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Bossing It: A Work-in-Progress with David&Goliath’s Robin Osborne


The managing director of the LA agency on the importance of empathy, learning, good mentors and friends for strong and supportive leadership

Bossing It: A Work-in-Progress with David&Goliath’s Robin Osborne
Robin Osborne is a seasoned advertising veteran who honed her skill of keeping multiple balls in the air while playing college tennis! She’s worked at major agencies in NY, Chicago, Minneapolis, and LA on a wide range of iconic brands including Heineken/Amstel Light, Kraft Foods, Best Buy, Target, Clorox, Pizza Hut, Dial Corporation, Sears, New York Lottery, and She leads a group of brands at David&Goliath including the California Lottery, Jollibee N.A., and the agency’s work with the United States Forest Service and Ad Council. She’s thrilled to have landed at David&Goliath almost four years ago, where she can employ her style of leadership in a culture aligned with her own values.

Check out Robin's incredibly thought responses to our Bossing It series below.

LBB> What was your first experience of leadership?

Robin> I guess going back to high school, when I served as co-captain on my cheerleading squad and captain of the tennis team my senior year. They were formative years and of course I was still figuring out who I was … but having this extra bit of responsibility was great experience.


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?

Robin> Early on in my career I had a boss who was a major micro-manager, wanting me to be exactly like her vs. fostering my strengths and encouraging me to lean into my own style of account management. She hovered so much and dictated every word of every email, and as you can imagine, I felt stifled beyond belief.  
On the contrary, my best mentors were those who saw my strengths and pushed me to be my best self; those who were inspiring and encouraging, rather than stifling.  
I do believe that we’re all still works-in-progress and I’m still learning and growing as a leader every day, however, I work hard at trying to be more the latter kind of leader – one who inspires and supports, rather than trying to create a bunch of ‘mini mes’.

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

Robin> I think by observing bad leaders and what not to do. Seeing people in leadership positions who were inconsiderate, judgmental or disrespectful, and observing how their actions made people feel. So, I guess, just learning from others’ mistakes and then striving to do better.
I’m an empath and have always had a relatively high EQ. My relationships are everything to me and I’ve always aspired to the idea of treating people as I would want to be treated. I’m also an optimist and tend to see the good in people. So, instinctively, it’s in my nature to want to foster the good, and help people shine. I try to do that through encouragement and propping people up.  
Over time, I’ve had a few direct reports who I loved and admired dearly, tell me how much my support and guidance meant to them and how I had helped them find their own stride.  It’s these moments that are the most rewarding for me, knowing how my actions positively impacted someone else.

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?  

Robin> I think I always dreamed about it and had big aspirations, but didn’t always believe I had it in me in the early stages of my career. Plagued by negative self-talk like so many young women growing up, it took others’ believing in me first to help me see that I had it in me. 

Too often, I’d sit quiet in a meeting, thinking of an idea or response, but not speaking up… only to have a similar idea or thought voiced by someone else in the room moments later. Over time, I started to realise, well, if I’m having these same thoughts and ideas, then I must belong here too. And with some prodding from good mentors and encouragement along the way, I grew my voice little by little, until I liked the sound of what I heard coming out and recognised that my comments were well-received and valued.  

I’ll never forget how terrified I was when I made the first big career jump from account supervisor to VP, management supervisor at a new agency in a new city. The role carried a significant title and salary bump and came with a lot of increased responsibility. I remember feeling like I had accepted a position I had no business doing. But quickly the team started speaking to me and then the clients did as well, and before I knew it, six months had passed and I was successfully doing what I thought I never could. More and more I began to realise that the only one holding me back from the things I wanted … was me, and the limitations I was putting on myself!

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?  

Robin> While there are certainly born leaders, I do think it’s a skill that can be acquired and honed over time. I have become a better leader by watching and learning from other great leaders I’ve been blessed to work with; observing them has fuelled my own growth.

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

Robin> I tend to seek harmony in all situations, and often play the mediator when there is conflict. So, conflict-laden situations such as giving constructive criticism, a bad review or having to let someone go is the most challenging part of the job for me by far. I imagine a lot of people feel that way. 
Naturally, over time you gain more confidence in these situations. But I think it has helped me to realise that sugar-coating something or not being transparent about someone’s opportunity areas, though may seem kinder in the moment, is actually doing them a disservice in the long run. A philosophy we embrace at the agency is ‘fail, to learn’ and by providing honest and necessary feedback, you may actually be helping to propel someone forward and fuel their growth. Even if sometimes it doesn’t feel that way for either party in the moment.  
So, I try to always approach these situations from a place of empathy, but then just deliver the information in a clear and straightforward way.  

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?  

Robin> Without failure, there can be no growth. It’s all part of the learning experience. But, earlier in my career, I had a tendency to want to find solutions before bringing my boss into the fold. I would try to work through any solution and have it completely figured out before letting my boss know there was an issue. In one instance, I waited too long to apprise my former boss of a tricky situation that was developing regarding a broadcast production talent situation, and it didn’t go as I had hoped. My boss was frustrated that he wasn’t brought in sooner to help be part of the solution vs. being kept out of it until the situation got worse. I learned a valuable lesson and it helped me to see that it’s ok to fail, we all will at some point, but that part of being a good leader is also knowing that sometimes more heads are better than one.  

