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How to Write a Crushing Cover Letter

If you're looking for a new ed leadership job for the upcoming school year, now is the time to put together a cover letter that crushes it.

What do I mean by “it”? The competition. I hate to say it, but it's the truth.

Too many cover letters are milquetoast, run-of-the-mill statements of fact that do nothing—nothing—to get the applicant in the “yes” pile.

If you want to land your next admin job, you've got to ace the cover letter. (Read on for a free downloadable template)

The Cover Letter's Job

The cover letter's job is to get you into the “definitely interview” pile.

If your cover letter fails to do its job, the whole process stops. You're out of the running.

You can only write a solid cover letter if you understand its purpose. Your cover letter is NOT:

  • An explanation of the simple fact that you exist and are interested in the position
  • A narrative restatement of your résumé
  • A note to the reader that you possess the minimum legal requirements for the position

No, no, and no! Cover letters that only cover the basics don't give the reviewer any useful information. They fail to do their job…so you fail to get your job.

Don't Be Perfunctory—Sell Yourself

This is hard for us to do as educators, but in your cover letter, you've got to sell yourself as hard as you ever will.

This doesn't mean that you:

  • Brag or boast
  • Make unsupported claims
  • Explicitly say that you're the best person for the job

…but you need to make the reader come to the inevitable conclusion that you're the best person for the job.

I've read tons of cover letters that waste space with perfunctory, vague, and ultimately worthless niceties that fill the page, but don't help the reader fill the job.

Understand that you're actually doing the reader a favor by making a clear, strong case about yourself. Most of the time, reading cover letters is a total waste of time for the person reviewing applications, because they don't actually say anything enlightening about the applicant—and as a result, they all sound the same.

This is a mistake to avoid, but it's also a huge opportunity for you. Write a strong cover letter that sells your candidacy, and you'll stand out above the rest.

Don't Duplicate Your Résumé—Bring It To Life

The place to list your certifications, degrees, and years of experience is in the résumé. Your cover letter has a different job.

When it comes to qualifications, your cover letter should:

  • Connect the dots for the reader—always explain how the qualifications you're highlighting actually make a difference. For example, “My extensive experience working with teachers as an instructional coach has allowed me to develop both the expertise and the relationship-building skills that it takes to be a principal who is truly an instructional leader.”
  • NEVER mention minimum qualifications, e.g. “I have a beginning principal's certificate from XYZ university”. Nothing screams “rookie!” like a cover letter that brags about meeting the job's minimum requirements.
  • Frame your qualifications in terms of benefits for the organization, and especially for its students, e.g. “My passion for restorative justice compelled me to lead the development of a behavior intervention program that reduced out-of-school suspensions by 63%.”

In other words, don't just share facts that are in your résumé (and certainly don't share facts that don't make you stand out).

Tell a story. Put the picture together for the reader, so they see how qualified you really are, and what a good fit you'd be.

For another take on your cover letter, check out this episode of Principal Center TV:

Download My Ultimate Cover Letter Template

I've created a simple, one-page template for you to follow as you craft your competition-crushing cover letter.

It's not a fill-in-the-blank deal—in fact, you won't be using any of my words. But you'll have a paragraph-by-paragraph guide to what your letter should accomplish.

Download »

5 The 48-Hour Brevity Challenge

I got this reply from a Principal Center Professional Member this week

"Just a question: Do you answer all of your emails personally? If so, I am very impressed!"

I do, but there's no need to be impressed.

It's just a straightforward application of the High Performance Triangle:

  • Strategy: Keep replies short, use stock phrases, and know when not to use email
  • Tools: TextExpander (more on this below); the phone
  • Habits: Inbox Zero; saving stock phrases

You probably answer most of your own email too, but chances are good that it takes more time than you'd like.

So I want to present you with a mini-challenge, to help you use email more effectively as a communication tool, while fitting it into less of your day.

To "sign up" for this challenge, just read on and leave a comment below. We're keeping it very simple.

An Email Response Mini-Challenge​

  • Try to go a day without sending any emails longer than 5 sentences 
  • Try to use no more than 20 different sentences, total (like Dr. Seuss did in writing Green Eggs and Ham with only 50 different words)
  • Save all of these sentences that you use for the day in a document

Too often, we try to use email for purposes it's not great for. There are some conversations that simply need to take place over the phone or face-to-face. No amount of wordsmithing an email can substitute for a real person-to-person voice conversation. 

