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A well-crafted message is based on two key aspects: your goal and your audience. The following section shows you how to get to know both intimately.

Defining your goal

Your first priority is to know exactly what you want to happen when the person you’re writing to reads what you’ve written. Determining this is far less obvious than it sounds.

Consider a cover letter for your résumé. Seen as a formal but unimportant necessity toward your ultimate goal – to get a job – a cover letter can just say:

Dear Mr. Blank, Here is my résumé. – Jack Slade

Intuitively you probably know that this isn’t sufficient. But analyze what you want to accomplish and you can see clearly why it falls short. Your cover letter must:

❯❯ Connect you with the recipient so that you become a person instead of another set of documents.

❯❯ Make you stand out from the competition in a positive way.

❯❯ Persuade the recipient that your résumé is worth reading.

❯❯ Show that you understand the job and the company.

❯❯ Set up the person to review your qualifications with a favorable mind-set.

You also need the cover letter to demonstrate your personal qualifications, especially the ability to communicate well. If you see that accomplishing your big goal, getting a shot at the job, depends on this set of more specific goals, it’s obvious why a one-line perfunctory message won’t do well against the competition.

A cover letter for a formal business proposal has its own big goal: help convince an individual or an institution to finance your new product, for example. To do this, the cover letter’s role is to connect with the prospective buyer, entice him to actually read at least part of the document, predispose him to like what he sees, present your company as better than the competition, and show off good communication skills.

How about the proposal itself? If you break down this goal into a more specific subset, you realize ideally the proposal must demonstrate:

❯❯ The financial viability of what you plan to produce

❯❯ A minimal investment risk and high profit potential

❯❯ Your own excellent qualifications and track record

❯❯ Outstanding backup by an experienced team

❯❯ Special expertise in the field

❯❯ In-depth knowledge of the marketplace, competition, business environment, and so on

Spelling out your goals is extremely useful because the process keeps you aligned with the big picture while giving you instant guidelines for effective content. Because of good planning on the front end, you’re already moving toward how to accomplish what you want.

To reap the benefit of goal definition, you must take time to look past the surface. Write every message with a clear set of goals. If you don’t know your goals, don’t write at all.

Try This: Invariably one of your goals is to present yourself in writing as professional, competent, knowledgeable, creative, empathetic, and so on, but don’t let me tell you who you are or want to be! Create a list of the personal and professional qualities you want other people to perceive in you. Then remember, every time you write, be that person. Ask yourself how that individual handles the tough stuff. Your answers may amaze you. This technique isn’t mystical, just a way of accessing your own knowledge base and intuition. You may be able to channel this winning persona into your in-person experiences, too.

Defining your audience

You’ve no doubt noticed that people are genuinely different in countless ways: what they value, their motivations, how they like to spend their time, their attitude toward work and success, how they communicate and make decisions, and much more. One ramification of these variables is that they read and react to your messages in different and sometimes unexpected ways.

As part of your planning you need to anticipate people’s reactions to both your content and writing style. The key to successfully predicting your reader’s response is to address everything you write to someone specific, rather than an anonymous, faceless “anyone.”

When you meet someone in person and want to persuade her to your viewpoint, you automatically adapt to her reactions as you go along. You respond to a host of clues. Beyond interruptions, comments, and questions, you also perceive facial expression, body language, tone of voice, nervous mannerisms, and many other indicators.

Obviously, a written message lacks all in-person clues. For your message to succeed, you must play both roles – the reader’s and your own. Fortunately, doing this isn’t as hard as it may sound.

Unless you’re sending a truly trivial message, begin by creating a profile of the person you’re writing to. There’s a really big payoff in doing this for people who are important to you, such as your boss. You emerge with illuminating guidelines on how to improve all your interactions with him or her, as well as knowing what to say and how to say it. This helps you with your face-to-face interaction as well as writing.

When the situation involves someone you don’t deal with often, or don’t know at all, the depth of the profile you create depends on how important the results are to you. If you’re responding to a customer query, you don’t need to know his decision-making style. If you’re writing to the department head with a request, you might want to find out how much information he prefers to have, what his priorities are, and more.

Before you try profile building, it might seem daunting to characterize someone when so much that drives each person is invisible. Trust me, you know much more about your audience than you think. In the case of a person already familiar to you, your observations, experience, and intuition go a long way. It’s a matter of drawing on these resources in a systematic manner, especially your memory of how she reacted to previous interactions.

Try This: Here’s the system I recommend. For now, suppose the person is someone you know. Begin with the usual suspects: demographics. Write down what you already know about the person, or take your best guess:

❯❯ How old?

❯❯ Male or female?

❯❯ Occupation?

❯❯ Married, single, or some other arrangement?

