Chapter 14

Writing Well to Manage Well

IN THIS CHAPTER

check Communicating to build your team

check Delivering bad news, good news, inspiration, and criticism

check Writing strategic messages to higher-ups

Most great leaders are admired for their powerful communication skills. Not a surprise: How else can you inspire, motivate, and persuade? But alas, most people’s direct experience is with managers who are not leaders and who fall short on this skill set. Gallup, the premier polling group, reports that two-thirds of American workers identify themselves as “unengaged.” Done every year, the report has consistently pinpointed poor relationships as the main cause, which often translates as poor manager communication.

Seen from the organization’s perspective, this rampant disengagement generates mistakes, misunderstandings, inefficiencies, and high turnover. A workplace with low morale is an unproductive one. Why so many organizations allow this huge limitation to persist connects with misplaced values, structures that reward people counter-productively, and lack of training.

While these problems can’t be solved easily, if you are a manager or aspire to join those ranks, this chapter can help you manage better by communicating better. All the techniques for writing and speaking I cover in earlier chapters give you useful tools to work with. Here the focus is on applying those ideas to typical management writing challenges, from thank-you’s to no-thank-you’s, good news to bad news, inspirational to critical.

This chapter also covers communicating to manage up, because we all report to someone, whether a department or division head, a CEO, the governing board, or a set of clients. We need to communicate gracefully with both those below and above us in the hierarchical chain of command. Fortunately, the guidelines are similar. Like so much of successful living, it’s all in the attitude, so that’s where I start.

Communicating as a Manager

You may think that the higher you ascend the management ladder, the more you can issue orders, and the less you need to care about the feelings of those who report to you or rank lower on the company totem pole. Big mistake! Even if you hit the top, autocratic ways of managing are both unpopular and ineffective in today’s work environment.

tip If you want people to work hard for you, help you perform well, feel enthusiastic about their work, and say nice things about you and the company, the word is: You must be more courteous, accommodating, and considerate than ever. This outlook should show in both your in-person communication and in what you write.

I do realize first-hand that the boss’s lot is not an easy one. The messages can be hard: “No, you don’t get the assignment or promotion or new office you wanted … No, the company won’t pay for your MBA … Sorry, I can’t let you work at home three days a week … The company had a bad first quarter so no conference requests this year … Everyone’s taking a 3 percent pay cut, well, maybe not everyone.” And then there are the routine written performance evaluations and critiques, which are seldom fun.

And those are just messages to subordinates! You must write with great care to your own supervisors and find ways to express your viewpoint even when they don’t want to listen. You must represent “your people” and try to protect them from any negative impact from higher-ups.

You’re expected to feed the chain of command’s need for better data or sales figures or productivity so higher-ups can, in many cases, take credit for your team’s accomplishments. You must win support for programs and innovations by writing reports and proposals they will only skim. You are probably required to explain and implement directives you don’t agree with. And you may have a host of new audiences to address: management peers, board members, donors, suppliers, and more.

tip Where to start on all this? Tone. To write strategically — that is, to accomplish your goals with people on different levels — it’s especially important to gauge your audiences as individuals, not just as cogs in a corporate machine. You can be most successful by relating to each person above and below you, both within terms of his or her role and personal perspective. Let’s look first at communicating with your staff.

Relating to your team members

If you head a department or work unit, you are fully responsible for how the group interacts and operates. This carries some ramifications that all too many managers appear to forget. When you’re the boss, you’re the role model; don’t look for any vacations from that. How you treat people and communicate with them is echoed in how they interact with each other. Remember also:

  • You’re always in the spotlight. People are intensely aware of any perceived unfairness, inconsistency, or favoritism on the boss’s part.
  • You set the standards for level of commitment and respectful behavior. Hard work, courtesy, and consideration are contagious when coming from the top.
  • You establish value. People naturally strive to perform in ways they observe the boss to value — if you write well, for example, they typically write more carefully, too.
  • What you say and what you write may be given far more weight than you credit or intend. Careless statements can have unintended consequences. Remember all those movies where a VIP said, “If only Smith wasn’t around to bug up the works …”?
  • Your communication style affects what your employees choose to share with you and how honest they will be. This also affects to what degree they’ll express their opinions.
  • Your tone in communicating has lasting impact. A badly thought-out or mean-spirited message may negatively affect your whole unit, while positive messages inspire and motivate.

Here’s an important corollary of the foregoing principles: Your responsibility as a manager requires you to control your own feelings and short-sighted reactions. If you want to be respected, letting negative emotions like anger, frustration, or bad moods rule will always work against you. The boss is key to the whole spirit of our work environment. We need her to be positive, cheerful, and even happy so we can feel secure and supported.

remember The best advice I’ve heard is that whatever the work, aim to build a team around yourself. Never get so lost in the numbers, pressures, or urgencies that you forget this basic commitment or run out of time to handle it. Use everything you write to foster good feelings and commitment.