And even when email is a great communication medium for the job, one message can't do everything. We aren't being considerate of the reader when we send messages that:​

  • Are far too long to be comprehended easily
  • Contain multiple action items or questions
  • Contain unfinished thinking...and the expectation that the reader will do the rest for us​

If you're writing in your diary, ramble on all you want, but if you're communicating, clarity is key. Clarity facilitates brevity, and vice-versa.

So if you want to ensure that you're being clear, hold yourself accountable for being brief.

If you want to go all-in on this idea, you can do what my friend Larry Fliegelman does and add a five.sentenc.es footer below your email signature:

Q: Why is this email five sentences or less?

A: Because brevity is the soul of wit. http://five.sentenc.es

If you need more space, send a separate email—it'll make replying easier for your recipient. Even better—talk in person if you can't cover the issue in five sentences.

Now, how can you crank out those five sentences even faster, without sacrificing clarity?​

Stock Phrases

Have you ever noticed that the older we get, the more we tend to use the same words and phrases over and over again? I realized I was doing this, at the ripe old age of 27, when I heard 5th graders repeating things I said on the playground—in a good-natured mocking tone, of course:

"OK, everybody, time to line up. All right, here we go, har har har..."

I'm pretty sure I didn't actually say "har har har," but even as a first-year principal, I had already established enough of a pattern that kids could joke about it.

We might think we're going around spouting unique gems of wisdom, but 90% of the time, we're saying the same things we always say—because they're relevant to the situation.

Of course, we can craft new phrases whenever we'd like.

But it's much easier, cognitively, to recognize a situation and retrieve the relevant response.

Here are some stock phrases I use frequently—not because I don't mean them or because I'm insincere, but because I've already decided how I want to express these ideas, and there's no reason to start from scratch:

Thanks for writing.

Let me know if I can be of assistance at any time.

Could we set up a quick phone call to talk about this?

Let's talk about this in personstop by when you get a chance.

Sounds good!

Let's put that on the agenda for our next meeting.

See you then!

Talk to you soon.

Let me know how it goes, and let me know if you need anything.

Thanks for letting me know about this situation.

I share your concern about this, and am committed to addressing it

Feel free to borrow from my list, but you'll no doubt come up with your own list very quickly.

A quick word on objections: many people resist this strategy because it seems insincere to re-use whole sentences.

I disagree: you're already doing this—just not on purpose.

See if you can answer all of your email for two days with just 20 phrases. As you write, save these phrases to a document, or copy and paste if you're re-using a phrase.

Your Challenge Starts Now

In the comment box below this article, share a stock phrase or two.

Then, strive to answer all of your email for the next 48 hours by:

  • Limiting all outgoing messages to 5 sentences or less 
  • Using no more than 20 different sentences, total, in all of your messages
  • Saving all of these sentences in a document

Give it a try, then come back and leave a 2nd comment and share how it went. If you leave an initial comment, I'll reply personally (remember how I'm good at that? :)) so you remember to report back. 

Going Further​

I've been building this habit for a long time, and I personally don't save my stock phrases in a document; I save them in an app called TextExpander, which speeds up my typing dramatically.

TextExpander can be a bit intimidating to set up, which is why the challenge above suggests just keeping a document open on your computer as you write.

But when you're ready, TextExpander is amazing. According to my stats, it's saving more several hours a month—time I'd otherwise just be typing, instead of thinking and getting other work done. It has helped me so much that we have a full course on it in our Members' Dashboard.

 You can sign up any time to get full access to my best strategies, detailed video tutorials on the tools I use, and (of course) how to develop habits for high performance in the work of school leadership.

How Habits Work

Show Transcript
Hi, I'm Justin Baeder. In this video, we're going to explore precisely how habits work. This is a critical area for increasing our performance in just about anything we want to get better at.
Throughout the day, about 40 to 50 percent of what we do is governed by habits. Think about the moment you wake up in the morning. You probably go into the bathroom and brush your teeth without even thinking about it.

You probably get in your car and drive to work without even thinking about your route. It's that fact that you don't really think about how to execute a habit that makes habits so powerful. Now, that's also what makes habits a little bit dangerous, because it's very easy to get into unhealthy habits, work counter-productive habits.

The power of habits can work for us, as well, because we can purposefully develop high-performance habits. I want to show you, now, how habits actually work. Habits start with a cue. We're going to draw this first as a loop.

