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The Art of Leadership: An Interview With Appointedd CEO Leah Hutcheon

Dominique Adams


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Leah Hutcheon, who will be speaking at DIGIT’s 3rd Annual IT & Digital Leadership Summit on the 30th of May, shares her thoughts on how to be an effective leader. 

As a prominent tech entrepreneur, Leah Hutcheon has won multiple awards for her leadership skills. She is the current NatWest UK Small Business Entrepreneur of the Year, is a Scottish EDGE Award winner, and has even been the subject of a BBC documentary on entrepreneurship.

According to Hutcheon, communication, company culture, and collaboration are crucial areas a good leader cannot ignore. Although she never set out to become a leader, by default she became the CEO of her own company, online booking solutions specialist, Appointedd.

As she puts it, leadership “snuck up” on her, but she knew what type of boss she wanted to be and the kind of traits she wanted to avoid. Hutcheon says that her experiences of dealing with certain managers earlier in her working life gave her a clear idea of the management styles she was keen to avoid, and this has helped to shape the person she has grown to become.

“Everyone has had good and bad bosses that they reflect upon – that was certainly true for me,” she explains. “From my experiences, I knew right from the start what kind of boss I didn’t want to be. I feel it’s important to empower your staff and be genuinely collaborative, and I knew I wanted to be the type of boss that encouraged that and led by example.”

Encourage a Collaborative Company Culture

“Because of the collaborative nature of my team, I don’t feel like I have to act like ‘the boss’. I’m certainly not controlling or didactic in any way. I want people to take ownership, which is why it was really important to me that everyone in the company had shares.

Generally, everyone acts in their own best interest, and having your staff invested in the company, encourages them to act in the best interest of the company.”

Hutcheon insists that leaders should help their teams “discover their collective superpower” while also acknowledging what each individual brings to the table.

Encouraging this culture, she asserts, helps to ensure that team members “play to their strengths both as individuals and as a collective”.

Good Leaders Facilitate Opens Lines of Communication 

Effective leaders need to focus on communication, which is one of the most important traits a good leader ought to have, she explains. The ability to maintain those lines of communication and encourage staff to share is a key component of cultivating a positive office culture.

“In the company, we have a very strong management structure, but it’s a fairly flat company structure,” she says. “On Mondays, we have an all-hands meeting and then on Friday, we have a breakfast huddle with bacon rolls.

“Friday afternoon we have a ‘show and tell meeting’, which is a chance for people to share their big wins and developments with the rest of the team.

“These meetings are important because regular communication helps us to stay really connected and helps empower the team. In a small company, you need everyone to be a starter and finisher.”

Don’t Dismiss Others Viewpoints

According to Hutcheon, focus, direction, tenacity, fairness and humility are also traits that all effective leaders possess, which can helps to steer a company through difficult times and maintain a strong focus.

“A leader needs to know and see where the company is going, and be able to do what it takes to get through the hard times. You also need to have humility, it’s important to know that you don’t know it all,” she says.

“To get the right answers you need to be able to collaborate with your team members and hear other people’s viewpoint without dismissing them. It’s important you’re able to accept you don’t have to be the star of the show, you must enable others to be stars of their own show.

“Be fair with your staff and never ask someone to do something you aren’t willing to do yourself. This one is huge for me as it was what my worst boss did frequently.

“There’s nothing more frustrating than being asked to do things you know they would never do. People need to know that you are willing to get your hands dirty,” Hutcheon adds.

Be Authentic to Your Company Culture 

For staff to feel confident enough to take ownership of their work, Hutcheon suggests, it is vital that leaders foster an environment where they feel staff can fail. If team members feel they cannot, then an effective leader must emphasise the importance of this work process.

“Don’t make your staff feel they can’t fail – you have to enable them to fail,” she says. “For example, at our company, we have a slack channel called ‘fail forwards’.” In this channel, staff are actively encouraged to own and share their mistakes on slack “without fear or shame”.

Hutcheon says: “The goal of the channel is to foster a culture of collective learning. I think that’s important for everybody to do, that comes from leadership, you have to set the example.

“We have to be empowered enough to feel brave enough to fail. If you’re not failing sometimes then you’re definitely not being brave enough, are you?

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“But you can’t ask people to be vulnerable and then chastise them for it. It’s so easy to slip, no matter how good your values are as a company. It’s a stressful environment in a startup,” Hutcheon continues.

“Everything is moving quickly. It’s very easy to fall back into using lazy ways of management. You can’t ask people to step up and then not live those values right through. Be authentic to the values you have as a company.”

To hear more from Hutcheon, and gain more insight into tech leadership skills, join us at the IT & Digital Leadership Summit on the 30th of May, at Our Dynamic Earth in Edinburgh.

The event will cover topics including key technology and business trends, the evolving role of IT and Digital, effective leadership skills and how to create a positive company culture. Hutcheon will be giving a talk titled ‘Using Disciplined Entrepreneurship as a Framework for Digital Transformation’, including an overview of the 24 steps of disciplined entrepreneurship.

For further details and to secure your place, visit

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Dominique Adams

Marketing Content Manager, Trickle

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