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

Robin> I don’t think there’s just one style of successful leadership. I also believe that every situation may require a tailored approach, and that’s part of the finesse in what we do. Generally speaking though, my personal style is one of communication and transparency and I tend to be very open with my teams. I think I’m a ‘lead by consensus’ person and often look to my team for their input before making a final decision.  

LBB> As you developed your leadership skills did you have a mentor? And on the flip side, do you mentor any aspiring leaders and how do you approach that relationship? 

Robin> I have been fortunate to have had many great mentors, both professionally and personally.  One of my first bosses in advertising was Mary Collopy, a management supervisor, when I was just starting out as an assistant account executive in New York. Mary taught me early on, in an agency dominated by male leadership at that time, that it was possible to be a strong, smart, respected woman in business, while still practicing empathy, compassion and understanding. She was also someone who identified my strengths and let me know she believed in me, perhaps even before I believed in myself. There have been many others along the way, but she was one of the first.  

Someone else I respect in the industry once said, “hire good people and then get out of the way.” And I firmly believe in that. I’m here to provide air cover, support and counsel … use me as a sounding board, but at the more senior levels with my direct reports, I don’t tell them exactly what to do. I offer guidance and my opinion as needed, but encourage them to find solutions that fit their own style and work for them. 


LBB> It's been a really challenging year – and that's an understatement. How do you cope with the responsibility of leading a team through such difficult waters?  

Robin> It has been an incredibly challenging year to be sure, but we’re all blessed to be working and we try to remind ourselves of that. It’s been challenging for everyone, both personally and professionally. I feel it’s important to stay in touch with people and connect, to ensure people feel engaged and part of something, part of a family really, and not isolated while working from home.  
In terms of how I cope, you mean besides the wine?! No, really, I just try to take time to ‘breathe’, so-to-speak. For me that can mean, fitting in a few minutes of meditation in the morning, afternoon yoga, or a quick walk outside with the dogs in between meetings. It’s important that I do what I need to do to stay grounded and level-headed, so I can be present and helpful to my teams. We also tend to laugh a lot as a team. Laughter does wonders for the soul and looking for opportunities here and there to find joy is important, especially in the face of so much negativity, uncertainty, and sadness that we’re bombarded with daily in the news.  

LBB> This year has seen the industry confronted with its lack of action/progress on diversity and inclusion. As a leader how have you dealt with this?  

Robin> Our agency has made a commitment to amplify DE&I initiatives and I believe is at the forefront of the industry, leading the charge through action. Just a few examples, we hired a director of empathy, Tiffany Persons, who is helping accelerate recruiting efforts to increase Black talent at every level and, has also helped enhance an environment that breathes recognition, growth and retention of D&G’s existing Black, Indigenous, and People of Colour (BIPOC) employees. Her workshops, ‘Aligned’, unlock empathy and empower inclusivity, aimed to inspire a shift in conversation by raising up the voices of those who have been previously unheard. Earlier this year we hired Blake Winfree as our chief of social impact to continue to inspire greater social responsibility and sustainable impact within the industry. 
So, for me, the agency has taken tangible steps and it’s about carrying that torch as a leader as well to our individual teams. I try to ensure that everyone feels safe to express themselves and to be heard, and that we’re fostering a team based on respect, understanding and empathy. 


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 in 2020?  

Robin> Our agency culture is everything. D&G has one of the most unique and special cultures I’ve ever experienced, having worked at many different agencies over the years. It’s a culture that promotes bravery, empathy, tolerance, connection, and being purpose-driven. It starts with our leadership who live the culture every day and then our culture team, in particular, has done an incredible job of keeping it alive during the pandemic. It’s hard because we’re all as busy as ever, but trying to make sure that we participate in those experiences and agency meetings to the extent possible.  
One of our Ten Brave Ways is ‘Join the family, not the company’ and so I do my part to keep that spirit alive every day, in every meeting. Just being there and fostering those relationships and the camaraderie that is such a unique part of who we are at D&G, beyond just the transactional nature of the business.

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

Robin> Finding a great mentor is key, of course, and their guidance has been invaluable to me along the way. But something else I’ve come to realise is that a mentor doesn’t have to be a boss or someone in a more senior position. Mentors come in all forms. And to that end, I would say that it’s important to surround yourself with positive, like-minded, supportive people and friends who you respect and admire. People who believe in you, who lift you up when you need encouragement, but also aren’t afraid to call you out when you’re off base. I have found that having a strong group of peers, and/or girlfriends in my case, to talk to and bounce things off, has been one of the greatest gifts, both in my career and in life; an invaluable resource to be sure. 

And of course, lastly, so many great business books and podcasts out there such as Ted Talks, HBR IdeaCast, Hidden Brain, or listening to people I admire like Brené Brown, Jay Shetty, or fellow ‘badass’, Jen Cincero. The resources and channels are unlimited, especially today, so the key is to find what works for you.

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David & Goliath, Tue, 27 Apr 2021 12:26:12 GMT