Set the stage for yourself by looking at your staff members as individuals. Build a profile for each with the tools presented in Chapter 2. Take special account of what motivates each person, his strengths and aspirations, and how he relates to the team.

tip Creating profiles of those under your authority gives you a super tool for deploying your forces well and promoting team spirit. Always cherish the differences. If we all had the same skills and enthusiasms, and looked at the world the same way, life would be a lot duller and organizations way less productive than they can be. The better you know your team, the better you can frame your written messages to each person as well as the full group. Let’s look at some helpful general guidelines.

Writing to inspire and motivate

The harder your staff works, the more you accomplish, the better you do your job, and the more kudos you gain. What’s not to like? Many ways of motivating people come down to surprisingly basic ideas. But they are so often ignored that it is easy for you to absorb them and stand out. Here are some communication-related guidelines:

  • Share information regularly. People like and need to know “what’s going on.” A new edict coming down from on high? Tell your staff as much as you can ASAP, and what it means to them. If people know they can depend on you to share important news, you diminish opportunities for gossip and wild surmise.
  • Give people the big picture. It’s motivating to know how the department and your own work fit into the organization’s goals. Keep your staff in tune with how the company is doing, and perhaps industry trends, to help them feel valued and make them better equipped to do their jobs.
  • Make the most of good news — and don’t hide bad news. If you’re recognized for an achievement that took a team, share the glory and celebrate. If there’s bad company news, tell it. The news will come out anyway so share it early rather than late if you want to maintain trust.
  • Keep a positive, upbeat attitude in all your communication. This projects that you like your job, know you do it well, and expect the best from everyone. Extend trust and most often, people will be trustworthy.
  • Let people know you are monitoring their work and holding them accountable. Beyond keeping them on track, this helps people feel valued and leads them to aim higher.
  • Actively encourage your staff to share their own information, ideas, and suggestions. Everyone complains about writing reports, but if your staff includes more than eight people or so, how else will you know what’s going on?
  • Show appreciation often: for work well done, an over-and-above contribution, and good writing! People repeat and amplify behavior that brings praise, while an unacknowledged good deed may remain a lonely one.

remember Always keep in mind that good communication is a two-way street. Technology has changed us: We expect to interact online, not just read, and we want to contribute ideas and opinions and be heard, rather than just listen and follow orders. People want to be part of the action rather than just recipients of information from on high. Practice the old one-way-trickle-down style (colorfully called “cascading”) at your own risk. Your most valuable people will not put up with it. Stay on the lookout for opportunities to encourage active participation.

tip This is especially important in managing Millennials and the younger Generation Z (Chapter 2). They value “the experience,” chances to learn, and knowing the why of everything. Such opportunities are more important than money to many young people, and they may quickly disappear themselves if kept on the periphery.

Let’s try these concepts out first with messages no one likes to write: bad news.

Delivering bad news

Suppose the head of technology, Hal, has been told that poor company profits for the past quarter mean there will be no raises this year. He’s been given a lot of profit-and-loss (P&L) statistics, but not much else to help explain the situation to his department. He knows that top management came close to cutting staff and will no doubt consider doing so should company performance not soon improve. He must break the news to his ten-person team.

First consideration: Should Hal deliver the news in person or in writing? When the news is bad, or you must criticize, always consider face-to-face interaction first. People often feel it’s cowardly to hide behind a written message in business — and they’re right, just as it’s cowardly to break off a personal relationship with a Snapchat post.

tip On the other hand, in many negative situations, a written message can be a good opener. It enables you to think through the facts and their meaning, and communicate them in a more controlled way that helps readers digest the information before reacting, or over-reacting.

In this case, Hal’s goal is to deliver the unwelcome news and minimize the bad feelings it will naturally produce. He considers his audience and his team members’ probable responses. This mental scan suggests that probably at least one person will respond with quick anger that will infect everyone else and set a bad tone for a conversation. Emotions are communicable! He envisions the whole group dwelling on the injustice of it all, making the situation worse.

Hal’s decision: Communicate the basic message in writing and follow-up face to face, with a short delay that gives everyone time to absorb the news and come to the meeting with relatively open minds.

