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What Your Boss Really Wants from You

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Take Charge of the Relationship That Matters Most to Your Career

Your most important work relationship is with your boss. You need it to go well. But even the best bosses can be hard to read, and some seem downright inscrutable. Your boss isn’t going to change for you—don’t waste your time trying. The solution lies in figuring out what makes your boss tick and adapting your own work style to make the relationship better. But how do you do that?

In this pragmatic and accessible guide, top executive coach Steve Arneson shows how to find the answers to fifteen essential questions that will help you understand your boss’s leadership style, goals, motivations, work relationships, and how he or she sees you. Vivid real-world examples demonstrate Arneson’s advice in action and show clearly how this process can be used to gain a more meaningful, productive, and enjoyable work life.

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1 When and how is he most approachable?

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This seems like a simple question, doesn’t it? Yet there is a great deal of insight to be gained by studying when and how to approach your boss. Like all managers, he has a particular style of interacting with his team. Some bosses are informal; you can talk to them anytime, anywhere. Others are more rigid and process oriented. The key is to figure out his preferred interaction style. For instance, can you knock on the door and get a minute of his time? Has he declared his preference about the office popin? If not, ask him directly: Are you open to me coming by your office with a quick question, and if so, when is the best time during the day? If that doesn’t work, ask one of your peers or just pay attention to the pattern of when you’ve been most successful. I once worked for a boss who literally wouldn’t allow the “do you have a minute” request—you had to set up an appointment to ask a simple question. Believe me, I wasted a lot of time and energy before I figured this out, and was getting worried that he didn’t like me. But it really had nothing to do with me. It turned out he preferred to read and prepare for any discussion and didn’t feel equipped to make decisions in informal conversations (this single insight explained a lot about this boss, by the way).

 

2 What is his preferred management style?

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Every boss has their own cadence and rhythm when it comes to getting work done; your job is to figure out what it is, and adapt to it. For example, does your boss like detailed work plans? Does he seek a lot of input before making a decision? Does he like to be hands-on when developing the presentation that goes to his peers and boss? Does he like to work one-on-one with you on a task, or does he pull in members of your team? In short, what’s the predictable pattern from start to finish on projects? How does he manage the day-to-day work that goes on in your department?

In my experience, bosses will have a preferred style for at least three basic work tasks. First, they will follow a set process for generating ideas. Some bosses prefer brainstorming; others want to generate their own list of ideas and have you react. Some bosses don’t engage much in this phase; they merely want to hear the ideas and then approve a final course of action. Do you know how your boss likes to generate and approve ideas, and why? Make a list of your recent ideas and how your boss reacted to each one. This insight will tell you a lot about him—how much does he want to be involved in this first step of the process?

 

3 What behaviors does he reward?

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Just like anyone else, your boss values some behaviors more than others. When it comes to your work style or behavior, do you know what he likes and doesn’t like? This insight is critical to establishing a good working relationship. Obviously, if you’re doing things that annoy him, that’s not going to create a solid foundation. You need to learn his preferences and try to work within those boundaries. Yes, that might mean adapting your style a bit, but if you want to improve the relationship, you need to figure out what he wants from you, and make adjustments.

For example, how does he feel about being on time for meetings? Is it acceptable to call and ask for more time on an assignment? Does he like you to run ideas by him, or does he let you make decisions? Does he want to know where you are throughout the day? Does he want you to e-mail back immediately, or do you have until the end of the day? How does he feel about you working from home? Does he want you to stay in touch when you’re on vacation? What does he think of your work space?

 

4 What is he trying to accomplish in this role?

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If your boss is any good at all, he has an agenda; he’s trying to accomplish something big in his role. This is a good thing; you want him to have a vision for the department. If that vision aligns with yours, everything’s great. But sometimes his mission is hard to interpret and that’s when you need to dig deep to study his true intent.

Start by determining his philosophical views about your function or discipline. How does he see the field? Which experts does he respect and follow? Is he a traditionalist, or does he want to take the function in a new direction? Get a fix on how your boss looks at his profession. Once you know his point of view, determine how it aligns with yours. Do you share the same beliefs about the future of your chosen field?

