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How managers look at their schedules

Photo by Katie Smith on Unsplash

While cooking, an unrelated thought:

Lately I’ve been planning my time more as an employee and not like a manager. An employee plans their schedule considering only the start time and length of meetings and tasks ahead of them. A manager, on the other hand, plans time intentionally for preparation and with other people in mind and .

A small example: tomorrow, returning from winter break, my employee schedule is, for the most part, wide open. I can become overconfident in the amount of free time I have and lack urgency because it appears all of my tasks could get done within the day.

However, a lately dormant manager mindset kicked in and said my overconfidence is wrong. Returning from break, you and your colleagues will want to talk about one another’s breaks. Tasks that weren’t done before break could suddenly become urgent and spring up, needing to be done immediately. It wasn’t hard to recall what those tasks might be. Suddenly my calendar isn’t as free as I thought.

A small example but not unlike cooking. Cooking can’t be a sequential activity where you do only one thing at a time in the order you want to do it. Making dinner without anything getting cold requires preparation, coordination, and consideration for what time is needed based on the ingredients you have. Our challenge is, then, how to plan accordingly.

Using a paper planner in 2018

An old planner, in those innocent days before smartphones have nearly wiped them out.

A strange thing is happening for a lot of us productivity geeks: we are nostalgic and pining for a paper-based planner while quickly adapting to having our phone and smart watches ping us to tell us where to be and when.

All the while we know that extra steps are counter-productive to efficient organization. Yet the allure is still there.

Typically you’ll find you already have to-do systems around you. Your inbox, calendar, and more than likely an app. Siri or Google Assistant are useful for adding miscellaneous tasks and setting location-based reminders.

Given this, a paper planner should be added to your routine once you realize you are likely adding extra steps and you are comfortable with the time this will take.

 The wrong way to pair paper & digital planners

For a while I tried using a basic dot grid Baron Confidant notebook as my paper planner. I wrote in all my tasks and priority events/appointments that day. I previewed my e-mail inbox to gather tasks from there and get a sense of what were my priorities.

It was a total waste of time.

There is no point in copying down events from your Outlook calendar when they’re already there and one-third are likely to change. E-mail should never set your priorities for the day, and when they do, it’s easy to click the priority button than write it down. Finally, seeing tasks from e-mail and then writing it down duplicates work and causes mental fatigue. Like the Getting Things Done rule says, if it’s two minutes or less, just do it right away and get it over with. No use adding it to a planner.

In first attempting to use a paper planner, I wasted valuable minutes trying to outline my entire day in a planner when I could have been acting on those quick hits or getting started on the important work that was due that day. Luckily I found a compromise that worked and my Confidant planner because much more useful.

 My “right” way of using a paper planner

I use Baron Fig’s 2018 planner to write my work priorities, not collect every task.

I quickly became tired of fighting the digital systems that were already there and working just fine. E-mail, unfortunately, is my top to-do list. OneNote is familiar because I use it for work and grad school and since most meetings (also unfortunately) are run from a laptop, the app is there and I type faster than I write.

So I shifted and found success in using my planner more for mindset than checklist. Now I write down my top 3 goals for the following day at the end of every work day. These are the 3 tasks that, no matter what, I am determined and need to complete. I find this helps me schedule my day accordingly and push myself to not let my e-mail take over those gaps between interviews, meetings and events. (Side benefit: I look at e-mail less, which is objectively a great thing.) Doing this at the end of the day works great for me because my focus and concentration tends to be best in the mornings and so I do actual work rather than writing about the work I should be doing. I also find therapeutic value to it: by writing down my goals, it’s not floating in my brain as an unresolved to-do. The act of writing it down lets me know I’m committed to it and so I spend less idle time in the evenings coming back to work.

My paper planner also becomes my place to record my long-term habits and see streaks in my habits so I (hopefully) continue hitting my goals. In the monthly view, I draw simple icons to represent going to the gym, closing all the activity rings on my Apple Watch, and reading for 20 minutes. At the end of every month I then tally up and divide by number of days in the month.

So what planner do i use?

As I mentioned before, I used the Baron Fig Confidant notebook as my to-do list. I love the dot grid layout and having less of a formatted layout made it versatile. However, this year I decided to get a formal planner so I could record my habits without having to write out a calendar space. I love Baron Fig’s 2018 planner because it’s well-designed, minimalist, and the format gets out of the way. I’m interested by the recent trends in planners to prompt people to reflect as well as plan — such as the Best Self Co.’s planner — but ultimately I don’t foresee myself wanting that daily prompt and a planner should not add any stress or fatigue.



2017 Fiction & Nonfiction Recommendations

This year was more about reading textbooks and peer-reviewed journal articles but somehow I found time to squeeze in a few books as well. Two books stand out and conveniently one is fiction and the other’s non-.

