James Bailey was the Managing Director of Waitrose & Partners, leading one of the UK’s most iconic premium supermarkets through significant transformation. With responsibility for £8bn in turnover across 300+ stores and 50,000 Partners, James brings deep expertise in navigating complex operational challenges. His career spans advisory work with private equity and investors, alongside support for emerging businesses. 

In this candid conversation with Melissa Reed, James explores what drives effective leadership in complex organisations, from setting clear direction and enabling great teams to constructively challenging the status quo. He discusses how the best leaders combine intellectual rigour with curiosity, the importance of cutting through organisational complexity, and why low ego is essential to building high-performing teams.

What does good leadership mean to you?

Setting a clear and simple direction, setting up crystal clear accountabilities and enabling great people to deliver it. A cliche I know but you’re not meant to have all the answers, just to keep asking the right questions. And wherever possible, always take the blame, never the credit.

What is the most important thing you have learnt in your career so far?

That businesses, big organisations in general, are nothing like the super-effective well well-oiled machines everyone assumes they are. They tend to be a permanent work in progress, ever-changing in an effort to improve or simply keep up. Once you realise that it gives you confidence to challenge the status quo, and if you can do it constructively, you’ll almost always find leaders willing to listen.

How did you get to where you are today? Did you take a strategic, planned approach to your career, or has it been more opportunistic?

Definitely opportunistic. I’ve never taken my career seriously enough to make a grand plan, and eventually you realise there’s so much you can’t plan for anyway. I always advise people to do two things: firstly, choose jobs you think you’ll enjoy, because you’ll always excel; and secondly, trust your instincts when making a choice. Your heart is usually right, but your head will try to take over and convince you to take that promotion in audit that you think would look better on your CV.

What changes to your industry do you anticipate over the next two years and are you excited by this?

Grocery is an exceptionally competitive and intense industry, which drives amazing benefits for customers, and that’s not going to change. But it tends to operate on long time scales – trends, cost pressures building up, technology etc. – so there aren’t many big surprises. Over the next couple of years, I anticipate seeing some notable examples of AI implementation in operations, although I also expect macroeconomic and political factors to continue creating short-term challenges.

What type of people do you like to work with and what makes them good leaders?

I try to bring together leaders who are smart, curious and have low egos. Smart isn’t necessarily about exams or qualifications; a lot of the most intelligent people I know learned it on the job. Curiosity drives improvement and bravery, that constant belief that it could be done better and you can’t stand still. And low ego, because great teams are all focused on the same prizes. There can be plenty of competitive energy, but if it’s coming from a place of personal ambition above all else, then it’s poisonous.

What fascinates you about your job?

I’m always fascinated by how complicated most businesses make things and how to cut through that complexity. There’s a constant flow of day-to-day challenges that are hard to predict, so organisations need to be resilient and flexible, and staying ahead of that is endlessly fascinating 

As a leader, what skills do you continuously work on to keep you at the top of your game?

Your people skills always need attention; e.g. improving your listening skills, managing important stakeholders or being smart about your impact. On top of that, there are always new developments you can choose to learn more about, like applicable AI or employment law developments, if you’ve got the time and curiosity.

What keeps you awake at night?

Not much, but if anything, the state of politics and the need for something to give. I feel optimistic about the UK, but there are risks and pitfalls and no guarantees.

What is the best way to switch off in your free time?

Families have a habit of forcing you to switch off! But failing that, I always find it’s something you can get lost in, whether it’s running, a good book or a round of golf.

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