Amanda is an expert in software development, and was struggling with her boss about the approach to take in developing new products. To clear the air, I brokered a meeting between Amanda and her boss that focused exclusively on their philosophical visions. By taking the conversation up a notch to their broader world views, we were able to find some common connection points. When it comes to interpreting the moves your boss is making, it’s important to first understand how he sees his craft; this will explain a lot of his initiatives and behavior.

 

5 What is he worried about?

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Believe it or not, your boss is worried—about something. He wouldn’t be human if he weren’t experiencing some stress at work. Do you know what it is? Is it a late deliverable? Is it a peer relationship? Is it a budget issue? Is he getting pressure from his boss? I guarantee something is at the top of his priority list, and you’d better know what it is, because that’s what he’s focused on right now.

Your boss’s priorities are the most transparent signal you’ll get about what he wants from you. Most bosses are pretty clear about their top priorities, and if they’re not, all you have to do is notice how they spend their time. If you can’t even get ten minutes with him, he’s probably focused on something important. If you’re not involved with this priority, what he wants from you is to leave him alone. Pestering him to look at your presentation, or bugging him to get on his calendar is only going to annoy him. To get a handle on what he’s concerned about, study his deliverables. Focus on his objectives, what he’s promised the organization, his deadlines, etc. The more you know about his commitments, the better. Again, if you need clarification, ask him directly.

 

6 What is his reputation in the company?

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This is a question that should be easy to answer, because it’s mostly an exercise in observation. Trust your eyes and ears to draw the insights you need about your boss’s reputation across the organization. Start with the basics—do people feel comfortable around him? Read the body language in meetings. Is there an easy dialogue, or are people afraid of him? Notice how he spends his time. Does he stay in his office, or is he out meeting with different groups? Pay attention to how he talks about other people, and how others talk about him. Is there a measure of mutual respect? Study what conversations he’s part of; is he being included in big decisions? Listen to what others are saying to you about him—do they envy or feel sorry for you?

The fact is your boss has a leadership brand, and it’s well known throughout the organization. His brand is how other people think about him or describe him; essentially, it’s his reputation in the company. So how is he perceived? Is he thought of as strategic, creative, or flexible? Is he seen as tactical, uninspiring, or stubborn? Do people trust him? Is he seen as a thought leader in the organization? Are his technical skills well respected? How about his people-management skills? What do people think of his background and qualifications for the role? What do they think of his results? Is his stock rising or falling in the organization?

 

7 Whom does he respect?

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The answers to this question contain a lot of insight because they tell the story of where your boss is building (or avoiding) relationships around the organization. All bosses want to work with people they consider capable and talented, and most won’t develop strong relationships with colleagues they don’t respect. So, what does your boss think of other leaders in the company? Whom does he respect? Whom does he not want to work with, because he doesn’t respect their style, experience, or outcomes?

Respect is a strong word in business. It means there is something about you that I appreciate, admire, or want to emulate; it’s really the highest form of corporate flattery. Given that it’s so important, your boss will likely be transparent about whom he respects in the company. He might say, I have a lot of respect for Bill; he does things the right way. He may also indicate whom he does not respect. He might tell you directly or it may be apparent in his body language or lack of interaction with that individual.

 

8 Where does he have influence?

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At first glance, it might seem that studying your boss’s reputation and level of influence would yield the same insights. Actually, they’re quite different. He might have a reputation as a difficult colleague to work with, but that doesn’t mean he can’t have impact across the organization. Reputation has to do with people’s perceptions; influence has to do with getting things done. Influence is gained by demonstrating a track record of success, having great ideas, and being able to execute. So, does your boss have influence? Does he have the power to get people to do what he wants? Is he a thought leader in the company?

Your homework assignment for this question involves two insights: 1) with whom does he have influence, and 2) what issues or decisions does he successfully impact? Let’s start with the senior managers he’s able to influence. Look at his track record and consider his success and failures. Is there a pattern? Does he have more success with male peers than female colleagues? Does he have more sway with new leaders or long-tenured executives? Does he have more influence with line leaders or staff leaders? Does he have impact in the field, or is it mostly in the home office? Take the relationship map that you created for question seven in Step 1 and highlight those leaders your boss tends to successfully influence. Where are they in the organization? What do they have in common? Is there any way to help him expand this list?