❯❯ Member of an ethnic or religious group?

❯❯ Educated to what degree?

❯❯ Social and economic position?

After demographics, consider psychographics, the kind of factors marketing specialists spend a lot of time studying. Marketers are interested in creating customer profiles to understand and manipulate consumer buying. For your purposes, some psychographic factors that can matter are:

❯❯ Lifestyle

❯❯ Values and beliefs

❯❯ Opinions and attitudes

❯❯ Interests

❯❯ Leisure and volunteer activities

You also need to consider factors that reflect someone’s positioning, personality, and, in truth, entire life history and outlook on the world. Some factors that may directly affect how a person perceives your message include the following:

❯❯ Professional background and experience

❯❯ Position in the organization: What level? Moving up or down? Respected? How ambitious? Happy in the job and with the organization?

❯❯ Degree of authority

❯❯ Leadership style: Team-based? Dictatorial? Collaborative? Indiscernible?

❯❯ Preferred communication style: In-person? Brief or detailed written messages? Telephone? Texting? PowerPoint? Facebook or other social media?

❯❯ Approach to decision-making: Collaborative or top-down? Spontaneous or deliberative? Risk-taker or play-it-safer?

❯❯ Information preferences: Broad vision? In depth? Statistics and numbers? Charts and graphs?

❯❯ Work priorities and pressures

❯❯ Sensitivities and hot buttons: What makes her angry? Happy?

❯❯ Interaction style and preferences: A people person or a numbers, systems, or technology person? Good team member or not?

❯❯ Type of thinking: Logical or intuitive? Statistics-based or ideas-based? Big picture or micro-oriented? Looking for long-range or immediate results?

❯❯ Weaknesses (perceived by the person or not): Lack of tech savvy? Poor people skills? Lack of education and training? No experience?

❯❯ Type of people the person likes, feels comfortable with, and respects, and the reverse: Who likes and gets along with him?

❯❯ Sense of humor, personal passions, hobbies

Do you know, or can you figure out, what your reader worries about? What keeps him up at night? His biggest problem? When you know a person’s concerns, you can create more compelling messages. I am not suggesting your aim should be manipulative. Taking the trouble to think within another person’s framework is respectful. Wouldn’t you rather be addressed in a way that acknowledges what matters to you most when you need to make a decision, for example?

And of course, your precise relationship to the person matters, as well as your relative positioning and the degree of mutual liking, respect, and trust – the simpatico factor.

I’m sure you’re wondering how you can possibly take so much into consideration, or why you would want to. The good news: When your message is truly simple, you usually don’t. More good news: Even when your goal is complex or important, only some factors matter. I’m giving you a lengthy list to draw on because every situation brings different characteristics into play. Thinking through which ones count in your specific situation is crucial and rarely hard.

For example, say you want authorization to produce a video explaining your department’s work to show at an employee event. Perhaps your boss is someone who’s enthusiastic about video. Or you may report to someone who values relationships and wants to cultivate a positive environment. This boss would probably welcome a way to show staff members they are valued. Or she may be a person who likes innovation and the chance to be first in the neighborhood. To gain approval, it’s best to frame the story differently for the specific decision-maker. I’m not saying you should distort the facts or omit any: The story you tell must be true and fair. But the focus and emphasis can be adapted.

You succeed when you take the time to look at things through another person’s eyes rather than solely your own. Doing so doesn’t compromise your principles. It shows that you’re sensible and sensitive to the differences between people and helps your relationships. It tells you how to frame what you’re asking for.

GENERATION GAPS: UNDERSTANDING AND LEVERAGING THEM

In almost every workplace employing more than a few people, generational differences present some major challenges. Sweeping generalizations based on when people were born may seem suspect, but we are all shaped by the culture and time period we grow up in. Our beliefs, communication and decision-making styles, interaction patterns, and expectations of each other can be at odds. Misunderstandings flourish. In response, consultants are at work explaining the groups to each other, marketers are researching the young people they must market to, and human resource specialists try to smooth cross-generational conflicts so their companies can function better.

Whatever age group you belong to, you will benefit from some empathy for the other cohorts. Supplement the following ideas with your own observations and you’ll discover ways to make subordinates and higher-ups happy without the risk of compromising your own values. Here are some tips to support sympathetic workplace relationships:

● Baby Boomers (born 1946 to 1964) are highly competitive and define themselves by achievement. Many are workaholics. Although Boomers wanted to change the world and fought for change (civil rights, women’s role), on the whole they respect authority, loyalty, position, and hard work that creates upward progress. They would like today’s young people to advance the same way they did: earning rewards (and confidence) gradually over time.

