CHAPTER THREE

Pleaser Power Plays

Most of us realize that success is a team sport. Pleasers go beyond believing this adage; they live by it. As Pleasers work their way up the professional ladder, many of them strive to bring out the best in their colleagues. Unfortunately, some Pleasers prove to be better at supporting others than at supporting themselves on the job. Until they understand the way that their family system may have conditioned them to look outside themselves for validation, Pleasers may be vulnerable to being “played” by Charmers and Commanders who dangle approval in front of them like a carrot on a stick.

In addition, Pleasers face a special challenge when it comes to managing up. Obviously, we all want to please the boss. Add this natural incentive to make your superior happy to the Pleaser’s occasionally exaggerated need for approval, and you have a recipe for anxiety and insecurity. To hold their own, particularly with a critical superior, Pleasers must become mindful of areas where they need to respectfully disagree, take a stand, and speak up for themselves if they want their full range of professional talents to be appreciated. Pleasers who don’t master these skills often pay the price of being passed over for promotion by peers who appear more confident to senior management.

We’ll come to this challenge later; we’ll start now with what happens when a Pleaser needs to manage down—an obvious test for someone who has a need to be liked beyond their need to take charge.

When the Pleaser Is the Boss

Pleasers often long to make love, not war. However, in managerial roles, the power reflexes of command are sometimes required. When put it charge, some Pleasers become anxious that they will not be liked if they take a stand to enforce their authority. This insecurity is rooted in the Pleaser’s longing for the approval of a preoccupied caregiver early in life. To lead effectively, Pleasers must keep a few simple principles front of mind to make sure that their collaborative talents aren’t undermined by their emotional insecurities.

Establish Clear Performance Standards and Enforce Discipline When These Are Not Met

Let’s face it: if you’re a Pleaser, the place where your emotions are going to wipe out your capacity for logic is any time you have to deal with conflict. And when you’re a boss, conflict is going to rear its head when members of your team aren’t performing at peak. Thus, you’d better figure out a way to strengthen your capacity to be objective when you need to deliver the uncomfortable message to one of your team that there are areas where they need to improve. What’s more, if you are managing a Charmer or a Commander, you need to lay out the consequences that are associated with underperformance, or these employees may be feigning agreement on the outside while they are yawning on the inside.

This kind of preplanning is a must for the Pleaser boss. You must clarify what your performance standards are and how they are going to be measured in a manner that everyone can clearly understand. You must also make sure that your employees understand how you are keeping score. Finally, you must accept that enforcing consequences when someone doesn’t cut it, even when it’s someone you like personally, is critical to the group’s ability to understand that you mean business—whether you enjoy it or not.

Project an Image of Strength

Pleasers should never underestimate how critical image is to keeping their staff in line. I learned this lesson working with the CEO of a prominent Fortune 500 company who lost ground not only with his board but with employees throughout his organization because his dedication to being a “nice guy” wasn’t giving them what they needed to feel hopeful in a contracting economy. While nobody wanted this chairman to be mean spirited, throughout the firm employees confessed that they longed for a “wartime” CEO who gave them a sense that someone decisive was at the helm. Pleasers need to realize that good intentions are necessary, but not sufficient, when it comes to leadership in an uncertain business climate.

To keep people on track, the boss must look confident, sound confident, and act confident as much as possible. Don’t ask for your employees’ approval; instead, clearly state your decisions once you are sure about them. Projecting an image of strength can be a strain for the Pleaser who often longs to let his or her hair down. Pleasers under fire must resist the urge to unburden themselves emotionally with their staff. Many employees, particularly Charmers and Commanders, see emotional vulnerability as a sign of weakness. Maintain a decisive image, and keep your reports busy with clearly defined assignments.

Embrace Pushback—It Means Your Staff Is Thinking

When the Pleaser’s need for approval is particularly acute, they may unconsciously equate agreement with approval. When the Pleaser is the boss (and a Commander as well), he or she may mistakenly believe that when someone disagrees with them, it’s because they don’t support them. Pleasers who confess they feel this way admit it’s illogical and counterproductive, when they consider their reactions objectively. This type of reaction undermines the Pleaser’s ability to lead effectively.

