Hyper Productivity Working With an Assistant

Background

Up until a few years ago I had never worked with an assistant. I hit a point where I needed to continue ramping up how much I could get done but I couldn't get past a number of things on my plate that really shouldn't have been there in the first place. Thanks to a suggestion from other busy execs I trust, I found an executive assistant (EA) and have been able to significantly boost what I can get done. Over the past few years I’ve worked with my assistant to refine the process of how we work together to best enable high productivity for me.

To help others in my companies with the same issue, I have collected the overall methodology of how I work with my EA to help them start the path to their own hyper productivity and wanted to share it to help others. A big element is continuing to refine the processes with new tools and standards to keep pushing the limits of productivity.

The key goal for an EA is adding scale to what an executive can accomplish. That includes owning many repeatable processes like communications and scheduling and many special projects. The EA is the executive's face to the world and needs to communicate a consistent message and caring about those on the other end of the communication.

Tools Used

We use many different tools for tracking conversations, tasks and data. Here’s a partial list that I’ll cover in more detail below.

1. Asana — task & project management system. Mostly web based but decent iOS app. I highly recommend the third party iOS app Hill 88 for Asana as well.
2. Evernote — note taking for everything
3. Slack — text messaging, great for less urgent discussions that will go back and forth for a while. Essentially replaces email for any discussion items.
4. iMessage — used for urgent real time communications
5. Calendar — Mac calendar running on top of Office 365
6. Away Find — email monitoring service & iOS app that notifies me when emails come from specific people or with specific topics
7. Fast Ever - iOS
8. Fast Ever Snap - iOS

Meeting Note Taking

I take all meeting, call or other notes are in Evernote. I use a couple different shared notebooks with my assistant in which she can immediately see and act on the notes.

“_Inbox - meeting notes” (the _ puts it at the top of alphabetical lists) — pretty much everything my assistant needs to see goes here. I title the note with the person’s name and capture notes using the short hand below. The Evernote iOS app itself is too slow for note creation (it’s better on the search & read side) so I use FastEver on iOS to more quickly capture text notes and add them to the notebook unless I'm on a call at my desk in which case I use the desktop version of Evernote.

“_Inbox - scans” — The second utility app is FastEver Snap or FE Snap. This app quickly takes pictures and adds them to Evernote. This is critical for capturing whiteboards or documents my assistant needs to take action on (like the forward looking paper calendar from an outside group and making sure those are in the calendar).

While Evernote could be used for capturing business cards, that’s done in Asana since it involves a executing on a task. See below.

My assistant takes all notes and copies them into the CRM attached to any people in the meeting and the business opportunity if one is involved. The contents of all notes are scanned for the short hand and additional actions are taken as appropriate. For example, I can just capture "T - follow-up call with Mike in 2 weeks” and my EA knows to run with scheduling a follow-up call in 2 weeks — I don’t have to think about it again.

The expectation is that all new notes are acted on within a business day.

One of the key elements I find is that there are always things that pop into my head during a discussion with someone that are unrelated and will require further action. I quickly jot those elements down in the Evernote note with the same short hand and can be confident that the actions will make it into the appropriate place.

Alex’s Note Taking Shorthand

When taking notes in a meeting or quickly scribbling on business cards I try to capture specific action items for both myself and my EA. Here’s a list of the short hand I use in those notes:

T <tag> - note
Add a new task to Asana. Tag it with anything before the ‘-‘ character (usually someone’s name on my team to add it to the agenda of our next meeting). If the task doesn’t include it, grab details about who I was meeting with to add context to the task when creating it. See below for more on Asana and tags.

L
Used on business cards to indicate that I need to extend a LinkedIn connection with this person.

OPTY - note
Create an opportunity in our CRM for this person with the note as the title

NL
Add this person to our email newsletter list in the CRM

S - note
I’m always looking to learn from other speakers. Their voice techniques, visual media and stories often given great ideas of things I can add to my presentations. This is my shorthand to add the note to a list of speaking techniques or content for future use in Asana.

I’d recommend keeping your list of abbreviations like this pretty short (less than 10) so you and your EA can both remember them clearly.

Regularly scheduled meetings

We try very hard to stay in sync on day to day items as well as what’s actually important. There are always urgent things to be addressed but continuing to focus on the important items moves my companies ahead. My EA and I use this general sync up schedule:

•Daily 10 min briefing (1-2) — she has batched up items that need quick answers from me or that I need to be aware of. That doesn’t mean running through every email that came in, just the things I really need to know about.

•Weekly task grooming & key project review (60 mins) — this is the opportunity to refocus on what those important projects are and look at what needs to be accomplished this week to move them forward. This typically involves my EA running with meetings/calls that will need to be scheduled out a week or two. Another key element is my EA recognizing projects that I need time to work on and getting that project time on the calendar. If I don’t pre-load chunks of time to get the work done, it’ll all become off normal hours projects and that just pulls me from my family and grinds down productivity.