Try This: Before reading the following version of the memo Hal might write, think about how you would write it. How would you generate a positive outlook without sacrificing honesty? Then read this version:

  • Subject: Next year salaries and planning
  • Dear Ellen, Jerry, Marsh, Quinn, Larry, Jackson, Emery, Jenny, Bob, Sue:
  • At the Leadership Team meeting yesterday, I learned that the company will award no salary increases for the coming year. This decision was reluctantly made by top management because our Q4 earnings fell 7%, in large part because the Mister Magic launch fell well below expectations.
  • The decision-makers could alternatively have chosen to make up the deficit with layoffs. While we all feel justifiably disappointed not to receive raises, I for one am grateful that the decision was to maintain full employment. So, none of us is now at risk, and we need not fear for our colleagues, nor worry about extra work burdens falling upon us.
  • I can also share that this year will see three new product launches. Our decision-makers are hopeful that results will be strong, the P&L picture will rebound, and we’ll all reap the rewards down the line. I’m optimistic — but I can’t tell you that we should be complacent.
  • What can our team do at this juncture?
  • I see a real opportunity for us to prove our value on a broader scale. My idea is that in the coming months, we could push ourselves to move above and beyond our own territory. I would love to see us share our project management know-how with other departments and help them adapt our systems to improve their own productivity. This helps the whole company, of course, and gives us a chance to spread the word on how valuable our work is and how well we do it.
  • Let’s meet on April 10 to brainstorm ideas. At that time, I’ll also reserve 10 minutes to talk about the wage freeze and answer any questions to my best knowledge. I’ll share the P&L statements if you want to see them.
  • Meanwhile, please think about my plan and bring your best thoughts to the brainstorming. Let’s identify departments that can benefit from our practices and create a preliminary plan of action.
  • I’m proud of the team we’ve built together, and I believe we can use our combined skills to contribute more and be valued more. —Hal

Why it works: Hal takes the “us” perspective throughout — we’re a team and we’re all in this together — but there’s no question about who is in charge. He strategizes his content and writing style to accomplish the goal and uses a matter-of-fact, low-key tone. The message acknowledges that readers will feel unhappy, but doesn’t dwell on it. He makes the likely assumption that people will not much be interested in the P&L statements, so gives that a light reference that he will supply the material if wanted. He spends the most time framing the bad news in a more positive light by:

  • Conveying confidence in the company: He points out that decision-makers could have made a less humane and acceptable choice, firing people, which suggests that the company cares about employees.
  • Creating a silver lining: Hal tells his people that though things are not as they would wish, they’re okay — and moreover, they can help underwrite their own prospects by pitching in above and beyond now.
  • Reframing his team’s attention from the inevitable “so unfair” complaints into an action possibility: The idea that as a team, they can work to demonstrate their value is energizing, and sets a positive tone for a think-tank session.

In such situations, it’s important to create a perspective shift without misleading people or offering false assurances. In many instances, it might seem hard to find a silver lining — but with a little creativity, you may be surprised at how often you do.

tip Notice that the message puts the bad news right up front — bottom line on top applies to bad news just as it does to cheery news. Delivering an unwelcome message in a “sandwich” framework used to be popular. For example, “We have really liked working with you. Unfortunately, we’re not renewing your contract. But we had some good times together, right?”

Today’s readers don’t react well to such tiptoeing. Get the bad news done and then move on to some kind of mitigation, insofar as possible. It must be genuine, or don’t do it at all. For example, if you’re turning down a job candidate, you might end with, “Here is the contact information of someone who I believe might like to know about your skills,” or “We’ll hire a new set of interns in August and would be glad to review your application again at that time.” Such offers mean infinitely more than, “We had so many great candidates but could only choose one.”

What if you have 1,000 applicants to turn down, or just don’t have anything helpful to say? Then just close simply but firmly. “Thank you for applying. We very much appreciate your interest in our company.”

warning Even worse than the sandwich technique is trying to obscure bad news in a torrent of irrelevant information, or news that’s good for people other than the reader. The CEO of a major international corporation made a fool of himself a few years ago by announcing big layoffs in an email that meandered on for seven pages about the company’s great future, then got around to announcing that a whole division was eliminated in the interest of this rosy future. Outraged employees immediately hit their share buttons and the whole world jeered.

The CEO overlooked this book’s governing principles — know your audience, know your goal, and strategize content within that frame. In announcing layoffs or other news that is calamitous to some, those at the top may forget that these messages have multiple audiences with different self-interests.

If you fire 500 people in writing, which is often the chosen medium, what’s the message to all the colleagues you hope to retain? Your goal for the laid-off folks should be to minimize their distress and hatred of you as a callous employer. Those slated to remain need to know that the company isn’t going under, and there’s good reason to stick with it and soldier on. The general public and media are only a click away, so you’re inevitably delivering the message to them as well. Therefore, you need to demonstrate that the firm is on solid ground, has made a difficult but valid decision, and isn’t unfeeling toward those losing their jobs.

How would you write such a letter, or email, telling 500 people they are laid off?

