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“5 Things I Wish Someone Told Me Before I Became the CEO of CharlieHR,” With Ben Gateley

Screen for cultural fit at the beginning of the hiring process, not the end — or you will end up using the person’s skillset to make excuses around why you should hire them even when they might not gel with existing key people in your company. We’ve had to fire people in the past for […]

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Screen for cultural fit at the beginning of the hiring process, not the end — or you will end up using the person’s skillset to make excuses around why you should hire them even when they might not gel with existing key people in your company. We’ve had to fire people in the past for not being a cultural fit, and we could have probably worked it out earlier than we did. We always welcome diversity and new perspectives, but if everyone on your team brings high energy to work every day, and a new hire is someone who works best when they’re left to their own devices, there can be negative sentiments that sprout from that divide. Division in a company is never a good thing. You risk tiring out the team involved in hiring and costing yourself money down the line by not having a cultural ‘meet the team’ aspect of your hiring process, and we’ve definitely had to learn that after a few missteps ourselves.


I had the pleasure to interview Ben Gateley. Ben is the CEO and co-founder of CharlieHR: an HR software used by thousands of small businesses worldwide. He has started and grown a number of successful companies since his teenage years — including BORN SOCIAL, one of the most successful social media agencies for challenger brands in the world. An outspoken champion of positive workplace culture, frequent volunteer and engaging public speaker, Ben is a passionate advocate for all things “people”.


Thank you so much for joining us Ben! Can you tell us the story about what brought you to this specific career path?

I’m one of those people who kicked off my career as an entrepreneur from the start. Rob, one of my best friends from school, and I began by organising club nights when we were 18 and started learning the ropes of running and marketing a business from quite an early age. We learned to work really well together as not just friends but as business partners who could play to each other’s strengths. Off the back of learning to market our events, we launched a social media agency (BORN SOCIAL) back in 2012.

As most entrepreneurs know, building a great team is really difficult — and we quite often spend more time on the admin that surrounds people rather than actually helping them to progress or improve. That’s where Rob and I spotted a gap in the market. We experienced the struggle of trying to run an amazing, growing team ourselves, while also trying to focus on growth and business development.

Managing our people — the daily admin of HR tasks like booking sick leave, checking holiday allowances when new requests came in or storing and organizing employee and company files, for example, was eating up loads of our time and energy. We looked for software to help us automate it, but found that there wasn’t anything on the market that met our needs as a small but growing company that was easy to understand and use as a non-HR pro, and was also affordable. We knew from our peers that we were far from the only ones struggling to juggle business and admin — so we decided to build the solution ourselves. That’s how CharlieHR was born.

Can you share one of the major challenges you encountered when first leading the company? What lesson did you learn from that?

In a nutshell, the most important thing is alignment across every role. Team, leadership, board, making sure everyone is really clear on what we’re doing and why we’re doing it.

From the start, we could have been more aligned on how we build our product and what we’re trying to build. Correctly managing the on-boarding process so that every newcomer is inducted into ‘our way of working’ is important when it comes to making sure the business runs smoothly and the team is working cohesively. In the early days of the business, this is especially crucial to not just the product, but the company’s survival.

What many companies miss in the very early days, is the continual research loop. It’s one thing to believe you’ve found a product-market fit, it’s another to slip into the mistake of thinking that the problem you understood and took as the foundation of your product isn’t constantly changing. Even as you’re working on the first iteration of your product. Research should be continual, even through the development process. Otherwise, you risk building something that solves a problem that no longer exists, or looks completely different- wasting time, energy and money.

What are some of the factors that you believe led to your eventual success?

For me, there’s always been one thing that’s been really important throughout — which is making work the best possible experience for the team in the room. Having a personal drive that aligns with the foundational ideal of our business is a big part of why being CEO at Charlie is such a logical and natural fit for me. A personal perspective that aligns with the business and a business partner who is also a best friend has been a huge factor in building companies whose successes are a source of great pride to us both.