If I have a cue, that can be anything in the environment. That can be a feeling like hunger. It can be the time of day. It can be an alert that you receive from your Smartphone. Just about anything can serve as a cue for what's called the habit loop.

I'm drawing on some research that's represented in Charles Duhigg's excellent book, “The Power of Habit” for this part of the presentation. The cue triggers, what we would call, a reaction or what Duhigg calls a sequence.

This is, basically, a sequence of behaviors that you carry out in response to the cue. Now, that can happen very rapidly, and it happens without a lot of thinking. Again, that's key to this actually being a habit. You don't have to think. You don't have to put forth conscious effort to carry out that sequence.

It just happens, because it's encoded in your brain. It may be encoded in your muscle memory, like driving to work. You just know where to turn. Once the sequence has been ingrained in your brain and in your muscle memory, it can be fairly difficult to change.

One of the reasons it's so difficult to change a habit, once you've learned it, is the third factor which drives the whole process, and that is the reward. Now, the reward shouldn't be confused with an effect or a consequence.

The reward is something that's almost always a feeling. It's almost always something that you experience internally after taking the actions in the sequences. If you're hungry, if hunger is the cue, and the sequence is having a snack or eating a meal, the reward is that you're no longer hungry.

That reward could be a new feeling, like the feeling of being full or the removal of some negative feeling. Some negative cue like hunger. In the classic, habit loop, this is drawn as a cycle. So cue leads to sequence leads to reward, and then we're back at cue.

That's how Duhigg describes it in the diagrams in his book. It's not actually so simple a cycle. There's another step that's omitted from a lot of the diagrams that I've seen about this, and that is anticipation.

Anticipation is what allows the reward to trigger the behavior in the future. When you experience the reward that reloads the anticipation for next time. Next time you experience the cue, you'll then experience anticipation. Then, you'll carry out the sequence which leads to the reward.

We can erase this arrow between reward and cue, because the reward doesn't cause the cue. We can erase the arrow between cue and sequence, because it's actually the anticipation that's triggered by the cue, and that triggers the sequence.

Let's go ahead and modify our diagram here a little bit. We can erase the arrow between reward and cue and between cue and sequence. What we have now, is no longer a loop. It is a better model of how habits actually work.

Once you understand how habits actually work, you have a lot of different leverage points for breaking bad habits, changing existing habits, and creating new habits for high performance.

Let's talk about how we can influence each element of the habit model. Now, a lot of the cues that you experience on a day-to-day basis are going to happen. They're outside of your control, because they're outside influences.

They're the time of day. They're things that other people do. We can't always prevent or control the cues, but what we can do is we can sometimes preempt them. We can say, “OK, at a certain time of day, I know I'm going to get hungry, so before that time of day, I'm going to have a healthy snack so I'm not tempted to just have some candy.”

The second thing we can do is we can seek to modify the anticipation. If you're anticipating something that's going to trigger a destructive sequence of behavior, then what you can do, is set up a negative consequence for yourself.

I have some examples in the habit guide that you'll find, also on this page that you can download, to go through some exercises on this. The sequence is where we usually focus when we're trying to modify a habit.

The golden rule of habit formation is to take an existing cue, an existing reward. Say, the cue is hunger and the reward is feeling full. Change the sequence. Maybe the sequence that I've been using is, “I'm eating a bag of chips to make myself feel full.”

It's pretty easy for me to substitute in a different behavior, a different sequence, and eat a salad, if that will trigger the same reward. Now, the problem with that is often that change of sequence, changes the reward that we experience.

It doesn't trigger the same kind of habit that we were trying to change. Then finally, let's look at the reward. If we're trying to develop a new habit, we may need to pick out a meaningful reward that we're going to be able to look forward to.

If we're going to install a new sequence, if we're going to commit to a new behavior, it's helpful to pick out a reward that we can anticipate so that we can reliably carry out that habit and make it a part of our daily practice.

Now that you have a model for how habits actually work, I want to challenge you to think about a habit that you want to develop, a habit that you want to eliminate, and a habit that you want to modify, and think to yourself, “What's the cue? What's the anticipation? What's the sequence, and what's the reward?”

What's the best point of leverage for modifying each of those habits so that you can get the results you want and perform at the level that you want to as an instructional leader?

I'm Justin Baeder. Thanks so much for joining me for this video.

Download the “How Habits Work” PDF Guide


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