Try This: If you’ve been faced with a challenge like this or can imagine one in the future, use this approach: Combine the goal-plus-audience strategy (Chapter 2) with the talking points technique (Chapter 8). Here’s how it might work if you’re responsible for letting those 500 people go:

  1. Define your audiences.

    Your primary audience is the 500 people you’re laying off. Your secondary audience is the remaining staff and everyone they might share the message with (the board, the media, the public, stockholders, competitors).

  2. Define your goals.

    Inform the 500 people that they are unemployed soon as sympathetically as possible. Reassure the remaining staff that the company is in good shape and that their jobs are currently secure and they will not be adversely affected. Reassure the other audiences and in doing so, avoid any suggestion that the company is mean or vulnerable.

  3. Brainstorm to create talking points.

    The talking points for this situation may be:

    • Decision was made by the CEO and Executive Leadership Team
    • They regret the need for making the cut
    • Reason: closing down of unprofitable division that is behind the times technologically
    • Remaining staff are secure in jobs but must pull together
    • Each laid-off employee will receive a generous severance package reflecting service time
    • The company is retaining a career counseling firm to help identify new opportunities for all the laid-off workers and counsel them one on one

Once you’ve articulated your audiences and clarified what you need to accomplish, the talking points give you good substance to work with. Here’s one way to use the points:

  • Dear ____:
  • I am sorry to share that the AeroWing Division will cease operation April 3 of this year, and that all division staff will be laid off. We highly value your nine years of service and regret that we will not be able to continue employing you as of that date.
  • I made the decision in close consultation with the Executive Leadership Team. We are responding to the division’s steady decline over the past five years, primarily because this product has been technologically outpaced by new competitors. We’ve concluded that unfortunately, the company is unable to support these losses and further invest in this arena at the expense of our other product lines, which continue to grow.
  • We want to offer you as much support as we can at this time. You will receive a compensation package reflecting your time with Aero that I am sure you will find generous. The Talent Management Office will shortly contact you to arrange a personal consultation.
  • Also, we are retaining a professional firm, BetterNextTime, to provide every member of the AeroWing team with one-on-one counseling. Ten counselors will work on-site for six months to help everyone affected find appropriate opportunities, and their full resources will be available to help you with your next career step.
  • I hope you will accept my personal good wishes for your every future success, and my appreciation for all your contributions to a division in which we will always feel enormous pride.
  • Sincerely,
  • Jack
  • John C. Berry, CEO

Why it works: The CEO and Executive Leadership Team take responsibility for the decision, and the CEO delivers the message in his own name. This may seem like a small point, but taking ownership matters to people. What is more annoying than bad news delivered in statements such as, “It was decided that …”?

The tone is low-key and matter of fact, but also somewhat formal, which is befitting the subject matter. The CEO expresses sympathy to an appropriate degree; going overboard with warm feelings would accomplish little and might be taken as hypocritical. The bottom-line reason for the layoffs is clearly stated in a way that doesn’t involve other parts of the company. The primary audience can’t argue with the numbers, and few will be interested in more detail.

Secondary audiences, such as the media and stockholders, may well want to see the financials, however, and the company would be wise to have backup material ready. More detailed information should also be tailored for a set of press releases, announcement on the company website, and other channels this company uses to communicate with its full range of stakeholders.

tip Writing with the structured approach I recommend always helps you think more analytically. In considering “audience” for this sample message, until I wrote the organized list, I overlooked the importance of stockholders and the company’s board of directors. Major clients might also need more tailored messages, as well as strategic partners and government agencies. If the organization is a nonprofit, a major announcement should be directed to supporting foundations, private donors, and volunteers. This suggests a broad principle.

warning When you’re responsible for communicating with a number of audiences, don’t forget them in reporting on an important event. Identify each audience and brainstorm how to customize the message for each: content, level of detail, language, tone. Keep WIIFM in mind — what’s-in-it-for-me.

And, know how to reach every audience. Board members may need hand-delivered information packets, different employee groups may prefer social media or email or printed memos, stockholders probably want a letter from the CFO. All too often, organizations unintentionally focus on communicating with a few audiences via their traditional channels, and overlook other venues more likely to reach other audience segments.

tip Research indicates that effectively handling bad news messages, such as announcing layoffs, makes a difference in how those who are losing their jobs react. Follow-up studies showed that departed employees who felt respectfully treated and understood the business situation harbored little bad feeling toward the company. Those who were treated carelessly remained angry — and found many ways to share that resentment.

Writing good news messages

Certainly, it’s a whole lot nicer to share good tidings, but you may have found that in fact, positive messages are difficult in their own way. But “thank you,” “good work,” and “congratulations” belong in the good manager’s portfolio, and this writing skill should be exercised often.

tip Many supervisors dwell on the need to criticize rather than offer messages of appreciation. But in many instances, appreciation is a better way to encourage behavior we want and wean people away from what we don’t want. Most employees aim to please their bosses and live up to expectations or exceed them. All too often, the problem is that supervisors fail to adequately communicate what they want! Many employee surveys highlight this unfortunate gap.