 

9 What is his relationship like with his boss?

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This is one of the most important insights you can develop about your boss. Like you, he’s trying to figure out what his boss prefers and expects. He’s trying to look good to his manager, and that has serious implications for you. My advice is to learn everything you can about this relationship—it will explain a lot of his behavior. Is there mutual respect? Does your boss enjoy working for his manager? The reason this impacts you is obvious: if he’s not feeling good about this relationship, he’s going to be stressed, and you’re sure to feel some of that. His relationship with his boss can impact what projects you work on, whether you get promoted, how you’re perceived by senior management, even your annual raise or bonus. Frankly, in order for your career to truly take off, you not only need a good relationship with your boss, you need him to have one with his manager, too. That’s why you need a lot of insight into this relationship.

For starters, look at how much time they spend together. Does he get face time with his boss? Does he get as much as his peers? Do they have regular one-on-one sessions? Obviously, you’re not in all of these meetings, but when you are, pay attention to their interaction style. Does he mostly take orders, or is he advising and influencing decisions? Is he comfortable around his boss? Does he get asked for his opinion? Is he listened to?

 

10 What is his primary motivation?

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Now we come to the most important epiphany of all—the insight into your boss’s single biggest driver of behavior. In my experience, there is one fundamental motive that steers a boss’s actions. I call it “primary motivation.” If you had to pick just one motive that accounts for your boss’s behavior, how would you describe it? There are a number of common boss motives: job security, advancement, money, recognition, risk aversion, results orientation, complete control (ego), and a desire to be liked by everyone. Do any of these motives explain your boss’s behavior? Let’s take a look at each of these in more depth.

Your boss may be motivated by job security (fear of losing his job). He may do anything to hang on to his position—every action and decision is made with an eye toward “not rocking the boat.” Maybe he’s primarily motivated by getting ahead in the organization; all of his behaviors can be traced to his desire to get promoted or look good to senior management. It’s possible he is driven by wealth creation; everything he does is about the rewards—getting the highest rating or bonus possible. Perhaps he’s motivated by praise and recognition; in that case, he’s constantly posturing to be noticed by senior leaders. Maybe he’s so risk averse that he’ll never make a bold move; his approach is all about not making mistakes or attracting attention. It’s possible that he’s motivated by perfection; he’ll do anything to get specific results that meet his exacting standards. Maybe he has a need to be right or in complete control at all times (high ego, with a micro-managing style). Finally, he may be driven by a need to be liked by everyone, so he avoids conflict at all costs. Your boss may be motivated by one of these typical drivers, or he may have a more specific motive that underlies his behavior. Whatever it is, your job is to figure it out so you can use that insight to make adjustments in your working relationship.

 

11 What does she value about you?

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I’m going to assume you’re a talented professional with a good blend of skills, experience, and ideas. In short, you’ve got what it takes to succeed at this level, and probably the next. But, does your boss see it that way? How does she view your full set of capabilities? Does she want more from you, or does she actually want less? What does she value most about you, and what does she not appreciate?

Try this exercise: Make a list of your strengths. What are you good at? What skills stand out? Next, place a check mark next to those strengths that fit the role you’re in now (some of your talents might not be needed in your current job). Now, move any of these strengths to another list if it’s something your boss truly values and leverages. How different are the two lists? I do this exercise with clients and they generally list 10–12 capabilities, most of which fit their current role. But when they select the talents they believe their boss values, the list shrinks to four to six capabilities. This second list doesn’t begin to represent the full contribution these people could be making to the business. Is this true for you, too?

 

12 How vital are you to her mission?

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13 What does she think you need to improve?

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Have you ever considered that your boss doesn’t think you’re perfect? That you’re not finished developing? It’s a safe bet she feels your skills could use a little polish. Since we all have development opportunities, what does she want you to work on? Has she told you? Even if she has, do you really believe that’s all she feels you need to improve?

This question can’t be answered by looking at your performance appraisal or development plan. Sure, you both agreed upon some growth areas in your most recent review, and those may be legitimate development opportunities. But what else does she want you to work on? Think about her motives and preferences. Is there anything she’s not telling you because it reveals too much about what she wants from you?

