What’s the grammar rule for this?

I’ve been asked questions like this numerous times. The person asking wants a black or white ruling, but the “correct” usage is often very gray. And very often, there is no “rule” but rather a choice to make, either on the part of the author or the editor.

The Chicago Manual of Style has a Q&A section each month in its online version of the guide. This is from the April 2013 Q&A section:

Q. Where in the manual will I find guidance to answer the question whether the adverb structurally in the phrase “structurally modify or upgrade” qualifies only the verb modify or both the verbs modify and upgrade? I have looked at paragraphs 5.143 through 5.161 (15th ed.) but don’t perceive the guidance I need.

A. Alas—the great and powerful manual cannot tell you what this writer was thinking. The only way to know for sure is to ask him or her. If you don’t have access to the writer, then you will have to settle for ambiguity. If you need to know the exact meaning because you’re involved in a lawsuit whose outcome depends on the technical meaning of this phrase, you’re at the mercy of the judge. If you are the judge, well, good luck.

So how do I decide what is the “right” answer? If I am not the author, I ask the author for more information. If I am the author or the editor, I try to write the sentence a different way to see if that changes the meaning or intention of the sentence. I review my source material to be sure I understand what it is I’m supposed to be writing about.

When I was studying French in college, the professor would ask us to answer a question about usage, and then ask why we think our answer was correct. The point was to help us learn how to apply the variety of rules one needs to know to speak (or write) French without sounding like a 2-year-old French child. I don’t recall the exact question now (having to do with liasion), but I gave my answer and then the professor asked, “Why?” I replied that “it just sounds right.” I heard mumblings from fellow students about how stupid my answer was, but the professor said, “Yes! You got it! It sounds right to you, because you’ve absorbed the rule and can apply it instinctively!” (Then he proceeded to ask the mumblers to cite the rule.)

Every day, we apply “rules” of grammar, sentence structure, and style based on our experiences. If we had to “look up” everything, we’d never speak, let alone get any writing published. Those of us who have studied grammar, sentence structure, style, etc. write and edit based on years of writing and editing a variety of works, making mistakes, learning from those mistakes, and remembering the corrections. I can’t cite every rule (I wasn’t an English major), but I know enough about it that if you need a ruling, I can Google the answer for you. (Or better yet, Google it yourself. You’ll remember it better that way!)

We don’t always have a written rule to follow. Styles don’t follow rules (other than the rules set by the person who wrote the style guide.) Do you think e. e. cummings followed rules and styles? Of course he did! But it was a style of his own making, which is not wrong (in poetry) when you apply the style consistently. Usually, we follow the rules for the type of writing that we are writing or editing. That is, the rules for writing technical user guides are not the same as the rules for writing poems or advertising copy (“Got milk?”).

And sometimes we have to go with our gut—or with whatever looks or sounds right.


There, Their, They’re, It’s OK!

Even experienced writers occasionally write the homophones (words that sound the same but have different meanings) there, their, they’re, and even there’re incorrectly. They don’t usually make the mistake on purpose; they just aren’t paying attention. When I’m writing an email or text, I don’t give it the same care and attention I give a user guide or technical article, so my fingers will often just type what sounds right. And since they all sound the same, you can’t really blame the fingers. For those of you who consistently get it wrong, here are a few tricks to help you remember which form to use without having to think too much.

It’s neither here nor there.

There (usually) references a location. The book is over there on the table. There contains the word here, which also references a location. If you replace there, their, or they’re with here and the sentence still makes sense, then there is the correct word. For example, The book is over ______ on the table. If you put here in the blank, The book is over here on the table, that makes sense, so the correct word is there.

Dude, where’s their car?

Their is a possessive pronoun: their car is the car that belongs to them. Her is also a possessive pronoun. In the sentence, Dude, where’s _____ car, you can insert her, so the correct word is their.

Who’s here? They’re here!

They’re is an easy one: if you’re saying they are, then the contraction they’re is the correct word. The trick for this one, if you really need one, is  Who’s here. They’re here. Who’s is a contraction and so is they’re. Or, using our tricks for there and their, Here here doesn’t make any sense (in this context) and Her here sounds like a toddler, so they’re must be correct. There’re is also a contraction, for there are. If in doubt, take it out (the apostrophe)!

