Work Happy: Flexibility and Trust in the Workplace

Business advice Meet the Work.Life team
Estimated read time: 8 mins
Published: 14/06/2019

On 12th June, we held the fifth event in our Work Happy event series, this time honing in on the effect of trust and flexibility on the happiness of your team.

We’re almost at the end of the Work Happy series, where we’ve been looking for ideas, tips and insights from entrepreneurs and experts who’ve made it their mission to help people find their best work-selves.

So far, we’ve heard from Henry Stewart of Happy Ltd. on empowering your people and owning up to your mistakes, Sally Lovett on how what you eat at lunch might ruin your day (a hard one to swallow), Jodie Cariss on mental health at work and making the unsaid said, Tony McGaharan on Google’s secret sauce, plus, a whole host of other clever humans on the highs and lows of engaging the future workforce.

This month, our speaker was Ben Gateley, Co-Founder and CEO of CharlieHR and Co-Founder of Born Social. Ben isn’t yet 30 and has launched and nurtured two highly successful companies that are proud to put their people first.


Ben started the conversation by explaining that, somewhat ironically given our topic for the evening, he fundamentally believes in “telling your team what to do”.

In his experience, Ben has found that too much flexibility breeds anxiety, confusion and imbalance.

Before he explained why, Ben wanted to highlight that for him, starting a business wasn’t about channeling his excitement for HR systems or social media. Instead, it was about creating a workplace where people wanted to come in in the morning, “We spend ⅔ of our lives in the office. I get out of bed to make Charlie[HR] a place where people want to spend that time”.

To do that, Ben has spent years pondering and trialling strategies to keep his team coming back everyday. He’s found that the world’s sudden preoccupation with flexible working has become overwhelming, “It’s on everyone’s lips, but can you have too much of a good thing? From our experience you absolutely can”.

When Ben and his co-founder, Rob, founded their first business together over 10 years ago, they were inundated with questions about policies, “We read all the books on amazing workplaces and thought about how we’d like to be treated”. The duo settled on being as flexible as they could and decided to offer unlimited holiday, reasoning, “we didn’t like it when people told us what to do or put us in a box”. They kept this policy for 10 years.


Ben’s first takeaway from a decade of offering unlimited holiday was, “high performers will always be high performers”. People that go the extra mile will continue going the extra mile, even when everyone else is on holiday. Ben found that these type of employees’ natural drive to work, meant it was almost impossible to get them to take enough holiday to avoid burnout, “they didn’t focus on looking after themselves”.

He noticed another divide in team members that had dependents and those that didn’t,  “people with families took lots of holiday because they had real reason to and so did people in relationships”. Ben also noted that people in lower paid roles took less holiday than those in more well paid positions. He saw the same divide across teams within the company.

When he approached staff about the policy, he found a lot of anxiety surrounding it, “people were asking, ‘So, what’s the right amount?’, ‘What’s too much?’”. With millennials experiencing higher recorded rates of anxiety than any other generation, Ben worried that leaving annual leave open was contributing to their stress.

People were also saving holiday to go on larger trips guilt-free, which Ben also found difficult, “people weren’t taking time off for three months, that’s not healthy working at the pace that we do”.

Finally, Ben explained that, of course, unlimited holiday doesn’t mean you can actually take as much holiday as you want, “You can’t even put it into a legal contract”.

Last year, after a decade of offering his staff unlimited holiday, Ben set a holiday allowance of 25 days plus bank holidays and Christmas days at CharlieHR.

Ben explained, “I really thought it would be hard to announce – but people clapped!”. The anxiety over how many days to take and what was enough and what was too little, ended up overriding the excitement of freedom.

CharlieHR now recommends everyone takes 5 days per quarter and Ben and the senior team have a dashboard which alerts them if anyone looks like they’re off track, “it shows people at risk of not taking enough holiday based on where we are in the year”. A manager will then check in with the team member to make sure everything’s okay.

Ben explained that now there’s a restricted allowance across the company, more holidays will be taken this year than ever before. For CharlieHR this is great news, Ben is comfortable in the knowledge that across the team, there is order, balance and equality.

For Ben, flexibility can’t exist without constraints, “in a world of flexible, easy come, easy go working, we are obsessed with not clarifying things as much as we should”. Ben told us that clear policies work for a reason, and knowing what the rules are “takes away so much of that anxiety”.

To finish, Ben gave the crowd some tips on implementing and creating great policies:

  • Freedom within guidelines
    • When it comes to holidays, this means giving a number. What the number is depends on your company values. At CharlieHR, they prioritise making everyone feel respected and valued.
  • Put it somewhere everyone can see it
    • Once it’s agreed, write it down and make sure every team member can find it without having to ask.
  • Ask people what they want
    • Does your policy make sense for your team? Ben has a young team and he takes into account the importance of holiday for wellbeing and mental health.