Writing is an ideal tool for making this connection. It feels more official and special when you deliver a written compliment rather than a spoken one, which is fleeting, and may not in the moment be well expressed.

remember The key to composing good thank-you and job-well-done notes is specificness. It’s easy to orient yourself to be specific if you apply the goal-plus-audience framework. Suppose your subordinate, Allie, has done a good job preparing a slide deck for your client presentation. You know a thank you is in order. Off the top of your head, you might say,

Hi Allie — Thanks so much for the slide deck, show went well. —Chuck

But this is short-sighted. If you more deeply consider your main goal — to encourage future good work — you’d probably see the challenge more concretely:

  • Reinforce Allie’s enthusiasm for such assignments.
  • Acknowledge her extra effort — she worked on this over the weekend.
  • Help her feel she’s a valued member of the team.
  • Help her feel good about working for me.

Here’s one way of meeting these goals:

  • Dear Allie,
  • I presented the show last night, and it went very well! I noticed that Bob, the prospect’s division head, smiled all the way through, and 20 minutes of good Q&A about our campaign ideas followed. It’s too soon to say if the account is ours, but I’m happy that we gave it our best shot.
  • So, thanks for helping me do that. You pulled the deck together on a tight deadline and translated the packaging ideas into effective visuals. The transitions you came up with tied it all together nicely.
  • Glad to have you on my team. —Chuck

remember Does this message sound like overkill — perhaps too effusive? As always, adapt the ideas to your own style and comfort zone. You don’t want to write notes like this every day, of course. But observe what a few minutes of strategic writing accomplishes. In telling Allie exactly what she did well and the results this helped achieve, Chuck shows Allie she is valued as a contributing member of the team; her hard work is appreciated by the person who matters most, her boss; and that boss is a great person to work for. Remember, relationship-building is an underlying goal for every message (see Chapter 2).

As Allie basks in feeling appreciated, her motivation can only grow. Will she work even harder to merit further praise? Put in extra time as needed? Come up with more creative ideas? Probably. Well-delivered praise is the best available way that you, as a manager, can promote alignment with staff members and get future work done outstandingly. But it only works when it’s specific and concrete.

Criticizing with kindness

It falls to the manager’s lot to coax team members to meet standards and perform better. Many supervisors are uncomfortable with this demand, but it’s essential to the role. The good news is that often you can accomplish your goals with a positive approach.

When I began presenting workshops early in my career, I realized that often when someone gives a speech, or reads an assignment to the group, listening to feedback is a terrifying experience. Although group input was always meaningful, at times people were unthinkingly (or thinkingly) cruel in their responses. The result was hurtful rather than helpful.

tip I stumbled across two techniques that mitigate these harmful interactions. First, invite the spotlighted person to review his own performance with a question such as, “How do you think you did? Anything you’d like to do differently next time?” Next, require that the group deliver only positive comments. I found that more was accomplished when following this positive-only rule than with open criticism. When everyone engages in looking for the good, strengths are highlighted, there are no worries about hurt feelings, and everyone learns more.

Try This: Telling someone what he did right reinforces the behavior you desire. Further, positive input generates ideas for improving in a more natural and friendly way. Often the process leads the “target” person to come up with better ideas himself. In a one-on-one meeting, you first might ask, “What did you feel went well with the project?” and then follow up with, “Looking back, what do you think you could have done better?”

tip Written messages, obviously, lack this back-and-forth potential. But the non-blaming spirit of the idea is nonetheless useful. Suppose Allie had not done a good job on her slide deck assignment. You didn’t like all the visuals, the transitions were uneven, the flow was shaky, whatever. You need to hold her accountable, yes, but the overarching goal is for her to improve next time. It’s probably counterproductive to tell her all of this, as crushing her initiative and confidence doesn’t accomplish any purpose at all.

Considering this, you might say:

  • Allie, I appreciate that you got the show done on such short notice. I know that was tough.
  • However, I had some problems with the deck. I don’t know what else is in your portfolio now, but your work is usually better. Let’s talk about it to understand what happened. —Chuck

remember A brief, less specific message does the job better. Unlike when you deliver compliments, when it comes to criticism, reviewing specifics often is best accomplished in a private conversation rather than in writing. The foregoing memo to Allie prepares her for a thoughtful discussion aimed at helping her improve.

You may need a “nudge” memo that is stronger, according to your judgment of the persona and situation. Here’s an example:

Gwen, you edited the workplan, but you missed a lot. I would have expected you to ask questions if some of the material was unclear to you. Here’s my own rewrite — let’s discuss.