Let us review:

  • It’s neither here, nor there. If you can replace the word with here, use there.
  • Dude, where’s their car? If you can replace the word with her, use their.
  • Who’s here? They’re here. If you mean they are, use they’re. (Or don’t use a contraction.)

The main point is to review what you’ve written before you send/publish it. (I’m sure I’ll find all of my errors tomorrow.)

A Review of (American English) Grammar, Spelling, Punctuation, and Usage


My degree is in communication, so I’ll start with a basic theory of communication. In simple communication, there are a minimum of four components: sender, message, medium of transmission, and receiver. A fifth component is often, unintentionally, introduced: noise. Rules of grammar, spelling, punctuation, and usage are an attempt to reduce the noise in communication.

Note: Many “rules” that we learned in school were actually style choices that were printed in books and then set as “rules.” Feel free to break some of these rules in your writing, but never forget your audience.

American vs. British English

Why do I say “American English”? Aside from the commonly known differences in terminology (bonnet vs trunk, torch vs. flashlight, lift vs. elevator), American English and British English have several differences in basic grammar and punctuation. For example, in American English, a comma always, always, always goes inside the quotation marks (unless doing so would confuse the reader). Similar rules apply to other punctuation in or out of quotation marks, and the types of quotation marks used (single or double). In British English, you will also hear phrases such as “The team are meeting to decide on the next play.” In American English, group nouns such as team are treated as singular. So, the same phrase in American English is, “The team is meeting to decide on the next play.” (I hear the narrator on “Mythbusters” often saying, “the team are” and it drives me batty!!) There are numerous websites dedicated to the differences between American and British English, so I won’t provide all the gory details here; just be aware that the information below is reflective of American English usage.

Grammar is:

  • The study of the way the sentences of a language are constructed
  • The establishment of rules based on norms of correct and incorrect language usage
  • Knowledge or usage of the preferred or prescribed forms in speaking or writing

Common Errors

  • Relying too heavily on spell check
  • Relying at all on grammar check
  • Not reviewing your work
  • Writing the way you speak
  • Believing that since you’ve “seen it that way before” it must be correct

Spell Checker

Spell check only checks the spelling of words; it doesn’t know if you’ve chosen the correct word. I suggest leaving the spell check feature turned on, however, so that typos are underlined in red for your attention (in Microsoft Word). (When in doubt, use a dictionary–or hire a tech writer!) Below are several words that are often misused.