If you are a Pleaser in charge, remember that it’s not your staff’s job to validate your seniority or your point of view. That validation must come from within. When members of your team push back on your point of view—rejoice! At least they aren’t asleep at the wheel. If you genuinely agree with their concerns, incorporate them. If you disagree, let them know you’ve heard their reservations but you have decided to override them. When you learn to operate with clarity, confidence, and courtesy on a regular basis, you won’t need people to agree with you to boost your self-confidence. What’s more, you are likely to set a tone where your staff feels motivated to think more deeply and share more freely about their perspective on your shared business goals.

Don’t Expect to Be “Friends” with Your Staff

To a certain extent, every type on the grid knows they need to please their boss to get ahead and tries to operate accordingly. That said, Pleasers, who sometimes have an exaggerated need to be validated, may be vulnerable to being manipulated by a subordinate who senses how to “game” their need for approval. We often see dramatic examples of this when a Pleaser is managing a Charmer. Charmers, who have mastered the arts of persuasion in preschool, are all too willing to spend time with a Pleaser boss to get what they want. However, in the same way they learned to manipulate an emotionally needy parent, Charmers will quickly intuit when the boss gets “hooked” on their approval and turn the tables sharply. This often results in a Pleaser boss dancing to the tune of an insubordinate report who has learned that he or she can get away with murder. Don’t try to become pals with this type of report, don’t indulge in lengthy personal conversations to clear up professional mishaps, and use praise sparingly.

Power Grid Case Study: A Pleaser Managing the Charmer

Bryan is a Pleaser who inherited his father’s celebrated restaurant and resort. Bryan has recently hired Dave, a Charmer, to be his general manager.

During the first couple of months of their working relationship, Bryan’s head was spinning from all the hard work and attention he was getting from Dave. It was the honeymoon period for a Pleaser managing down to a Charmer, and Bryan loved it. Dave worked long hours to get up to speed and arrived early in the morning to brainstorm with Bryan. Bryan was particularly flattered when Dave began sharing some of his personal life with him, trusting him with stories of his off-work hours. Bryan became comfortable enough himself that he talked about his personal life with Dave too.

To be an effective boss, you must be able to operate with enough formal power to get your employees to toe the line. The challenge for Pleasers is that they hope so much that their employees will like them personally that it can be a struggle for them to set the limits necessary to manage others effectively. While Bryan’s father might have left him with a potentially prosperous business, he also left Bryan with a huge self-esteem issue because he had focused so much of his attention on that business rather than on his son when Bryan was a little boy.

The classic dynamic we see when an emotionally needy Pleaser is managing an entitled Charmer is a role reversal. Since Charmers can be quite ambitious, they will often go out of their way to please the boss so that they themselves can get ahead. Charmers may even resort to manipulation. If it takes unstructured personal chats, the Charmer will paste on their most sympathetic smile, show up, and listen to the best of their ability. Basically, in the beginning of the relationship, the Charmer will try to fulfill the Pleaser’s longing to be validated. This is precisely what Dave did with Bryan up until the moment it no longer suited his own needs. When Dave felt safe enough to stop “pretending” that he cared so much about the minutia in Bryan’s world, things started changing.

As we’ll see in chapter 4, the simple truth that Charmers learned from managing their caregivers is that once they get an authority figure hooked on their approval, it’s simpler to get what they want from them. How does the Charmer know when someone is hooked? When that person starts to compliment them too often. The risk for the overtly positive Pleaser is obvious.

Once the Charmer senses the Pleaser is emotionally hooked, the romance stops and the role reversal begins. At this point, it’s hard to tell who’s the boss.

After a few months, Dave began getting moody, showing up late for work, and getting peevish over minor details. Because Bryan felt that he had bonded “so personally” with his general manager, Bryan found himself unable to take Dave to task.

If you are a Pleaser, know that most Charmers have been falsely empowered by an authority figure from their family system. This is because, in many cases, the Charmer was raised by caregivers who turned to them for emotional support and guidance. Thus, Charmers begin most relationships with an inflated view of themselves. Praise a Charmer too much, and they will start doing less and demanding more. Often, they will start demanding a raise, and if they really think they have the Pleaser hooked, they will sulk until they get it. Pleasers need to remember to use praise sparingly with Charmers and be prepared to enforce concrete consequences if they underperform.

Bryan needed to learn to practice some of the strengths we associate with the Commander to get this working relationship back on track. First, he needed to set some clear performance expectations for Dave. As he did this, he needed to consider the way that his need for personal attention had undermined his leadership. Second, he needed to have a no-nonsense chat with Dave to make sure that his expectations were clearly communicated and understood. Finally, he needed to establish consequences and be prepared to enforce these if Dave dropped the ball. Once Bryan started setting some clear limits, both for himself and for Dave, they were able to reestablish a positive working rapport.

