Alicia Diamond

Actionable advice for passionate business builders

Actionable advice, tips, and musings from a 2x Chief of Staff & passionate business builder

How I stay organized

My intention is for this to be a living, breathing document that outlines my personal system for staying organized and prioritizing my most transformative ideas into action. I firmly believe that you must have a system. Not an app, not a tendency, but a system. Start with how you already work, take the time to think about what about it works for you and doesn’t work for you, and document your system. 

But what if I don’t know what works best for me?

It’s okay! Your system should be flexible. Start with something small that we all manage: email. Think about the following:
- When do you check it?
- When you read email, what device are you using (laptop, tablet, phone)?
- What does it look like (device, time of day, physical location) when you manage your email and feel accomplished? Write this all down. 

This is the beginning of your system!

Here are my responses for my professional email account:
- I check it in the morning just before I officially start my day.
- I read it on my phone in the morning, on my laptop throughout my work day, and on my phone in the evening at home. 
- When I manage my email well (and feel accomplished), it’s because I’m reading it on my laptop. I prefer to craft longer responses on my laptop rather than on my phone. I don’t know if an email will warrant a long or short response until I check it, so when I check it on my phone I often find that: 
- I read the email
- I start thinking about how I want to respond
- I realize it’s a long response
- I decide to wait until I’m on my laptop
- Meanwhile, the email is already marked as read.
- When I get to my laptop later, that email is already marked as read, and all of my initial thinking from when I first opened the message is gone. I have to start thinking from scratch.

So, what did I learn from that?
- I prefer to manage email on my laptop.
- I should probably design a system that makes it possible for me to check email from my laptop regularly so that I can be responsive in a timely fashion. 

Based on this, here is the first version of my email system:
- I try to only check my email from a laptop.
- I check my email at loosely scheduled times (when I know I'll be on my laptop): at home 7:30 am, at work 10 am/1 pm/4 pm, at home 8 pm.
- I work with colleagues in Asia, so I need to know what if they've added important inputs to my day before I schedule and prioritize it. The 7:30 am check from home is a cursory "what looks important" check. I strategically glance through before I commute to work so that I can use my commuting time to consider how I might incorporate these new inputs into my day. 

What do you mean by "inputs"?

Most of our lives are dominated by inputs. Email exists only to add inputs to our lives. If we don't have a system to manage these inputs, we lose control of our day. (It has happened to the best of us!) Inputs without a system, or as it's scientifically known Wack-a-mole, is the least productive method to accomplish your biggest tasks for the day. We'll talk more about structuring your entire day later on. 

So, email is providing inputs. I can be diligent about planning my Tuesday before I finish work on Monday, however, in reality, I need to acknowledge new inputs before I dive into work on Tuesday. Think of it this way: you know that when you come home from work on Monday, you want to cook dinner and do laundry. When you walk in the door, your kitchen is flooded, and your faucet is gushing water. Do you simply ignore the problem and go about preparing dinner? Of course not! You walked in, received new inputs, and adjusted course. 

So, I have a version 1 of my system. What now?

Use it! Commit to using the system for a week. Any given day has enough variability, and we don't want a "false positive" or "false negative" result in our experiment. This means: did we think the system worked well only because our day was more/less chaotic than it usually is? The goal is to see how the system holds up after a few typical days. 

But what happens if my system stops working for me?

I’m a tinkerer and tweaker by nature. I like to push the boundaries just as soon as they are defined in the name of “continuous improvement.” My system is defined such that I run experiments. Sometimes for a week, sometimes for a month. If the experiment goes poorly, it reinforces the efficacy of my existing system. If it goes well, I incorporate what worked into my new system.  

Let's say that I stuck to my email system version 1 and found that when I checked it at 4 pm, I had a lot of new requests (since 1 pm) that needed to be addressed before the end of the day. This caused me to be stressed out and to have to work later than intended. Was the experiment a failure? 

Yeah... the system sucked. WRONG.

The entire point of the experiment was to determine what about the first version of our system worked well and didn't. We got important feedback that the schedule didn't work well. We need to make a change and now we know where to start. Some potential solutions:
- Add an additional email check between 1 and 4 pm. 
- Look to see when the majority of my inputs arrive: if they're coming in the afternoon, I can shift my day to do focused (interruption-free) work in the morning and "whack a mole" in the afternoon. 

Do you see how this all works? This is only for email, but I hope you can see how it extends to other sources of inputs. Here's what I hoped you took away:
- Think regarding inputs. Where are you getting information and tasks from? Manage when and how you receive those inputs. 
- Be realistic. Your system must be customized to you. Only you know when you work best, how you work best, and the reality of your life. Don't be stubborn!

What's your system? What about it works for you and what about it drives you crazy?

Without further ado, here's my system (version 723?), circa January 2018:

1. Gmail for email, both professional and personal. 
- Text snippet turned off. (This means I only see the sender and the subject line until I click into the email. Why? Because when I glance through my inbox on my phone at 8pm, I know that an email from my boss is worth opening, but an email from Amazon with an order confirmation is worth delaying. I don't want to get distracted by the Amazon tracking information at 8 pm...)
- Phone alerts off. I'm fortunate enough to be in a position where I can schedule dedicated email time with some regularity. I know that if I get an alert, or if my phone displays a badge, or if my laptop "dings" when I get a new email, the interruption (an input!) will pull me out of my focus. And for what? I'm going to get to those inputs. My team knows that something urgent deserves a text, a chat, or a pop-by. 
- Tabs turned on. This is an experiment I'm running right now. I hate that I can't rename the tabs, but I'm using them to differentiate between "importance of inputs." I'll explain more in a later post. 

2. The Todoist app. Oh, has this been a gamechanger for me! I kicked off this experiment in January 2015, and it stuck. Hard! I have a paid account for personal and professional use. Todoist lets you turn emails (inputs) into tasks. Genius! You can also add random thoughts as tasks "buy milk" or "check if Amazon order already shipped". Once you see your entire task list, you can prioritize and execute in order of priority. 


Alicia Diamond