In our ongoing “Leaders Fail Too” series, we sit down with leaders who’ve learned that failure isn’t the opposite of success, it’s often the pathway to it. This week, we’re talking to someone very close to home: Paul Dutnall, COO of Work.Life, about his most transformative “failing forward” moment and how it completely revolutionised the way he thinks about leadership.
Paul’s story will resonate with anyone who’s ever felt the weight of responsibility on their shoulders, convinced that they need to have all the answers. Spoiler alert: they don’t, and neither do you.
“I’ve taken it on myself thinking I need to figure out how to do everything, I need to know everything, it’s on me to find a solution,” Paul reflects, describing a mindset that will be painfully familiar to many leaders, especially those building companies from the ground up.
As COO of Work.Life, Paul found himself caught in the classic leadership trap: believing that being a good leader meant being the person with all the answers, the one who could solve every problem, master every skill, and handle every challenge that came his way. It’s a natural instinct, especially for driven, capable people who’ve succeeded by taking ownership and getting things done.
The challenge? This well-intentioned approach was actually limiting Work.Life’s potential rather than unlocking it.
“There are a lot of things I could be calling on to reflect on, and more to come,” Paul admits with the kind of honest self-awareness that comes from experience. This isn’t a leader who’s figured it all out, it’s someone who’s learned that admitting you haven’t figured it all out is actually the beginning of real leadership growth.
Paul’s transformation didn’t happen overnight. Like most meaningful change, it came through the gradual realisation that his approach, while coming from a good place, wasn’t serving the company’s best interests. The very dedication that drove him to take on everything was actually holding back the team’s potential.
“One thing I’ve learned as a leader is not how but who,” Paul explains, describing a fundamental shift in perspective that revolutionised his approach. “Finding amazing people who are far better than me at the things we need to accomplish and problems we may need to solve and find, inspire and enable those people to do well.”
This shift from “how” to “who” represents more than just a change in strategy, it’s a complete reimagining of what leadership actually means. Instead of being the person with all the answers, Paul learned to become the person who finds the people with the answers. Instead of trying to be the best at everything, he focused on being the best at identifying, attracting, and empowering people who excel in their specific areas.
Paul’s experience highlights a common leadership challenge: the belief that good leaders need to handle everything personally. This mindset is particularly prevalent in startup environments where resources are limited, stakes are high, and there’s often a culture of ownership that can inadvertently become a culture of over-ownership.
The limitations of this approach become clear when you consider the bigger picture:
Capacity constraints: Even the most capable leader has finite time and energy. When everything flows through one person, growth becomes limited by that person’s bandwidth rather than the team’s collective potential.
Underutilised talent: When leaders handle everything themselves, they inadvertently prevent team members from developing their skills and contributing at their highest level. Amazing people want to do amazing work, not just execute someone else’s decisions.
Missed perspectives: Different challenges benefit from different expertise and viewpoints. When one person tries to solve everything, the organisation misses out on the diverse insights that come from empowered, engaged team members.
Strategic distraction: Leaders buried in operational details can’t focus on the high-level strategic thinking, relationship building, and vision setting that actually drives long-term success.
Reduced innovation: Teams that aren’t empowered to solve problems and make decisions become less creative and proactive. The innovative solutions that come from engaged, autonomous teams get lost when everything requires approval from the top.
Paul’s shift from trying to do everything to focusing on empowering others “transformed the way I think about leading our business.” This transformation didn’t just change his daily experience as a leader, it fundamentally changed how Work.Life operates and grows.
Building sustainable systems: By stepping back from handling everything personally, Paul was able to focus on building systems, processes, and team structures that could scale effectively. Instead of being the system himself, he could build actual systems that would support sustainable growth.
Unlocking team potential: When Paul stopped trying to be the expert on everything, his team members had space to become experts in their areas. This didn’t just improve outcomes, it improved job satisfaction and engagement across the organisation.
Creating scalable leadership: By focusing on “who” rather than “how,” Paul was building a leadership approach that could grow with the company. Instead of being the bottleneck, he became the person who identifies and removes bottlenecks by ensuring the right people are in the right roles.
Improving decision quality: Decisions made by people with deep expertise in specific areas are generally better than decisions made by well-intentioned generalists trying to cover everything. Paul’s new approach improved the quality of decisions across the business.
Accelerating growth: With the right people empowered to excel in their areas, Work.Life could move faster and more effectively than when everything required Paul’s direct involvement.
Paul’s experience offers valuable insights for leaders at every stage of their journey, whether they’re running startups, managing teams in larger organisations, or anywhere in between.
Recognise the pattern: The feeling that everything depends on you, that you need to have all the answers, that stepping back means letting people down, these are common leadership challenges, not personal failings. If you’re feeling stretched across too many areas, it might be time to reconsider your approach.
Redefine leadership strength: Real leadership strength isn’t about being able to do everything yourself, it’s about being able to build teams that can accomplish more together than any individual could alone. The strongest leaders are often those who are most comfortable acknowledging what they don’t know and finding people who do.
Invest in people development: Paul’s transformation required him to “find, inspire and enable” amazing people. This isn’t just about hiring, it’s about creating environments where talented people can thrive, feel empowered, and contribute at their highest level.
Focus on systems and culture: Instead of being the system yourself, focus on building systems and culture that enable teams to operate effectively with appropriate autonomy. This includes processes, communication structures, decision-making frameworks, and cultural norms that support independent excellence.
Practice strategic letting go: For many leaders, the challenge isn’t knowing they should delegate, it’s actually doing it effectively. Start with areas where team members have clear expertise, build trust gradually, and resist the urge to micromanage when approaches differ from your own.
Paul’s honesty about having “more to come” in terms of learning and growth reflects an important truth about leadership: it’s an ongoing journey of development, not a destination you reach. The best leaders aren’t those who’ve figured everything out, they’re those who’ve learned to navigate uncertainty, adapt to new challenges, and continue growing alongside their teams.
His experience at Work.Life demonstrates that some of the most important leadership lessons come not from dramatic failures, but from the gradual realisation that our well-intentioned approaches might not be serving our teams and organisations as well as we’d hoped. These moments of insight, while sometimes uncomfortable, are where real leadership growth happens.
Paul’s story also highlights the importance of environments that support leadership development and learning from experience. At Work.Life, the culture that allowed Paul to recognise the limitations of his approach, experiment with new methods, and build better systems is the same culture that supports all team members in their growth and development.
This is particularly relevant for the entrepreneurs, startups, and growing businesses that make up Work.Life’s community. These environments provide not just physical workspace, but communities where leaders can learn from each other’s experiences, share challenges and solutions, and support each other through the inevitable evolution that comes with building successful businesses.
The flexible workspace model itself reflects many of the lessons Paul learned about leadership: instead of trying to control every detail, create frameworks that enable success and then trust people to make the most of them. Instead of being everything to everyone, focus on creating environments where different people and businesses can thrive in their own ways.
Paul Dutnall’s journey from trying to handle everything to focusing on empowering others offers a masterclass in leadership evolution. His willingness to share both his learning process and the insights gained demonstrates the kind of authentic, growth-minded leadership that builds strong teams and sustainable businesses.
The next time you find yourself thinking you need to figure out how to do everything, remember Paul’s insight: it’s not about how, it’s about who. The most effective leaders aren’t those who can do everything themselves, they’re those who can build environments where everyone can contribute their best work.
Watch Paul’s Leaders Fail Too… here!
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