How to write for a bad, hard-to-please boss

Reading time: Just over 3 minutes

In the 25 years I spent as a wage slave (an employee, rather than a contractor) I had exactly ONE good supervisor. But I learned plenty about how to write for a bad boss….

I was standing in the middle of the newsroom — an open-area office with about 115 people — having a disagreement with my boss. He started to yell: “How dare you question my judgment!” he screamed, at full volume. Behind his back, we called him the Tartan Tornado or McBagpipes because he was Scottish, opinionated, loud and relentless. I quickly suggested that we adjourn to his office. Not to prevent embarrassment to me. But to prevent it for him. Because he was wrong.

Although this exchange occurred more than 25 years ago, I remember it as if it were yesterday. He was a terrible boss. But he was a bully and bullies are relatively easy to deal with if you react to their tantrums with a cool, calm demeanor.

I thought of McBagpipes recently when I received an email from reader Dennis Roberts (I’ve changed his name for obvious reasons.) Here’s what Dennis wrote: 

I work for a large corporation. Over the past several months, I have learned that my boss and I have different expectations for the writing process and what defines the “voice” of the author. In your words from your blog, I don’t have the permission to write a bad first draft (of course, I’m not talking punctuation and typos). Feedback or “editing” is often just to rewrite the entire piece. 

How do you deal with a difficult editor, publication director, supervisor, coworker that has a different style or expectation? When you work with clients, how do you ensure that you hit the target the first time?

Here is my advice for Dennis, and anyone else facing a similar situation:

1) If your boss is a bully, stay calm. Bullies like to target people with low self-esteem so don’t appear to be vulnerable. Stand tall and speak to the person calmly. If their behavior is inappropriate tell them this, neutrally. You might say something like, “You’re not describing what you want me to do. You’re yelling.” If necessary, document these conversations and report them to Human Resources.

2) Make sure you are getting very clear instructions. This MUST include:

  • A word count. (How can you write if you don’t know how many words you’re allowed?)
  • A description of the audience. For whom are you writing? What’s the male/female breakdown? What’s the average educational level?
  • An understanding of exactly what your boss wants your readers to do. Is he or she hoping to change their minds about something? Sell something? Inform?

3) Understand that most bosses often haven’t thought much about what makes “good writing.” A humourous definition of the word “editor” says: someone who knows what they want — but only when they see it. Bosses are much the same way. So, get around this problem by asking your boss to provide you with samples of writing that to him or her exemplify excellence.

Once you have the sample(s), read them carefully and slowly. Here are some questions to consider:

  • Did the writer use first (I), second (you) or third (he/she/it) person?
  • How many stories, anecdotes and examples did the writer give?
  • Is the piece written mostly in passive or active voice?
  • Does the writer favour concrete vocabulary (table, light bulbs, 2x4s) or abstract (organization, success, freedom.)
  • How skillfully does the writer manage connectors, transitions or bridges?
  • Then, run the piece through readability stats and determine the average number of words per sentence and the grade level. Ensure your own writing matches these metrics. If your boss’s favourite writing averages 20 words per sentence, aim for the same. And if it hits a grade 10 level then go for that. Ditto if it matches a grade 6.
  • Finally, copy the piece(s), word for word. (I’ve been a professional writer for more than 35 years and I still try to spend five minutes a day copying.  It’s the best self-instructive tool I know.)

Understand that “good writing” has no objective measure. It’s almost entirely subjective. Others may loathe writing that I like (and vice versa.) If you’re really having problems coming to grips with this, ask you boss to give you a fresh “good writing sample” with every assignment you receive. (If this turns around your writing style, your boss surely won’t object.)

4) Always aim to write a crappy first draft but know that no one else should see it. That draft is for your eyes alone. Why would you need permission for something no one else sees? I wonder, perhaps, if your sole mistake has been giving this draft to your boss?

5) Understand that you should always write as quickly as possible and edit as slowly as you can bear. Interestingly, good writing does not come from working slowly and mindfully. It comes from getting the first draft as soon as you can and then editing more forcefully and more frequently. Try the Hemingway app  to help yourself edit but know that you also need to read your piece, aloud — slowly — to ensure it makes sense and that the rhythm is good.

Most of all don’t let the negativity of your boss get into your brain. It’s important that you understand you can write. If you keep reciting to yourself, “my writing is no good,” or “my boss is never going to like this,” you will be sabotaging yourself.

Don’t do that! Instead, replace that shoulder devil as soon as you can (here’s how). And vow to figure out what your boss really wants. Then give it to him or her with some careful editing.

How do you deal with toxic bosses? We can all learn from each other so, please, share your thoughts with my readers and me in the “comments” section of my blog. Anyone who comments on today’s post  (or any others) by March 31/15 will be put in a draw for a copy of the beach-read novel The Vacationers, by Emma Straub. Please, scroll down to the comments section, directly underneath the “more from my site” links, below.

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