Bossing It: Why It’s “Clarity Above All” for Sandi Preston
Sandi Preston is currently the chief strategy officer of creative solutions company Translation, occupying the role for the past five years. She contributes her Chicago-bred work ethic and journalist-trained storytelling sensibilities to her day-to-day role where she is responsible for guiding brands towards work that is award-winning at the least and culturally seismic at best.
Throughout her tenure over the past 14 years, Sandi has led accounts with a distinct point of view, always upholding the virtue of clarity as the means to drive breakthrough and connection.
LBB> What was your first experience of leadership?
Sandi> Join me in my way-back machine: My first leadership experience was when I became co-editor of my high school newspaper. It was the first time I felt both my point of view and decisions had a direct impact on an outcome. While any editorial experience I had post high school was short-lived, my capacity for leadership continued to expand.
Once I began working at agencies, being able to form a compelling POV and make decisions that influenced those around me increasingly became not only a demand of the job, but also a determining factor of how far I would go in my career.
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?
Sandi> I don’t believe I “figured out” what kind of leader I wanted to be -- my leadership voice and style came to me organically as I had more experiences that shaped my voice and style of working with others. It’s been an evolution of sorts where I am constantly learning from what worked well for me (or didn’t) in achieving a desired result.
I aim to learn from mistakes versus repeat them -- all the while, still allowing mistakes to happen. There’s not a singular archetype of leadership I’m aiming to achieve, but rather with commitment, steadily become a better leader.
I’m open to iterating as I go, otherwise if I reach a point of feeling like I’ve mastered it all, I would not feel like I’m growing. As actress Ruby Dee once said, “I am always becoming.”
LBB> What experience or moment gave you your biggest lesson in leadership?
Sandi> From the standpoint of my resume, the experience that provided me with my biggest lesson in leadership has been taking on the role of chief strategy officer at Translation. In this role I’ve had to hone both my own strategic prowess and hone that of an entire department. Thus, leadership in this capacity has also meant teaching.
Luckily, or perhaps serendipitously, I’ve also taught yoga for over a decade and if there is one skill from the studio that transfers directly over into the office it is the capacity to guide and compel others to follow my lead.
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?
Sandi> Becoming a chief strategy officer was not on my vision board at the onset of my career. When the opportunity first presented itself to me, I actually was hesitant to take it, but the tenaciousness within me would not allow me to pass on the challenge. I grew up pretty shy and introverted. Writing became my way of being heard without being seen.
But as my career trek shifted from storytelling to essentially storyselling, leading in a very outward way -- and doing so with conviction -- was a mandate of my growth. I quickly had to get comfortable showing up and commanding many rooms.
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?
Sandi> When you lead a discipline, i.e., strategy development for brands, the start of your career is all about learning the fundamentals and putting those learnings into practice. The more you practice, the better you get. I think the same can be said for leadership development, however, there is a fair amount of soft skills that are being learned along the way.
I think naturally everyone has different hard and soft skills that come easily to them. Who you develop into as a leader depends a lot on your awareness of where your natural skill set lies, and being clear on what you put into practice to improve upon those skills in a way that is most authentic to you.
LBB> What are the aspects of leadership that you find most personally challenging? And how do you work through them?
Sandi> A great mentor of mine once told me that our greatest strengths are often a signal, if not a foil, of our greatest weaknesses. On the side of my strengths, I am empathetic. Everyone loves an empathetic leader, right? Sure. However, on the side of my weaknesses, I’ve had to learn when/how to face conflict more head-on.
At times, I’ve avoided confrontation in order to preserve harmony. But all that creates is a false sense of harmony.
As a leader, you have to be able to address issues directly to prevent tensions from going unresolved. Doing so can involve many uncomfortable conversations, hard decisions, and a wide range of emotional responses that for an empathetic leader, can be quite overwhelming.
The goal is maintaining balance -- upholding the high standard of emotional intelligence inherent to empathetic leadership but also being able to unemotionally navigate the tough situations that the role so often demands.