An important exception to this less-is-more approach is when you need to create a written record of insufficiencies, such as for legal documentation. Then write in excruciating detail. A lawyer or HR person is probably available to give you these guidelines.

Writing requests and giving orders

The same principles of thoughtful communication apply when you assign work. Routinely see everyday messages as building blocks toward better performance and good relationships. Which request in each of the following memos would you prefer to receive from your boss?

  • Jake, here’s the material for the Collins report. Due date Wednesday, no fail! Better, get it on my desk Tuesday for review. Thnx.
  • Jake:
  • Here’s everything you need for the Collins report. I believe all the sections are covered, but please take a look at the attachments and let me know ASAP if you find anything missing.
  • This is high priority, and I count on you to get the full draft to me Tuesday. Then I’ll do a quick review for delivery to the client on Wednesday. If you run into any problems call me, day or night.
  • I know this deadline is tight. Thanks for pitching in.

The second message tells Jake why he’s doing the work on short notice and that it’s for the team. He feels respected and included. Who doesn’t want to feel that way? When I talk about this in workshops, often someone says, “But that’s my assistant’s job! Why do I have to cajole him into doing it?” You don’t. But if you want the work done with enthusiasm and resourcefulness, perhaps with unacknowledged overtime, you need to care how the person feels.

tip Make it a habit to visualize whom you’re writing to (see Chapter 2) so the person is real and individual to you. Decide to use every message to build that team around you. People work harder for a manager who cares about them and tells them why their assignments matter.

I know a young, successful department head who frames every request to staff this way: “Would you do me a favor and … .” “Of course they have to do it,” she explains, “and they always say ‘sure.’ When I put it like that, it sets a tone that says I appreciate what they contribute. They’re happier to ‘help me’ than if I just said, ‘do this.’ So, I just give all my orders that way.”

Writing to Higher-Ups

You don’t need me to tell you that when you write to a superior, every message should be carefully thought out, well written, and scrupulously edited. If your boss sends you cryptic, confusing, or non-explanatory messages (such as, “No!” or “Not now!”), do not take that as a reason to write abrupt, careless messages yourself.

remember I recommend developing a written profile of your supervisor, drawing on the approach I detail in Chapter 2. You can much more successfully present your requests, suggest ideas, and build trust when you take the time to understand the person, especially his communication style and decision-making preferences. Does he want a lot of detail, the big picture, or the bottom line? What problems does he want to solve, what keeps him up at night? What’s the best time of day to ask for something you want? (Research says that many people are most well-disposed and open after lunch.)

See through the boss’s eyes and you’ll automatically find the right words and persuasive framework. The same process I present in earlier chapters for writing emails, reports, and proposals apply when the audience is your manager. But pay close attention to some characteristics that I am 98 percent sure your boss possesses by virtue of position. She feels:

  • Always short of time
  • Pressured to show results for her domain
  • Faced with conflicting priorities

And, of course, she reports to a boss of her own, with all the attendant challenges.

warning Remember that an email or document sent to your supervisor may work its way up the management line or be included in a report or other material. So even if you enjoy a comfortable relationship with your boss, as a guiding principle, assume all upward-directed messages may have a larger audience and use your best thinking and skills. Let’s look at how to take account of the three common characteristics I cited for bosses.

Most often, with variation based on your profile of your supervisor, your best strategy is to write brief, straightforward emails that stick to one subject. Long detailed emails may be skimmed or not read at all, especially if the subject line and lead don’t get to the point right away. In general, any time you’re addressing a higher-up, such as board members, donors, executives, and government regulators, aim to:

  • Be direct. Begin by clearly stating your reason for writing and end with a call to action — what do you want?
  • Take a positive tone and position. Better to be perceived as a problem-solver than a problem-bringer or complainer. Stay upbeat and sound objective and in control; provide solutions or alternatives when you can.
  • Write super-concisely. Don’t include extraneous thoughts or words. Use simple language and short words, sentences, and paragraphs.
  • Write correctly. Use full sentences, good grammar, correct spelling and punctuation, and clear transitions. Be suspicious of abbreviations and beware of emoji!
  • Create self-contained messages. Include just enough context so your multitasking reader doesn’t have to look up previous material, do research, or ask basic questions.
  • Write with extreme courtesy. Take time not to sound abrupt or as if you’re issuing orders or calling him to account.
  • Employ good visuals. Make the information easy to access and grasp. Draw attention to important points with subheads, bold lead-ins, and plenty of white space. A plain typeface in the 12-point range is best.

Here’s an example of an email that follows these guidelines.

