Bob Keiller on Leadership, Legacy, and Tackling Big Challenges

Bob Keiller’s name is synonymous with bold leadership, value-driven business practices, and a deep commitment to community. From his instrumental role in a £236 million management buyout of PSN to his recent community-driven projects with Our Union Street, Bob’s journey reflects a leader who embraces challenges with resilience and purpose. In this article, we explore how Bob has applied his unique mindset to entrepreneurship, mergers, and navigating difficult situations while giving back to the community.

Taking Bold Steps in Entrepreneurship

Bob’s career is a testament to making tough decisions when the stakes are high. One of his most significant achievements was leading the management buyout of PSN, but as Bob explains, entrepreneurial success is never guaranteed. Faced with uncertainty, Bob’s driving force wasn’t the certainty of success but avoiding future regret for not taking the leap. He accepted the risks, knowing failure was possible but resolvable. It’s this willingness to tackle uncertainty head-on that distinguishes Bob’s leadership style.

In guiding future entrepreneurs, Bob avoids prescribing one-size-fits-all advice. “Every situation is unique,” he states, adding that resilience and accepting risk are essential when making high-stakes decisions.

Navigating Uncertainty: Leadership in Crisis

Leading through uncertainty has defined much of Bob’s career, notably during the 2008 financial crisis. At the time, Bob was managing investor expectations and had borrowed $100 million for acquisitions, just as the bank withdrew its facility. In response, Bob had to adapt rapidly. He and his team moved from quarterly to weekly forecasting, focused on cutting unnecessary costs, and ramped up business development efforts. Crucially, Bob ensured that his staff was involved in every step of the decision-making process, fostering a sense of trust and shared direction.

This period of financial crisis tested Bob’s resilience and highlighted the importance of transparency and flexibility in leadership. His ability to shift gears, execute Plan D when Plans A, B & C were no longer viable – when others would have panicked, and keep his team on board was key to weathering the storm.

Ensuring Successful Mergers Through Cultural Fit

One of Bob’s most valuable lessons from his time leading PSN and Wood Group is the importance of cultural alignment in mergers and acquisitions. Bob and his team were highly selective, rejecting 95% of potential acquisition targets. The reasoning was simple: even if a company had stellar financials, if its culture didn’t align with values, it would not have worked. As Bob explains, “Over 80% of M&A deals fail, often because cultural alignment is overlooked.”

For Bob, ensuring that teams share the same fundamental values creates a foundation for success. Whether it’s integrity, safety, or teamwork, these values drive decision-making and allow companies to grow without losing sight of their mission.

Scaling PSN with Core Values

Bob’s leadership philosophy was central to PSN’s growth from a small business into a global enterprise. Core values were not just posted on the wall but lived through every decision made at PSN. “Having deeply held core values is a huge asset for growth,” Bob explains. By ensuring that everyone in the organisation understood and embraced these values, the company was able to make decisions with integrity, safety, and transparency.

Bob emphasises that when you value integrity, dishonesty cannot be tolerated. When you value safety, cutting corners is non-negotiable. These principles not only safeguarded the company’s growth but also created a unified team, aligned in purpose.

Turning Setbacks into Learning Experiences

Leadership is about learning from failure, and Bob is no stranger to setbacks. One difficult moment occurred during the merger of PSN with Wood Group, where delays in implementing safety standards had a tragic outcome. This experience left a lasting impact on Bob, who reflects on the importance of decisiveness in leadership. “Had I been more decisive, a life might have been saved,” he admits. It’s a sobering reminder that while leaders can’t predict everything, they must always prioritise the bigger picture.

For Bob, every setback is an opportunity to reflect, learn, and improve. This focus on continuous improvement is a hallmark of his leadership approach.

Mentorship and Empowering the Next Generation

Throughout his career, Bob has been a strong advocate for mentorship. He believes that leadership is a journey, and part of that journey is bringing people along with you. Bob mentors young entrepreneurs and shares key lessons on resilience, authenticity, and communication. As he puts it, “If no one is following you, you’re not leading.”

Empathy, people skills, and a focus on communication are crucial qualities in leadership, according to Bob. These traits allow leaders to connect with their teams and build a shared sense of purpose.

Redefining Success Beyond Profits

Today, Bob defines success not by profits or corporate accolades but by the success of others. Much of his time is now spent working with charities, social enterprises, and young entrepreneurs who lack the resources for professional consultants. His work is offered for free, with the expectation that those he helps will, in turn, help others. It’s a ripple effect of positive impact, rooted in the idea that success should be shared and multiplied.

Building Meaningful Relationships

With a network of over 150,000 LinkedIn followers, Bob understands the importance of meaningful relationships. He advises others to focus on trust and reciprocity. “People are more likely to support you if they know you, trust you, and believe you’d do the same for them,” he explains. Building a strong network takes time, but the relationships Bob has built throughout his career continue to be a source of support and opportunity.

Revitalising Union Street: Combining Business and Social Impact

Bob’s recent work with the Our Union Street campaign demonstrates his commitment to community revitalisation. Bob partnered with Derrick Thomson to take on this ambitious project with no funding, authority, or expertise. Despite initial scepticism and criticism, Bob and his team have pushed forward, embodying his belief that “If not us, who? If not now, when?”

This project reflects Bob’s broader belief that business success and social impact are not mutually exclusive. Leaders have a responsibility to give back, and Bob uses his skills and experience to make meaningful contributions to his community.

Looking to the Future: AI and Innovation

Bob remains passionate about the future of artificial intelligence and its potential to transform decision-making processes. He envisions a future where real and artificial intelligence are combined to create powerful solutions. His curiosity about the possibilities of AI underscores his forward-thinking approach, always looking for ways to innovate and improve.

A Legacy of Leadership and Impact

Bob Keiller’s journey is one of resilience, values-driven leadership, and a commitment to giving back. Whether through his corporate successes with PSN and Wood Group or his community-focused initiatives, Bob continues to inspire the next generation of leaders. His approach to leadership is clear: embrace challenges, lead with integrity, and always find ways to make a positive impact on the world around you.

To learn more about Bob’s work and community projects, take a look at the stories he shares on LinkedIn.