Bossing It: Why Personality Is a Big Part of Leadership with Jonathan Harris

Co-founder and executive creative director of Wild Gravity, Jonathan applies his expertise in creative problem solving to help clients clarify their vision and message by establishing a trusted creative partnership and producing world-class deliverables.

Prior to starting Wild Gravity, he earned over ten years of agency creative experience and an additional five at Microsoft marketing some of the world’s largest brands. His time spent client-side helped develop and hone a powerful skillset that he’s proud to translate into Wild Gravity’s success.

LBB> What was your first experience of leadership?

Jonathan>  At the beginning of my career I worked at a boutique agency in Seattle. I was the sixth employee and the two guys who founded the agency were landing big business, and talking to big clients. Marketing Directors, CMOs, people like that. But they were also in the trenches with me, the junior new guy. When I pulled in in the morning, they were already there. We concepted together. They listened to my ideas. Treated me like an equal when they had so much more experience and talent than I did at that point. They didn’t bring any ego into the workplace and they became successful by grinding it out. I took a lot away from the way those guys led their shop and the way they treated their people.

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?

Jonathan> When I worked for those guys I wanted to always do my best and go the extra mile for them because of how they led. At each place I worked I picked up management styles I liked and noticed ones I wanted to be sure to avoid. 

Jon Sneider and I founded Wild Gravity over six years ago and we have a printed list of values that help guide our small shop. The very first one is, “Do The Right Thing.” We often say, you’re never wrong when you do the right thing, which sounds corny but it’s proved to be a really valuable guiding principle for me in forming my leadership style. 

I strive to lead by example. I like to be the first one here and the last one to leave. I like to empower my employees, but I’m deeply involved in every project. I care. I care about the work and I care about every one of my employees. We take care of them because we genuinely care about them. 

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

Jonathan> I watched a past manager fight hard for an idea of mine when the strategy was challenged in a large cross-organizational meeting. That really stuck with me. I’ve always loved my managers that had my back no matter what. That’s when I’ve been inspired to do my best work. It made me look forward to the day I could do the same for my employees. 

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?

Jonathan> I mean, this was always the dream. I think any entrepreneur has that internal voice of, when I get my chance this is how I want to lead. Then when you finally make it, it can be quite overwhelming. 

I had to take a step back and remind myself not to be carried away by the urgency of the day or by the emotions that I might be feeling about a larger issue, and to focus on the leader I wanted to be in the moment to the employee that was in front of me at any given time.   

I never really had the opportunity to flex that muscle until we launched Wild Gravity and I learned that like any muscle it’s one that has be built up. 

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?

Jonathan> When you’re coming up you think it’s all going to be natural, that you’ll just be cool. But when you’re the leader you realize the real skill is being cool when things are not cool. That’s something you need to learn. 

You can’t be freaking out on the outside worried about making payroll while you’re giving direction on a project or your employees going to be looking for a job rather than working on the project, for example.  

In past jobs one of the things that I saw my bosses do that I admired and what I try to do is lead by example. Be here first. Be involved in every process. Bring great energy. You have to be willing to lead, and that means willing to work…and doing it all while you might be nervous that the lease on your building is falling through. 

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

Jonathan> Time management is tough. Wild Gravity is a small shop, Jon and I are the heads of the business and we’re very close to the work. We manage people, but we also do a lot of the work ourselves. So on top of all the business administration stuff we have to do such as business development, employee reviews, company culture, staff meetings, finances, we’re writing, directing, producing every day. That’s a lot of spinning plates so when you have an employee demanding your help and you’re neck-deep writing a script, that’s hard. 

But we’re growing fast so we’re able to do more leading the work than doing the work, which feels great. 

 It also helps to have a wildly talented team to rely on when you reach capacity. 

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?

Jonathan> We have a lot of little sayings here and another one of them is, the difference between success and failure is picking yourself up off the matt that one extra time. A failure is only a true failure if you fail to learn from it. 

We’re constantly challenging processes in search of new efficiencies, new ways to the best finish. So it’s inevitable that we fail, but if you can keep the failures small and grow from them you can mitigate the risk while improving your process.

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?

Jonathan> At Wild Gravity, we’re as transparent as we can be. Part of the job as leader is to create an environment for our team to be successful and that means being open and honest with our team. But as I alluded to earlier there is certain information that shouldn’t be shared with employees as it would be detrimental to the employees, the business, or both. 

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?

Jonathan> At Wild Gravity we like to say we’re happy to share our secret sauce because it’s experience. In my experience I never had a truly great mentor so it’s been great to work with Wild Gravity President, Jon Sneider. He’s been the closest thing I’ve ever had to a mentor. He’s taught me everything I know about business, and in many ways has turned me into the leader I am today. 

As for mentoring aspiring leaders, for me it comes back to leading by example. It’s been a true pleasure to watch some key people at Wild Gravity grow as leaders, take the reins and really rise up to any challenge. 

LBB> It's been a really challenging few years - and that's an understatement. How do you lead a team out the other side of a difficult period?

Jonathan> It feels like business is finally getting back to normal but It’s been the toughest we’ve ever experienced. Covid was only a blip compared to the tech-sector cutting spending and laying off tens of thousands of workers, some of which were our main points of contact. As a small business focused on the tech sector it could have been deadly.  

To lead the team out the other side is really to lead side by side with them. You grind. You pound the phones, so to speak. You focus almost all your energy on biz-dev. Jon and I were just biz-devving almost fulltime. Finding projects to fill the gaps and doing everything we could to make payroll every two weeks. We had to cut a lot of costs, say goodbye to a few people, all while trying to stay cool for the team. 

LBB> What are some ambitions and plans you have for the company and yourself in the coming year? 

Jonathan> Last quarter and this quarter, we’ve seen some incredible growth. It feels like business is finally back to normal. We see this next year being a growth year for us as we’ve established some significant new lines of business and our pipeline is looking strong. 

The next year is all about taking advantage of all the streamlining we’ve done over the last 18 months and applying our learnings to the future of the business. 

Personally, I plan to empower our top employees to become stronger leaders and offer them more opportunities for project ownership.

LBB> What have you noticed as the biggest changes in the industry during your career thus far? And do you have any predictions for future trends or themes? 

Jonathan> Remote work was/is a big one. We support the concept in general but when our client teams stopped going to the office they also stopped talking (about us, about projects, about opportunities to collaborate). We saw a sharp decrease in project volume across the board. As soon as the call-back to the offices happened, that same week we had emails coming in, even the phone rang with projects. It was wild. Sometimes the water-cooler chat really does matter. Based off that, and the continued investments in Tech real estate (in our area at least) I predict the trend to continue this way. Expect in-office presence to increase. 

LBB> How important is your company culture to the success of your business?

Jonathan> Company culture is huge. When you first start a business you’re not thinking about that. You’re thinking about landing clients and keeping the lights on. Then you start to grow, and maybe the vibe starts to change. If the vibe goes south, everything suffers. We want our team happy, engaged, and excited to make beautiful videos. Culture is something we keep a close eye on, and I think we’re in a good groove in that regard. 

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

Jonathan> Nothing is more important than collaborating with your team. Our brainstorm sessions, our status meetings, our post-mortems, they’re all priceless opportunities to grow as a leader. Listen to your team. Be open to new ideas. Challenge the norm. Break the process. That’s what Wild Gravity was founded on.