Success is also an ongoing thing. It’s long term and I don’t really consider it to be a destination. To continually be on the road to success, or a road on which you feel like you’re succeeding, perspective is really key in my experience. The world is big and life is short — nothing that we’re doing is life or death. Perspective helps us stay calm. It allows you to make decisions that account for all the facts and take as much emotionally based nuance out of it as possible. Yes, your business and your job are important, but it’s not the only thing in life.

To maintain perspective, I always think of our people first. As a CEO it’s your job to teach others and to take the time to appreciate others — by focusing and investing in your people, and developing a workplace where you and your team are happy to make the daily 9–5 a pleasure to work. Spending ⅓ of your life in the office is significant, so for the sake of yourself, your team and in turn, your business, working hard on creating a great company culture is vital.

What are your “5 Things I Wish Someone Told Me Before I Became CEO”? Please share a story or example for each.

  1. As mentioned before, a big one for me is alignment in the business. It really is so important that everyone knows not just what you’re working towards, but what the route to that end product should look like. With proper alignment on the way you work, and not just what you’re working on, you’ll have a more unified and productive team whose minds can work together in a more constructive way without clashing.
  2. Screen for cultural fit at the beginning of the hiring process, not the end — or you will end up using the person’s skillset to make excuses around why you should hire them even when they might not gel with existing key people in your company. We’ve had to fire people in the past for not being a cultural fit, and we could have probably worked it out earlier than we did. We always welcome diversity and new perspectives, but if everyone on your team brings high energy to work every day, and a new hire is someone who works best when they’re left to their own devices, there can be negative sentiments that sprout from that divide. Division in a company is never a good thing. You risk tiring out the team involved in hiring and costing yourself money down the line by not having a cultural ‘meet the team’ aspect of your hiring process, and we’ve definitely had to learn that after a few missteps ourselves.
  3. Avoid heroics as a CEO. The answers lie within your team, not just in your own head. Sometimes as CEO you might feel like it’s your responsibility to come up with all the answers — and that’s a false assumption to be making. Trust in the amazing talent you have around you, and let them solve those problems for you. Our new product that complements our original HR software for small businesses, is affordable bespoke HR Advice — also for small businesses. From a business development point of view, we were running short on ideas for generating new leads and getting the word out there that our new service was live. In the end, we had a company-wide brainstorming session. Everyone was able to bring fresh eyes and minds and new perspectives to the problem, and we came away with a long list of exciting possibilities. It doesn’t lie solely with the CEO to solve all the problems of the business.
  4. Hire slow, fire fast. If something feels wrong within the first three months, the likelihood is that your gut instinct is right. Use your probation periods properly, don’t sit around waiting for things to get better. We’ve certainly had situations where the team have known that a hire was wrong and we’ve not done anything about it. It always feels like a difficult decision to make, but at the end of the day, you have a responsibility to the rest of the team as well to make sure they feel like everyone they work with is delivering at a high standard. You risk demotivating your team and slowing down their development by dwelling too long on difficult but necessary decisions.
  5. Run retros. When things do go wrong, whether that be in hiring, a team project or something else, make sure you bring the team together and run a retrospective on the whole experience. Use those learnings to improve your processes. There is no perfect process, you need time and learnings to continue to improve and change them. They do a great job at creating a release for any tension that might exist between individuals. Working in a start-up is hard and having the opportunity to decompress and share your frustrations is important to the longevity and productivity of the team and everyone’s working relationships.

What advice would you give to your colleagues to help them to thrive and not “burn out”?

Consistency allows you to maintain peak level performance over a long period of time — especially in the world of small businesses and startups, we’re running a marathon, not a sprint.