Word Meaning
accept, except accept: to admit or agree; to regard as normal or usual, true, or right; to take in stride [a verb]; except: to exclude; an exception to [preposition]
affect, effect affect: to influence, to pretend (verb) “to affect change”; effect: a result (noun), to accomplish or bring about (verb) “to take effect”
alternately, alternatively alternately: in turn; one after the other: “We alternately spun the wheel in the game.”; alternatively: on the other hand; one or the other: “You can choose a large bookcase or, alternatively, you can buy two small ones.”
all ready, already all ready: all is ready; in a state of readiness; already: existing, completed
all right, alright all right: [correct form]; alright: [incorrect form]
will, shall will: to promise, to require to; shall: to make an absolute promise (a stronger form of will)
advise, advice, inform advise: [verb] to offer suggestions; advice: [noun] an opinion or recommendation; official notification; inform: to provide information
between, among between: for two things [as a general rule]; among: for more than two things [as a general rule]
biweekly, semiweekly biweekly: once every two weeks; semiweekly: twice each week
can, may can: is able to, is capable of; may: has permission to
compliment, complement compliment: to praise; to say something favorable, kind, or flattering; complement: something making up a whole; work in accord with; suit well
comprise, compose comprise: to include or contain “The whole comprises the parts.” (The phrase “is comprised of” is always poor usage.); compose: to form by putting together”The parts compose the whole.”
continual, continuous continual: repeated frequently, lasts but with breaks or pauses; continuous: without interruption
discreet, discrete discreet: prudent, knowing when to be silent; discrete: separate, disunited, discontinued
further, farther further: more, additional (to further an idea); farther: distance
fewer, less fewer: a number; fewer than 10 items; less: a quantity or volume; less water
imply, infer imply: to suggest or hint [done by the speaker]; infer: to surmise or conclude [done by the listener]
insure, ensure, assure insure: to protect; ensure: to guarantee; assure: to pledge or make safe [used with people]
lie, lay lie: to recline in a prone position [used with people]; lay: to put or place [used with objects]; Lay is transitive, associated with a direct object — “Lay that pencil down.” “Yesterday, I laid that pencil down.” “That pencil has been laid down.” Lie is intransitive—“Lie down.” “Last night, I lay down.” “It was my plan to have lain down already.
like, as like: similar to [a literal comparison]; as: in the same degree or amount
precedence, precedents precedence: precedes or comes first; takes priority over; comes before; precedents: plural of precedent; a standard or norm, or a significant event that is a turning point
principle, principal principle: a fundamental law, doctrine, or assumption [a noun]; principal: most important or influential [an adjective]
regardless, irregardless regardless: in spite of, without concern; irregardless: no such word! Do not use it! (“without without regard”?)
stationary, stationery stationary: solid, unmoving; stationery: a piece of paper
that, which that: preposition used with a dependent clause that contains essential information; which: prepositions used with an independent clause that contains nonessential information
a while, awhile a while = noun phrase “A while later…”; awhile = adverb “Sit for awhile longer.”
since, because since should be used only to refer to time; because: by reason of; EFFECT, because CAUSE
regrettably, regretfully regrettably: unfortunately; regretfully: full of regret
persuade, convince persuade: motivate someone to do something; convince: lead someone to understand or believe
may, might may is factual or possible (or permission); might is hypothetical
libel, slander libel is written defamation; slander is spoken

Grammar Checker programs

Here is an example of a sentence that was marked by grammar checker as having errors:

The managers of the organization meet each morning.

Grammar checker suggested the writer should use meets instead of meet; however, meet applies to managers, not organization, so “managers meet” is correct, not “managers meets.” Grammar checker assumes the writer will place modifiers next to the words they modify, which is normally a correct assumption.


Many words and phrases are misused so often, we sometimes forget which is the correct usage.

Incorrect Correct
Please try and finish the report on time. Please try to finish the report on time.
The report simply alluded to the problem, rather than stating it clearly. The report simply eluded to the problem, rather than stating it clearly.
The discrepancy in the report eluded the author. The discrepancy in the report alluded the author.
The wind tunnel did not effect her hair style. The wind tunnel did not affect her hair style.
(affect is a verb)
What affect did it have? What effect did it have?/What was the effect?
He was already to start work on the project. He was all ready to start work on the project.
He was ready to start work on the project.

different from vs. different than

In formal writing, the preposition from is used with different.

  • The fourth-generation computer is different from the third-generation computer.
  • Different than is acceptable when it is followed by a clause.

Than vs. Then

  • Than is used for comparison: One is smaller than two.
  • Then is used for time: First I’ll go home, then I’ll put my feet.

Whom vs. Who

If you can use him/them, you should use whom:

  • Do you need to call him?
  • Whom do you need to call?
  • You need to call them?
  • You need to call whom?
  • “Who ya gonna call? Ghostbusters!” s/b “Whom ya gonna call?” But in this case, its obviously informal communication.

Who, Which, That

Who refers to persons. That and which refer to animals and things. That, rather than which, should be used with restrictive clauses.

Hint: If you can surround it with commas, use which.


After John left his house, which is on the corner, he went straight to work. (nonrestrictive)
A company that diversifies often succeeds. (restrictive)

Latin Words and Phrases

ad hoc (for this) no hyphen: The ad hoc committee will meet this Thursday.

per diem (per day) no hyphen: The field service reps will be paid $30 per diem.

i.e. (id est, that is): The big dog (i.e. the Golden Retriever) is sick.

e.g. (exempli gratia; for example, such as): Big dogs (e.g. Golden Retrievers and Great Danes) make great family pets.

sic (thus) verbatim: “I aint gonna (sic) do it!”

Mixed Construction/Parallel Sentences

Mixed construction occurs when a sentence contains grammatical forms that are inconsistent with one another.

