Bossing It in association withLBB's Bossing It

Bossing It: Learning and Leading with Dotted Line CEO Lauren Sweeney

Advertising Agency
Richmond, USA
Dotted Line CEO on funding for learning, starting a business from the ground up and how leaders are built, not born

Lauren Sweeney, founder and CEO, Dotted Line, was recently tapped by Virginia Business for its annual Women in Leadership Awards, in recognition of her efforts to build a culture of collaboration and develop future leaders

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?

Lauren> The people in my personal life have had direct influences, starting with my grandfather, who owned an oil-and-gas company in rural Virginia. I saw first hand how he treated his employees with high esteem while also setting a high bar for his expectations, and how he engaged across his network. He taught me that it’s hard to be a great leader if you don’t love people.

As a young entrepreneur, I’m learning and leading at the same time. Before starting Dotted Line, I was in a corporate role where I experienced the positive impact of employee learning and development programs. For this reason, I’ve instituted learning and development programs at Dotted Line to grow our people’s abilities. And I’ve watched my husband, a fellow entrepreneur and a voracious learner, take time to educate himself on every facet of his scope of responsibility and build a successful business as a result.

I’ve found that teams are only as successful as their individual members. When individuals are growing and stretching their abilities, the team grows with them and performs at a higher standard. I want Dotted Line to be a workplace where people can always be growing in all areas of their life, not just professionally.

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

Lauren> Starting my own agency from the ground up and turning it into a successful business. One of my biggest lessons from this experience is the importance of modelling a growth mindset as a leader. For example, Dotted Line’s leadership team and I faced a watershed moment where we needed to decide how ambitious we wanted our agency to be and what it would take to get there. At the time, we were winning with our clients, building a great internal culture, and hitting profitability goals. But we were hungry for new opportunities: to land bigger clients and do the next level of creative work. We had to make a big investment in ourselves first, where we strategically built out our team to demonstrate we had the breadth of talent, perspective and expertise to deliver flawlessly at higher levels. It was a huge step, personally and professionally for me. It underscored how focusing on the potential of what something can be, rather than getting stuck focusing on limitations, can help your team achieve goals, one step at a time. The proof is in a threefold jump in our number of people and nearly doubling of our revenue from 2020 into 2021 alone.

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?

Lauren> Strong leadership influences were on display for me early on from growing up in a family of business owners. During my corporate time, I regularly volunteered to lead, whether it was the company’s internship program, a group status call, or a major presentation. I don’t remember explicitly saying “I want to take on a leadership role” but I was always eager to learn and grow.

As I’ve realised the potential of Dotted Line and our people, I’m mindful that every business is limited by its leaders. I started to dedicate more time to intentionally grow myself so I can help our teams grow and the company as a whole. The people leadership component is a top priority to me.


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?

Lauren> I truly believe that leaders are built, not born. Anyone can be a leader, despite what most stereotypes dictate. It’s not true that leaders are always extroverted, visionary and dominant; they can also be introverted, pragmatic and compassionate. Our industry has a huge opportunity to remove these leadership stereotypes - which are often gendered – and get more diverse leaders at the top for others to emulate. This is also why mindset as well as learning and development are so important, to give all people the skills they need to lead others effectively. The power is that anyone can choose to be a great leader, but they need to invest the hard work and discipline that is within their control. Every day, I walk into the agency and strive to be a great leader for my team.

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

Lauren> As a leader, your job is not to have all of the solutions. Your job is to inspire and uplift your team so they can uncover the solutions themselves in their own way and learn and grow from that experience. Out of my desire to help, I have to remind myself on a regular basis to step aside and be the coach on the side lines, not the player taking shots on the court.

Relationships are incredibly important when it comes to driving results through other people. My personality tends to be more focused on the results. I’m constantly learning how to better connect with others so they can do their best work. I’m also constantly sharing that I’m leading and learning at the same time. I believe it’s OK to be vulnerable as a leader and articulate if (and how) a situation could have been handled differently.

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?

Lauren> I definitely have moments where things don’t work out the way I want them to or expect them to. Over the years, I’ve learned from those failures, such as client pitches where we weren’t adequately prepared or didn’t deliver on the targeted ask. On the people front, I underestimated what it would take tomorrow transition a new senior leader and to introduce a new capability.

I look at these moments as opportunities for growth. I learn from those experiences, and I’m vulnerable and own where I don’t meet expectations. I encourage my team to have that same mindset. People understand failures if they see how that drives smart change. Failure is essential to being human and being a leader and a by-product of really pushing the limits is that sometimes you amaze your client (and yourself).