•Monthly project review & setting (60 mins) — This monthly time is used for reflection on what the key projects for the month really should be. Since we run the companies using EOS (the Entrepreneur Operating System) we set critical goals quarterly and I’ll want to ensure I’m personally tracking to my goals.

Projects & Tasks in Asana

Asana is my core tool for getting work done. This is the first place I reference for what I should be doing next. I push hard to avoid checking email myself and getting distracted.

The key elements of Asana are projects, tasks and tags.

Projects are created for any effort that is going to require at least a couple tasks to accomplish. This way I can refer back to the project list and ask myself what else needs to be done to move the project forward, not just what the next task already recorded is. I’ve found that it’s easy to get pulled into the tasks that have been defined but miss which important tasks to address something important aren’t yet on the list.

I create projects for key client deliverables that I’m heavily involved with, company quarterly goals that I’m the owner for, presentations I’m creating - any effort that involves getting input or deliverables from others or any other effort that is going to take more than a calendar day. Ideally all projects have a due date and can be marked as completed. Projects generally should not be dumping ground for a collection of tasks but something that can be completed.

I also have a few general bucket projects such as:

• Bizdev - anything related to sales/relationship building
• EOS - tasks to bring up during our weekly EOS leadership meeting
• Presentation techniques - this is where snippets and ideas picked up from other presenters go

When tasks are initially created in Asana they often don’t yet have a project or priority (I’m not thinking about that when I first create the T tag in a meeting note). My EA adds them to Asana and then we run through them as part of the weekly review to categorize them into projects (goal is for every task to go into a project). It’s usually a red flag if a task doesn’t have a project to ask the question of if the task should be done at all.

I create tags with specific people’s names on them - typically my direct reports or anyone I’m interacting with regularly. Any time I have something I need to delegate or discuss with one of these people, I add a task about it and tag it with their name. When I sit down with that person I just bring up the list of tasks tagged with their name and I have a ready made agenda for our meeting. In my shorthand during a meeting I use:

“T - Will - talk about financial report” for adding a task that is tagged to “Will”. When I next meet with Will I have a list of topics to discuss already in hand and have avoided sending him a flurry of tiny emails throughout the week.

Business Card Handling

Using the Hill 88 Asana iPhone app I add a task in Asana for each business card (usually with the title ‘card’) assigned to my EA. If there are special actions to take with the card I add that shorthand to the task title (like L for sending a LinkedIn connection). In that task I attach a picture of the card (taking it right then in the app). The expectation is that the card is added to the CRM system within 24 hours and any actions noted are recorded as well.

Calendar & Scheduling

My EA owns my calendars and I try to stay out of scheduling anything directly. I will ask her to own picking times for discussions and coordinate with other execs or their assistants. If I need to schedule something myself I let her know that I added it in case she had a time out floating for someone else to schedule in.

I use 4 separate calendars for keeping track of my work life. First is the general ‘work’ calendar that contains a majority of calendar events. The ‘work’ calendar is the one primarily shared with other team members in the company. If an event is occurring after 5pm or on a weekend, I also use a ‘work evening’ calendar. The ‘work evening’ calendar is shared with my wife so she can see things outside the normal work day without having the noise of the rest of the day. This works well for my travel details for example.

My third calendar is ‘evening’ for anything personal, also shared with my wife. This calendar requires a deep level of trust with my EA as it has things like my tennis league and family events. Having this knowledge my EA can proactively ask great questions to see if I need help or need to do anything ahead of these events.

The final calendar is called ‘notes’. This is a private calendar with my EA on which parallel events to scheduled meetings are included. Every meeting on the ‘work’ calendar should have an entry on the ‘notes’ calendar with the overall goal and purpose of the event and any special reminders. As I’m moving through 10-20 meetings in a day it’s invaluable to be able to check the calendar for a quick reminder of how I met the person I’m about to sit down with or why exactly I’m meeting with them. Events on this calendar are typically short titled with something like “G - Mike” which will contain the goal of the meeting with Mike.

If a calendar event changes significantly (time shift, attendees), something new is added or something removed that is going to occur in the next 24 hours, my EA will notify me via iMessage of the change too. I look at my calendar at the start of the day and have a plan for that day. If something changes I may not notice it without this update notice and end up with a last minute surprise I haven’t prepared my thinking for.

If I have a call scheduled with someone the event notes will clearly state who is calling whom (I typically prefer to be the one making the call) and what phone number to call that person on (again, just a tap on the number in iOS dials the call).

If the event is a meeting with someone, we put both my cell number and theirs in the note so that if anything happens last minute we both have easy access to contact the other participant.