  • Subject: Hiring consultant by Thursday
  • Hi, Elaine:
  • Here are the three best responses to our RFP for a benefits consultant on the Chandler Project, filtered from 39 candidates. It would be great if we can announce the decision by Thursday; then we can put the paperwork through in time for board approval on June 4.
  • If you want to talk this through, just let me know. I believe all three candidates are strong and would meet our needs.
  • If you are able to get back to me by end of Thursday, it will be very helpful in moving forward on schedule.
  • Thanks. —Sam

Guarding your tone

warning The most frequent complaint upper echelon managers make about employee writing — especially when done by younger people — is that they are “tone deaf.” In other words, they address VIPs, including clients and top executives, in the same spirit and language they might use writing or texting to friends. This doesn’t come across as respectful. If you feel that respect must be earned, not automatically awarded for reasons of age or relative importance, I won’t argue with you. But you can damage your prospects. You’ll gain more respect for yourself by communicating in line with the high standards most upper-level people expect, or insist on.

Try This: If you need to develop your ear for tone, make a practice of reading your emails aloud and consider: How does it sound — like my natural voice? Does it give the impression that I’m annoyed or frustrated? Or don’t like the person I’m writing to?

tip Be especially mindful of how easily a piece of writing can communicate actual feelings such as anger or dislike. Choice or words, cadence, and sentence structure can almost magically give away negative feelings. Notice when you read messages from other people that you sometimes intuit an emotion without being able to pinpoint what carries it. The takeaway for you: Try not to betray negative emotions!

warning Should you fake respect or good feelings when they’re not genuine? Yes, sometimes. When you communicate in ways that lead others to feel badly, rejected, or disrespected, it may never be forgotten or forgiven, especially if you do it in writing. You need to build relationships, not undermine yourself.

Try This: Accept that your negative reactions, or assessments of other people, may not be always be fair or balanced. We all have limited perspectives and can misperceive other people’s words or actions. Experiment with giving difficult managers — and everyone in your work environment — the benefit of the doubt. Treat others with generosity, even when you don’t like them or think they’ve offended you, and you may find yourself bringing out their better side.

The bottom line: Monitor your tone in every message to see if it’s negative or can be misinterpreted in any negative way by the reader. When it’s important, ask a trusted colleague to review what you wrote. Do you need more incentive to read between your own lines? Consider that your superiors won’t let you near a customer, client, or VIP of any sort if they can’t trust you to be in control and represent their interests well.

Here are some extreme examples.

Version 1:

Marge, didn’t I already ask you five times to review the draft I spent 23 hours writing and give me your input? Remember? I’m at a standstill! If I don’t hear from you by 3:30 tomorrow, I’ll assume you have nothing to say and go ahead on my own. —Matt

Version 2:

Marge — I’m still waiting for your input on the draft I sent Tuesday. This is creating problems. Any chance you can get back to me this week? —Matt

Version 3:

  • Hi, Marge,
  • I know what a busy time of year this is, but we’ll really appreciate your input on the Marshall draft. You may recall we promised to deliver it Monday. Is it possible for you to take a look by the end of the week?
  • It will be a big help.
  • Best, Matt

I take for granted you don’t write emails like Version 1. If you read it aloud, it sounds accusatory, impatient, whiny, and childish. If Marge is Matt’s boss, she will feel attacked and regard him with suspicion henceforth. If he’s a client, Matt may soon be job hunting. If Marge is a coworker, she’ll feel angry and uncooperative.

Version 2 is less offensive but still has a negative intonation — I’d call it passive-aggressive. Marge may do as asked, but won’t feel warmly toward Matt.

Version 3 is courteous and deferential. If you read it aloud, the tone is neutral and feels respectful. It carefully avoids casting blame. This message has the best odds of achieving its goal, to coax Marge to give the draft a few minutes’ attention and regard Matt as perfectly reasonable.

Avoiding the blame game

Version 3 suggests another good strategy: finding a way to let another person, especially a VIP, save face if he or she errs. No one likes to feel chastised, belittled, or implicitly criticized by anyone, let alone someone on a lower level. If the boss or a client ignores your plea for a response, or fails to return a phone call, or even stands you up for an appointment, how can you handle it?

tip A good general principle is to let that person off the hook without relinquishing what you need. In Version 3, Matt does this by saying that he knows this is a busy time of the year for Marge. It can take a moment’s thought to figure out an appropriate mitigating statement for the other person and use it to frame what you want in a more acceptable way. For example:

  • I know you’ve been traveling and how hard it is to catch up …
  • This may have fallen through the cracks when so much is going on …
  • I know everyone’s pressing you for figures this week …
  • It looks like we had a miscommunication …

A person who feels well-disposed is much more likely to help you out or rectify an oversight than one who is put on the defensive.

remember Don’t overlook another tool in your strategy kit — the thank-you note. I talk about the value of expressing appreciation to subordinates earlier in this chapter, and the approach is equally effective with supervisors. Executives rarely receive compliments or thanks from people who report to them. Writing to thank them for good advice or a special favor makes you notable. A respectful compliment is also welcome. A message such as, “Tom, thanks for being such a great mentor and helping me grow so much,” may be in order once in a while. More immediate compliments may be best delivered in person. For example, “I admire the way you handled the Burke problem and learned a lot from it.”

