Change management key to retail veteran’s stellar career

Retail veteran Penny Winn enjoyed a stellar career with Woolworths holding various roles across logistics, information technology and customer engagement. She was responsible for overseeing some of the most complex projects rolled out by the retail giant during her 16 years with the company.  A life-long learner, Penny took up key board positions with Port Waratah Coal Services, CSR and Caltex Australia when she left Woolworth in 2015, seeking out new challenges for the next phase of her career. 

In this week’s Success Story, Penny talks with Catherine Robson about managing people through change, what a university education really gave her and how mindfulness meditation gives her a professional edge.


A gifted student who was awarded the Zonta prize at UTS for the most outstanding female MBA graduate, Penny believes the currency of academic credentials depreciate more and more quickly in the current environment. If you focus on how you learn more than what you learn, it’s a skill that can set you up for life.

“University is a great thing to teach you how to think and how to learn. People get wedded to the technical things they learn at university and that’s not actually important. It’s the ability to be able to see a problem, pull it apart and evaluate it from lots of different ways,” says Penny.

That problem-solving ability and a trusted relationship with mentor Roger Corbett, Woolworth’s former chief executive, helped Penny pull off the sort of career growth within one organization many people jump between companies to achieve.

Handed the responsibility to oversee some of Woolworths most complex projects, including the transformation of it’s financial services and end to end supply transformation, Penny was challenged to really stretch seemingly beyond her capabilities at the time.

“It’s a zigzag route but you’ve got to think; I can actually probably do this and if someone believes I can do it, I’m going to work darn hard to make sure their trust in me is also warranted,” says Penny.

Often faced with opposition and change resistance from individual store managers, getting key players on board with new systems proved to be one of her biggest challenges. Penny persevered, honing her change management skills, something that has paid off throughout her career.

“I think one of the best things you can do when you come up against a brick wall is stop, think and evaluate who it is you’re trying to change,” she advises.

“You also need to leave your ego at the door. If you’re going to be successful in these things, it’s not about you being “Aren’t I wonderful?”…it’s actually about making that person look good, the one who wants to deliver the numbers,” says Penny.

After a stellar 30 year career in retail, Penny went on to join the board of Port Waratah Coal Services as Chair, Non-Executive Director of CSR Ltd and a Non-Executive Director of Caltex Australia Ltd.

Needing to digest a huge amount of industry knowledge to stay across industry trends in her board roles, Penny reads and networks as much as possible.

“I think building the network is really important, you learn so much from your network because you’ll hear what’s going on and about new trends.”

“The other thing is, you’ve just got too keep reading.”

“Before a board meeting, I’ll spend 5 days prepping for it but also just doing other research, so I can add value and know that I’m asking the right questions, so I am drilling down on the things I need to,” she says.

A broad depth of industry knowledge isn’t the only way Penny stays on top of her game. She turned to meditation some time ago to relieve stress, but discovered it also gives her a professional edge.

“About 7 years ago, I would wake up at 3 or 4 in the morning and I’d be worrying about this or that. I thought this is just crazy, I’m getting old before my time. I decided to change my life in some ways and I took up mindfulness meditation,” she recalls.

“Everyone else is worrying about everything, you can actually get a real business advantage by just being present in the moment. I think it’s just the best thing. And I haven’t woken up at 3 or 4 in the morning for years and years,” she says.

Listen to the full podcast to hear Penny’s insights about the importance of mentors and the career changing opportunity that took her to the UK.