CHAPTER FORTY

CREATING A PERSONAL OPERATING SYSTEM

Without question, your time is your scarcest resource. There is only one of you in your company—and you can't hire a second you. Figuring out how to get the most out of your day is a critical skill. Figuring out how to optimize your team is an incredibly important part of managing yourself.

In this chapter, I'll discuss managing your agenda, managing your calendar and managing your time. Think of these three sections in descending order of abstraction. Managing your agenda means understanding generally what you're supposed to be doing. Managing your calendar means making time for those things. Managing your time means being as productive as possible at those things as well as doing all of the important (or unimportant) distractions that invariably come up in your day.

While I'm going to talk about a few different tools for managing my time throughout this chapter, I generally refer to all of these tools together as my Operating System. Just as your company has an Operating System, you should have one, too.

MANAGING YOUR AGENDA

Having a really tight Operating System starts with having a really tight agenda. Your agenda is your job description, overlaid with a sense of current priorities. (If you're struggling with the overall picture of your job description, this book should have been a good starting point for you!)

Here are some questions I keep in the Agenda tab of my Operating System document:

• Strategy. Are we doing enough here to build sustainable competitive advantage?
• Plan. Do we have the right plan in place to scale revenues and profits?
• Market. Am I spending enough time with clients, resellers and partners?
• People. Do we have the right people? Are we investing enough in development?
• Culture. Is this an awesome place to work? Are we staying nimble enough?
• Execution. Are we executing on our plan? If not, why not?
• Financing. Is there enough cash in the bank? For how long?
• Board. Do we have the right directors? Am I using them enough?
• Me. Am I doing enough to learn and grow as a leader?
• Current. What's most important, right now?

In my To Do tab, I input the answers to all of those questions—especially “What's most important, right now?”—and turn them into tasks and projects. Each item on the To Do tab has a due date for its next step. That column is color-coded around its deadline (red = “Today/Past,” yellow = “Upcoming in the Next Week,” white = “Further Out in the Future”). The column is sortable by topic area as well as due date. Again, this spreadsheet is up on my second monitor all day long, so any time there is a spare moment, I can review it and start working on the critical upcoming items.

Once a month, I go back, review the Agenda tab, make sure it's current, then review the To Do tab to make sure it flows from the Agenda tab.

Since my agenda is, in some respects, the company's agenda—and since I follow David Allen's principles in Getting Things Done of having all of this stuff listed in one place—my Excel document has a series of other tabs in it as well:

• Delegated. This tab tracks all tasks I assign to others on my team, with next steps and due dates (color-coded, as in the To Do tab). It's an easy mechanism for following up and making sure things are getting done on time.
• Company scorecard. This tab lists the company's scorecard and stated goals for the year or the quarter, so I can easily check on this as I'm assigning tasks to myself or others.
• Development plans. This tab lists my and my direct reports' development plans so they're also handy for one-on-one and staff meetings. A development plan doesn't do anyone any good unless it's being actively reviewed and worked on.
• Networking. This tab lists everyone I need to meet, internally (skip-levels) and externally. It has specific columns for location, so my assistant and I can schedule meetings in a given city when I travel there, as well as desired frequency of meeting, with the simple logic that turns a “schedule” flag red when it's time to set something up.
• Thoughts. This is a catch-all tab that lets me write stuff down as it appears in my head. I review it every month or quarter when I reset my agenda.

All-in, tight management of your agenda, with whatever system you use, is a critical starting point for managing your time.