  1. Life and business should be a balance — create balance in your life by making sure you have other projects you’re passionate about, work is important but not everything. You’ll avoid feeling like your whole world crashing down when one element of your life isn’t going too well by diversifying your interests and investing in your passions.
  2. Understand yourself — make sure you know what gives you energy and what takes it away from you, and learn how to manage that. If an afternoon run gives you the juice to be productive for not just that day, but to clear your head all week, don’t let anything work or otherwise related get in the way of you committing to that personal time. Your personal life, and your work will suffer.
  3. Invest in yourself — diet, exercise, therapy, coaching, yoga, cook for yourself — your mind and your body are your product so you need to look after it with the same attention and care you would a business you started yourself.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

My biggest advantage, which is also my biggest disadvantage, is that I’ve only ever worked for myself. While this grants total freedom to choose your own projects, it also leaves you open to being terribly lonely and could make it difficult to challenge yourself and check your assumptions. I however, have been very lucky to have worked with my best friend from school, Rob, for the last 13 years.

Having such an honest and long-term relationship with my co-founder has been such a blessing, and has really helped us both develop our leadership skills through an honest and dynamic relationship in both our personal lives and at work. Rob was both my fellow co-founder at Charlie and my best man at my wedding last month.

So many businesses fail because the founding team can’t work together or put aside their differences, which is understandable — founding a business is hugely intensive work and puts a strain on any relationship. Having worked and been best friends with Rob for so long, we’ve almost evolved the way we work to suit each others’ strengths. We’re both incredibly lucky to have found someone who complements the others’ weaknesses. For me Rob is the person I’m most grateful towards for sure — if our luck hadn’t been aligned to push us both towards starting a business together I’m sure we wouldn’t have made it this far or this long by ourselves. Long may it continue.

What are some of the goals you still have and are working to accomplish, both personally and professionally?

My goals remain largely the same as when Rob and I first started CharlieHR. I want to enjoy working Monday to Friday. I’ve been very lucky that work has been a very positive aspect of my life over the last 10 years, and I’d like that to continue.

My second goal is to continue to help the team that we work with to achieve their goals and ambitions in their lives in the small ways that we can. Not only this but we as a team want to bring some of the Charlie ideals to the small businesses we have as clients. We continue to work off genuine feedback from small business leaders, founders and team members to improve and build new tools for them to make their companies more efficient, to foster and enable an ongoing feedback loop to bolster improvement for both the businesses we work with and the individuals we help them manage. In a grander statement, both the team and I here at Charlie continue to work with a keen focus on empowering both small businesses as companies, and the individuals who work in those companies.

By making the difficult, repetitive but important administrative aspects of running a business easy and effective, we hope to improve that ⅓ of people’s lives that they spend at work, and to also help them to do great work.

What do you hope to leave as your lasting legacy?

I’d like people to think they’re better because they worked with us. I’d like to think I’d be able to contribute to someone’s personal development, their happiness, their enjoyment both at work and outside. The prevailing way that we do that is by focussing on the individual rather than on the company — and by focussing on the individual’s growth, we’re feeding the company growth too.

You are a person of great influence. If you could start a movement that would enhance people’s lives in some way, what would it be? You never know what your idea can trigger!

Make work better. Most people are not engaged by their work (70% of US workforce). We believe that our generation will work a lot longer and with greater overlap between work and personal life than ever before. What we’re trying to do at and with Charlie is to make work better for our team and the people who use our product. The impact we can have on people’s lives by making their Monday to Friday environment more engaging is huge. Imagine a world where people don’t live for the weekend. As idealistic and naive as it sounds, we like to think we’re making the steps in our product and writing articles on our blog to not just enable, but to help educate and present work-life enhancing ideas to those in a position to implement positive change.

How can our readers follow you on social media?

We run a blog that covers everything from founder stories and experiences to our own trials, errors and successes of building and running a business while managing open and diverse company culture. The blog can be found here: charliehr.com/blog. We’re also on Twitter @JoinCharlie, LinkedIn @CharlieHR and of course, I have my own Twitter @gateley.

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