The Fundamentals of Time Management

Mastering the Calendar: An Intro to Time Management 

When I started supporting Dick Costolo at Twitter as an executive assistant, day 1 on the job was my first experience calendaring for someone. Hard to believe they trusted me with so little experience and without any training. Make no mistake, I quickly realized that an organized and well-managed calendar is the foundation to successful time management which leads to a successful executive.

There is no doubt that we have all seen the pitfalls of a disorganized calendar. One-on-one meetings get scheduled over or meetings getting double booked. Having your executive go in and out of the office wastes a ton of time. If you have a fire drill, everything gets pushed to later in the week.

Time organization is the most critical component to calendar organization. I also advocate for healthy calendar habits in Do Not Schedule time, commonly referred to as DNS. This will allow you to break the bad habits and to create room for the good ones.

Dick and I had a great process we established early on to communicate setting up meetings. I’ll share with you our pro-tips, broken down into three comprehensive parts.  

Getting Organized Starts with Proper Time Organization

First and foremost, no one should be allowed to book anything on your executive’s calendar, including the executive. Anything that goes on without your permission should get declined. Without this element of control the calendar is out of control. I am not asking you to be a gatekeeper. Quite the opposite. I am asking you to create the right boundaries to ensure your success, and the success of the person you are supporting, Once people know you are their advocate and want to help them find time with your executive, they start going through you for everything. This builds trust with other team members all while giving you the control you need to create well organized days and weeks for your executive. 

Prioritizing the days of the week is your first step at a well organized calendar and exercising your responsibilities as an administrative executive. When we have a hierarchical approach to the week, we can easily find times that work and what will not. This will make room for the meetings that matter the most. 

Most of the executives that I have worked with find Mondays to be overwhelming. They are backlogged with emails from the weekend, have a ton of requests they need to sort through for the week, and also a list of to do’s on their mind. Imagine feeling this way, and then finding out you have to be out of the office on a Monday?

Make Monday the highest priority day. This means everything scheduled on Monday is a meeting your executive needs in order to accomplish their priorities for the week.

Move all Tier 1 one-on-one meetings to Monday

  • This requires you to discuss with your exec to distinguish their top-tier players. You most likely need to divide their direct reports and put tier 1 on Monday and tier 2 on Tuesday.
  • Staff meetings should always fall on a Monday
  • High priority project check-ins
  • Most importantly, create a time block (30 mins to 1 hour) for DNS time to catch up from the weekend. If you need to give that time away for a meeting, you have a time slot to provide weekly.

Tuesday becomes a day for Tier 2 one-on-ones and allows for rescheduling one-on-ones from Monday. You can easily reschedule over Tier 2 meetings without feeling a huge sacrifice. 

The key is to create a program that works for your executive. A weekly routine creates what I like to call FLOW.

Flow is when a day is set up to make sense and the exec has smooth transitions from one thing to the next. I often spent my early mornings at Twitter trying to create flow before Dick got in to review his schedule. If there was something out of the ordinary, such as a quick coffee meet up outside the office that wasn’t moveable, and he only had five minutes to get back to the office, we discussed it ahead of time. He knew what to expect and we agreed on the madness together. This sets the expectation that disorganization is not the norm and you aspire to have a daily FLOW that works. How else can anyone get anything done!?

Designate days your executive can easily have meetings out of the office. For example, if that is Tuesday and Thursday afternoon, the executive will start to catch on to the routine and will start to offer up those days to their business partners. As we know, going outside the office wastes a ton of time. Once you have designated days, you will offer up those days first when scheduling with other EAs. 

There will always be fire drills and meetings will need to be rearranged.

By having a prioritized calendar, you can move a group of high priority meetings over to a day that has easily moveable meetings. Here are some additional ways prioritized days of the week can drastically improve the flow of your executives calendar:

  • Creates clear openings for booking travel 
  • Time optimization for being in and out of the office
  • High priority meetings and projects don’t get rescheduled over
  • Creates openings for deep work 

Your executive’s schedule is often dictated by inbound requests and your decisions dictate the flow and organization of their day. Be rigorous about the schedule, only prioritizing the meetings your executive needs to have to move the company’s strategic initiatives forward successfully. In other words, what the exec NEEDS vs what people WANT. 