For our panellist discussion, Ben was joined by Emily Parsons (Slack) and Sarah Sich (Work.Life), as our host, Nat, probed the trio on ways to implement flexibility in the workplace and the importance of trust.

Emily works in Workplace Operations at Slack, a communication platform which enables companies to connect with their colleagues and remote workers in companies around the world. Emily is passionate about making and facilitating spaces (virtual and in the real world) where people can do the best work of their lives.

Sarah is the Head of Marketing at Work.Life and is passionate about workplace happiness and team engagement. Having always had a side-hustle, Sarah is an advocate for flexible working, and a strong believer that trust is the key to innovation and productivity.

Nat kicked off by asking about the trio’s experience of flexible working and what it means to them.

Emily explained that at Slack, the team can work from wherever they want: “We’re trusted to get our work done wherever we are. We have remote workers around the world and Slack is the perfect tool for remote communication”. Emily finds that it’s just as easy to get hold of remote workers as it is someone in the office, and the freedom to choose where you base yourself means the team feel valued and trusted. 

At Work.Life, Sarah explained that members generally choose their coworking space based on its proximity to their home, as they’re keen to avoid long commutes and unnecessary travel: “Everyone is different. Traditionally, flexible working was only something families required but it’s not always about commitments. You might be a morning person, work better in the evenings, or at home without distractions”.

Sarah says that the flexible nature of Work.Life’s memberships means members can visit multiple spaces across London, “we try to encourage people to roam, as a change of scenery can do wonders for creativity”.


At Work.Life, the team use Slack to communicate across their UK locations. Sarah has found it to be a seriously useful tool to keep people in touch with each other and share internal communications.

However, she acknowledges that company culture is key, “flexibility and communication can exist but if you don’t trust that everyone on your team will do their job unless they’re right in front of you, then you can’t have flexibility”. For Sarah, that means hiring the right team.

Ben agreed that technology doesn’t create the working environment; company values do, “If you put Slack into an extremely corporate, traditional company, it’s not going to be used the way it was intended”.


When it comes to applying flexible working at work, our panelists found it works best when it’s embedded in a culture of openness and transparency. Ben said that at CharlieHR, some of the best policy changes have come from staff members, not management, “It’s key to give the opportunity for feedback at all levels, so that if someone wants change, they feel like they have the ability to make it happen”.

Emily said that there’s a similar openness at Slack, “For us, flexibility and trust comes from keeping communication lines open. I can direct message someone from the American office and hear what’s happening or I can message the CEO”.

Sarah agreed, but noted that after working in very restrictive workplaces as well as more flexible ones, she’s found that staff members can adopt flexible working better if they can lead by example, “I think it has to come from managers and go down the chain. People need to see flexibility in action at a senior level”.

Ben told us that he operates on the belief that workplace trust can only come from building strong interpersonal relationships, “relationships where you truly know the person as an individual, not just as a staff member. You have to deeply care”.

He has found it takes longer with some people than with others but that you end up being able to be honest with each other for the better of the business, “you can push and pull each other quite ferociously”. Ben explained that a culture of caring opens a channel for honest feedback that can only exist where there’s trust.

Emily then told us that when face-to-face communication isn’t an option, there are ways of building relationships remotely, “Slack have integrations like Kudos Drive and Donut where you can give feedback or chat to a randomly allocated member of the team to catch up on a personal level”. She also said that video conferencing means face-to-face communication is only a click away.

Sarah agreed that video tools are useful but believes “nothing can replace real interactions when it comes to building relationships”. She has also found that speaking to someone outside of the office environment can deepen that connection too.


Ben thinks it’s personal, “I see people evangelise a small number of companies. We read a book or go to a talk and try to follow their example, but the reality is that they were in the right place at the right time”. Ben thinks it’s important to look at your specific personalities, processes and requirements to find out what’s best for you, “not just what works for Facebook”.

He also warns of talking about time as a unit of input or hard work, “You can’t compare one hour of someone’s time to someone else’s. We have core hours of 10-3 and outside of those hours, people can decide what they want to do”.

Emily agreed that the culture of packing up and leaving on the hour isn’t productive, “My manager is in Dublin and he never really knows where I am. When I hire people for new offices overseas, I want to build that same level of trust”.

Work.Life is focused on providing happy workspaces and we hope that this event series will help others to understand how better to promote happiness in their workplace!

The final event in our Work Happy series, Work Happy: Why Design Matters, takes place in our Fitzrovia space on Wednesday July 10th – where we’ll be grilling experts from Nyde and Dr Martens. Thanks to everyone who made our fifth Work Happy event so great and we hope to see you all at the next one!

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