience with, then I'm not going to be as confident in it. But I'm just curious, just in general, is this something you think about at all as a leader or in life All

Jonathan Hicken [03:58]:

The time. In fact, there's a project in my professional sphere that I am working on right now and have been for about a year and a half where I felt completely unequipped to lead this particular project. I mean, the level of specialized knowledge in order to get the job done was so niche that I wasn't, I often question am I the right guy to do this? So absolutely, and that's just one small example where my confidence has taken a hit or if I make a decision where the results aren't what they need to be, my confidence takes a hit. Absolutely. And certainly in my personal life, I think for me, my struggles with confidence often have to do with relationships or even how I look. So those struggles absolutely exist for me.

Eric Ressler [04:48]:

Yeah, it's kind of interesting. I remember this is making me reflect on something. In the early days of Cosmic, we had a friend and a partner who introduced us to a client and the client needed a video produced, shot and filmed and packaged and everything. And our friend at the time, I had just started falling in love again with video and film work, which I did a lot of when I was younger and then hadn't really done professionally, but I was getting back into it, had some cameras and some gear, not a ton, very, very minimal setup. My friend at the time was like, oh, well you guys need a video, these guys can do that for you. And I remember the client turning to us and saying, oh, you guys do video production? And I was like, yeah, we could do that. And so it was this moment of just really having to take a leap of faith and having to essentially fake it till you make it.

[05:43]:

And I think there's some amount of that that is just entrepreneurial is about building a business is about growing as an organization is like if you're always in your comfort zone, you're not growing by definition. And there's obviously a way to take that so far that you're essentially being a fraud or we talk a lot about imposter syndrome in modern culture and I think there is a lot of imposter syndrome and then there are actual just imposters too. And so where is the line there? I don't think it's necessarily clear, but I think there is a need sometimes to embrace a space of growth and even a space of stretching where you actually are as a leader or as an organization and it's not going to be comfortable. And how do you build confidence around I can get through this. And I think that's really, maybe that almost starts to get more into the term like resilience of like, okay, well we've gone through hard things before and we've made it out. I know that although this is hard for me right now either because I'm going through a difficult time as a person or as an organization or we're taking a big leap of faith, I know that we're going to get through this. And so there's I think this interesting balance between confidence and resilience and growth. I think confidence, it

Jonathan Hicken [07:03]:

I think confidence, it begs the question of what are we confident in? Is confidence in my inherent value as a person or as a leader, am I confident and that the destination is the right destination? Am I confident in my skillset? Right. I don't know, this is occurring to me right now that there's an element of where do you place your confidence and where do you embody that confidence?

Eric Ressler [07:40]:

To tie it back to the topic at hand here, embodying confidence as a leader, maybe we should just start by agreeing or disagreeing or debating should leaders be confident? I'm going to go out on a limb and say I think they should. And I think that the reason for that is building confidence is a good skill to have and to do it authentically means that you are stretching and growing as a person. And also if you are going to lead, you need to be confident in your leadership and if you want people to follow and to support and to be part of that, if you're not confident and you come across as being wishy-washy or indecisive or whatever flavor of non-confidence that you have. My sense and my experience frankly has been that that is a not constructive way to be as a leader.

Jonathan Hicken [08:32]:

I agree. And I think that it's important to note that being a confident leader does not necessarily mean being an asshole.

Eric Ressler [08:43]:

I will double click on that.

Jonathan Hicken [08:44]:

Yes, right. I mean, I think we can sometimes conflate those two concepts that confident leaders are assholes and maybe they are. Sometimes I am sure some people in my universe would think that about me and I'm comfortable with that. But I do think that you can be confident and humble, you can be confident and a quiet leader. There are different flavors of confidence.

Eric Ressler [09:13]:

Totally agree. And I think we should, let's talk about when confidence goes too far and kind of the pitfalls of being overly confident. So you described a really classic example of someone who's confident but also kind of an asshole and that can work, right? I don't think that's probably what anyone should aim for. And I think sometimes people are actually being an asshole because they're not confident. In my experience, a lot of times, especially the world's smartest people or the leading expert in any given field, sure they have some level of confidence, but they actually also usually have a contradictory trait, which is being extremely humble if not second guessing themselves a lot. Or I think another way of saying this is the longer that you do something in any given niche or field, the more you realize how little you actually know about that work.

[10:10]:

I think about this a lot in doing branding work and marketing work. I've been doing it my entire adult life. I've been running cosmic for 15 years and there are days and times where I wake up and I'm like, God, there's just so much to learn here still. And the thing that I thought I knew that I was so sure about a year ago, two years ago, five years ago, I actually don't think that's right anymore. And maybe that's because the world is changing. Maybe that's because my perspective is changing, but I actually think that is a more confident essence than someone who just assumes they're right all the time, who might seem confident on the surface. But if you start to peel the layers back, you realize it's actually coming from a place of lack of confidence or other deeper emotional issues that they might have.

