Balancing Vulnerability and Authority with Charly Gillespie-Smith

Charly Gillespie-Smith is the creative mind behind Lasting Lemons. Before founding the agency, she launched and grew Little Moons' TikTok presence in 2019, producing an online craze and national obsession resulting in massive business growth.

A natural storyteller and trendsetter, Charly took the opportunity to shake up the social media landscape and put the fun back into social. Driven by her ADHD and dyslexia, she champions her neurodivergence as the secret to her boundary-pushing creativity. Today, she's building a team of sky's-the-limit-thinkers who embrace the unconventional.

LBB> What was your first experience of leadership?

Charly> My first experience of leadership came when I founded Lasting Lemons. It was a huge adjustment, going from being the most junior in a business with no experience of leadership or management, to suddenly running an entire company. The shift was both exciting and overwhelming, and I had to learn fast.

Everything from operations, HR, finance and people management fell on my shoulders, and I quickly realised that leadership wasn’t just about having a title, it was about taking responsibility for a long-term vision and helping others work towards it.

LBB> How did you figure out what kind of leader you wanted to be – or what kind of leader you didn’t want to be?

Charly> When I started the business, I was controlling and, in some ways, a micromanager. I wanted everything to be perfect. But I soon realised that approach wasn’t sustainable. I had to learn to trust my team and delegate properly. That shift shaped the leader I became, and I developed into someone focused on building a culture of trust.

It also changed how I grew my team. I began looking not just for skill but for people I genuinely trusted, and people who brought different perspectives but shared the same commitment to quality and creativity.

LBB> What experience or moment gave you your biggest lesson in leadership?

Charly> The best advice I ever received came from my grandad (Papi). He told me to “build a business that runs without you.” That one sentence changed how I viewed leadership. It encouraged me to step back and trust the systems (and people) had put in place.

Letting go was difficult. Lemons was my baby, something I cared about deeply. But as I took a step back, I found that not only did things run as smoothly, but my team grew more confident. Mistakes happened, but they became learning moments. I saw people develop, take ownership, and grow into leaders themselves.

LBB> Did you know you always wanted to take on a leadership role? If so how did you work towards it and if not, when did you start realising that you had it in you?

Charly> Truthfully, I never set out to be a leader. I started my business based on outside encouragement, and because I had a unique skill set that no one else seemed to be offering at the time. At first, I missed being part of a team and not the person people looked to for decisions. It felt strange being the one others relied on.

But over time, I’ve found joy in the freedom that comes with leadership. I was suddenly in charge of my own time allowing me to spend more time with family, travel, and prioritise my health. It’s taught me that being a business owner is as much about mindset as it is about skill. Sometimes that means making difficult decisions without emotion, and that can be tough.

I still struggle with imposter syndrome. It started in school, where I had undiagnosed ADHD and dyslexia, and it's something I carry to this day. But I’ve come to accept that leadership isn’t about being perfect and instead, it’s about being self-aware and committed to learning.

LBB> When it comes to 'leadership' as a skill, how much do you think is a natural part of personality, how much can be taught and learned?

Charly> Some people are born with natural leadership qualities, but I believe it’s absolutely a skill that can be learned over time. I’ve had to learn by making mistakes, adapting, and constantly reflecting on what’s working and what’s not.

I also believe that great leaders need to know how to follow. In my role, I often have to follow the client’s direction e.g. their brief, timing, feedback and adjust our creative process accordingly. That dynamic has taught me a lot about adaptability, an important aspect to leadership.

Because I didn’t have leadership experience when I started, I try to give my team the kind of exposure and learning opportunities I wish I’d had. Whether that’s leading client calls, owning pitches, or managing others, I want them to feel confident stepping into leadership roles before they’re officially given one.

LBB> What are the aspects of leadership that you find most personally challenging? And how do you work through them?

Charly> The hardest part of leadership, for me, has been learning to separate personal emotions from business decisions. Early on, I took everything personally. I felt guilty when I had to make tough calls, especially when it came to people.

I’ve had to accept that my team sees me as their boss first, not their friend. That shift in mindset didn’t come naturally, but it’s helped me become more objective and clear-headed.

I’ve also hired more senior team members who help share the weight of decision-making and offer perspective when I need it.

Another challenge has been balancing vulnerability with authority. I want to be open and authentic, but I also have to give my team confidence in our direction. I’ve learned that you can admit when you don’t have all the answers, as long as you show that you’re committed to figuring them out together.

LBB> Have you ever felt like you've failed whilst in charge? How did you address the issue and what did you learn from it?

Charly> Yes, without a doubt. During the first year of running Lasting Lemons, I went through some difficult personal changes and was later diagnosed with depression. I didn’t tell the team at the time and instead I just pulled away. I’ll always feel like I let them down during that period.

Since then, I’ve become much more open with my team and introduced wellness-focused initiatives. We now have ‘wellness hours’, mental health days, and a strong encouragement to avoid working outside of core hours unless absolutely necessary. I want to create an environment where people feel supported, where they can take care of themselves and not feel guilty about it.

LBB> In terms of leadership and openness, what’s your approach there? Do you think it’s important to be as transparent as possible in the service of being authentic? Or is there a value in being careful and considered?

Charly> I’ve always tried to lead with transparency and authenticity. In the rare moments when I haven’t, I’ve felt like I was going against the culture I’ve worked hard to build.

My team knows I had no leadership experience when I started this journey. I remind them that I’m learning just like they are. For us, openness builds trust and it creates a space where people feel safe to speak up, share ideas, and be honest about challenges.