When the Pleaser Is a Peer

Because they have an emotional trigger that drives them to seek the approval of others, Pleasers often abdicate their opinions in favor of those of their peers. However, if the Pleaser’s peers begin to suspect that all it takes is a little raw aggression to push them aside, the workplace can begin to feel like the dodgeball field in no time. To maintain the respect of their peers, Pleasers need to embrace some life lessons that other types on the grid may already grasp.

Know Your Boundaries and Protect Your Turf

It’s a simple lesson, and one most people learn playing “king of the hill” in preschool. Why is this one such a toughie for the Pleaser? Because many Pleasers didn’t learn how to protect their turf on the playground. In fact, some of them never made it to the playground at all. Pleasers were often dashing home as kids, making sure they took care of whatever their caregivers were too preoccupied to deal with. The upside for the Pleaser is that these men and women don’t snap under pressure; they maintain an even tone that keeps them out of hot water. The downside is that they often don’t do anything when an aggressive colleague simply shoves them out of the way. It’s not as if they had the benefit of involved parents who were emotionally coaching them on how to handle raw aggression.

On the job, the equivalent of playground shoving is the colleague you don’t work for who treats you as if you do. Many Pleasers report that when a peer starts barking orders, they often find themselves rushing around obediently before they rationally realize what’s going on. This can leave the Pleaser seething with resentment on the inside but without the tools to recognize what’s wrong. Thus, if you are a Pleaser, make sure you know the boundaries of your job description before you get subtly (or not so subtly) subordinated. Use the rules of the system to protect your professional boundaries, and keep a written job description on hand at all times.

Prioritize Respect over Affection

When Pleasers are unaware of how their drive to form strong personal alliances differs from the priorities of other types on the grid, they may make the mistake of being overly solicitous, hoping their colleagues will return this behavior in kind. It seems like only yesterday that a lovely and brilliant young Pleaser in my coaching practice was struggling with investment banking colleagues who were playing head games with her by questioning her competence, staffing her on substandard deals, and making innuendos to senior management that she “wasn’t that bright.” In fact, the problem was that this young woman was a walking brain trust whose mere presence brought out the dysfunctional side of some of her insecure colleagues. One afternoon, she was blinking back the tears as she asked me, “Do you think they’ll ever like me?” Answering her, I realized I was making a point I’d been repeating to many Pleasers when I found myself saying, “It doesn’t matter if they like you. It matters that they respect you.” (This woman, by the way, has gone on to become an investment banking superstar. Her clients adore her—and respect her.) Grasping this lesson can be tricky for the tender-hearted Pleaser who longs to make “friends” on the job. That said, this is one of those lessons the Pleaser is destined to learn at some point in their careers.

Negotiate Practical Issues First and Personal Reactions Second

Pleasers, who long to keep the peace, can get rattled when a colleague blows up at them under pressure. This is because, in their family systems, Pleasers were often conditioned to be nurturers. When someone’s upset, the Pleaser wants to fix their feelings first and the problem second. When a Pleaser is working with a peer on the job, these priorities need to be reversed. To stay on track professionally, the Pleaser must learn to stay focused on resolving the professional issue at hand and mopping up any hurt feelings later. When the Pleaser can get his or her colleagues focused on what they can do practically in the present—meeting the deadline, correcting the mistake, saving the client, and so forth—that solution-oriented mind-set can sometimes serve to repair the hurt feelings at the same time.

Accept Conflict as Constructive

Pleasers, whose collaborative instincts are often the glue that holds a culture together, can tire easily when faced with conflict. They just want it to go away; they want people to “play nicely,” and hope that if they bury their heads in the sand long enough, the problem will blow over and all will be forgotten. This attitude misses an important point. Sometimes, conflict can be extremely healthy for an individual and for an organization’s development. Conflict signals passion. It’s a sign that there are stakes worth playing for and that people are in the game. When approached in a healthy manner, it can even be fun. As Pleasers develop a more balanced power style, and cultivate the tools they need to embrace conflict constructively, they begin to learn that the ability to resolve conflict often creates powerful professional alliances among peers. Avoiding conflict can sometimes signal that you are avoiding engaging with a professional peer in a fully involved way.