Kevin is in this situation. At his mid-year review, Kevin’s boss suggested he work on his coaching and delegation skills (Kevin agreed these were opportunities). However, he also suspects the boss wants him to work on listening and taking direction more effectively. Why? Because whenever Kevin doesn’t follow his boss’s specific direction, she gets upset. She wants Kevin to do exactly what she tells him to do, and whenever Kevin follows his own path, he feels the boss’s wrath. Why doesn’t Kevin’s boss just come out and tell him to improve these skills? Because she knows it will sound silly; the only examples she can give Kevin are times when he’s not done precisely what she wanted. She’s savvy enough to know it looks petty to suggest a development need that really isn’t there. Still, if Kevin is right, how long should he ignore this unspoken development suggestion? My recommendation was to start demonstrating deeper listening behaviors now, to get ahead of what may well become a career-derailer if the boss’s perceptions don’t change (after all, Kevin can always use improved listening skills). The idea is to infer what your boss wants you to improve, even if she’s not telling you directly.

 

14 How does she represent you to others?

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One of your boss’s responsibilities involves evaluating your performance and potential. In doing so, she will be sharing this assessment with other leaders in the company. If you work in a large firm, this happens in the formal talent review process, where senior leaders gather to discuss you and your peers. If you’re in a smaller company, it’s more informal, but she’s still sharing her evaluation of you with her boss and others. So, do you have an idea of how she’s representing you? How she’s describing your performance, attitude, and work ethic? Whether she supports your potential to advance in the company? This might be the hardest of all insights to read and verify, but it’s important that you have some idea of how she’s presenting you to the organization. There are at least three evaluations she’s making at all times, and each has to do with what she wants from you.

First, she’s comparing you to a standard or model of what she expects from a direct report. If she has been managing people for a while, she has a strong sense of what she wants in an employee (remember her preferences). Try this exercise: Write down the qualities of her ideal employee and compare yourself to this list. How well do you match up? This is the first test of whether you’re delivering what she wants, and most of this is likely to be about your makeup. Do you match her ideal profile of work ethic, attitude, passion, teamwork, etc.? While this may seem like a comparison to a fixed standard, it’s more than that. Fair or not, your boss is talking to other managers about how you match her perfect-employee model. In fact, there may be cultural norms that make this prototype fairly common across the organization.

 

15 What is her history with you?

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The final question to consider from your boss’s perspective has to do with your complete history of working with her. Has her opinion of you evolved over time? Has the relationship improved lately, or is it in steady decline? If it’s the latter, can you point to a specific incident that caused the relationship to go off the rails? Your track record with your boss provides a number of insights that can be quite revealing, especially taken in context with all you’ve learned thus far about her motives and views of you. Let’s look at three historical dynamics in particular: 1) how the relationship started, 2) how it evolved, and 3) where it is now.

Let’s start with how you got together in the first place. Did she hire you? Did she join the team after you? Was she a peer who became your boss? Each of these scenarios has different implications for what she wants from you. If she hired you, she probably believes she was clear about what she wanted from you. Think back to those conversations. Did you get a clear sense of mission, and if so, have you strayed from it? You may have forgotten this, but chances are she hasn’t. In the interviews, did you trust your instincts about her or ignore them? Were there signs even then that you overlooked just to get the job? If so, you can’t really fault her consistency—she sent signals about what kind of boss she would be (this isn’t particularly helpful now, but it’s a good lesson for next time).

 

STEP 3 Take Responsibility for the Relationship

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Sections 1 and 2 were all about awareness and understanding. The questions were designed to open your mind by taking a deeper look at your boss’s motives, and by seeing the relationship from his or her perspective. Equipped with these insights, it’s time for you to take responsibility for the relationship. Remember, you’re not going to change your boss; improvement will come by modifying your attitude and behavior. In this section, I’ll provide general tips and techniques for making these adjustments, and offer specific recommendations for four common boss/motive scenarios.

Let’s start by discussing the most important adjustment you need to make—your attitude. Any progress you make with your boss has to be rooted in a new way of looking at him. You’ll never successfully change your behavior if you don’t first adjust your attitude. I believe these two concepts are equally important; you need to be intentional about changing your attitude and your behavior. Adjusting your attitude starts with changing the way you view your boss.

 

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