That said, I do believe there’s a balance. Some situations require consideration and strategic thinking. But overall, I’ve found that being human is one of the best leadership tools I have.

LBB> How important is your company culture to the success of your business? And how have you managed to keep it alive with increases in remote and hybrid working patterns?

Charly> The company culture makes Lasting Lemons. There is no business without the Lemons. From day one, I’ve believed that a strong culture isn’t just about perks or slogans. It’s about creating a space where people feel respected, trusted, and empowered.

We do have set office days to encourage in-person collaboration, but I’m also flexible. If someone needs to work from home for personal reasons, they can. I trust the team to get their work done whether they’re in the office, at home, or out on a shoot.

That trust is mutual; if someone isn’t pulling their weight, it affects the whole team, and everyone knows that.Thankfully, we’ve built a culture where people take ownership and look out for each other.

Recently, I put a big question to the team: what if we removed all structured working hours, holidays, and office days? At first, everyone loved the idea. But as we talked more, it became clear that some structure is necessary. Not just for productivity, but for fairness. That conversation was really insightful. It reminded me how important it is to involve the team in decision-making. Giving people a voice is part of my leadership style, and it’s also what helps keep the Lemons culture.

We also make an effort to stay connected beyond the work. From regular check-ins and ‘weekly wins’, ‘Lemon of the week’ and shoutouts to the team on our socials, I try to keep morale and momentum going even when we're not all in the same room. Culture, to me, is about how people feel day to day.

LBB> What are the most useful resources you’ve found to help you along your leadership journey?

Charly> The most valuable resource I’ve had is other people. I’ve learned so much from asking for advice. From fellow founders, mentors, and even team members. I regularly meet with other business owners and creatives to exchange stories, share insights, and keep each other grounded. It’s helped me realise I’m not alone in the challenges I face and everyone is figuring it out as they go.

I’ve also started using AI tools more frequently. They’ve been unexpectedly helpful for checking things like industry standards, career progression frameworks, or even how to word a tough email. When you’re running a business and don’t always have someone to bounce ideas off, being able to ask quick questions (even just to sense-check) makes a big difference.

I also follow a lot of founders on TikTok. It might sound unexpected, but there’s something so refreshing about seeing people share real, unfiltered stories of running a business. Whether it’s advice on hiring, client management, or just venting about the hard days, it’s relatable and helpful. That kind of content makes leadership feel less lonely and more accessible.

LBB> As you developed your leadership skills did you have a mentor, if so who were/are they and what have you learned? And on the flip side, do you mentor any aspiring leaders and how do you approach that relationship?

Charly> I’ve been fortunate to have a few key people support and guide me throughout my leadership journey, though not always in a formal mentorship way. Some of the best advice has come from those who know me best and understand that I don’t lead in a ‘traditional’ way. That perspective has helped me stay grounded and trust my instincts.

But perhaps the most important influence has been my dad. He was written off work due to burnout and depression, and witnessing that firsthand had a huge effect on how I think about leadership and wellbeing. It made me aware of the dangers of overworking and the importance of protecting mental health, not just for myself, but for the people I lead.

Beyond that, my dad also has a huge amount of experience when it comes to running businesses, and I honestly couldn't have done this without him. He’s given me advice, helped me with difficult situations, and always offered a grounded perspective. His insight, paired with his experience, has been invaluable in helping me become the kind of leader I want to be.

I haven’t officially mentored anyone yet, and I think imposter syndrome plays a part in that. I sometimes feel like I’m still figuring things out myself. But when I take a step back, I know I’ve gained valuable experience, starting and running a business, leading a team, navigating setbacks and I hope that one day I’ll feel ready to share that with someone else more formally. That said, I do try to create mentoring moments within my team. I give people space to lead, try things, and grow because I know how much I would’ve valued that when I was starting out.

LBB> In continually changing market circumstances, how do you cope with the responsibility of leading a team through difficult waters?

Charly> The most important thing for me is always making the team feel secure. The past few years have shown that change is constant, whether it’s the potential TikTok ban in the US, the rapid rise of AI, or the ongoing cost of living crisis. All of these affect how we work, how we lead, and how our teams feel day to day.

In moments like these, I try to lead with calm, honesty and flexibility. When platforms like TikTok face disruption, we don’t panic, we pivot. When AI began transforming creative workflows, I encouraged the team to embrace it as a tool, not a threat. And with the rising cost of living, I’ve made wellness and fair pay a priority. Things like mental health days, flexible hours, and open conversations about stress or financial pressure are built into our culture.

For me, leadership isn’t about having all the answers. It’s about showing up with empathy, direction, and trust in your team.

LBB> As a leader, what are some of the ways in which you’ve prioritised diversity and inclusion within your workforce?

Charly> Right now, Lasting Lemons is an all-women team. This wasn’t intentional, but happened organically as I hired the best people for each role. I think that’s a testament to what happens when you focus on talent, not just ticking boxes.

We’re also a neurodiverse team, with several of us (including myself) having ADHD and dyslexia. That’s made me much more aware of how important it is to create an inclusive environment that supports different working styles and ways of thinking. It’s shaped everything from how we communicate to how we structure deadlines and meetings.

Beyond the core team, I’m very aware of the importance of diversity in all its forms, especially in creative work that speaks to broad audiences. When it comes to video content, we make a conscious effort to collaborate with a wide range of freelancers from different backgrounds, cultures, and perspectives. Representation matters both behind the camera and on screen, and we always consider that.

For me, diversity and inclusion aren't a tick box or checklist. It’s about building a culture where everyone feels seen, supported, and empowered to do their best work.