How to create an entrepreneurial culture in any business

One minute briefing: Octopus Group’s CEO and co-founder Simon Rogerson on getting people comfortable with failure.

by Stephen Jones
Last Updated: 20 Jul 2020
Also in:

Large businesses will often talk about the need to be more like start-ups. 

The problem is that the core rules of being agile - moving fast to snap up new opportunities, being comfortable with making mistakes and allowing things to fail - can be at odds with the bureaucratic and risk-averse culture that’s so often found in large, listed firms. 

It is possible for big corporations to be entrepreneurial, says Octopus Group co-founder and CEO Simon Rogerson, but it’s a challenge. It requires keeping more nimble parts of the organisation at arm's length and creating a company culture that is comfortable with feedback.

It’s an approach that has seen Octopus grow from an investment start-up in the year 2000 to a group with 1,400 plus employees, spanning real estate, energy and financial services. 

Speaking at Management Today’s Leadership Lessons Live conference in June, Rogerson explained that there are several other things firms can do to create an entrepreneurial culture. 

Role model failure

The only way to get people to take risks and think differently is if you celebrate failures and the lessons you learn from them. Where many organisations go wrong is they discourage making mistakes. 

There's a great expression: perfect is the enemy of good. In many industries you’ll tend to hire people who are fairly typical. They’ve done really well in their exams at school and excellent at university; they’ve never really failed at anything. That creates the wrong mindset. If you have a mindset driven by an education system where everything is encouraged to be perfect you won’t move anywhere near quick enough. 

“One of the great signs of leadership is vulnerability, it’s being open with your colleagues and organisation both personally and in terms of corporate vulnerability: what you got wrong, why did it happen and why it’s not going to happen again.

“It’s about role modelling, it has to come from the top. I have role modelled failure well over the years. Some things have worked, some things have gone absolutely terribly but I’m okay with that because I know that I’ve pushed things pretty hard.” 

Create entrepreneurs 

Ownership has probably had the biggest impact on Octopus. We were completely founder-owned when we set up 20 years ago; now our employees own 20 per cent. It changes mindset and changes behaviour. Owners feel more accountable and they start to think long-term.

“So much entrepreneurial talent gets lost in a big organisation because people either think they need to have an idea (they don’t - it’s all about execution), or they don’t want to take the risk. You can encourage entrepreneurialism quite literally by making people entrepreneurs. 

“The best programme we have introduced at Octopus in order to encourage people to act like entrepreneurs is called Octopus Springboard. It’s designed to encourage employees who are thinking about leaving to start their own thing to do exactly that. They pitch an idea to us and we back their idea for a small equity stake. That’s the ultimate safety net, so that if - in six months, nine months, a year - their business hasn’t worked out, their role is safe for them back at Octopus. 

“I do that safe in the knowledge that these people will be so much more valuable having tried and failed then having never tried at all. It doesn’t just have benefits for the small amount of people who go through it, it changes the attitude of other employees towards risk taking. It gives them permission to think they can do it.”

Flatten decision making

“The first rule of thumb is the bigger the decision, the smaller the group that should be working on it. 

“When we’re deciding to do new things strategically, we tend to have a group of no more than three or four people involved in the decision. That doesn’t mean ideas don’t come in from the wider organisation, but the ultimate yes or no is decided by the small group. 

“Keep it small, keep it tight and encourage a culture of really candid feedback, so that when you do make mistakes and get things wrong you hear about it really quickly. That is empowering people within the organisation because it gives them a voice.” 

Image credit: Octopus Group

Stephen Jones

Stephen Jones recommends

Why Amazon banned PowerPoint

Read more

Find this article useful?

Get more great articles like this in your inbox every lunchtime

Where have all the people gone?

Why are businesses moaning there aren’t enough people to fill their vacancies? Are employers looking...

What's in store for 2022?

To help glide into 2022 more smoothly, MT asked a range of experts to share...

How to manage addiction and maintain sobriety

Struggling to cope? Try this 5-4-3-2-1 coping technique.

What's Lord Alan Sugar really like as a leader?

Lord Alan Sugar is back on our screens as the formidable boss in the latest...

How to boost staff morale

MT Asks: What is your company doing to motivate staff as another year of the...

"Learn from my mistake - don’t be reliant on one supplier'

5 Minutes With… Rosie Khandwala, ethical beauty pioneer and founder of Sugar Coated.