  • I will check your report, and then it will be returned to you. (active to passive voice)

To make it parallel, change it to:

  • I will check your report, and then I will return it to you.

The bulleted list that follows is not parallel:

The following recommendations were made regarding the position statement:

  • Stress that this statement is for all departments
  • Start the statement with “If the company”
  • The statement should emphasize that it applies both to department managers and staff
  • Such strong words as obligation, owe, and must should be replaced with words that are less harsh

To make it parallel, make each bullet an imperative (do this, do that):

The following recommendations were made regarding the position statement:

  • Stress that this statement is for all departments
  • Start the statement with “If the company”
  • Emphasize that it applies both to department managers and staff
  • Replace such strong words as obligation, owe, and must with words that are less harsh.

Note: In a list, use bullets for steps that do not have to be completed in any particular order. Use numbers ONLY if the steps must be completed in that order:

  1. Open the microwave door.
  2. Insert food.
  3. Close the door.
  4. Select cook time.
  5. Press Start.

Where possible, only put one step per bullet. If there is only one item, it should not be in a bullet. Either make it into a sentence or note, or add more bullets.

Sentence Structure

Identify the parts of speech in the following sentence: John often throws beach balls with his feet.

Subject Adverb Verb Adjective Direct Object Prepositional Phrase
John throws balls
John often throws beach balls with his feet

(Compare: The beach balls were thrown by John. Balls is now an indirect object.)


A coordinating conjunction is used to join parts of a sentence or to separate clauses that are equal in rank. Using coordinating conjunctions makes the reading more smooth, less choppy. For example: He was angry. He got over it. He was angry but he got over it.
  • and
  • or
  • but
  • for
  • nor
  • yet
  • so
Correlative conjunctions are coordinating conjunctions that are used in pairs. Correlative conjunctions need parallel sentence elements. For example: He was not only handsome, but also very intelligent.
  • either, or
  • neither, nor
  • not only, but also
  • both, and
  • whether, or
Subordinating conjunctions connect sentence elements of varying importance. Although no one will actually follow her advice, she spent hours putting together the grammar presentation. The phrase “Although no one will actually follow her advice” is subordinate to the phrase “she spent hours putting together the grammar presentation.”
  • Most common are:
  • so
  • although
  • after
  • because
  • if
  • where
  • than
  • since
  • unless
  • as
  • before
  • though
  • when
  • whereas

Dangling Modifier

Phrases that do not clearly and logically refer to the proper noun or pronoun are called dangling modifiers. They are usually caused by overuse of the passive voice.

  • While eating in the cafeteria, the computer malfunctioned. (Was the computer eating in the cafeteria?)
  • While the operator was eating in the cafeteria, the computer malfunctioned.
  • The man rented a house with his son, which cost $400 per month. (Did the son cost $400/month?)
  • The man and his son rented a house for $400 per month.


Personal pronouns refer to the person(s) speaking or being spoken to or about. I am very tired right now.
  • its
  • them
  • they
  • his
  • he
  • your
  • you
  • mine
  • me
  • I
Demonstrative pronouns must have an antecedent. I keep finding typos in this presentation. (Presentation is the antecedent, i.e. the word to which “this” refers.)
  • this
  • that
  • these
  • those
Relative pronouns link a dependent clause to a main clause. I am the technical writer who created this presentation.
  • who
  • whom
  • which
  • what
  • that
Interrogative pronouns ask questions. Who am I?
  • who
  • whom
  • what
  • which
Indefinite pronouns specify a group of person or things rather than a particular person or thing. All good things must come to an end.
  • all
  • any
  • another
  • each
  • both
Reflexive pronouns indicate that the subject of the sentence acts upon (reflects) itself. (See examples below this table.)
  • myself
  • yourself
  • himself
  • herself
  • oneself
  • themselves
  • ourselves
  • itself
Intensive pronouns act like reflexive pronouns but give emphasis to their antecedents.  I myself asked the question.
Reciprocal pronouns indicate the relationship of one item to another. People should always respect one another.
  • one another
  • each other

Compare the following sentences that use personal pronouns:

Incorrect Correct
Me and him went to the store.(Me went to the store?) He and I went to the store.I went to the store.He went to the store.
He went to the store with she and I.He went to the store with she.He went to the store with I. He went to the store with her and me.He went to the store with her.He went to the store with me.
Please call my assistant or myself to make an appointment.Please call myself to make an appointment? Please call me or my assistant to make an appointment.Please call me to make an appointment.