How do I become a Chief of Staff (COS)?

If you are an Executive Assistant, you may be considering becoming a Chief of Staff (COS). You may be wondering:

  • If I am a senior Executive Assistant, should I be working towards a promotion to COS?
  • Do I have the skills to move from Executive Assistant to Chief of Staff?
  • What will be expected of me?
  • What does this mean for my career? 

There are a lot of questions that go along with starting the journey to becoming a Chief of Staff. So, let’s get started!

A Chief of Staff may be defined in a few different ways. I’ve outlined the various types of COS roles and how they ladder up and contribute to the success of an executive, a team or a business. Read more about this in my post about defining the role of Chief of Staff. If you are a CEO looking to hire a Chief of Staff, I’ve also got you covered with these tips from my previous post. 

If I am a senior EA, should I be working towards a promotion to Chief of Staff?

I’d like to turn this question back on you. After reading through the blog about what a Chief of Staff is and what they do, do you feel like you are already doing a lot of this same work?

If your answer is “yes,” then: YES you should be working towards this title promotion. A lot of the work I was already doing in my role as Dick Costolo’s executive assistant was at the Chief of Staff level. Having that title promotion set me up for future work in that role and allowed my peers and colleagues to look at me as more of their partner in the goals we were trying to achieve. 

If you are not quite there in the Chief of Staff responsibilities, start to work towards this by making the first step by embedding yourself in understanding and helping your executive to tackle their priority work. Understanding your executive’s priority work will not only change the way you tackle your job on a day to day basis, but it will also change how your executive tackles their own work. This makes you indispensable to them in getting their work accomplished.

Being a Chief of Staff is being a partner.

How can you work toward becoming a Chief of Staff? You can take gradual steps to position yourself. Here are some high-level tips you can implement right away to begin making that transition:

1. Become an integral part in helping your CEO set priorities and tackle them. Priority Setting – every week your CEO needs to get a bunch of stuff done and you are the conduit. Take a step back, have you gone over with your executive what they need to accomplish over the next 6 months. It could be a key hire for a VP Engineering or managing the communication around a product launch. Regardless, you need that list and that acts as your weekly/daily guide on what to prioritize, refocusing your CEO daily on the key items they need to accomplish. Pretty soon you will be the roadmap to getting shit done.

2. DNS (Do Not Schedule) Working Time: The only way to get shit done is to find the time to do it. Carving out 1-2 hours of your CEOs time a day to accomplish these priority items is the only way. Guard that time with your life, and your exec will actually feel like you are there to help them succeed. Because now you have found the time for them to actually get work done. Imagine that. Going to work and being able to actually accomplish this, instead of sitting in meetings all day listening to people talk about what they need from you.

As a CEO, do I need to hire a Chief of Staff?

The role of a Chief of Staff (COS) is so important. I recently reflected on the various types of Chief of Staff roles and how a COS contributes to the success of a team and business. The CEO’s right hand position is absolutely pivotal in any company. Read more about this in my previous blog post. here

A CEO’s success completely hinges on how their Chief of Staff or Executive Assistant helps them tackle their priorities to ultimately help them succeed. A COS is leaned on to make sure things that cross the CEO’s desk are handled the right way. They ensure people are being taken care of, and that the company goals are met. 

Are you a CEO looking to fill a COS position?

As you think about what you need, and the daunting task of finding that perfect person to fill this role, here are some quick tips that can help in your search:

1. Often the person you need already exists in your company.

Finding someone who understands the company, what it took to get there, who the players are, and understands the product already is most helpful. There is a long learning curve to overcome if you are asked to be a leader behind a leader without knowing much about the company.

2. Look for people that are confident, business minded, humble – almost egoless, and a great communicator.

You want this person to have zero ego in it. They should just want to help you and the company succeed. Often this is why when I explain the two types of Chief of Staff roles. The Management Consultant never stays in the role longer than two years because they want to become the boss, and their ego gets in the way. More detail from my first post here. 

3. Don’t discount a potential candidate.

If you have an incredibly good executive assistant already, but are worried they might not have the right business experience to take on this role, I encourage you to NOT discount their abilities. Sometimes just enough business sense, mixed with good EQ (emotional quotient), and project management skills is all they need to get going as a Chief of Staff. 