Power Grid Case Study: Separating Personal Feelings from Professional Goals

Dave, one of the oldest directors in the information technology division of a large investment bank, is a Pleaser. He has been repeatedly passed over for promotion and has worked with the firm for over a decade. Paul, an Inspirer, is a new hire who comes to the firm from an Internet company.

Dave’s challenge in working with Paul shows us that Pleasers may have to manage more than their workload as they deal with their peers. Sometimes they have to manage their envy.

Like many Inspirers, Paul exhibited a natural charisma that drew others to him from his first day on the job. When Jeff, their boss, began to gravitate Paul’s way, Dave found that he was so overwhelmed with jealousy that it was getting difficult for him to concentrate on his work.

Dave’s feelings began to really get the better of him one morning when Jeff strolled down their floor, passed his office, and lingered in Paul’s doorway “just to chat.” One thing that made this scene particularly hard for Dave to witness was that Paul seemed so maddeningly nonchalant about a scene that would have had Dave dizzy with happiness if it had happened to him.

While Dave was trying not to stare at Paul and Jeff through the glass wall of his office, he was secretly hoping that Jeff would notice how industrious he looked as he hovered over his computer. Instead, he heard peals of laughter as the two grinned over some shared joke. Dave began swallowing hard and racking his brain for topics that would work for lighthearted small talk if Jeff decided to make the rounds and come by to chat with him. While Paul was a classic Inspirer, taking popularity for granted, Dave, like many Pleasers, was obsessed with the popularity scorecard.

As envy got the best of him, Dave began using the office grapevine to spread innuendos that Paul was positioning himself with the boss at others’ expense. The pain that Dave felt at being overlooked turned itself into this toxic strain of gossip. However, a few months later, when Dave discovered that Paul had complimented his work in a couple of memos to Jeff, Dave quickly backed off his smear campaign.

How exhausting to be Dave! If his colleagues suspected how he was torturing himself to get the boss’s attention, they probably would have suggested he take a vacation and get some perspective—for everyone’s sake.

The lesson for the insecure Pleaser is, the moment you get triggered to stab someone in the back is the moment when it’s best to be direct. Dave’s strongest move would have been to simply go to Paul, acknowledge how well he seemed to be fitting in with the boss, and to ask for feedback on how to get his best ideas across to Jeff more effectively. Unfortunately, employees who harbor hidden agendas aren’t inclined to deal directly. This is why, to operate clearly and powerfully with their peers, Pleasers need to separate their personal longings from their professional goals.

When a Pleaser Is a Subordinate

Being direct and succinct can be challenging for Pleasers. The Pleaser often hopes that by chatting personally with his or her superior, a bond will form that will fulfill the Pleaser’s longing for attention and approval from an authority figure. This type of emotional agenda frequently backfires. To get ahead and stay ahead, the Pleaser needs to stay focused on their professional responsibilities and seek validation for their work rather than their capacity for office socializing.

Make Sure Your Opinion Matters as Much as Your Output

When a Pleaser describes the hard work they did to create a report, and then goes on to say that they will not be included in the discussion when the report is reviewed, I consider this a person who needs a power upgrade. You want your superiors to value your subjective opinion as well as your analytic output. Don’t give everything away at once. Ask leading questions when you present material so you encourage people to think about what you are presenting to them. Focus on establishing a sense of personal presence, as well as a reputation for factual reliability, when you share your work with others.

Learn When to Push Back

Pleasers, who are overly focused on seeking the approval of others, may miss crucial opportunities to point out things their boss may have overlooked. This is not only risky for their organization, it may cause their superior to draw a far darker conclusion than that the Pleaser is tongue-tied. When problems or overlooked information come to light later, and this is often the case, a frustrated superior may come to the erroneous conclusion that the Pleaser didn’t say anything because they simply weren’t all that bright. While it’s always wise to be cautious about when and how one pushes back, particularly if the boss is a Charmer or a Commander, Pleasers must train themselves to speak up respectfully when they have a strong view. Pleasers who learn the art of when to articulate their intuitive hunches tend to be highly valued on the job.