Communication style: Good with confrontation and face-to-face; hold meetings often; like the telephone, email, and detailed information; get information from newspapers and television; many use Facebook, LinkedIn, and Twitter.

React badly to: Younger people’s perceived lack of respect, low commitment level, expectations of fast progress, constant need for mentoring, arrogance about their own superior technology skills, and careless writing!

React well to: A can-do attitude, willingness to work hard and overcome obstacles, respect for their achievements and knowledge, and well-planned and proofed messages.

● Generation X (born 1965 to 1980) is a relatively small generation literally caught in the middle. They are often middle managers and must translate between those they report to and those who report to them. They are hard-working, individualistic, committed to change, and seeking life balance. They value opportunities to build skills.

Communication style: Depend on email, preferably short and efficient; would prefer to skip meetings; comfortable with new technology and social media (especially Facebook) to varying degree, but without the full enthusiasm of younger people; refer to television and to a lesser extent, newspapers, for information.

React badly to: Autocratic, unappreciative managers; an air of entitlement from subordinates and subordinates’ need for constant attention, encouragement, and supervision, and unwillingness to go the extra mile and adapt to workplace needs; impatience; “unearned” confidence.

React well to: Resourcefulness, independence, sense of responsibility, attention to detail, willingness to take on “uninteresting” assignments, good communication.

● Millennials (also known as Generation Y) (born 1981 to 1996) belong to an especially large generation and face strong competition but fewer opportunities. They are highly social and communal-minded, preferring to work in teams and in close touch with everyone else inside and outside the office. They want responsibility – quickly – plus intensive mentoring. They expect to spend their careers job-hopping and experimenting with other income sources. They are non-materialistic and typically leave jobs quickly when unengaged, even without another in sight. Accord high value to active experience, inclusiveness, and tolerance.

Communication style: Digital all the way; prefer to interact through texting, instant messaging, and social media, especially Facebook; draw news and information from the Internet; use email only as required; unenthusiastic about telephone contact, meetings, and confrontation.

React badly to: Lack of respect; insufficient encouragement, appreciation, inclusion, and fast rewards; not being given reasons for assignments; not being accommodated in lifestyle preferences; being required to work with old technology.

React well to: Coaching, opportunities to learn and grow, sense of purpose, being valued, explanations, new experiences, constant communication, teaming, and insights into the big picture.

● Generation Z (also known as the Homeland Generation) (born 1997 to 2010) is an unknown element of the workplace as yet. Growing up with the experience of a Great Recession and the War on Terror, this most parent-protected group of all shows signs of being more conservative, fearful, pragmatic, and concerned with privacy. They are the first “true digital natives” and use their smartphones for all information, entertainment, and communication, but few phone calls. In social media, they prefer the ephemeral Snapchat and Instagram.

Brainstorming the best content for your purpose

Perhaps defining your goal and audience so thoroughly sounds like unnecessary busy-work. But doing so helps immeasurably when you’re approaching someone with an idea, product, or service that you need him to buy into.

Suppose your department is planning to launch a major project that you want to lead. You could write a memo explaining how important the opportunity is to you, how much you can use the extra money, or how much you’ll appreciate being chosen for the new role. But unless your boss, Mark, is a totally selfless person without ambition or priorities of his own, why would he care about any of that?

You’re much better off highlighting your relevant skills and accomplishments. Your competitors for the leadership position may equal or even better such a rundown, so you must make your best case. Think beyond yourself to what matters most to Mark.

A quick profile of Mark reveals a few characteristics to work with:

❯❯ He likes to see good teamwork in people reporting to him.

❯❯ He’s a workaholic who is usually overcommitted.

❯❯ He likes to launch projects and then basically forget about them until results are due.

❯❯ He’s ambitious and always angling for his next step up.

Considering what you know about Mark, the content of your message can correspond to these traits by including:

❯❯ Your good record as both a team player and team leader

❯❯ Your dedication to the new project and willingness to work over and beyond normal hours to do it right

❯❯ Your ability to work independently and use good judgment with minimal supervision

❯❯ Your enthusiasm for this particular project, which, if successful, will be highly valued by the department and company

Again, all your claims must be true, and you need to provide evidence that they are. For example, you could include a reminder of another project you successfully directed and handled independently.

Your reader profile can tell you still more. If you wonder how long your memo needs to be, consider Mark’s communication preferences. If he prefers brief memos followed by face-to-face decision-making, keep your memo concise, but still cover the major points to secure that all-important meeting. However, if he reacts best to written detail, give him more information up front.

Creating a reader profile enables you to create a blueprint for the content of all your messages and documents. After you’ve defined what you want and analyzed your audience in relation to the request, brainstorm the points that may help you win your case with that person. Your brainstorming gives you a list of possibilities. Winnowing out the most convincing points is easy, and you can organize simply by prioritizing, as I show you how to do in Chapter 3.