If you aren’t familiar with the concept of EQ, check out this comprehensive article from the Harvard Business Review, where they define EQ as “the self-awareness of emotions, both others’ and your own.” 

The only major differences in the role they have now, and the new role, is being able to hold their own with other business leaders in the company. Can they work alongside your team to execute on a project? Have they earned the respect and trust needed to get shit done

Now it is time for you to get out there and hire a Chief of Staff. What are you waiting for?

What is a Chief of Staff, and what do they do?

Over the past decade, I have seen a gradual pick up in the number of Chief of Staff (COS) roles supporting CEOs within the tech industry. In the past three years, this number has picked up dramatically and I am seeing a trend that CEOs sometimes hire a COS before they even hire their assistant.

I often get asked for advice about how to get the most out of your COS. Let’s start by defining the role.

So, what are the types of Chief of Staff Roles? There are two types of COS roles:

1. The Management Consultant

This is more like a business operations (biz ops) role, someone who specializes in management consulting, has an MBA, or is looking to get their MBA. They have a 1-2 year shelf life in the role. They dig into organizational inefficiencies to help provide data to support business decisions.

  • The COS takes on special projects that are high priority for the success of the business that the rest of the executive team doesn’t have time for. They act as the center of gravity, pulling all the pieces together from various teams to execute on the project.
  • Example: Company Z needs a new revenue channel to boost earnings from 100M to 120M by the end of this year. COS takes this and starts to route through different channels in the Sales, Business Development, and Marketing orgs to pull together a few hypothetical models that could work. Once the direction is chosen, the COS might help to assemble the team and launch the new revenue strategy alongside the head of sales, until the head of sales can take it over.

2. The CEO’s “Right Hand”

The majority of my experience, and what I have seen be most successful in an organization, is this type of Chief of Staff role. I am calling it the CEO’s Right Hand, because the COS is completely integrated into the CEOs priorities to help them succeed.

At a high level, they are leaned on to make sure everything that comes through the CEO’s office gets done the right way. They ensure people are being taken care of and that company goals are met. This role is far more satisfying then the first. 

What does the Right Hand Chief of Staff do?

If you are a CEO reading this and wondering what you need to be successful, look no further. You need a Right Hand Chief of Staff that will help you succeed.

This role covers three main areas:

Area 1: The CEO’s Success

Focusing on the following:

  • Priority setting
  • Delivering on goals
  • Time management
  • Communication with the Executive team & overall company

Area 2: The Team’s Success

  • Take on strategic projects for the team, as needed. The key here is the project shouldn’t take the COS too far away from their daily tasks that support the CEO’s success (area 1). The COS should still be accessible. Often times, this means no direct reporting…only facilitator-type work.
  • Support communication up the stack to the CEO, and help team members prepare and understand what the CEO wants to know, including prep for meetings, and one-on-one meetings.
  • Ensure the team is working well together. Mitigate office politics and create a transparent environment.

Area 3: Company Culture

This last area can be flexible and more adaptive to your environment. However, due to the nature of being very close to information at the top, the COS can be vital in understanding where the disconnects exist. It is really important to facilitate messaging from individual contributor to the CEO. This can help in a number of ways, such as encouraging (or repairing!) a healthy balance of communications, work and fun within a company culture. Specific activities include:

  • Putting an ear to the ground to understand where things are falling through the cracks. The COS needs to be proactive in understanding the issues and seeking to facilitate a solution.
  • Assisting in communicating to the company, through steering the messaging based on what people need.
  • Fostering a healthy culture through the right amount of communication, gatherings and team building.
  • Relationship preservation with key original employees who may not get as much face time with the CEO.

The Chief of Staff role is such a vital part of any organization.

Don’t just take it from me. There is proof in nearly every successful organization. In fact, I enjoyed reading about Julia DeWahl’s experience and recommendations about the role, and encourage you to check out her recent post on Medium. Julia was the COS at Opendoor when the company grew from 200 to 800 employees in a year! And, this is just the tip of the iceberg. If you want support, training or coaching, join the mafia via the link below.