Personal pronouns and gender-specific wording

There is no singular personal pronoun in English that refers to both sexes. He is traditionally used when the sex of the antecedent (the noun that he refers to) is unknown. The use of a masculine pronoun (he/his) to refer to both sexes can be offensive. It is better to rewrite the sentence in the plural or avoid use of a pronoun altogether. (Many American and English writers [Shakespeare, Shelley, Dickens] have used they and its forms to refer to singular antecedents, but it’s considered a “no-no” by many editors.)

  • The engineer cannot do his job until he understands the concept.
  • Engineers cannot do their jobs until they understand the concept.
  • The technician should take care in choosing his equipment.
  • The technician should take care in choosing equipment.
  • If we hire another nurse, she could help us complete the task.
  • Hiring another nurse would help us complete the task.

While we’re on the subject of offensive phrases…

Based on a survey of 7,500 managers and executives enrolled in writing programs, the following phrases were deemed offensive:

  • “To be perfectly honest” suggests that everything else has been dishonest.
  • “Needless to say” contradicts whatever follows, so skip it.
  • “Enclosed herewith, please find” is wordy and dated; substitute “enclosed is” or “enclosed are”
  • “As you know,” “as you are aware,” “as per our conversation” are unnecessary and may sound insulting; omit them.
  • “I am writing this letter to inform you” states what is obvious to the reader.
  • “Please rest assured” sounds “as if you’re asking the reader to take a nap,” said survey respondents.
  • “Please be advised that” wastes time and says nothing.
  • “At your earliest convenience” and “as soon as possible” are too vague; provide a specific date.
  • “If you should have any further questions, please do not hesitate to contact me” is overused. Find a fresher expression, such as “Please call if you have any questions.”
  • “For your perusal,” “review,” “consideration” are outdated and pretentious. All of these phrases should be avoided by contemporary business writers.


Anything that modifies a noun functions as an adjective.


Indefinite Definite Demonstrative Possessive Numeral
  • a
  • an
  • all
  • none
  • some
  • any
  • the
  • this
  • that
  • these
  • those
  • my
  • his
  • her
  • your
  • our
  • their
  • two
  • first
A dog was barking. The dog was barking. That dog was barking. My dog was barking. Two dogs were barking.


Just as body language cues us in to what another person is saying, so does punctuation clarify what is written.

Commas are used to:

Introduce a word or phrase:

  • He needed only one thing, encouragement.
  • (Or: He needed only one thing: encouragement.)

Separate independent clauses:

  • He did not like his work, and his distaste for it was evident to everyone.
  • (Comma optional here. Since they are two independent clauses, they could also be two separate sentences.)

Enclose parenthetical words, phrases, clauses:

  • Note, for example, the illegally parked bus.

Indicate omission:

  • He takes his work seriously, himself lightly. (He takes is omitted in the second half.)

Make a series more clear:

  • I request that all of my worldly goods be split equally between Jim, Jacob, Sarah, and Susie. (Each gets 25%, right? Well, maybe 20% each–the lawyer gets his share, too!)
  • I request that all of my worldly goods be split equally between Jim, Jacob, Sarah and Susie. (Do Jim and Jacob each get a third, with Sarah and Susie sharing the other third? The law says, yes.)


Ellipsis dots are not used to introduce a series or a bulleted list. Do not use ellipsis dots for any purpose other than to indicate omission, such as when quoting a source from which you have edited words. Be careful when you do omit words to not change the overall meaning.

  • The letter states “the programmer and the developer must create a system flowchart.”
  • The letter states “the programmer … must create a system flowchart.”

