Bossing It: Leadership Rooted in Accountability with Jamie Falkowski

As chief creative officer and partner at Day One Agency, Jamie Falkowski helps to grow and inspire an agency that’s built for the next 10 years and 24 hours.

Since joining as one of the agency’s early employees in 2015, Jamie’s leadership and creative vision have helped Day One attract and grow creative assignments for clients like American Express, Beam Suntory, Chipotle Mexican Grill, Converse, Ferrara, and Nike.

Founded in 2014, Day One Agency is a creative communications agency with the ambition of moving the world with stories that earn a place in culture.

LBB> What was your first experience of leadership?

Jamie> While I had the random experience of school group projects or clubs in college, my first true leadership experience really came into play during my time at Alldayeveryday.

Transitioning into leadership is a funny thing and sort of felt like it crept up on me – I went from being the one doing a lot of work to suddenly being a big part in shaping the output of a team.

In this role I worked closely with the partners and became a conduit between their knowledge/feedback and the team's ideas and insights. While many were working on the projects it became very clear—the success or failure of these things stops with you. 

Leadership is rooted in accountability – it is often thrust on those willing to do what others won't.

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?

Jamie> We often hear the phrase, “great artists steal,” and, for me, as a leader, I believe “great leaders reflect". 

Over the years I’ve had the opportunity to work with a lot of great leaders, both on the agency and brand side, and I’ve tried to pick up the things I like about how they work and adapt to the things that bothered me or didn’t cut through. Anything in life that is truly meaningful takes time. You need the reps and trial and error. I feel for those I managed early on. I didn’t really know how to get the most out of them or how to focus on the right things. 

Now, I focus so much on adapting my own style to fit others and to help them succeed. I mentioned ‘reflect’ earlier and yes, it is in stealing and embodying the great from other leaders but it’s also in managing creatives. I need to change and adjust my style subtly to build trust and a relationship that allows for good collaboration. 

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

Jamie> We learn the most, unfortunately, through failure. A project gone wrong. An employee leaving. A botched new biz pitch. In all of these cases (here it is again) you “reflect” on the lesson and try to figure out how to adjust. We can’t keep doing the same things and expect different results and failure teaches us how to get better. But failing is only valuable to the entire team if you know how to clearly communicate it and share from the pain. Be an open book. 

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?

Jamie> When I look at my profile from a tool like Insight Discovery, there are a lot of subconscious clues that indicate that I was likely to end up in a leadership position. I like to shape things and to help navigate complex problems. 

I’ve been with Day One Agency for nine+ years and I’ve played a number of different roles. A couple years in I saw our trajectory taking off and the evolution of the work accelerating. During a conversation with Josh Rosenberg, our CEO, he asked me what my long term vision was for myself. I knew I wanted to shape and figure out what a different agency model could be and where I sat mattered less than the challenge.

In my previous role I had a close relationship with Allday’s managing director, Kevin Kearney, and respected the way he tried to drive and shape the business. I knew that was a role I wanted to take on to help Day One Agency navigate to what was next.

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?

Jamie> It is a classic nature versus nurture conundrum.

Being a leader is a lot about the soft skills –  it is probably 70% natural instinct, which will get you very far if you have the right balance of empathy, self-consciousness, and confidence. You need to be able to see outside of yourself and have a bit of a sense of how others might view you.

I will say that the last 30% — the skills you develop through training and adapting past what you inherently know — is the hardest part. Being a good leader is something I believe you have to work at. Know your weaknesses and know when you make a mistake. Be humble, communicate it, and take ownership. Let others see you working at getting better and actively looking for feedback. 

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

Jamie> Leading and managing require two different skill sets. To me, managing boils down to communication which can be an ongoing challenge as you need to regularly reflect and adapt to each person's style, often slowing down in the process.

As a leader I have learned there is power in clarity, and you have to be okay repeating yourself. I often feel like a broken record, but in today’s hybrid world where so many are multitasking, things get missed. Be comfortable repeating what is important.