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?

Lauren> Transparency and communication are everything, particularly for today’s workforce that is seeking more meaning in their day-to-day work. As leaders, we have to convey the WHY behind company decisions and actions. Keeping open lines of communication and determining the right level of transparency is an essential ingredient to a healthy work environment and solid team morale. This is why I send out a company-wide message on Tuesdays to share what’s top of mind about Dotted Line’s business and culture. Transparency is not the same thing as having no filter, however. I put a great deal of thought, consideration and intention into how and what I communicate to my team and our clients. Words have impact, and the team is watching closely.

For example, when the pandemic hit, the leaders and I quickly created different scenarios for the potential impact of losing clients: bad, horrible and worst. We agreed on steps to take to put the team first, such as not taking pay for a time. Then, we created worst-case scenario plans. This exercise helped us be ready if we suddenly lost a big client - a risk in any business.

We communicated this exercise to employees at a high level. While that wasn’t an easy message, people appreciated the transparency. The team dug in to go above and beyond for our clients during this uncertain time. Fortunately, we never needed any of our plans. Our business actually grew significantly in 2020.

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?

Lauren> Great leaders never operate in a vacuum. Seeking outside expertise and guidance is essential. I believe in leveraging different people in different capacities, and right now about a dozen personal advisors are helping guide the business, serving as an informal board for the agency. My early mentors helped me learn the fundamentals of running a business and developing the agency’s culture. Today, I learn from individuals who own much larger agencies, business advisors and exceptional female leaders. I gain different things from different conversations. What’s important is identifying what you hope to learn and focusing your engagements to make the most of the experience on both sides.

I’m also working closely with a business coach to aid in problem-solving in the moment and leading effectively through the ups and down of our growth phase. I’ve extended coaching to the leadership team, which is helping to broaden alignment on how to achieve our shared goals and enrich our interactions.

Meanwhile, I’m building new relationships through the YPO (Young Presidents Organisation) and the Virginia Council of CEOs. On the flip side, I’m serving on the board of the Virginia Chamber of Commerce, where I hope to share my voice and experience to support new entrepreneurs.

LBB> How important is your company culture to the success of your business? And how have you managed to keep it alive with staff working remotely or in a hybrid environment?

Lauren> Dotted Line’s culture is the most important ingredient contributing to our success. We knew that building and maintaining culture as our company grew would be a challenge, so we took active steps to prepare, including a proactive, strategic plan designed to scale our culture and deliver great work.

We’ve established six core values for the agency. Everything we do ties directly back to those and they are integrated across the employee experience. We also have a year-long Leadership Development program and culture committees that are run by employees.

We also make a significant investment in our people. The agency model means having a workforce that feels engaged, challenged and growing. But we also have to create an environment that is healthy and stable so the teams can do their best work. Our Leadership Development program is one step toward building confident, team-based leaders as our staff numbers grow.

Like many other businesses, we’ve seized the virtual experiences of the past two years to refine our capability to work effectively and efficiently. Communication is critical and even more so with a hybrid culture. We heavily rely on Slack for status updates, team kudos and other means of communication. Making this fun is an important part.

Because our clients love our uniquely collaborative approach, we built internal systems to recreate that as a virtual experience. Employees work remotely up to up to three days a week, and we’re constantly listening to cultural cues and adjusting to meet their evolving needs and expectations. For example, we’re looking to establish one day where everyone is in the office and to create a special tradition for that day.

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

Lauren> I am a voracious reader. Reading is how I learn about new concepts and expand my horizons. In 2019, I read one business book per week to build on my knowledge as a business owner and marketing leader. Reading is also a big component of Dotted Line’s culture overall and in our Leadership Development program. Supplemental readings are given to participants to accompany a workshop or speaker session. Our office has a library vault with a whole host of inspiring and educational books. We also have a curated reading list for our employees to reference in their own free time.

EntreLeadership has been an exceptional resource for me as a small business owner. Dave Ramsey’s book, conferences, and online programs are some of the best out there.

The One Thing, written by Gary Keller, chairman of Keller Realty, is a game changer. This book is about focus and prioritisation on the one thing that is most critical for you to succeed. .

The Confident Mind by Dr. Nate Zinsser is one of the best leadership books I’ve read this year. It’s about building a genuine confidence that is optimistic and demonstrates mental resilience.

I have always prioritised funding for learning – coaching, conferences, development programs, such as EntreLeadership. I believe no investment is too large when it comes to growing your capacity as a leader.

Work from Dotted Line