The Many Balancing Acts of Leadership with Karan Singh

As general manager of Vistar Media UK, Karan Singh leads the company’s efforts to connect advertisers and media owners to the world’s largest global OOH marketplace. Under his leadership, Vistar provides innovative, data-driven solutions that help brands capture consumer attention with precision and scale.

With over a decade of experience in data consultancy, retail media, and ad tech, Karan has held pivotal roles driving growth and fostering strategic partnerships, most recently leading international advertiser partnerships at Microsoft.

Beyond his professional accomplishments, Karan is passionate about fostering diversity and inclusion in the media industry. Since August 2020, he has served as a mentor at Media for All, supporting the development of Black, Asian, and other ethnic talent within the sector.

He sat down with LBB to reflect on early lessons of leadership as cricket captain for his university, building his own leadership style, and the transition to a management role…

LBB> What was your first experience of leadership?

Karan> My first experience of leadership was when I was at university.

We had a University of London union cricket team made up of the best players across all the different colleges. In my second year, I was made captain of that team.

I thought it would be an easy transition since I was a senior player, but it was actually a real wake-up call. It exposed all my flaws and taught me that treating everyone the same way – the way I would want to be treated – doesn't work.

People responded very differently, sometimes adversely, to that approach. It was my biggest schooling in leadership at that early age.

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?

Karan> I learned from experience and from watching others. I took inspiration from people who had either managed me or others that I'd watched closely, taking the good from those I admired. But probably more importantly, I had witnessed bad practice and saw some not-great leaders in the market.

I learned a lot from them in terms of how not to do things, how not to come across, how not to manage people, and how not to show empathy.

This made it quite black and white for me in terms of building my own leadership style, taking the good from others, and avoiding the bad, bringing that into my own approach.

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

Karan> COVID was probably my biggest wake-up call in leadership. It was a shock to the system – learning how to manage a team remotely, keep people engaged through something unprecedented, and manage uncertainty from both macroeconomic and personal perspectives.

The challenge was keeping people on mission and engaged while balancing business needs with personal needs.

It taught me how to be responsive and flexible while maintaining the human element in management. You can go down the rabbit hole of focusing everything on work and business, but there's a balance to be had.

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?

Karan> I don't think there was any one point where I decided I wanted to be a leader. Naturally, my personality has lent itself to the perception that I would be a good one. If you look at how you are within friendship groups, it's often obvious who takes others on the journey they're going on, and I think I was always that person.

But that doesn't necessarily translate into being a good leader – that's a learned process. You can have leaders who aren't officially leaders, leading from a peer level, but it's a big transition when you have to step back and lead from a different level.

That was definitely something I had to learn through experience and not getting it right 100% of the time.

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?

Karan> I think people typically have a natural disposition to enjoy being a leader or not. But actually, a lot of it can be taught.

You can teach someone, even those more reluctant, the skills to be a good leader. The Holy Grail is when you have someone who aspires to be a leader, has that natural disposition to lead, and wants to lead, and then they learn the skills.

So it's got to be both to a degree. You can teach most people, but the best ones are those who enjoy it as much as they're willing to work on it.

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

Karan> I'm a sales guy at heart, and sometimes the most challenging aspect is stepping away and letting other people grow and flourish.

Leadership isn't about jumping in and taking the reins. It might not be delivered as quickly as I'd expect, it might not be as polished as I would do it, and it might be in a different style.

The bit I find quite challenging is relinquishing that control and taking one step back to let people thrive. It's a delicate balance because sometimes it can feel like you're being standoffish or not involved, but actually, if I'm involved in anything, I like to take control over it, which can sometimes be detrimental to the team.

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?

Karan> While my natural disposition is to be open and shoot from the hip sometimes, I've learned there's value in being careful and considered. I learned this from a particular leader – that sometimes you need to manage a process or situation by drip-feeding things, taking people on a journey, being thoughtful about how you position and frame things.

Rather than radical transparency, where you can be very direct and to the point, you might lose the context around a decision or the reasoning, and you can't take people on that journey.

They might just have a bad reaction to it.

LBB> As you developed your leadership skills, did you have a mentor? If so, who 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?

Karan> I haven't had an official mentor, but I've always looked up to certain people within the industry.

Danny Clayman at Microsoft, a previous manager of mine, is someone I'll speak to about certain decisions in my career because he's been there and thinks about things differently than me in a way that gives me perspective. It's really important to have someone who can share a different point of view so you can think about things from almost a 3D lens and then make a holistic decision.

I do a lot of mentoring for a media organisation for diverse talent within the industry - future leaders of the business. For me, it's about sharing perspectives and experiences I've had, but ultimately letting people come to their own conclusions.

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

Karan> One of the most critical aspects of diversity and inclusion is ensuring that we make our interview process inclusive. While we always go for the best talent for the job, I try to ensure that when we're dealing with recruiters, whether internal or external, we have the most diverse view of talent possible in the process – otherwise, we reject it.

We've even had recruiters rewrite job descriptions because we found that certain language used by sales directors tended to get more male applicants. When we changed the wording, we saw a better balance. Those are some of the practical steps we've taken to adjust that balance.

LBB> How important is your company culture to the success of your business? And how have you managed to keep it alive with the rise of remote and hybrid working patterns?

Karan> Culture is everything. It's really important that you enjoy being at work. I find that if you enjoy something, you're better at it. Enjoying the people you're around and being allowed to be yourself is something I always try to foster.

Culture is determined by the people in it. When we're hiring, we're very purposeful about hiring people who are slightly different or bring something different to the table, but can work collaboratively to foster that culture. If you have a bad apple, it often spoils the culture. It's super important because it means people show up way more than we prescribe them to – if they enjoy being there.

We've become a destination where people want to come and work, and subsequently, we get more inbound enquiries about people wanting to work at our business. That's entirely down to the people we've hired and who run the business.