Bossing It: Understanding What Makes People Tick with Oli Roberts

Oli is the owner & founder of Oskar illustration, a top 20 UK based illustration & animation agency based in the UK; he has completed work for brands such as Nike, Adidas, Apple, BBC, Wired, Uniqlo & Ikea. Oli has taken what he has learned from his time spent in event production and advertising to form his own leadership style.

LBB> What was your first experience of leadership?

Oli> My first real job after university was building and running experiential marketing stands up and down the country, at music festivals or in shopping malls. Something unexpected would always go wrong. From being stormed by angry English football fans in Sheffield after we got ejected from the World Cup, to a generator getting stuck against the back doors of the back of a Luton van 30 minutes before the client was due to arrive. People always looked to me to deal with the hitches. That included getting Leeds fire brigade to cut the back door open to free the generator and giving them 400 yoghurts for their trouble.

 

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?

Oli> I never really wanted to be a leader. I was more comfortable being hands on and sorting out my own challenges. Leadership found me as I climbed (without wanting to) the career ladder when I worked in ad land. When it became part of my role to lead, I chose to lead by example. Treat people with respect, work hard, ask for help and offer support when needed. Building trust for me is key. You need people around you who have your back. And you theirs.

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?

Oli> Leadership was not something I chased, but I realised I had it in me when colleagues started coming to me more and more for guidance.

 

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?

Oli> A bit of both. I suppose Elon Musk is a leader of sorts but I certainly wouldn’t follow him into battle. You need to understand what makes people tick and have empathy. Take the time to find out how they like to work, what keeps them motivated and what gives them a headache. Agree on common goals. Then share responsibility to let them make it happen. And build a culture of learning from failure. I’ll only cut ties with someone if they lose my trust.

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

Oli> Giving feedback on something that didn’t go well is always the hardest. I try to find out if there is anything outside of work or personal circumstances that might have hindered their performance. And I try to listen. Let it come from them. Then we both agree on how we can overcome blockers that got in the way and build a better framework for the next time. Essentially both signing up to a better way forward.

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?

Oli> Yep. Feeling the weight of responsibility for other people’s well-being as well as their performance can be crushing. Asking for help always…helps. Also asking for feedback on your own mentoring or leadership style.

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?

Oli> Both. Depends on the situation and individual. I can’t really do anything but be authentic. This is generally a good thing I think but sometimes one might meet need to dial down the glaring truth and reframe it to get a better response.

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?

Oli> I’ve never really been taught any leadership skills. When I worked at Grey London, Clive Woodward came in to talk about performance and leadership which I found inspiring. His ‘bottom up’ leadership strategy really stuck with me. Identify the problem or challenge as a team. Discuss and then agree how to overcome it. Then everyone can hold each other accountable to achieve that common goal.

 

LBB> In continually changing market circumstances, how do you cope with the responsibility of leading a team through difficult waters?

Oli> Business is all about people. If they are unhappy, unwell or disillusioned, the work will suffer. Nothing is more important than someone’s health & wellbeing so it’s about creating an environment where your door is always open and people feel comfortable to speak to you. And you have to feel confident to help or point the person in the right direction to someone who can.

 

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

Oli> We regularly talk to our artists and agency team about doing self-initiated projects that can make a difference or drive awareness of a particular issue. Again, asking the questions and then listening is key. Then action.

 

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?

Oli> Alongside the uniqueness of our work, it’s the most important thing. Oskar is a family to us. We try and meet our artists in person when possible. Difficult when they’re all dotted around the globe. But we try! And we have monthly online team drop in’s, a team WhatsApp group and regular 1:1’s to help foster connectivity. Sometimes a good ol’ phone call is all that’s needed.

 

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

Oli> Human beings. Talking to other folk in leadership roles. Asking and listening to what works for them. Following top tips on a website doesn’t work for me. Some podcasts are good though like Uncensored CMO. Rory Stewart’s words and demeanour also inspire me.