CHAPTER 22

What If My Boss Doesn’t Want to Win and Doesn’t Care About Their Soul — or Mine?

“No man chooses evil because it is evil; he only mistakes it for happiness, the good he seeks.”

–MARY WOLLSTONECRAFT

You’re working hard to be a manager who wins well, but what if your boss is more of a User, Gamer, or Pleaser? How can you still win well?

• • •

Jamie shut the door and began the emergency meeting. What he had to say wasn’t easy, but he knew his people could handle it. That’s why they “get paid the big bucks.” He minced no words. Stock prices, competitive pressures, time to get it together. Now. The intimidation factor was high. His face red and blotchy, he barked, “Fix it fast or else!”

He would never speak this way to the front line. He’s an inspiring communicator, and his people love him. He trusted his leaders would translate the message in a meaningful way.

Grace, the new vice president, left Jamie’s meeting a bit shaken but clear on the message. She called an emergency huddle with her direct reports. They were in the midst of executing plans to address key issues, but she worried it wouldn’t be fast enough. She needed to show progress right away. She took Jamie’s remarks to heart and was pretty sure her job was on the line.

She didn’t usually rely on fear and intimidation. Most of the time she was a role model of Winning Well behaviors, but she was still learning the culture and figured that people were accustomed to this. Plus, her team was full of seasoned leaders who understood the pressure. She would never speak that way to the front line, but she trusted that her team would know how to communicate the message in a meaningful way.

Grace’s technical manager, Bill, left their meeting a bit shocked. “Wow,” he thought. “Grace has never acted this way before. She doesn’t even seem to want our input. She just told us what to do. Something must be really wrong. If this is what she’s telling us, I wonder what she’s holding back.”

Bill was concerned that his team of operations supervisors wouldn’t buy into her plan. After all, it had been a crazy couple of months, and they were all about to tip over from exhaustion. Plus, he knew the decision was shortsighted, would reduce quality, and would cause rework down the line.

Clearly, though, the situation was serious, so he decided to just be a good soldier and salute. He was behind on his mortgage, and his daughter was headed to college. This was no time to stand out as a naysayer.

Bill called a meeting of his operations supervisors and laid it all on the line. He needed to get their attention, so he figured a little bit of intimidation couldn’t hurt. Plus, he knew he was on the short list for a transfer to another department. He wouldn’t have to deal with the downstream effect.

So Bill told his supervisors, “I want you to fix this, by whatever means necessary. If anyone complains, write them up for insubordination.” Bill knew he was being a bit rough. He would never talk that way to the technicians. But he had good supervisors who he trusted would buffer the message.

Imagine you report to Bill? What are the chances you would use Winning Well behaviors as you talk to the technicians?

INTIMIDATION SNOWBALLS

Be careful. Gamer, User, and Pleaser characteristics are contagious. Don’t let the bad behaviors rub off.

You can learn as much from a bad boss as a good one.

First, pay close attention to how the stress impacts you, your people, and your family. Find folks who will tell you the truth. Be sure you’re staying true to your leadership philosophy.

Find ways to ground yourself: think of a lightning rod. It absorbs the energy from the lightning and disburses it into the ground without allowing it to damage the building. Exercise, mediation, and prayer are all good options to ground you. Remember that you know how to win well, and your boss is just one transient person in your life. This season will end, but you will live with who you are becoming forever. Once you ground yourself and regain your bearing, consciously choose how you will interact with your people. Even in moments of high stress, you do have a choice. Choose based on your values, on confidence paired with humility, and with a focus on relationships and results.

Second, keep in mind that you can learn as much from a bad boss as a good one. Pay close attention to the impact your boss’s behaviors have on you and your teammates. Keep a journal or make a running list. Commit to never being that person.

If any of the managers in the above example had had enough confidence and humility to ask a few strategic questions or taken some time to discuss the best way to solve the problem by focusing on results and relationships, they would have likely come up with a more effective solution.

By shutting up and protecting themselves, they sold their souls and made matters worse.

HAVE A CONVERSATION

Karin recalls a time not too long ago when she felt her own soul slipping way. It had been a tough couple of weeks. The cocktail of challenges had impacted her team’s normally high performance. They needed strong results immediately. She didn’t realize how much her stress showed on the outside until a trusted manager on her team called her and said bluntly, “You’re changing.”