Quotation Marks

Both double (“) and single (‘) quotation marks are for enclosing words, phrases, clauses, sentences, paragraphs, and groups of paragraphs. Quotation marks are used for:

  • Direct quotations
  • Lengthy direct quotations
  • Change of speaker
  • Titles and names (Underlining or italics s/b used in word processing)
  • Quotation w/in a quotation

Place marks correctly with reference to other marks. (British usage is exactly reversed from American usage.)

The comma and the period always come inside the quotation marks.

  • “Well,” he replied, “I’m not sure.” Then he inquired, “What do you think is fair ?”
  • He referred to it as a “gentlemen’s agreement,” but to me it was sheer ” bunk.”

A question mark, exclamation point, or dash come outside the quotation marks unless it is part of the quotation, as in the first example:

  • “What will my starting salary be?” asked the manager.
  • Did he say, “I have enough money”?
  • The performance was a “flop”!

The semicolon and colon come outside the quotation marks:

  • Study the following in “Human Anatomy”: Bones


A colon is used for:


  • My goal in this job is simple: success.

Separation (as in subtitles)

  • Education for College: Improving the High School Curriculum

General rules of usage:

  • Never use a colon directly after any verb, or the conjunction that.
  • Do not place a colon between a preposition and its object


Hyphens may be used to avoid ambiguity and difficult reading, but if misreading is unlikely, the compound may be closed.

  • re-create (vs. recreate)
  • biomedical
  • multifaceted
  • interrelated
  • anti-inflammatory (double vowel)
  • co-opt

Compound adjectives should be hyphenated, as in

  • labor-intensive report
  • two-digit date fields
  • on-staff engineers
  • Y2K-Compliance Assessment (vs. Y2K Compliance)

New Words

Many words in common use today are relatively new, or are old words being used in a new way. Therefore, the “rules” for their use are not firmly established. Some examples are:

  • Internet (capitalized)
  • intranet (not capitalized)
  • online
  • email, e-mail, or E-mail (AKA “evidence mail” Keep that in mind when you send them!)
  • Web page (capitalized)
  • website
  • browser, site, server
  • protocols
  • logon, log on: The Logon dialog box appears. (noun); Log on to the network. (verb)

Compound Words

  • An open compound is a combination of separate words that are so closely related as to constitute a single concept, such as stool pigeon.
  • A hyphenated compound is a combination of words joined by one or more hyphens, such as mass-produced goods.
  • A closed or solid compound is a combination of two or more originally separate words that are now spelled as one word, such as notebook.

For some years now, the trend in spelling compound words has been away from the use of hyphens. This is a trend, not a rule. After they are in common use for an undefined amount of time (usually, after they make it into a dictionary), they go from being temporary compounds to permanent compounds. When a compound is used as an adjective before a noun, it is often hyphenated to avoid misleading the reader. For example:

  • Bob’s first-floor apartment is hyphenated to make it clear that you mean an apartment on the first floor, rather than it was Bob’s first apartment.
  • The phrase, sixty-five-year-old men is hyphenated to make it clear that the men are 65 years old, rather than there being 60 five-year-old men.
  • However, the phrase much loved friend is understood as is and requires no hyphen for clarification.
  • Note also that foreign words and phrases are usually not hyphenated, as in ad hoc reports.

There are pages and pages of rules and exceptions having to do with hyphenated compounds. For example:

  • half-baked plan is hyphenated (as are most half compounds) but halfway house and halfhearted attempt are not. (These are examples of temporary compounds that have become permanent compounds through widely accepted use.

By the way, words ending in ly are not hyphenated since ambiguity is unlikely.)

When there are multiple adjectives in a compound, each is hyphenated, as in Do you manage other customer- or business-sensitive data, to indicate, in this case, that the data is both customer sensitive and business sensitive. Without the hyphen, the sentence is asking two separate questions: Do you manage other customer? (which makes no sense) and Do you manage business-sensitive data?


Most of the examples and “rules” in this presentation were taken from:

  • Handbook of Technical Writing bySt.Martins Press
  • Punctuate it Right! by Harry Shaw
  • The Computer Encyclopedia by Alan Freedman
  • TheChicagoManual of Style by theUniversityofChicagoPress
  • “Don’t Use These Phrases!” Winning Strategies for Corporate Communication,Springfield,Virginia: Communication Concepts, 1991.