Fiction: My Absolute Darling by Gabriel Tallent

I’m not sure I would read this if I just looked at the book jacket or an Amazon review. It came as a recommendation from my sister Larraine and I’m glad I followed her advice. My Absolute Darling is an extremely challenging read; it centers on an 8th-grade girl who calls herself Turtle and lives off the grid in NorCal with only her father, as he “prepares” her for a post-society world. Turtle’s dad sexually abuses her and there are many scenes, whether sexual, psychological, or physically violent, where I cringed as I read. Through that, though, is a book where you learn about a unique, brave character whose voice is so clear it becomes ingrained in your mind and you think about her long after you’ve read the last page.

Non-fiction: The Gatekeepers by Chris Whipple

Part of our post-election delusions is that someone might be able to control Trump. It wasn’t Priebus, Jared, Ivanka or now Chief of Staff Kelly. The Gatekeepers is about the history of the Chief of Staff position and covers Chiefs of Staff from the Nixon White House to Obama’s. The book covers failed approaches like the “spokes of the wheel” model used and abandoned by Gerald Ford or having no Chief at all, which hurt Carter. It also gives insights into how Chiefs mold their office and approach depending on the Presidency as well as how Hillary and Obama made Chiefs of Staff course-correct early Presidencies. I’d recommend this book if you’re into politics, organizational design, management/leadership, and team dynamics. I shared more details about The Gatekeepers in an earlier post as well.

My other 2017 reads:


  • Homegoing
  • The Last Novel (re-read)
  • Harry Potter and the Order of the Phoenix


  • Work Rules!
  • The Everything Store
  • The Happiness Industry
  • A More Beautiful Question
  • Chaos Monkeys
  • The Coaching Habit

One down, one to go

Last year on December 15 I was accepted to Regis University’s MBA program. In the past year I’ve taken classes in project management, business law, leadership, HR, and accounting/finance. I’ve also met a great cohort and received a high level of support from the Regis staff.

With one year left until I graduate, I feel anxiety about what I should learn next. Maybe this is what Reid Hoffman, founder of LinkedIn and host of the podcast Masters of Scale, would consider a drawback from being an infinite learner. Ideally I would find a scholarship to attend graduate school for free, possibly Penn State’s online Organizational Psychology program, but that’s doubtful. The two options I zeroed in on, then, became either learning Spanish or code. So, much to the delight of my Middle and High School self, I’m going to pick up coding again and learn Swift.

Graduate school was never a given for me and equally improbable was that I would attend a Jesuit program. I continue to be surprised by the doors that fortunately open for me, and how often those doors reconnect me to earlier themes in my life.

The Gatekeepers

“It has the most awesome responsibilities of any corporation in the world, the largest budget of any corporation in the world, and the largest number of employees. Yet the entire senior management structure and team have to be formed in a period of seventy-five days.”

This is the intro to The Gatekeepers, a book from Chris Whipple about Chiefs of Staff in recent history, starting with H.R. Haldeman in the Nixon White House and ending with Denis McDonough in Obama’s. The Gatekeepers is a quick, fascinating read and doesn’t necessarily require you to be interested in politics. If you are interested in Organizational Design, how you manage competing power structures, and the ultimate coaching up situation, you will highlight many excerpts and take away several lessons.

My intention is to give a broad overview and not any sort of Executive Summary-like substitute for reading the entire book. In fact, if you’re reading the first two parts and find yourself enjoying it, just go ahead and purchase the book right away. I could have knocked it out in a day.

Finally, most of the excerpts I’ve selected are focused around the discipline and structures that Chiefs of Staff did — or didn’t — maintain in the White House. While the book covers several policy and political moments in recent history, it ultimately came  back to the dynamics in the White House that either diffused or poured gasoline on these events.

. . .

How the Chief of Staff position was created

When Ike made his first entrance into the Executive Mansion, the story goes, an usher handed the new president a letter. ‘Never bring me a sealed envelope!’ Ike barked. Nothing, he decreed, should come to the president without first being screened by someone he trusted. Soon Adams was installed as the president’s gatekeeper—and the first White House chief of staff was born.


The “Spokes of the Wheel” system doesn’t work

From the start, Gerald Ford’s White House resembled a kids’ soccer game, everyone running toward the ball. Ford had announced that he would govern with eight or nine principal advisers reporting directly to the president—a circle, with Ford at the center. He called it “the spokes of the wheel.” But the result was chaos and dysfunction.

As Ford wrote later: “I concluded he was right. The ‘spokes of the wheel’ approach wasn’t working. Without a strong decision-maker who could help me set my priorities, I’d be hounded to death by gnats and fleas. I wouldn’t have time to reflect on basic strategy or the fundamental direction of my presidency.”

Carter, who many regard as the most intellectual President in the modern era, didn’t learn from Ford and the errors of decentralization.

The day after the election, Watson gave a memo to the president-elect, titled “Some Thoughts on Organizing the Executive Office of the President.” At the beginning at least, I think your five to eight top aides should be equal in their status, salaries and access to you. In effect, you should act as your own chief of staff. There is no way for you to predict how your choices for the top jobs will cope with the unique challenges of the White House. If a “first among equals” naturally emerges later, and you decide that designation of a chief of staff would help you, you can name him then. Watson would later admit that he had trimmed his convictions to match Carter’s. “What I believed was that the chief of staff was imperative for a smoothly functioning White House, but that was not going to happen.”