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?

Jamie> Yes, of course. I think it is an inevitable part of the job and, as mentioned, where we learn the most. We ask so much of our teams and want them to set the bar high on what they do. In practice, those marks might be missed. The same is true for me. I can’t expect them to push and stretch if I don’t try myself.

When we fail we try to not only own up to it but to dig into why – that’s where the true lesson can be found.. Sometimes things that look like they are working are actually broken. If you see it broken, fully break it—and communicate why. 

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?

Jamie> It is a balance. We’re extremely transparent with the team around our goals, ambitions, shortcomings and where we need support. Still, you want to evoke confidence and a sense of trust with the internal team and with partners. I’m honest when I feel like we screwed up but I also will let anyone who listens know when we’ve got the answer and a great path forward. That time in between when figuring it out? I may keep that close to just the people who need to see me sweat. 

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?

Jamie> I’ve reflected on the best of so many leaders over the years. I’m lucky to have amazing clients partners to watch and learn from like Kory Marchisotto, CMO at e.l.f. Cosmetics and Kamauri Yeh, VP of digital marketing at Nike. I watch how they navigate, what they share closely with me and more broadly with their teams. 

Internally, my business partners, in particular Josh Rosenberg, our CEO, have taught me so much. Today, I have the opportunity to learn and lead alongside him and Brad Laney, president, and Rob Longert, managing partner but before becoming a partner they were the ultimate guides. They have always been vulnerable in what they didn’t know and headstrong in what they believe to be true. 

From a mentorship perspective I have a large number of direct reports and get to spend time with a talented creative team. I try to mentor them in the ways I believe will materialise in personal growth and development for the business which is to say, I have to treat them all individually. I try to listen to what they need and help them to see and maximise their strengths.  

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

Jamie> Keep your eyes/ears open and pay attention to what isn't being said. I try to ask them a lot of questions and to get to the root of how they are feeling. Our team is extremely sharp and the right ideas are often in our own walls. My job is to edit and amplify the best.

Beyond that, I share what I’m thinking openly—I write a weekly brain dump to the entire agency senior leadership team—and take feedback for improvement. I look for opportunities to reiterate what is important and on repeat let everyone know our business is changing. I’m the first to adapt and evolve when needed and the team needs to be comfortable with that change, too. 

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

Jamie> We certainly prioritise diversity when it comes to staffing teams. It’s extremely important to me to meet as many varied thinkers and creative people as I can and typically interview 100+ candidates a year. 

Additionally our Employee Resource Groups (ERGs) are important programs and investments that help to create a sense of belonging and community. Our ERGs boast high engagement rates, as 97% of the team is involved in at least one group. We see the camaraderie that comes from giving different team members the space to get together and connect on a human level.

I’m forever grateful to Randi White who oversees so many of these initiatives for us and exemplifies inclusive leadership at Day One Agency. I try to be a little bit more like Randi in my day-to-day work life. 

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?

Jamie> Day One (like every agency) is just the people. Sure, we have a point of view and a logo, but it is made up of brilliant individuals who can do something greater when they all come together.

The truth is that a remote/hybrid workstyle requires more work than ever. You have to be paying attention and ignoring the distractive ping of Slack, email, or any other red dot on your iPhone. Is it possible to do breakthrough work via zoom? I think it can happen, but only if you have a solid relationship and have built trust and camaraderie with the people you share those small squares with.

To me, that starts with building connections—and in turn culture—offline. That doesn’t just mean sitting at a desk. It means breaking bread, taking in art and culture, and making time to debate and celebrate. 

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

Jamie> When I was first transitioning into leading more work I came across the '10 Lessons' from W+K’s John C Jay. I often go back to these because they are so simple. I also greatly enjoyed, 'The Ride of a Lifetime', by Bob Iger and try to regularly read leadership books—trying to find the next thing I’ll steal for personal reflection.