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Every Day is Bosses Day

Regardless of your position in a school district, you will always report to someone.

Teachers report to an administrator.

Administrators report to a superintendent.

Superintendents report to the school board.

And regardless of supervisor, there are always tasks to complete. Whether it’s completing paperwork, collecting information, or creating presentations, meeting a boss’s expectations is a way of life.

When a supervisor asks you to complete a task, how do you respond?

Does the request become a top priority?

Or, does the request fall through the cracks?

While addressing the needs of peers and direct reports is important, few things determine your professional trajectory more than how you respond to the demands of a direct supervisor.


In The Principal, Surviving and Thriving, Andrew Marotta discusses the importance of meeting a supervisor's expectations. Consider the following:

Take care of items and issues for your bosses right away. You cannot miss your boss's stuff. Replying to emails, attending meetings, dealing with things. In spite of whatever is flying at you, make sure you see and tend to your boss’s stuff. If you miss a couple times, they will start to doubt you and lose trust in you.

While meeting a supervisor's expectations seems like a no-brainer, many school leaders struggle with this concept. Whether it’s a missed deadline, incomplete paperwork, or an unanswered email, some school leaders have a habit of making life difficult for their boss.

“What difference does it make it if comes from a boss, a peer, or a direct report?” you may be thinking. “Isn’t everyone important?”

While responding to requests from peers and direct reports is important, replying to a supervisor's request is more important. Why? Because your boss determines your professional fate. While others’ opinions play a role in your success, your supervisor is the only person responsible for measuring your job performance.

“Yeah, but what if your boss is unreasonable?” you may wonder. “My boss sucks.”

Working for an unreasonable boss is a whole different issue and deserves its own chapter. While the rest of this section assumes you work for a halfway competent boss, understand there is a silver lining for anyone who is stuck with a horrible supervisor: you learn what not to do. Great leaders often use these personal adversities as a source of motivation … vowing never to put others in similar circumstances.

Finally, take comfort in knowing that your time will come. Given the mass exodus of people leaving educational leadership, those who stay focused and commit to professional development and lifelong learning will have their pick of jobs in the coming years.

Assuming your boss is halfway competent, let’s continue.

As a general rule, approximately 90 percent of employees regularly meet their boss’s requests. Assuming bosses have reasonable expectations, most employees meet those demands without issue. However, what about the other 10 percent of employees? What about staff who struggle to meet supervisor expectations?

Consider your school for a moment. Are there teachers who can't be trusted to update grades, turn in paperwork, or call back parents? Whether they lack organizational skills - or think a boss's orders are important - these individuals cannot be trusted to complete even the simplest of tasks.

Beyond teachers, many school leaders also struggle meeting supervisor demands. Although we assume administrators are inherently dependable, some administrators struggle more than teachers. Whether they fail to upload a report, document a conversation, or respond to an email, each district has leaders who cannot be trusted.

I once supervised a leader who constantly missed deadlines and failed to follow through on commitments. Regardless of task, I always had a hunch that I would need to watch this employee to assure duties were completed.

As a leader who preaches "Assume the positive!" and encourages workplace autonomy, having a weak link on our team was maddening. Whereas I could trust other team members to complete tasks without worry, I spent considerable time and energy asking for missing work and reinforcing expectations with this individual.

After a few years of working with this employee, I realized our partnership could not last. I was spending far too much time managing this (highly-paid) employee as opposed to doing my own work.

Eventually – using the steps outlined in this blog – this leader was removed. While dismissing an employee is hard work, replacing subpar leaders with strong performers is vitally important. Making leadership “upgrades” not only allows you to get you work done, it eliminates the stress felt by managing a poor employee.

Consider the leaders you supervise:

Is there someone who struggles taking direction?

Is there someone who creates more harm than good?

Is there someone you can’t trust to get the job done?

Few things limit a school's potential more than inept leadership.


Let’s face it: moving up the school leadership ladder is a bit of a game. As much as we wish promotion was straightforward and merit-based, politics and posturing will always play a role.

One of the quickest ways to master the game is by ensuring your boss’s work is done at a high level. Here are five key ideas to consider:

Capture: Employees must have a reliable system to track commitments. Whereas some leaders stubbornly rely on memory to recall responsibilities, efficient leaders develop a system for keeping track of duties. Notecards, post-it notes, and electronic documents all are great places to start. I prefer using a 5” x 8.25” Moleskine Notebook to track my to-do list.

Communicate: One surefire way to lose your boss's trust is poor communication. High functioning bosses demand effective communication from direct reports. Whether it be email, text, or phone call, employees must respond to their supervisor in a timely manner … or quickly find themselves in the doghouse.

Clarify: School leaders are very busy, meaning sometimes they don’t define what they need from direct reports. As was discussed in Learning Curve, highly effective employees seek clarity by asking "dumb questions.” Rather than guess what the boss is wanting, ask questions to ensure tasks are done correctly.

Control: School leaders must learn how to effectively manage the day-to-day responsibilities of their position. From a superintendent’s perspective, few things are better than principals who “keep their house in order” while limiting the major issues that leak from their building. Want to earn a promotion in your district? Learn how to put out fire before they reach your supervisor’s desk.

Check-In: Direct reports who want to ensure they are meeting their boss’s demands may want to request a recurring 1:1 meeting with their supervisor.

Employees who initiate these alignment conversations not only build relationships, they also hold their boss accountable for clarifying job duties and expectations.


National Boss’s Day is celebrated annually on October 16th.

On this day, employees give bosses cards, flowers, and gifts.

While all are nice gestures, most bosses would gladly trade employee donations for employee dependability.

Rather than celebrate Boss’s Day once a year, start treating every day like Boss’s Day.


If you liked this article, you'll love my new book Learning Curve!

Learning Curve is 360 pages and PACKED with useful ideas on leadership, education, and personal growth.



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