Jonathan Hicken [10:59]:

It sounds to me like you feel really confident in your own ability to learn and adapt and rise to the occasion or rise to the challenge. That's what I'm hearing. I relate to that. So my career has been a bit of a winding one. I haven't been in social impact my whole career. I started in academia. I thought I was going to do that. That didn't work out. I moved into tech, I was in tech, then I moved into the social impact space, but have been in different sectors of the social impact space. And the thread for me all along through all of that had to do with skill. So I was confident in a certain set of skills, even if I wasn't a content matter expert, but I knew that my skills in research and in team building and in strategy and in fundraising were going to serve me and be transferable kind of, no matter where I went. And so for me, the fun was actually kind of exploring and finding where I was going to end up. But the confidence came because I knew I was confident in my skillset and I was confident that I could transfer those skills to these different areas.

Eric Ressler [12:08]:

I think that tracks, and I think I've experienced that in my own way in building up my own set of skills more broadly around creativity and branding. And I think the skill that I've become that's the most built over time, that wasn't necessarily inherently part of my skillset, was understanding how to apply my passion for creativity and design specifically in a way that could actually create business outcomes, that could tie into strategy, that could serve and move organizations forward and not just be an art project. And I think to some degree, I always understood that I've had a pretty good intuition for business sense in a way that's served me quite well, and I'm very thankful for that. But I think it's honestly maybe come from a place of this lack of confidence and having to build that and wanting to make sure that I'm, because I don't want to let people down because I don't want to have an expectation that I set in a conversation and then not come through on that for a client or for a partner or for my own team or whatever it is.

[13:17]:

Another thing I've noticed is that even my own personal confidence in myself, there's also I think as a leader, a confidence in your team and your organization and your ability to meet your mission. That's also at stake here. At least that's what I've experienced. So as a personal example, throughout the pandemic period and making a transition from being a very brick and mortar studio where we had a big table, we all sat around and a lot of our networking and work came in through just referrals and people understanding that we exist because of our location. We had to make a really big transition into being a remote first global agency, which we've done, which has been something I'm very proud of, but was a really bumpy road. And I realized actually quite recently, even just this year, that I had created a set of limiting beliefs for myself and for my agency around how successful we were ever going to be able to be because I kind of recalibrated my vision and my expectations for what I could achieve based on some of the challenges that we went through in that period.

[14:36]:

As an example, looking at just particular revenue goals or even thinking about growing the team to a certain degree. We've tried things over the years and failed and after a certain amount of attempts and failures, there's kind of a logical conclusion that's just like, well, it's a limiting belief based in fact and reality versus personality deficiencies. But I don't think you can actually separate those things as cleanly as I had in my brain. I kind of reset my expectations for what I could accomplish, what cosmic could accomplish. And I think frankly, I put that bar way too low. Maybe it was a mix of some burnout. Maybe it was because I was going through a time in my life where I have a lot of focus on family and raising my two kids and wanting to make sure to be there for that. And that just, I only have so much energy and attention that I can give to the world. And some of that was taken away from cosmic and given to my own life and my family, which was a choice that I made. But I actually think that it was a lack of confidence or a kind of calcification of limiting beliefs that was happening subconsciously because of trials and tribulations. You're

Jonathan Hicken [15:50]:

Inspiring me to do some inner work here, understanding how I'm positioning myself at the Seymour Center and what's possible for us. But one of, something you said just sparked some inspiration, which is around letting go of myself a bit in terms of my personal journey to confidence building where it's like it's not about me. And I actually think having a kid accelerated that accelerated that perspective. And I think any parent out there probably can relate to this where there's this celestial shift in the way that you see the world and in a way that I think I'm still undergoing that transformation as a social impact leader. And I think I do sometimes over index on my own impact on the organization, and I'm learning and starting to see, and it's a really liberating feeling to be like, it's not about me and I'm just one player with one particular role. And there's something very confidence building about that perspective where it's like, oh, I have a role in this. I have a place, but I'm just one of many. And that can feel really powerful. And for me, it's actually given me quite a bit of confidence, especially when I'm pitching a new program or a new concept or a new vision because I'm able to divorce myself from the conversation and really embrace this idea that this has nothing to do with me at all.

Eric Ressler [17:30]:

So for you, it's kind of like that shift in perspective takes a little bit of the pressure off.