Respect the Value of Your Superior’s Time

In a competitive work environment, Pleasers need to remember that the boss may be constantly thinking of the value of time. If we take this one step further, it’s likely that the boss is thinking that their time is more valuable than that of their subordinates. For example, if you are below them in the system’s chain of command, the Commander feels your job is to serve them. In tactical terms, the Commander views a business hierarchy much like a military rank. Can you imagine a private lingering in the tent of a general before the battle, wanting to brainstorm with his or her superior officer about the next campaign? This is what it feels like to Commanders when one of their reports wants to kick ideas around with them. Wherever the Pleaser suspects his or her boss may fall on the Power Grid, it’s important to know when to get to the point quickly and curb the desire to bond conversationally. Pleasers must be mindful of the value of their superior’s time and watch for subtle cues that the time for “informal chatting” is over.

Stay Focused on Professional Priorities

Many Pleasers slave away in the hopes that they will get the validation on the job that always seemed to elude them in their family systems. The flaw in this strategy for the Pleaser is that if the firm is going through a crisis or the boss happens to be a Charmer or a Commander, they’re going to be waiting a long time for a compliment. Let’s face it: managers are trained to focus primarily on one thing—the commercial point. While it often appears on the surface that Pleasers are focused on the organization’s mission, motives may be lurking at a deeper level that can sabotage the relationship between a Pleaser and his or her boss. For example, when an Inspirer is the boss, basking in the glow of such an altruistic superior can get addictive for the emotionally hungry Pleaser. Bosses from any quadrant on the grid will eventually get burned out if the Pleaser needs too much “me time” with them. Thus, as Pleasers become more aware of how their need for attention can drive their behavior, they need to monitor the amount of time and attention they request from their superior.

Power Grid Case Study: When a Pleaser Meets His Commander Boss

Andy is a Pleaser who works as an engineer for a large aircraft manufacturer. His new boss, Steven, a Commander, was a recent hire brought on from one of their competitors to help them work on securing an important military contract.

Andy grew up in a farming community in rural Pennsylvania. His father worked repairing large machinery, and his mother helped run a local bakery. One of five children from a loving but financially strapped family, Andy learned to look out for himself early in life. One of the ways he did this was to make sure he knew what was going on with the people he worked with personally as well as professionally. Andy was a really friendly guy.

Andy’s misguided attempt to make a good first impression with his boss shows us how the Pleaser’s dream of bonding with authority can sometimes be a dangerous fantasy.

Andy approached Steven on his first day at the new firm for an informal chat about what was going on in their division. This seemed like a good idea to Andy because, after all, this is what any Pleaser would have welcomed from a new team member.

Andy was surprised and stung by the terse and unwelcoming manner in which Steven looked up and greeted him with a demanding “Yes?” when he saw Andy standing in his doorway. A Pleaser who was easily hurt by being rebuffed, Andy stood like a deer in the headlights for a few uncomfortable moments and fumbled to explain why he had decided to just “drop by.” He thought he had been coming by to earn a few points with his new supervisor—and instead he was losing ground as the seconds ticked by.

Here’s a clear example of how the Pleaser and the Commander can see the same situation very differently. From Andy’s point of view as a Pleaser, an informal chat gave colleagues that important moment to bond personally. For a Pleaser longing for attention, this is what the heart and soul of business is about.

While a Commander presents a dramatic example, a boss from any quadrant on the grid finding a new employee in the doorway may sense a dilemma. For example, a new boss may hope to establish discipline among new reports in order to keep them focused on the job. If this is the case, the boss may wonder how he or she will be able to make a department run successfully if the employees feel free to wander in with idle chitchat.

While Andy’s situation looks grim on the surface, it’s important to bear in mind that Pleasers can have fabulous careers reporting to Commanders as long as they remember what to focus on when they interact with this type of boss. In Andy’s case, it’s helpful to remember that Commanders can be structure junkies. In other words, they never met a rule they didn’t like. As we know, Pleasers are great with details. Thus, one way a Pleaser can win the heart of a Commander is by becoming an expert on the rule book. Regardless of the quadrant the boss falls in, Pleasers will be headed in the right direction when they turn their laserlike focus on the details their superiors care about rather than longing for more face time.

Conclusion

Self-confident Pleasers rise to the top. This is because once they have learned to trust their intuition under pressure, Pleasers are able to balance a keen eye for business detail with a keen sense of what motivates others in a way that can take their colleagues’ breath away.

Pleasers who have learned to “kick the habit” when it comes to their addiction for approval still approach their careers with an innate tendency to support others. What they have learned is how to do this without sacrificing themselves in the process. This makes them leaders who can envision and execute business solutions that are profitable for their cultures and their cash flow simultaneously.