top of page
Jonno circle (1).png

Thank you to the 1,400 leaders who’ve generously done the 7 questions!
I hope reading

7 Questions with Matthew Singleton

helps you in your leadership.



Jonno White

7 Questions with Matthew Singleton

Name: Matthew Singleton

Current title: COO

Current organization: OLR Retail Ltd

As the COO I am accountable for governance, optimisation, culture, plans and procedures, creating and adopting a strategic approach and delivering the CEO's vision.
HR, Recruitment, Infrastructure and Legal all directly report into me, plus, I head up our Application Managed Services Business Unit which accounts for over half our revenue and headcount.

7 Questions  with Matthew Singleton


1. What have you found most challenging as a CEO or executive of a large enterprise?

Culture change.

Delivering a strategy, with a well defined plan is easy in comparison to changing the culture in a well established organisation.

Culture is intrinsic, with a formal way of measuring the success or progress, add in to that, there is a natural reluctance to any change.

2. How did you become a CEO or executive of a large enterprise? Can you please briefly tell the story?

Finding the right organisation that gave me the opportunity to demonstrate my abilities.

I have a strong (and long) background in IT and had always been very technical, which pigeon holed me to a degree in large organisations. In IT, there is a natural path to CTO, but these roles were generally being filled by Developers, which was not a role I wanted.

So I worked towards operations Management with a strong focus on strategy.

3. How do you structure your work days from waking up to going to sleep?

Lets just recognise I am not a morning person! So getting up at 6am 3x a week and going for a run is a huge accomplishment for me.

Usually, I would get a train around 7.30am to work, get home at 7.30pm, I really like to go to the gym at lunch time not just to work out but also to have a shower and reset the batteries ready for the afternoon.

When I get home, I have dinner with the family and time with my boys. I take them to football training 3 times a week.

I then usually do more work from 9.30pm for an hour or two - as I said - I am not a morning person.

4. What's the most recent significant leadership lesson you've learned?

Empathy and critical thinking are vital skills a leader needs.

Being able to truly understand what someone is experiencing and from their perspective allows you to lead instead of manage.

Critical thinking gives you the ability to see all sides of a challenge - plus, you need this to be self reflective. This does mean formulating opinions is a longer process but, in my opinion, crucial.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

"5th Generation Management" by Charles Savage. I did a Master's Degree in Leadership and Strategy 6 years ago and during my literature review I came across this book, it was published in 1996 and I was amazed at how forward thinking it was.

I have always been an advocate of highly qualified, small teams delivering work, rather than silos of skills and departments delivering work. This book is very focused on co-creation which resonated with me.

Like all good books, it's (probably) a classic!

6. How do you build leadership capacity in a large enterprise?

Clarity, focus, performance, objective, diverse, empathy, sincerity, driven, highly motivated, trustworthy, loyal etc are all springing to mind but given the size of this response box I have I am settling for 'Strategic'.

A leadership team must be able to think and act strategically. I see, too often, people who can create a plan, deliver a plan, manage a plan but are unable to be strategic.

Driving a company forward takes a strategy, delivering that strategy takes a plan.

7. What is one meaningful story that comes to mind from your time as a CEO or executive of a large enterprise so far?

Ayrton Senna once said "you can not overtake 15 cars in sunny weather.. but you can when it's raining" - this has made so much sense in the last 18 months with the pandemic.

I am not sure if that is a story but I do like it.

bottom of page