For School Executives, “How” is a Four Letter Word


“How am I going to get it all done?” he sighed.

Jeff sat behind his desk with his head in his hands, looking at the mountain of work in front of him. He was in his second year as a middle school principal and his office looked like every other school administrator’s office I had ever seen: stacks of paper all over the desk, sticky notes around the computer monitor, “CALL ME BACK” slips taped to the telephone. As his eyes darted across the endless piles of “to-do’s” he was visibly stressed and confused. “Where do I start?” he asked me.

I was Jeff’s personal Breakthrough Coach and I felt for him. I have spent my career working with administrators just like him- competent, capable educators who spend countless days and nights fighting to keep up with the daily deluge of paperwork, rather than being in classrooms doing the critical work of improving teaching and learning.

If Jeff’s situation sounds familiar, you may also have tried any number of hints, tips and techniques to manage yourself more efficiently, but none have helped you get and maintain control of your time. The problem isn’t that you have yet to find the right solution. The problem is that you’re asking the wrong question.

Two different questions

Malachi Pancoast, President of The Breakthrough Coach, asserts that it’s a school administrator’s job to keep two key questions in the foreground at all times. The first: “What results are we trying to achieve?” The second: “How are we going to achieve them?” These two questions may relate to large strategic concerns like annual test score targets, or to specific tactical moves like scheduling a meeting with a parent. In my experience, the most successful, results-oriented school leaders spend the bulk of their time answering “what” questions: “What outcomes do I want to achieve?” The ones who struggle waste countless additional hours trying to figure out “how”: “How am I going to achieve them?”

According to Pancoast, school principals serve as first-line managers in their organizations. The job of a first-line manager is to clearly articulate to staff the answers to the big “what” questions. Answers such as:

  • “We will increase 3rd grade math proficiency scores by 20 points this year“
  • “We will cut 7th grade discipline referrals in half by mid-winter break.”
  • “By the end of September, we will develop a rainy day schedule that allows students to eat and return to class without extending the lunch period.”

The job of staff is to then figure out how to fulfill on a manager’s what. This is the primary distinction between managers and staff: Managers say “what”; Staff says “how”. School leaders like Jeff who continually attempt to resolve both questions themselves end up overwhelmed and burnt-out.

The “What-How” Dance

This relationship particularly applies to school secretaries and the principals who manage them. A keen observer can watch this what-how dynamic play out between the two in either healthy or unhealthy ways by observing how site administrators complete their yearly teacher evaluations. For administrator-secretary teams who have the what-how dance down pat, the process flows smoothly. For principals who insist on answering both “what” and “how” themselves, the process is a source of endless headaches.

In a well-choreographed what-how dance, the principal makes the first move by clearly articulating to the secretary the result to be accomplished:

“I need to have all of my evaluations done and submitted by April 30, 2016.”

In this example, the principal answers the what question: “Evaluations submitted by April 30, 2016.” He then fleshes it out with details:

  • A 30-minute goals conversation with each teacher by December 1, 2015
  • Three 45-minute observations for each teacher by the end of each semester
  • A pre- and post-conference with each teacher on the day of their observation
  • Thirty minutes scheduled for me to write up each observation feedback
  • Forty-five minutes to write each final evaluation
  • A 30-minute final evaluation conference with each teacher

Once the principal declares what needs to happen, the secretary then takes the lead in determining how. As the administrator’s Scheduler-In-Chief, it is her job to open the administrator’s calendar and map out the process through to completion. She takes the long view, scheduling observations on Coaching Days and deskwork on Office Days. She notifies teachers of their appointments and prepares the paperwork for each meeting. Most importantly, she keeps her principal on track by reminding him of his stated commitment – “Evaluations done by April 30, 2016,” – and nudges him in the right direction. When she says it’s time for the goals meeting with Teacher Smith, she hands him the paperwork and the principal sits down, ready for the meeting. When she sends the principal to a classroom to conduct an observation, he goes. When the principal sees “Observation Write-Up Time” on his calendar, he shuts his office door and starts writing.

But what if the administrator isn’t in the mood to write when the secretary nudges?

It doesn’t matter. An effective administrator understands that once he has identified the destination, his secretary is then responsible for delineating and reinforcing the roadmap for getting there. When he grants her this authority and respect, he achieves the desired outcomes, minus the aggravation and suffering.

Many administrators find that letting go of the how to their staff feels counterintuitive and disconcerting. They’ve spent so many years asking themselves “How am I going to get it all done?” that this default way of problem solving courses relentlessly through their veins. They encounter paperwork on their desks and they immediately ask themselves the confounding how question. Then they spend hours, days, even weeks, stuck in the quagmire of inventing how answers. And the work piles up.

The way out: Notice when your sentences start with how, (both out loud and in your head), and immediately stop talking…stop mind-chatting. Instead, jot down the overarching purpose of your work. What are you trying to accomplish right now? Identify who on your team is best suited to support your efforts and go talk to them. Lay out the what, and humbly ask them for the how. Allow yourself to be both amazed and grateful when they fire-off multiple how’s – how’s you would have never imagined no matter how much time you spent cogitating. Then empower your people to run with their solutions and get out of the way. The more you practice the what-how dance with staff, the more adept and graceful you get at it. This translates into increased results and greater job satisfaction, in less time and with less wasted energy on everyone’s part.