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Calendar Heroes: Chris Parsons, Co-Founder & CTO at Lollipop

In this edition of Calendar Heroes, we talk to Chris Parsons, co-founder and CTO of Lollipop, to learn about his style, tools, and methodologies for balancing priorities while leading the early stage startup that's building the fastest and most enjoyable shopping and cooking experience in the world. Follow Chris on Twitter at @chrismdp and on LinkedIn.

Tell us a bit about yourself and what you do

I'm a co-founder and CTO of Lollipop - a startup that's making the mundane task of grocery shopping magical. We're about 12 employees right now and growing rapidly, so I'm moving from a hands-on role into an oversight position. I've been on this scaling journey before - it's always an interesting and bumpy ride!

I'm also raising three kids with my wife Ellie - two teenagers and one pre-teen - which easily fills the rest of my calendar!

What does a typical work week look like for you?

I work in London two days a week, working from my home office in Winchester the rest of the time. The entire company comes to the office in London on Mondays and Wednesdays. Monday mornings is a planning morning for our squads, then we do an all-hands check-in to catch up as a company and hear the squad goals for the week.

I'm working on our next hiring round at the moment, so the rest of the week is currently taken up with reviewing and writing job descriptions and tweaking our hiring plan. I'm also the only developer that's not on a product squad right now, so I'm often working on things that make the product teams go faster such as build improvements and timely code reviews.

What techniques do you use to manage your time?

I try to have most of my 1:1 meetings face to face on my office days. Despite us all getting better at remote working during the pandemic, there's nothing that beats chatting with someone in person. I try to do all my video calls from home, as there's not a lot of space in the office and I'd prefer to take the chance to spend time with people face to face.

I currently treat my whole time in the office as "office hours" - I'm interruptible when I'm in the office for small requests. On home days, I schedule large blocks of time as deep work so I can guarantee not to be interrupted, and I try to avoid small meetings that break up the day.

What tools do you use to make you more productive?

I'm a big fan of Todoist, using due dates on tasks for things I'd like to get done by a certain time. My to-do list is semi-organised, and could do with some work to structure it more strategically by area: currently it's a little too tactical for my liking. This is partly a reflection of starting to move from a hands-on role to a more strategic one.

I use tasks with far off due dates for people that I want to catch up with every few months - rather like a personal CRM - and I use shared lists with my family for things like shopping.

I tag tasks with people's initials so I can be sure to mention something when talking to them. I've also started running a Notion page for a series of conversations for the people I collaborate with closely so I can define agendas and take shared notes. This works really well to capture the state of conversations over time.

Reclaim is great for time blocking. I use it for a lot of my big tasks that take longer than one hour, especially if meetings are starting to take up more of my time in a particular week. It's great to be able to rely on my calendar to tell me what I should work on next, as well as blocking time out from the inevitable meeting requests. I also use Reclaim's Habits for important things I want to do weekly - for example I have a "Big Picture" Habit that only schedules on days I'm not in the office. This forces me to take a step back and think about those important (but not urgent) higher level things.

What's the best piece of advice you've ever received?

Find a mentor. Everyone needs someone a little ahead of you; someone they can trust and can confide in absolutely. I've had many mentors over the years in both my professional and personal life and can't recommend it enough for boosting confidence and enabling me to be the best version of myself.

Calendar Heroes are real stories from very busy professionals across all types of roles and industries to learn more about how they manage to make time where there is none. We're highlighting these stories to help share tips and ideas for working effectively, improving your time management skills, and boosting your productivity.

If you know a Calendar Hero who has awesome productivity hacks that you'd like to recommend we interview or want to be interviewed yourself, let us know! You don't have to be a Reclaim user to be featured as a Calendar Hero: these stories are about anyone with an interesting approach to managing a complex schedule.

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