Back to school - and learning how to take a decent holiday (from the job)

Hello, I’m Poss, a Chief Operating Officer (COO) working in technology, and I like talking about some of the themes behind running a business. 

I’ve been quiet over the summer months, which was sort of deliberate, and now, as we ditch the shorts and turn the heating on, I’ve got that excited “back to school” feeling. 

Summer is important to me. My dad was a cobbler and self employed. He would shut up his small shop in South London at the end of July and not return until I went back to school in September. For those 5 weeks each summer, we would holiday in Cyprus. My dad, the man who worked 55-60 hour weeks, would spend the majority of his time in his speedos on the beach, smoking Alfred Dunhills (oddly only on holiday) and hanging out with old friends. He worked hard, but chilled harder. 

I feel that legacy today. The trouble is, us Brits aren’t the French. We can’t switch off for the whole of August, but I will take a good vacation (sans the speedos or the Dunhills). So returning to work after a summer break can often feel like a daunting task, especially for COOs juggling multiple responsibilities and stakeholders. 

Some of the key things I think you need to get the best from the “back to school” period. 

Put the work in up front and set clear expectations: Ensure your team and those around you understand their responsibilities and deadlines. Double down on the planning, map out the dependencies and strategise mitigation tactics. Even if this feels over the top, that strategic thinking is never wasted and you’ll reuse it as your business grows anyway. 

It might sound obvious, but who is responsible for what when you’re away? Delegate tasks clearly and provide guidance on handling unexpected issues. Handover documents and out of office messages aren’t rocket science, but they enable trust and confidence. 

Whilst this is the holiday season for everyone, asynchronous communication is your best friend. Invest in writing, document decisions and processes. Tools like Slack, or project management software like Monday or Trello, allows for flexibility and avoids overwhelming your team with the disruption of people being away. 

Trust your people. You can be as organised as possible and be great at communications, but fundamentally, you’ll need to trust those working on your behalf. That trust not only pays off in the short term, but builds relationship equity. Any senior executive taking 2 weeks off is a challenge that many people looking for practical experience, will relish taking advantage of. Use that to your mutual advantage. 

And lastly, nothing beats a good post holiday catch up over a coffee. Maybe this is just me, but I love that first catch up, knowing what’s worked well (phew), what is stuck (and goes onto my to-do list) and what gossip there is! This is another reason the “back to school” vibe is great. 

As society’s view on the workplace and work-life balance shifts, I think it’s even more important than ever to talk about practices that make the transition from work - to life - more effective. So if you have any views or ideas, please share. Otherwise enjoy the bit of autumn, before it gets REALLY cold… 

Thanks,

First written on 15 September 2024