BLOG: 5 Big Questions

Into 2022 and beyond, we’re asking 5 Big Questions

always possible CEO, Richard Freeman, sets out the focus of our work for the foreseeable future

It may be cliché, but its true – the 2020/21 pandemic has brought many structural problems into sharp relief. And if nothing else, it has forced people to prioritise.

I’ll put my hand up and say that one thing I’d been sometimes forgetting to do was to be clear about what problems I was trying to solve. Our work is broad and wide – troubleshooting with a national charity one day, a tech-led architect the next, a government agency the next, a school the day after. And the methods and threads between our work is clearer than ever. But, if you boil it all down, we need to be clear about the questions we’re trying to answer.


  1. How do we properly measure change and impact?
  2. How are growing enterprises preparing for the future?
  3. What sort of workforce will we need for whatever comes next? 
  4. How is creativity helping to solve problems?
  5. What does better collaboration look like?


I think I’ve arrived at 5 big questions. That encapsulate where the company is at, the team, me, our clients. These questions might/will change in the future. They might evolve into better questions soon, but fundamentally, this is what I want to know. I’ll expand my thinking a little.


1: How do we properly measure change and impact?

In the 21st century, it’s easy to drive change. It’s the only constant. Every politician promises it. Every citizen asks for it. Every entrepreneur is selling it.

But how do we know that the decisions we make and the actions we take lead to genuine progress?

My team has some brilliant researchers and evaluators – honing tools that create insights out of data, stories and observations. Our new research team, led by Vicky Tremain, gets under the skin of what is being measured, why, how, for whom. But, most of the time we shouldn’t be needed. There is no organisation that wouldn’t be more successful with some in-house ongoing evaluation.

It’s a scarcely taught skill, and unless a business or charity has found a diamond researcher and data-head to join the staff team it will almost certainly be a hole in the business.

Good evaluation processes means time saved. More money. Better results. Happier service users. Higher profile. Stats to shout about. And, more crucially, a culture of learning and improvement that just means you’ll be around when others fall away.

If you know what impact you’re having, you can have more of it. So why don’t we learn how to measure it better?


2: How are growing enterprises preparing for the future?

I don’t like the naff, zeitgeisty, Nathan Barley-esque phrase: ‘future-proofing’. We don’t want to protect ourselves from the future; we want to charge in head-on! But I get it. And I use it. The will to charge-in headfirst to a new idea is nearly always undermined by the shock of the risk when the future charges back.

And the pushes and pulls on any growing organisation in 2021 are profound.

In the past week, people have told me – and the new always possible Business Support team lead Sam Hawkins – about their challenges with recruitment, digital transformation, sustainability, feeling invisible, governance, purpose, scaling, being heard, whether to get an office pet etc

Office? What’s an office?

The struggle is very real.

But for most, it genuinely is. Although we have a growing entrepreneurial culture in the UK – we also have infinitely more things to derail anyone willing to stick their neck out.

We’ve delivered a constant range of bootcamps, mentoring, workshops, troubleshooting sessions and research projects over the last 2 years. And picked the brains of people in every sector, working out which to foot to pit in front of the other, in The Possibility Club podcast.

But we want to scale it up. There are too many good people with good ideas, providing employment and social value, that get lost in the slipstream.

We’ll be sharing more of the honest learning, not just the encouraging platitudes. And something for everyone, wherever you are on your business journey.

I’ve just joined a new peer group of CEOs and MDs, and that will be a new game-changer, once we remember how to be vulnerable with each other.


3: What sort of workforce will we need for whatever comes next? 

Gavin Williamson wrote an article earlier this year, saying that the purpose of education was purely to prepare people for work. You’ll know I’m not making a political point to suggest that the honourable gentleman added about as much value to his brief as a set of broken nail clippers. Nadhim Zahawi, the new Education Sec, has a bar set so low, that by saying nothing at all since the reshuffle he has already achieved more than our Gavin.

Education should prepare you for work, but not only. And what the future workforce needs is not simply to be prepared for employment.

There is a terrible synonym between ‘preparation for work’ and ‘preparation to be quiet and do as you’re told each day until the ordeal is over’. That is sooo 2019.

What about a workforce that has coding, care and communication skills in equal measure? Teams built on diverse thought, shared energy and channels for your good ideas regardless of your job title.

What if haulage drivers, elder care workers and quantity surveyors all had autonomy, mastery and purpose in their work? Maybe we wouldn’t be in the mess we’re in?

If we talked about careers instead of jobs, recognising that your typical Gen Z (currently in late teens/early 20s) will have at least four careers and have run three of their own businesses before they reach the statutory retirement age of 94.

What does the workforce need in 10 years time? If my careers adviser failed to suggest to me that training as a drone operator would lead to riches 20 years ago, what lacklustre guidance are we peddling today?

More people need to be part of this big question.


4: How has creativity helped you to solve problems?

I was disappointed how few people, outside of the creative industries, shouted about the need for the creative industries during the pandemic.

Norman Cook told me it’s because no one is betting on culture. As long as people are betting on sporting events and the stock exchange then the public and politicians will move heaven and earth to keep big leagues and big business afloat. It’s a theory.


Either way, despite report after report, dataset after dataset, the OBJECTIVE TRUTH that creative play, story-telling and artistic making are good for:

  • Health
  • Well-being
  • The economy
  • Cultural identity
  • Child development
  • Social cohesion
  • Reducing crime
  • Innovation
  • Solving problems
  • Thriving places
  • Quality of life
  • Social mobility
  • etc
  • etc
  • etc

is still completely undervalued or ignored in most strategic thinking.

I understand the different between creative practice (eg writing a song) vs creativity in context (eg designing a turbine blade to mirror the aerodynamics of a swan) – but  conversations about both of their values still feel niche and restricted.

How can we get everyone to value creativity around them in the same way they value natural light?


5: What does better collaboration look like to you?

Our events programme is ramping up, co-designing moments of gathering and connection with organisations as diverse as Bucks New University and University of Sussex, Coventry City Council and Brighton Chamber of Commerce. The new always possible events and engagement team is led by Steph Danvers – we’ve got big plans!

A new book has come out recently, called ‘Aftershocks & Opportunities 2: Navigating the Next Horizon. Lots of thinkers from around world have contributed chapters on everything from the crypto-economy to enterprise in the developing world, sustainable food production to intergenerational society.

My chapter is an optimist’s take on post-traumatic growth and how businesses might behave better in the coming years. As well as thinking about skills, ethics and strategy, I make the case that collaboration is happening in ways unlike before.

Whether we are in a post-capitalist age or not, the mood for collaboration has become more robust and exploratory. Cross-sector, private-public, in innovation and service design.

During the pandemic many organisations realised that they were too big or too small, too vulnerable or with rapid growth potential. New realities of digital set-up, homeworking, extraordinary supply/demand disruption, mental health management, logistics, crisis control and ripping up the rule book meant that people have had to reach out and ask for help.

When collaboration works – it is gold dust.

If you want to buy the book, that would be lovely:

But if you want to ask me for more information about our 5 Big Questions, get in touch.