Thinking through how to profile your reader works equally well when you’re writing a major proposal, a business plan, a report, a funding request, a client letter, a marketing piece, a blog, a Microsoft PowerPoint presentation, networking message, or website copy. Know your goal. Know who your intended audience is and what that person or group cares about. Then think widely within that perspective.

Another way to think about your content is to consider that everything you write is an “ask.” Even a message that just conveys information is asking your audience to read it and act upon it in some way, if only to absorb or file it. An event announcement asks the recipient to take note and usually, you’re asking her to feel motivated to participate. A “congratulations on your promotion” note asks the lucky person to notice that you’re on her side.

Try to think of a written communication that doesn’t ask for something. It’s pretty tough. There’s an advantage to seeing every message as a request: Doing so sets you up to frame your message with the right content for the person to whom you’re writing.

Writing to groups and strangers

Profiling someone you know is relatively easy, but you often write to groups rather than individuals, as well as to people you haven’t met and know nothing about. The same ideas covered in the preceding section apply to groups and strangers, but they demand a little more imagination on your part.

Here’s a good tactic for writing messages addressed to groups: Visualize a single individual – and/or a few key individuals – who epitomize that group. The financier Warren Buffet explained that when writing to stockholders, he imagines he’s writing to his two sisters: They are intelligent, but not knowledgeable about finance. He consciously aims to be understood by them. The results are admirably clear financial messages that are well received and influential.

Like Buffet, you may be able to think of a particular person to represent a larger group. If you’ve invented a new item of ski equipment, for example, think about a skier you know who’d be interested in your product and profile that person. Or create a composite profile of several such people, drawing on what they have in common plus variations. If you’re a business strategy consultant, think of your best clients and use what you know about them to profile your prospects.

Imagining your readers

Even when an audience is entirely new to you, you can still make good generalizations about what these people are like and even better, their needs. Suppose you’re a dentist who’s taking over a practice and writing to introduce yourself to your predecessor’s patients. Your basic goal is to maintain that clientele. You needn’t know the people to anticipate many of their probable concerns. You can assume, for example, that your news will be unwelcome because long-standing patients probably liked the old dentist and dislike change and inconvenience, just like you probably would yourself.

You can go further. Anticipate your readers’ questions. Just put yourself in their shoes. The dental patients may wonder:

❯❯ Why should I trust you, someone I don’t know?

❯❯ Will I feel an interruption in my care? Will there be a learning curve?

❯❯ Will I like you and find in you what I value in a medical practitioner – aspects such as kindness, respect for my time, attentiveness, and experience?

Plan your content to answer the questions your readers would ask, and you won’t go wrong. You’ll save time, too. How many memos do you send or receive daily, asking for clarification or trying to sort out some kind of confusion? Careless communication is a huge concern for business leaders. One badly written email sent to ten people can waste many hours of collective work just to retrieve the situation. An even bigger worry is the impact of mistakes generated by poor communication. Recently an auto company’s engineers failed to clearly describe a safety problem to upper management, with disastrous consequences. On an everyday basis, minor variations on this theme occur everywhere.

Notice that in addition to being “me”-centered, nearly all the questions asked by the dental patients are emotional in nature rather than factual. Few patients are likely to ask about a new doctor’s training and specific knowledge. They take that for granted. They’re more concerned with the kind of person he is and how they’ll be treated. This somewhat counterintuitive truth applies to many situations. Good salesmen don’t pitch themselves – they pitch their ability to make the customer’s life better. Notice also that the questions would be essentially the same for a new accountant or any other service provider.

When writing, you may need to build a somewhat indirect response to some of the questions you anticipate from readers. Writing something like “I’m a really nice person” to the dental patients is unlikely to convince them, but you can comfortably include any or all of the following statements in your letter:

I will carefully review all the records so I am personally knowledgeable about your history.

My staff and I pledge to keep your waiting time to a minimum. We use all the latest techniques to make your visits comfortable and pain-free.

I look forward to meeting you in person and getting to know you.

I’m part of your community and participate in its good causes such as …

Apply this audience analysis strategy to job applications, business proposals, online media, and other important materials. Ask yourself, whom do I want to reach? Is the person a human resources executive? A CEO? A prospective customer for my product or service? Then jot down a profile covering what that person is probably like and what her concerns and questions may be.

Everyone has a problem to solve. What’s your reader’s problem? The HR executive must fill open jobs in ways that satisfy other people. The CEO can pretty well be counted on to have one eye on the bottom line and the other on the big picture – that’s her role. If you’re pitching a product, you can base a prospective customer profile on the person for whom you’re producing that product.