MANAGING YOUR CALENDAR

With your overall agenda set, you can now start planning out your calendar in weeks, months, quarters and even a full year. Here are some of the key building-block elements to my calendar and how I think about them in relation to each other and to the rest of my Operating System (note that these track pretty closely with some of the main elements of the Company Operating System that I described in Chapter 17):

• Board meetings. These have to get locked in early and tend to be anchor points for other things going on at the company.
• Staff meetings. Whatever your meeting routine is, mark off the big staff meetings—like quarterly offsites or all-day meetings—early. We usually schedule offsites sometime about a month prior to a board meeting to make sure we're hitting execution points and surfacing issues we need to discuss with the board.
• All-hands meetings. It's good to mark these off so other people can schedule around them. At Return Path, they typically follow board meetings by a week or so, since we use board materials to prepare for them.
• Company events. Summer party? Holiday party? Community Service week? Whatever the events, you will want to schedule around these as well.
• Staff 1: 1s. I usually set these as recurring appointments in my calendar, though not all staff members have the same length of meeting or frequency.
• Blocking off work time. I know some people who block off a handful of hours in the middle of the day each day or once a week for work time, so that their calendar doesn't fill up and they can use the slot to catch up on their own work. I assume it can work but I've never been a fan of this for a CEO because time in the middle of the day is prime time for others to need access to me. My “work time” tends to be before 9 and after 5.
• Industry events. These dates are usually known well in advance and almost always involve travel.
• External things. If you're on outside boards or have a CEO forum or something like that, you will want to note all of those dates in advance.
• Vacations. Critical to plan these out early, even if there's no natural forcing function like kids' school calendars to align to. If you don't map them out and keep the dates clear, you will never take time off.

MANAGING YOUR TIME

Having the major building blocks of your calendar set for a year or a quarter means you're likely to avoid scheduling conflicts with your most important meetings. That's a good start. Once you have all of that set, you can start to manage your time more effectively.

I have historically been very open with my calendar. For most of my career, people who want to meet with me, both internally and externally (with the exception of random vendor solicitation) generally have gotten to meet with me. Some of this is generosity but I'm also a compulsive networker and have always made time proactively to meet with people just to meet them; learn more about different pockets of the industry or finance; meet other entrepreneurs and find out what they're up to or help them; and connect more broadly from there. I've also routinely been on multiple boards at the same time, as I've found that's a very helpful part of my management routine.

As the company has gotten larger and more geographically spread out—and as my kids have arrived, accompanied by a house with a longer commute—I've taken to being more judicious with my time. I could probably do an even better job at it but I've started taking control much more of the minutes in my day. As anyone on my team will tell you who pops into my office, sends me an instant message or calls me, my initial response is always, “just a second,” as I insist on finishing whatever quick task or thought I'm working on before engaging with the person. I'm increasingly reducing meeting times from 60 minutes to 30 or from 30 to 15. I'm also more frequently responding to requests on my time with things like “can you send an email for starters?” so I can respond asynchronously. I have to respond to requests for meetings with the occasional “no, that's just something I don't have time for now.”

My executive assistant (see the following chapter) has been playing a larger role in helping me structure things so that I have blocks of free time during the day and I make sure I “schedule” time to work on major things that I know will take up a lot of time.

FEEDBACK LOOPS

One tool I've developed over the years to serve as a feedback loop or check on my Operating System is a simple time allocation model.

First, I am religious about keeping an accurate calendar—including travel time between meetings or on planes—and I go back and clean up meetings after they have happened to make the calendar an accurate reflection of what transpired after the fact. At the end of each quarter, my assistant downloads the prior three months' worth of meetings and we categorize them to see where my time went. Then, we make changes to the upcoming quarter's calendar to match targets based on my agenda. For what it's worth, my categories have changed over time but they have always been pretty high level. Currently, they are “Free,” “Travel,” “Internal,” “Board,” “Client/External,” and “Non-work” (by which I mean outside business activities like serving on other boards). See Figure 40.1 for a sample of this time analysis.

FIGURE 40.1 Sample Quarter-over-Quarter Time Analysis

Looking at the buckets in isolation in a given quarter isn't so useful but looking at the trends over time and comparing them to where I tell myself I want to be spending my time has been really helpful in keeping me proactive and on track. I routinely generate conclusions like “Wow! I need to cut back on travel!” or “I wasn't in-market enough last quarter.” The kinds of shifts you can make are to be proactive instead of so reactive; to cut meetings, shrink them or group them when appropriate internally; to use video-conferencing instead of travel where possible—and to be just a little more selfish and guarded with your time.