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?
Sandi> There absolutely have been moments of failure throughout my leadership as CSO. I think about the times I should have made a call, but didn’t. I think about times that I could have set a boundary, but didn’t. Or, in the most self-critical way, I think about what I would have done differently to drive a different outcome than what occurred.
I’ve had to learn that failing is a part of the learning process. But, progress happens when we learn to fail forward; meaning, not just hamster-wheel our thoughts in shoulda, coulda, wouldas, but to actually draw lessons from our failure and do something about it by doing something different the next time.
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?
Sandi> I live by a mantra of “clarity above all.” I think transparency is important to foster honest and meaningful connection within whatever community you are leading. But there’s a nuance between being clear and being transparent, a nuance that has distinct implications, especially in leadership.
For instance, transparency fosters trust and openness by revealing information, whereas clarity ensures that the information is easily grasped. Transparency may sometimes involve complex, detailed explanations that provide context, whereas clarity aims to strip away what’s inessential to being understood.
Ultimately I believe that the most authentic leadership achieves a balance of both, ensuring that the necessary information is shared (transparent) while also being easy to understand (clear).
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?
Sandi> I’ve been fortunate enough to have worked with several people along my career path that I’d deem mentors. My former boss, John Greene, shaped me quite a bit as a leader in that we not only worked directly with each other for eight years, but he also dropped gems (some of which I’ve dropped above) that truly became core to my management style.
Prior to John, I bore witness to women in the industry who were, in my eyes, in such command of their roles, that I desired to be like them as I grew in my career. These women notably were Alima Wheeler and Laura Luckman Kelber. As I continue growing as a leader I do indeed believe that growth is not just vertical -- it’s lateral -- and in that way, I expand by mentoring others who I work with directly and indirectly in nurturing their leadership journeys as well.
LBB> In continually changing market circumstances, how do you cope with the responsibility of leading a team through difficult waters?
Sandi> Coping with the responsibility of leading a team through difficult waters for me involves one central rule: embrace change and inspire others to do the same. Tough times are tough. But, they are also impermanent. When we have to ride a wave of difficulty, I try my best to maintain a relaxed mind, knowing that it will pass. Doing so requires facing bouts of doubt that surely arise but then overriding those feelings with a greater sense of trust in whatever transition, or transformation, that is underway.
LBB> As a leader, what are some of the ways in which you’ve prioritised diversity and inclusion within your workforce?
Sandi> I do not see diversity and inclusion as priorities on their own as much as they are elements intrinsic to any action that I prioritise. That said, the way that I make sure that diversity and inclusion remain elemental to my leadership approach is partly in challenging myself to stay receptive.
No matter what I think I already know or understand, I actively push myself to place myself in the shoes of others, see their context, and take in the reality of the circumstances around us without projecting my own emotions and experiences onto it.
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?
Sandi> Company culture is essential to the success of our business. Company culture is the one thing that feels uniquely ours within an ultra competitive industry and hence motivates the best talent to not just come here, but stay here.
Keeping it alive amid increasingly changing working patterns has required adapting -- being flexible and open to new ideas around employee engagement and well-being, while holding true to the shared values and beliefs that makes us who we are.
Times may change, but when the core principles of the company hold true, company culture remains strong even as we evolve how we work together.
LBB> What are the most useful resources you’ve found to help you along your leadership journey?
Sandi> Meditation is an incredible tool to build self-awareness, and self-awareness strengthens intuition. I find that operating from a place of both intuition and experience is critical to leadership success.
Another useful tool is simply reading. Reading, particularly thoughtful and diverse works, broadens your knowledge base, improves critical thinking, and ultimately enhances the ability to lead effectively.
Continuous reading also exposes leaders to new ideas and perspectives, which sparks creativity and innovation. I rarely pass on a highly recommended book, no matter its genre. The more inspired I am by the thoughts and visions of others, the more I can go on to further inspire the thoughts and visions of others. Reading is such a generative leadership practice.
