Bossing It: No Judgement, No Agenda - Just Support with Neil McKenney
Neil McKenney, chief operational officer at DOOH.com. Neil has worked with DOOH.com, out-of-home specialists, since 2014 when it was founded. As part of this role, Neil leads the day-to-day business of DOOH.com. This includes managing operations and business development in the UK, Ireland and around the world after helping to successfully establish DOOH.com as an industry leader in the UK.
LBB> What was your first experience of leadership?
Neil> Before entering the world of OOH, my first real experience with leadership came in the police force, where I worked as an operational intelligence officer. I was responsible for organising surveillance and warrants, often bringing together teams to gather intelligence, ensure safety, and execute the operation at hand. Even though I was a police constable, I often found myself leading operations, which involved briefing people with ranks above mine. It was a high-stakes environment, and I had to trust my judgement and rally others in critical moments. That experience taught me a lot about responsibility, communication, staying level-headed under pressure, and how to be a leader in general.
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?
Neil> Like many, I wanted to be a “good” leader, but I also had some specific values I wished to emulate as a mentor to others. Fairness and respect are really important to me, and I wanted to create an environment where people felt they belonged and could grow. But it’s not always easy; in any team, there will be people you just don’t naturally click with. I keep myself in check, making sure I don’t judge anyone based on a gut feeling. Everyone deserves respect and the chance to show what they’re capable of, and I work hard to ensure that’s the case in my team.
LBB> What experience or moment gave you your biggest lesson in leadership?
Neil> My most significant learning experience arrived during a challenging period, as is often the case with important lessons
I had just taken over the daily running of the company officially in January 2020, and three months later, we were facing a global pandemic. It was an uncertain and nerve-wracking time, but Andrew, our CEO at DOOH.com, and I prioritised our people. We took pay cuts ourselves before asking anyone else to, and we were completely transparent with the team about the challenges we were facing. Keeping our team together was our number one priority, and that experience grounded me and reminded me of the importance of leading by example and putting people first. I’m proud to say throughout the unprecedented times of the pandemic, we managed to keep all staff onboard.
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?
Neil> I wouldn’t say I always knew I wanted to be in a leadership role, but it’s something that unfolded as I gained experience and took on new challenges. I’ve always been a natural problem-solver – my mind gravitates toward solutions, sometimes maybe too much – and that instinct drew me toward leadership in unexpected ways.
My time in the police was a turning point. Even as a police constable, I often led high-stakes operations, and it was in those intense moments that I realised I had the ability to bring people together toward a common goal.
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?
Neil> I think it’s quite a mix. While some of it is natural, a lot of it is learned through experiences – good and bad. Some traits, like problem-solving and resilience, come naturally to me and certainly help, but real leadership takes time and experience to develop.
My journey has shown me that while certain instincts are valuable, learning how to lead effectively—especially through setbacks and challenges—is something that can and should be honed over time.
LBB> What are the aspects of leadership that you find most personally challenging? And how do you work through them?
Neil> One of the biggest challenges I face in leadership is dealing with imposter syndrome. Despite my experience, there are moments when I question if I truly know what I’m doing or if people should even be looking to me for guidance. It’s a strange feeling—knowing I’ve handled complex situations, yet sometimes doubting myself in quieter moments.
To work through this, I lean on trusted colleagues for perspective and remind myself that even seasoned leaders are always learning. That balance—acknowledging my growth while accepting there’s always more to learn—helps me stay grounded and focused on what’s best for the team.
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?
Neil> ‘Failure’ is something that means something different to everyone– some may see time spent working in a different career and then moving on to be a failure or a particular opportunity they may have missed.
Of course, I think everyone has had moments they wish they could sometimes redo something, but I wouldn’t say I’ve “failed” as much as I’ve had moments where things didn’t go as planned or where I realised I could have done better. However, these situations have been some of my greatest teachers. They’ve helped me to learn resilience and sharpen my approach to leadership.
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?
Neil> I believe in being open and transparent as a leader, but there’s definitely a balance to strike. Authenticity is important to me. I want my team to feel informed and connected, especially during tough times. But I’ve also learned that not every detail needs to be shared. My approach is to be honest and open where it truly matters while being mindful and thoughtful about what I communicate.
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?
Neil> Andrew Newman, our CEO and founder, has been a major influence, and we’ve both learned from each other over the ten years of DOOH.com.
I’ve also been fortunate to have John Davidson, from Kinetic Worldwide, as a mentor. We held similar roles in our respective companies, but his additional experience leading such a successful organisation brought invaluable insights. He’s been my sounding board over the years, providing me with perspective and encouraging me to think critically.
When it comes to mentoring others, I aim to encourage my team to lead with confidence and make their own decisions. I’m there to support them but avoid micromanaging.
LBB> In continually changing market circumstances, how do you cope with the responsibility of leading a team through difficult waters?
Neil> During tough periods, it’s crucial to keep communication open and prioritise the team’s well-being. COVID-19 was a major test, and our team’s resilience during that time really inspired me. It taught me that being present and transparent during difficult times is essential, and we came out of it stronger.
LBB> As a leader, what are some of the ways in which you’ve prioritised diversity and inclusion within your workforce?
Neil> We’re committed to creating a workplace where everyone feels they belong. Mental health, inclusivity, and support for diverse backgrounds are at the forefront of our culture.
As a gay man, my own experiences have given me a deep appreciation for the importance of acceptance and respect. This perspective has influenced my commitment to fostering an environment where everyone feels valued and supported, and I actively work to create a culture that encourages people to bring their whole selves to work.
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?
Neil> Our culture is everything to us—it’s what keeps us grounded and moving forward. For me, it’s personal. I’ve had my own struggles with mental health and know firsthand what it feels like to be in an environment where you don’t quite belong. That’s why creating a space where everyone feels truly supported and included is so important to me. As a mental health ally, I make it clear that anyone at DOOH.com can reach out if they need someone to talk to. No judgement, no agenda—just support.
We work hard to keep things real with open communication and regular check-ins. It’s not just a “nice-to-have” for morale; it’s about building a workplace where people feel valued, motivated, and like they’re part of something bigger. I want everyone on our team to know they’re seen, they’re heard, and they’re part of a community that has their back, no matter what.
LBB> What are the most useful resources you’ve found to help you along your leadership journey?
Neil> For me, it’s all about people. My team, my mentors, and the relationships I’ve built have been the best resources. I didn’t go the traditional route with formal education, so I’ve leaned on those around me to grow and learn. Learning from those around you, especially from different backgrounds, walks of life, and even industries is the best way to ensure you’re constantly learning and moving forward.
