Bossing It: Andy Silva on Knowing When to Step Out of the Way
Andy Silva’s global advertising experience on both the agency and client side provides him with a nuanced understanding of what modern marketers are facing. His journey began at Saatchi & Saatchi New Zealand, a formative experience that led him to join 72andSunny in the U.S. where he directed global advertising for top brands including Samsung, Adidas, Google, and Smirnoff.
Transitioning to a client-side role, he became Head of Accounts for AT&T’s internal marketing group, further mastering agency-client relations and marketing strategy. Since joining Party Land in 2020, Andy's vast experience has enhanced the agency's strategic prowess and partnerships, making him a pivotal figure in clients' success.
LBB> What was your first experience of leadership?
Andy> My first experience of leadership came unexpectedly early in my career. I had just started at a small agency, and within two weeks, my direct boss was fired! With no immediate plan to backfill the position, I found myself stepping into his role and leading the department. To be honest, I was shitting myself.
It was trial by fire, but it pushed me to adapt quickly, make decisions with confidence, and learn how to support a team through uncertainty. This experience taught me that leadership isn’t always something you choose. Sometimes, it chooses you, and when it does, it’s on you to rise to the challenge. (And not shit yourself.)
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?
Andy> Having experienced a few horrible bosses in my career, I knew early on that I didn’t want to lead from a place of fear or ego. I wanted to be the kind of leader who listens more than speaks, fosters collaboration, and builds trust. Empathy became a cornerstone of my approach. I’ve seen first-hand that people produce their best work when they feel valued, supported, and respected. And I wanted to lead in a way that allowed people to bring their whole selves to work.
Setting expectations early and often is a crucial aspect of effective leadership. Clear communication from the start helps everyone understand their roles, responsibilities, and goals, which minimises confusion and keeps the team aligned. Regularly reinforcing those expectations ensures that as projects evolve, everyone remains on the same page. This approach builds trust, accountability, and gives people the clarity they need to perform at their best, knowing exactly what’s expected of them at every stage.
LBB> What experience or moment gave you your biggest lesson in leadership?
Andy> I remember early in my days at 72andSunny, I made a dumb mistake — I sent a client a quote that was incorrect by $250,000. When I went to my manager for help, his response was, “What do you want me to do about it?” He wasn’t trying to be a dick, but he was right.
It was a tough lesson in accountability and problem-solving, but it made me realise from that day forward I was responsible for finding my own solutions. It wasn’t about looking for someone to fix things; it was about stepping up and owning the outcome, no matter how challenging the situation.
LBB> Did you know you always wanted to take on a leadership role? If so, how did you work toward it? If not, when did you realise that you had it in you?
Andy> I always knew I wanted to take on a leadership role. From early in my career, I was drawn to the idea of guiding a team and helping shape the bigger picture. I worked toward it by observing great leaders, learning from their approach, and seeking out opportunities to step up whenever I could.
For me, leadership has always been about more than just managing—it’s about inspiring others, creating a space where people can thrive, and driving toward a shared vision. I was always confident I had it in me; it was just a matter of time and experience.
LBB> When it comes to 'leadership' as a skill, how much do you think is a natural part of personality, and how much can be taught and learned?
Andy> I believe leadership is a blend of both innate qualities and learned skills. Traits like empathy, emotional intelligence, and authenticity often come naturally but can be refined. The more technical aspects of leadership—like navigating difficult conversations, managing expectations, and making tough decisions—are learned through experience. A good leader is always learning, always evolving.
LBB> What are the aspects of leadership that you find most personally challenging? And how do you work through them?
Andy> One of the most challenging aspects for me is balancing transparency with discretion. I value openness, but there are times when you need to shield your team from unnecessary stress. The key is knowing when to be fully transparent and when to protect your team from too much information that may hinder their focus or morale. I work through this by considering how the information will impact them and always ensuring I’m honest without being overwhelming.
I’ve learned that one of the most valuable things you can do as a leader is simply say yes or no, and then step out of the way. Most people aren’t looking for someone to make the decision for them—they usually already know the right answer. What they really want is reinforcement and the confidence to move forward. By giving clear direction and then trusting them to take it from there, you empower people to own their decisions and thrive.
LBB> Have you ever felt like you've failed while in charge? How did you address the issue, and what did you learn from it?
Andy> Yes, failure is an inevitable part of leadership. There have been times when I’ve misread a situation or made a decision that didn’t land as I’d hoped. When that happens, I believe in owning it—both to myself and my team. Admitting mistakes is crucial for growth. The lesson I’ve taken from these moments is that failure can be a powerful teacher if you’re open to learning from it and using it as a way to improve.
LBB> In continually changing market circumstances, how do you cope with the responsibility of leading a team through difficult waters?
Andy> Change is constant, especially in advertising. Right now, it’s the rise of AI disrupting industries and a political storm brewing. There’s always going to be something.
I’ve found that staying calm, grounded, and adaptable is key. You can’t control market shifts, but you can control how you respond to them.
My focus is on being a steady presence for my team, keeping communication clear, and reinforcing the idea that we’ll figure it out together. When you cultivate a culture of trust and resilience, your team can weather any storm.
LBB> As a leader, what are some of the ways in which you’ve prioritised diversity and inclusion within your workforce?
Andy> Diversity and inclusion are non-negotiable for us. A team that reflects different backgrounds, perspectives, and experiences is not only more creative but also more representative of the world we’re speaking to in our work. We actively prioritise diverse hiring practices and create an environment where everyone feels they belong and can contribute meaningfully. It’s not enough to hire diverse talent—you have to ensure they feel seen and valued.
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?
Andy> At Party Land, play and fun aren’t just perks—they’re essential to our culture and to generating great ideas. As a comedy agency, we know that the best creative work comes from an environment where people feel connected, relaxed, and ready to explore the unexpected. Even as a fully remote agency, we’ve made it a priority to foster that sense of play.
From impromptu virtual hangouts to our #partylandoutofcontext Slack channel, we make space for moments that spark creativity and keep the energy up. It’s all about keeping the fun alive because when we’re having fun together; the best ideas tend to follow.
LBB> What are the most useful resources you’ve found to help you along your leadership journey?
Andy> The most valuable resource on my leadership journey has been finding great mentors. Having someone to guide, challenge, and inspire you is hugely important, and if they’re not in your organisation, don’t hesitate to seek them out elsewhere.
You’d be surprised how open people are to offering help—I certainly am.
Beyond mentors, books have been a game-changer for me. There are countless great reads that push you to think differently about yourself and how you respond to the world around you.
Leadership is an ongoing journey of learning, and the key is to always stay open to new ideas and perspectives, whether they come from people, books, or the experiences you gain along the way.
I can’t emphasise enough the importance of always being willing to learn and staying open to the possibility of being wrong. Just because something was true for you once doesn’t mean it will be true forever. Adaptability and a willingness to rethink your assumptions are key to growth.