White House staff would be surprised at how many large memos Carter would read in one night, returned with corrections on typos. Clearly not the way a President should spend their time, but Carter, even after his Presidency, maintained that his early research did not show any clear result that a Chief of Staff was a necessary position.


Baker as the model for successful Chiefs of Staff

Baker, who served as Chief of Staff under Presidents Reagan and Bush 41, is widely considered to be the most effective Chief of Staff since the role had been conceived. A few key tenants of his leadership follows:

  • Surround yourself with really good people. “The most successful managers are those that are secure enough to surround themselves with extremely strong-willed, talented people.”
  • Focus is essential. Baker created three goals in the Reagan agenda, and all three were tied to the economy.
  • Know when to say “no” to the President.
  • In Baker’s bible, preparation was the first commandment. He wrote everything down, logged 16-hour days, and returned every phone call, no matter the hour.
  • Maintaining a servant leadership mindset. “The people who don’t succeed as White House chief of staff are people who like the chief part of the job and not the staff part of the job,” says Baker. “You’ve got to remember that you’re staff even though you’re powerful.”


How Clinton and Obama express disappointment

This passage is a sad “what if” for me. Bill Clinton ran an undisciplined White House early in his first term and Hillary, “with lawyerly precision,” explained the unhealthy and unproductive dynamics hampering the President’s agenda. Hillary can be knocked for campaign staffing issues but I doubt that would carry into governance:

The first lady’s frustrations finally came to a head at a meeting ostensibly called to discuss a gas tax. Instead, it became a day of reckoning. With lawyerly precision, Hillary Clinton delivered a brutal critique of White House management. The economic team and the political team were not communicating. The communications team was ineffective. She was furious. “This is unacceptable and unfair to Bill,” she said.

And this excerpt about Obama, at a low point in his Presidency when the demand of web traffic caused the Healthcare.gov site to crash when it was unveiled. Obama knew he had to take the blame but from the beginning he asked McDonough to have weekly status updates to make sure the technology was there and the site could handle the traffic:

[Obama] did a slow burn. He did not yell—which only made McDonough feel worse. “He didn’t say much. That was the problem. If I could’ve had it out with him—that’s better, you know? Finally, he said, ‘Look, I asked you to put together a meeting a week. I said at the end of the meeting what I needed. And this is what I got. What the hell?’

. . .

I reflect often on my experiences as a member of a team and a leader of teams. Teamwork has many variables that require a constant, mindful attention toward balance. If you have a laissez-faire mentality, leadership and delegation leads to decentralization, which will often lead to a clot in some area within the organization. On the flip side, a dictator will often engage the wrong behavior and lead to both sides digging in their heels. Teams in that space play a low-stakes game because fear and lack of commitment prevent them from doing truly amazing work.

My takeaway from reading The Gatekeepers is how discipline is the most important function for a Chief of Staff. Discipline determines the systems, processes and efficiency that leads to outcomes. While our decisions are not dictating the world stage, we can learn so much from the organizational effectiveness of a disciplined White House.


My favorite time writing was freshman year of high school. It wasn’t when I paid thousands of dollars to go to college and joined the paper. It wasn’t in my 10+ years of writing fiction that tried too hard to be Faulkner and accomplished only his run-on sentences but without the art.

Freshman year was when I blogged for the first, and longest continuous, time. It was before Blogger itself, when you needed to know code.

What made writing great then was I had little to no expectations. Whatever I thought I wrote and what I wrote I lightly edited before hitting publish. Over time I learned how to improve my writing and learned how much I liked to set aside time for it. There was a small community of like-minded geeks and it was thrilling when they added a link to your site on their sidebar. That was it. That was the milestone and the rest was just writing, as it should be.

. . .

The second-longest blog I wrote is still around on Tumblr, and it’s relatively recent. It was when I moved to Philadelphia at age 25 to work in education and it lasted when I moved back to Denver. Between high school and my move to Philly there were many false starts in writing, many blogs that are now gone with the services that hosted them.

With my Tumblr it was easy to come back and start posting again. Throw up a photo, a quote, a link and even if no one else clicked the heart you could always go back through the archives and there was an adequate notebook for you to review. It was a rare break from the posturing and branding we find ourselves constantly doing online these days.

Tumblr was started, like almost all Internet services, as an independent company that was swallowed up by a larger company (Yahoo) before that larger company stalled and was absorbed by another large company (Verizon). Sadly, it’s not hard to imagine Tumblr getting data mined for profits before disappearing.

. . .

I bring up these stories to explain why this blog exists and why it’s self-hosted. I want a place to think and write about organizational culture, leadership, and why we commit ourselves to missions. I want this to be at a place where my writing isn’t considered content that is monetized and then validated through likes, hearts, and stars. I want a corner of the Internet where this exists for however long I choose to pay. My favorite part of the Internet isn’t social media apps and services; it’s independent blogs. 1

Like my Tumblr before this, I’m excited for the index of writing, links, quotes and photos that will accumulate over time for me to review. Extra points if it ends up being a resource for you and others from time to time too.

Here goes.