Any calendar event with an address on it needs to have the address in the notes field at the very top (not in the location field). This makes it touchable on the iPhone to jump right into maps with that address. The address shouldn’t contain a suite number in the part that will be touched so that needs to be moved below like:

Lextech
1431 Opus Place
Downers Grove, IL 12345

Suite 200
Ask for Alex

That calendar entry will be blue on the iPhone and touchable. Note the blank line after the address just to be sure it recognizes the address. If the suite number was listed above or the format is different than that it won’t be touchable or even worse it could point maps to the wrong location (I’ve seen maps choke on a strangely formatted entry and try to take me to a different part of the city).

Near Zero Time in Email

I strive to stay out of email almost all of the time. My EA triages everything and determines when she can insert herself into a conversation or run with directly. Anything scheduling related or something that another person is more appropriate to handle is tackled without me worrying about it. Any emails I do need to be aware of are either added as Asana tasks for me to work on or if they’re urgent, I receive an iMessage alerting me to something critical. This means my EA and I strive to never email each other (that’s what Asana, Slack or iMessage are for).

When sending outbound emails that I want to know the response directly myself, I append a couple special characters to the end of the subject line of my outbound email. I added a rule to the AwayFind tool to watch my emails for those characters and I receive a push notification on my iPhone alerting me to the message so I can jump on it. I also configure AwayFind with key email addresses that I want to be alerted about immediately.

All emails should be linked in the CRM system to the person involved. That means checking to see if someone is already the CRM at a different prior company and updating their contact information (with my data going back into the late 90s most people have changed companies a few times). Anyone not in the CRM gets added along with any contact info in their email footer.

If a conversation is related to a business opportunity, that should also be linked (and created if necessary) in the CRM.

All emails should be linked to the CRM, whether mine or the EA’s. That way we both know what was last said to someone and can act accordingly. This is a place to quickly confuse someone if both of us are reaching out or saying something different because the email wasn’t linked.

iMessage vs. Slack vs. Asana

The general rule for how my EA and I communicate is based on the urgency of the item and if it is a part of a project. We use a couple tools and avoid email at all costs.

Using comments in Asana is the target whenever possible. That keeps a conversation related to a task/project in one place for easy reference and access to prior information or other tasks in the same project. When handing a task back and forth, we will enter a comment in the task and then assign the task to the other person. For example, if I need research on a company I’m talking to, I’ll create a task asking for the specific type of information I need and assign it to my EA with a due date. If I wasn’t clear or the information coming up in the research prompts a question, my EA will add the question as a comment and assign the task back to me. I’ll see that task in my Asana inbox, add a comment to answer the question and assign it back to her.

For something more generally discussion related we use Slack (questions about desired travel options or a quick heads up about a news tidbit related to a client.

iMessage text messages are used for urgent communications related to today’s schedule, someone arriving at the office or other time sensitive items.

Travel

Traveling can add a lot of stress if the right information isn't available when it's needed. With some standard formats and expectations, I have what I need right in my calendar.

Flight entry format

MDW SW #1234 8:30am - FLA 11:15am ABCDEF
(Origination airport) (airline) (flight #) (local departure time) (destination airport) (local destination time) (confirmation number)

The times in the title are local times so I can sanity check an entry and never be worried about if the calendar adjusted or not. Having the confirmation number in the title makes it quicker to get to.

Start/end time
The take off and landing times needs to match up with the local times my phone will automatically change too. For the example above going from central time to eastern time the event would need to be created from 8:30am central to 12:15pm central.

Notes
The confirmation number is usually the only note.

In addition to the flight itself, calendar events are created for the travel time to the airport, time in security, time at the gate and boarding. That way if there is a call I have to take while traveling we can target it for time during travel or gate, not in the midst of security. We typically use:

My travel to the airport is about 45 minutes so I target to be heading out from home or office 3 hours before the flight. I’d rather have a few extra minutes at the gate than ever be rushing around. It just takes a lot of stress out of the travel equation and gives me time to catch up on things at the gate.

Flight time - 3 hours to -2:15 hours travel to airport
-2:15 hours to -1:30 hours security
-1:30 hours to -30 minutes time at gate
-30 minutes boarding

For any travel to/from airports with a car service, the driver’s name and number (or the service number) goes in the notes of the travel to/from airport event so it can be tapped on the iPhone to dial it.

All travel items need to be duplicated on the ‘Work - evening’ calendar so my wife can see them as well (even if they’re during normal work hours).

Wrap-up

I’m always looking at ways to improve communication and coordination with my EA. I hope that this overview of the process we’ve created so far is helpful to those with the same desire to scale up their productivity.

If you have experience with other tools or processes that have helped you be more effective working with an EA, please share them.