Diary of a CEO – How I went from freelancer to Chief Executive Officer

photo of people near wooden table

My first hand experience learning to delegate and manage a new team

A serendipitously well-timed meeting scheduled with our accountancy team gave me a breakthrough moment in my learning journey as a new Chief Executive Officer this week. After 10 years as a freelancer, with almost sole responsibility for everything related to my entrepreneurship, I’ve found adapting to my new role as team leader and business manager a major challenge. I’ve learned some important lessons in delegation and where to focus the bulk of my time while we get this business off the ground.

In the meeting, I was astutely reminded that not only do I now have in-house assistance in place thanks to my fantastic team, but I also have access to an increased budget for external services, such as accountancy, legal, and technical support. Essentially, this means I need to be delegating as many tasks that don’t immediately fall under my primary responsibilities in the business as possible. Rather than trying to do a bit of everything myself, I need to focus on my core duties. In other words, planning our strategic activities, raising our company profile, networking, fostering partner relationships, marketing, and generating sales leads. Naturally, I also need to concentrate on producing copywriting and Finnish to English content that is optimised by what I bring to the table as a translator and content creator. This will allow me to dedicate more time to brand building and generating revenue – safe in the knowledge that my exceptionally capable team has my back completely. 

Becoming the Chief Executive Officer – the ‘Delegation Dilemma’ 

Two words spring to mind – trust and insight

Trust. I’m not referring to an inability to let others carry out tasks that were previously my job alone. I’m talking about trusting myself. I sometimes find it hard to trust my own judgement and, now that my decisions are potentially much further-reaching in their impact than those made in the relative comfort of my freelance career, I struggle even more to confidently and assuredly delegate a task to my team or an external service provider. Don’t get me wrong, this feels like the reverse of a control complex. What if they think the task I’m giving them is redundant? What if I should be doing the task myself and asking them to work on something more important? It’s a rabbit hole that can feel inescapable!

Insight. After working as a team of one for so long, I’ve learned good and bad habits in relation to collaborating with colleagues and clients. The last time I worked in such a close-knit team setting was during my nursing training, before the pandemic. There, the hierarchy was clearly defined. I was either a student on placement, one of a handful of mature students bringing a wealth of industry knowledge and experience to the table, or I’d been assigned a role by a course teacher. And this made it much easier for me to utilise my team as a resource to lighten my workload, allowing me to focus on the big picture and organisational questions, or to accept my role as a mentee working underneath a qualified nurse, occupational therapist, or social worker.

The Chief Executive Officer as part of the Team – Honesty and integrity

Now that I’m the CEO of a small business and lead a core team of three language services professionals who each have similarly extensive and diverse experience, knowledge, and expertise, I find navigating the division of labour much more challenging. How can we as a new business efficiently tackle this situation to prevent us getting bogged down by a lack of clarity? As a result of long COVID complications and the hectic nature of starting any new enterprise, a future stuck in the mire was possibly lurking around the corner prior to our proactive, watershed discussions. It took an effective combination of pragmatic and honest self-reflection on my part and some justified and empowered questioning from my team to clear away the fog of confusion and set us back on course. We honestly asked ourselves who we are and what we want this company to be, and there we re-discovered ourselves and our USP. That’s what I call integrity.

Early on in our regular team meeting this week, we quickly realised that home truths needed voicing for us to troubleshoot this potential bottleneck. We saw that we needed to stop, take stock of what we had and hadn’t achieved on our journey so far, and clarify the processes we needed to follow to achieve the business growth and success we strive for. This will ensure we continue to have clear role delineation and a robust and overarching system for rallying the team when one of us isn’t able to carry out a core function due to our availability, for example. After all, we are all parents of young children, work from home, and, like most of the world, have been dealing with the impacts of the coronavirus pandemic while starting a new business and learning roles that marry the unfamiliar with the tried-and-tested. We’ve adopted a 100% remote and collaborative model, so it’s essential that we adapt our system to this model from the start, in order to successfully function.

The next step: consolidation and systems development

Going forward, we’re going to double-down on planning our tasks and goals more concretely and transparently, and will remind each other to proactively seek clarification when we need it. After all, it’s the approach we’ve successfully followed with our respective clients for years.

The key decisions we’re actioning following our eureka moment are

  • Ensure that we use our team calendars effectively
  • Set aside time for regular business development discussions
  • Strike a balance between team meetings and independent research
  • Finalise our meeting agendas early on the morning of the meeting (not 15 mins before the meeting starts!)
  • Block time when we’re all available to work on processes together
  • Schedule weekly and monthly check-ins to track progress and revise goals
  • Create dedicated task and discussion channels in Google Workspace to avoid unnecessary overlap and facilitate ease of traceability
  • Guarantee that we all have some protected thinking time!

Do you have experience of developing new business processes and insight to offer on how you overcame organisational and systems bottlenecks during your start-up journey? We’d love you to join the conversation in our social media channels or in the comments below.

If you’re a sole trader or business based in North Lancashire or Cumbria and you’re looking for a super responsive and dynamic accountancy service that flexes to provide the best service package for your needs, MDLS can’t recommend the Blend Accountants team highly enough. They don’t upsell for the sake of it, they don’t give you pipe dreams to chase, and they don’t treat you like a name on a form. Instead, they honestly appraise you of your best strategic options, encourage you to clarify and share your goals with them, and they listen to you and want to get to know you as a person.

MDLS – Your authentic voice in Finland and the UK
“We’re a translation and communications company run by linguists for linguists. And our clients, of course, We’re in it 100% for our clients, too.”

Mike Dutton, CEO of Michael Dutton Language Services

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