Have you ever wondered how someone who runs a productivity company stays organized?

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During my time in university I didn’t even keep a to-do list. When I worked in investment banking, at most I’d scribble some notes in my notebook that would get lost in between stacks of papers on my desk. This is to say, this is coming from a perspective of someone who cannot deal with admin, but had to change his ways when confronted with the challenge of building a company.

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I will let you in on my method as of August 2023. As I improve my system, I will be releasing newer versions of this article. 

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Let’s break down the principles of my personal project management system and how I’ve implemented it in Skippet.

Project Management Productivity Principles

Let’s start with the “why” of my personal productivity system.  Below are the three principles that are the foundation of my project management system, from most to least important.

Principle 1: Needs-driven

My project management system is not merely there to remind me of my tasks. It serves to keep me on track. The biggest risk for a startup founder is spending time on the wrong things. In asset management, Return on Investment is driven by factors such as margin or revenue growth. For Skippet my (and the team’s effort) is the main input. So, ROI is simply time x value generated. time is mostly fixed in the long-run and it is a given that you work hard. Value can be 0 or, in theory, infinite. 

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It is therefore important for me to see where I spend my time, and prioritize according to business needs.

Principle Two: Lightweight & Easy to Use

Principle 1, by itself, would make you track all your data to optimize your productivity which would take way too much time. For most people, and definitely for me, this would lead to failure. Therefore, I wanted my system to be lightweight – to have just the amount of detail required to stay on top of my work and priorities. I’m a firm believer in the Pareto principle – 20 percent of the effort gets you 80 percent of the way (in most things). Just like with dieting or working out, the biggest risk is not following through and abandoning the system before it becomes a habit.

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This also means that I wanted my system to be convenient to use and visual, requiring minimal cognitive load.

Principle Three: Connected & Visible

It is important to me that my project management system isn’t siloed from the rest of my work and our company’s data. Other databases and people should have access to my information (or at least the ones I want them to!). This facilitates coordination with others, fosters transparency and makes my system scalable into the future (see the last section).

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Luckily, as you will see this is covered in Skippet.

My project management system (v1)

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High-Level Priorities: Table of Projects

The primary purpose of this table is to establish high-level priorities and understand where I am spending my time accomplishing principle 1. It also helps the team see where I fit in (principle 3).

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I have considered having an even higher level than “projects” related to our Board “Management Agenda” (i.e., three to five company-wide priorities) but I decided to keep it simple in line with Principle 2.

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This table mitigates two risks:

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1. Spending time on the delightful stuff that is already taken care of by other people. For example, product design is something I love that is very well covered by our product designer with significant valuable input from my co-founder & CEO.
2. Spending time on non-business-critical tasks that are merely ticking items of a to do list. This is often business admin where perfectionism adds little value. 

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Day-to-day Tasks: Table of Tasks

This is a simple to-do list with a few notable features:

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1. Notes: Associated with each task, so that I don’t take notes in random places
2. Linking to projects: So that I know where I’m spending my time as detailed above
3. Deadlines: Every task needs a deadline - if there is none it’s probably not important/necessary
4. Status: I keep track of all tasks, even the ones completed, on hold or cancelled. I never delete tasks. It’s a basic database principle that I adopted.
5. Priority: Self-explanatory – the combination of priority & deadline determines where I spend my time.

Effective Visualisation: Work-in-progress tasks & color-coded calendar

In theory, the projects and task tables could satisfy my principle 1 & 2 of being needs-driven, and lightweight and easy to use. I can guarantee I wouldn’t use this system if that were the case.

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There would be too many clicks involved and too much cognitive load associated with a simple task.

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Two solutions address this issue:

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1. A view of tasks that are not-started or work-in-progress (same for projects but this is less relevant). Importantly, I remove the tasks that are “on hold” – if they become important, I will consider them – otherwise they are just a distraction. The tasks are ordered by deadline. I use this view day-to-day. I have a separate view displaying just the High priority tasks. 
2. Colour-coded calendar with all my tasks based on priority. The tasks are fed there automatically. This makes it easier to view my tasks along the time dimension. I leverage this view when I’m busy and stressed and want to feel that I’m in control.

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Next Steps for My Project Management System

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So, this sums up my first iteration of my project management system that I’ve been successfully using for the last few months.

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I’m playing around with several ideas to expand this system to further support the outlined principles:

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1. Linking clients to tasks: Since we use Skippet as our CRM for our sales-assisted funnel, this is a natural evolution of the system. As we are still in the early days of marketing Skippet, I don’t feel this is necessary yet. When I do, I will create a new version.
2. Tables of notes & meetings: I have a separate table of notes linked to projects with more information about notes. Since I’m not yet consistently using this, I decided to omit it from this post. 
3. Team-wide projects & to-do-lists: I would advise this to any service-based company. Given the small size of our team and the fact that many of my projects don’t involve that much day-to-day collaboration, this is probably not yet necessary. The engineering workflow is kept in github (we don’t yet have a github integration) so this has limited utility.

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There are also several neat updates coming to Skippet which will help me update this system. They include an AI which will generate all the above for you considering your exact needs – after all, my system may not be “one-size-fits-all”.  

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Sign up to Skippet’s beta for free to build your project management system.