Making it easy to respond

tip Here’s another idea that gives you better results when you need something from a supervisor, VIP, or peer: Make it easy for that person. Recognize that realistically, your messages won’t get much attention. Managers spend a lot of energy putting out fires, and the broader their perspectives, the harder it is to keep everything in mind and focus on detail. Here’s a theory: In general, the higher up the hierarchy you go, the briefer your messages need to be. Or if not brief, the more easily grasped in record time. Aim to give your superiors just enough to make a good decision, ask important questions, or take other action.

See this demand for brevity as a compliment: These busy people trust you to decipher what matters, tell them what they need to know, and filter out the rest. Here are some techniques to help you do this:

  • Be clear in each case what the manager needs to do — or what you want her to do — upon reading the message. Make a decision? Take an action? Evaluate something? Stay up-to-date? Figure out what is necessary for that goal and include the right amount of background and detail.
  • Pay attention to the visuals. Even an email can use headlines, subheads, and bold lead-ins to direct attention to high points and support productive skimming. Dense material is uninviting and a challenge to absorb. Follow the rules for short sentences, paragraphs, and words.
  • Lead with an executive summary. What, for an email? Yes, if helpful. The reader may have a particularly short attention span; or you may want to set him up to read the body of the material in a certain light. If this is the case, compose a mini-version of an executive summary, which I cover how to do in Chapter 7.
  • Keep a backup in your pocket. Have a “stage 2” communication ready should the boss want more detail or context.

tip Another way to make it easy for a higher-up is to offer active help. Extending the example in the preceding “Guarding your tone” section, Matt could have improved Version 3 of his memo to Marge this way:

I know what a busy time of year this is, but we’ll really appreciate your input on the Marshall draft this week. Would it be easier to talk about this by phone for a few minutes? I could then make the changes for you. If this would be helpful, just give me a call when convenient.

tip An ingenious supervisor I know reports to her own short-attention-span supervisor in a government office this way: She sends him an email and also prints it out. She brings the printed copy to the conversation and gives it to him. He reads it in her presence, talks about it as inclined, asks questions, and makes notes on the printout. She is thus assured that he read the message thoroughly and is well-equipped for a decision. His annotated printout gives him a secure platform for proceeding.

Writing Backup Memos

When communicating with subordinates, superiors, and peers, it is often smart to confirm mutual understanding in an email or other internal communication format. This can save a great deal of hassle later if those involved emerge with a different memory or interpretation of the matter at hand. Make these memos concise and to the point.

For example, to a supervisor:

  • Subject: Confirming action on Melody
  • Dear Luke:
  • Thanks for taking the time to talk through the Melody account with me this morning. Here is my understanding:
  • We will recommend two possible courses of action for our client, Gray Builders:
    • Option A is to start the project in June.
    • Option B is to delay project start until October.
  • To flesh these alternatives out, I will:
    1. Ask Terry Thompson in Accounting to crunch both sets of numbers for us.
    2. Put my staff to work researching the permits from the EPA, municipal authorities, county housing office, etc.
  • If any of this doesn’t accord with your understanding or needs further thought, please let me know. Otherwise I’ll proceed on this basis early next week.
  • Thanks, Jenny

Take a similar tack when assigning something significant to a staff member, and in addition, consider whether the person you’re writing to is fully equipped for the task. Does he need specific instructions? A way to learn something? Connection to necessary resources? Access to people or files?

remember If you want your team to function efficiently and with confidence, provide easy access to more information and a comfortable way to ask questions. Avoid forcing people to guess what you want or how you want them to do it: Take the time to brief them fully and then trust them to deliver. But encourage your team to bring problems to your attention at any point in time, as soon as possible.

It won’t surprise you that one of the most empowering things you can do for your staff is to set a good example as a communicator, in both what you say and what you write. In addition to the example you set by demonstrating this skill set, consider an appropriate level of training. Your employees will thank you as they discover the value of better writing, and they will do you credit.

And this, dear reader, is where I leave you. Now you have it — the A to Z of business writing I promised, starting with the often overlooked but important emails you produce every day to your staple business documents, spoken communication, online presence, and special communications challenges.

But don’t go away quite yet: The following “Part of Tens” chapters give you three sets of quick helpful insights about using your writing skills to advantage.

I hope you will take the foundation this book gives you to enjoy writing, practice it in your daily work life, and keep learning. I know this investment will always reward you — often in unanticipated ways.

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