Jonathan Hicken [17:35]:

It takes pressure off, but to me, pressure is not the problem for me at least. I can handle pressure. It's more of maybe it's a shedding of fear, which is for me, kinda plays into my ability to be confidence and embody confidence and show confidence. And when I can see our mission as completely divorced from my own contributions to it, that to me washes away some of the fear and I think helps me show up as a more confident leader.

Eric Ressler [18:12]:

So let's talk about when this can go too far, and I think it actually shows up in a couple of different ways. We talked about the asshole version of confidence, which is not recommended, even if it might sometimes be effective, although I do think that that is usually a short-term effectiveness or a trade-off that maybe just doesn't need to happen. But there's another common version of this that I've actually seen, which is the really charismatic leader. And I think we all understand the power of charisma, and I think a lot of people are trying to work towards that. But I think a lot of these, what I've experienced and what I've observed is that these charismatic leaders seem to just be born this way, and they can be extremely powerful and extremely effective in rapidly moving an organization forward, whether they're the founder of the organization or a new board member or CEO or executive director who maybe wasn't the founder.

[19:09]:

These people can seemingly move mountains, and that might translate to fundraising or partnerships or networking. These people are often also very highly networked because people who are charismatic or attract a lot of other people. But I think that if that charismatic leader is taking on too much of the burden of the organization and too much of the ability for that organization to survive and thrive is based on that one charismatic leader, that can be a problem. I've seen that happen multiple times where a charismatic leader is essentially carrying the organization and then that leader retires or moves on or gets in a fight with the board chair or whatever it is, and then all of a sudden their presence is gone and the whole house of cards just kind of crumbles down.

Jonathan Hicken [19:57]:

I've worked in an organization like that, and lemme tell you, being in it while it's happening is very exciting. And there are downfalls, and I won't get into the details right now, but I think some of that happened when this particular charismatic leader left the organization that there was a period of dip, and understandably so because they were so charismatically powerful.

Eric Ressler [20:23]:

I think the solution to some of these investing too much in confidence of just a given leader is that as much as I think we want leaders to build healthy confidence, we also need to build organizational confidence and competence. So if you have a charismatic leader or an effective leader or whatever, you just have to make sure that you can build out the support structure and the operations to support that leader. And also in a way that the leader is not carrying too much of the burden or leaving a big hole if they do leave for whatever reason. So the other thing that I think is important in terms of how do we build confidence and competence at more of an organizational level, and I think this will only strengthen a leader's ability to be competent, is to be really strong on some of the foundational things that we talk about a lot on this show.

[21:17]:

Things like owning a niche, having a strong brand, having effective marketing and communications and fundraising because all of that is going to better position your organization against other similar organizations in your space or competing organizations in your space in a way that will give you confidence because it's earned, right? It's earned confidence and earned confidence. And I think that as I've been building cosmic and I've watched other nonprofit organizations and social enterprises build, one thing that is clear to me is that with or without a charismatic or confident leader, the organizations that are the most effective and by extension the most competent and confident are the ones that have done that hard work and have meaningful answers to those questions. And that if you don't have that strong foundation, then it just becomes harder to build that confidence because you're not really building it on a strong foundation.

Jonathan Hicken [22:15]:

And confidence, I think, breeds confidence.

Eric Ressler [22:19]:

Yes.

Jonathan Hicken [22:20]:

And so when you start to develop excellence and competence in those areas, I think it's kind of one of those snowball effect kind of things. So I think it's really important actually for organizations that are small or starting up or getting going to nailing all these fundamental piece early on because that's going to help you attract talent that's going to help you attract funding and board members and all of the necessary ingredients for a high performing social impact organization.

Eric Ressler [22:51]:

Yeah, I agree. And there's actually a term to describe that, which is called the Matthew Effect, which is a term I wasn't familiar with until just recently, but it confirms that exact observation, which is that, yeah, confidence breeds competence and competence leads to more competence. And I think I've experienced this with my own organization and watching others as well. And so how do you get that traction, right? I think that's a lot of what we are exploring in this show. To kind of wrap it up here, I think I want to make a claim, and I think hopefully we agree on this, which is that I think working to build confidence as a leader, if you do it with the right intentions and you do it healthily in a way where you're not also an asshole, in a way that you're not overextending, that confidence as a crutch for the rest of the organization, I think is a worthwhile goal. I think it's a worthwhile endeavor, and I think the ways that you do that are also synergistically just going to help you be a more effective leader in general. So I think we should all be striving for this in a healthy way. I would love to hear stories from listeners and the community around how you've struggled with this, but Jonathan, this has been a fun one, kind of an interesting topic, so thanks for dissecting it with me.

Jonathan Hicken [24:02]:

Yeah, it felt like we were opening the kimono a bit. Thanks,