The words stung with fierce truth. He was right. On the inside, she was worried about their mission, their cause, and their careers. But on the outside she was acting more like a User. She was showing up like the boss she’d refused to become. Her passion to protect her team had taken on an ironic intensity. Her supportive style morphed into frantic control. She invited herself to line-level conference calls and required more rehearsals before executive presentations. Instead of trusting her competent team, she scrutinized every page of every PowerPoint deck.

Her efforts to protect her team from stress had backfired.

The words still echoed from the first conversation when her phone rang again. Another one of her managers was calling. At that moment, Karin realized that the two managers had talked before and coordinated the conversation. The second manager said, “Your style works. Stay the course. We believe in you, in us, and the mission. Every one of us has your back. Just tell us what you need.”

David has heard those words, too, in very similar circumstances. Kevin, a trusted colleague and one of his direct reports, said, “You’re not David anymore. What’s going on? How can we help?” Sometimes bosses need to see themselves as you see them. When you hold this kind of conversation from a place of support and compassion, it’s a heck of a lot more productive than being ticked off at your boss and talking behind her back.

We were the ones who needed reminding of what Winning Well looks like. Our teams reminded us that:

Over the years, we’ve had employees tell us how we’ve hurt their feelings, overlooked their efforts, embarrassed them, or overreacted. Every one of those conversations has helped the team to be stronger and helped us to be more effective.

Sometimes the best way to win well is to help your boss see the impact of his behavior on the results and people.

There are also more lighthearted ways to approach such situations.

One vice president we know had such highs and lows that her team gave her two nearly matching Barbie dolls for her desk. The first was immaculately dressed in typical Barbie fashion: matching shirt, shoes, and pearls. The other doll had felt-tip marker on her face that made her look evil, and hair that looked liked it had been eaten by a cat.

They chose a “good Barbie day” to approach her with their plan. Their request was that she put out the doll that best portrayed her mood as a warning sign. Her team then knew if evil Barbie was lurking, they needed to lie low. She accepted the gift with a smile and used the dolls as requested to lighten the mood. She even became comfortable when one of them would go to her shelf and switch the dolls to tell her the team was having a rough time with her.

Despite an occasional, frustration-induced mood swing, she was a brilliant, inspiring, deeply devoted leader. Everyone who worked for her grew under her care. If the team had stopped caring because of her outbursts, they would have missed all she would teach them about Winning Well.

Chances are that if your boss isn’t Winning Well, he doesn’t feel particularly good about it. If everybody’s frustrated, it’s likely your boss is too. Messy relationships are always a two-way street. Be sure you do everything you can to work on the relationship.

Conversation Starters

Here are some questions you can ask your boss to get a conversation started.

MANAGING UP WITH CONFIDENT HUMILITY

Confidence and humility are cornerstones of Winning Well. They’re also vital in maintaining an effective relationship with your boss. Remember some of the confidence-leveraging behaviors: know, own, and use your strengths; stand up for what matters; and speak the truth. Be brave enough to have and share your opinions, even if they differ from those of your boss.

Of course, every boss is different. Understand and play to her style. If you struggle with persuading your boss, try the following tips:

1. Don’t confront her in front of your peers, her peers, your team.

Have the conversation privately. Let your passion inspire your argument, but don’t emote. Stay calm. Appeal to his heart and mind, but don’t wear your heart on your sleeve. It might help to tell a story, but think it through first. Overly emotional appeals will weaken your argument.

2. Do your homework.

What are her goals? What keeps her boss awake at night? Put your concern in terms that are important to her. Prepare for questions. Do the math. Do more math. Do the math her way. Poke holes. If she doesn’t like math, collect stories. Do more math, just in case.

Yesenia managed a group of insurance company accountants. Her group had low morale because of a problem they’d uncovered but couldn’t solve. The customer service department was taking shortcuts that cost the company $3 million annually. The accountants had tried to talk to the customer service department without success. Yesenia approached the CEO to discuss the problem. She didn’t lead with, “My group has a morale problem.” She started with, “My group has discovered a way we can save $3 million annually. It will take some coordination with another department. Would you like to hear more?” Of course the CEO took the time to listen—because Yesenia had done her homework and shared the issue in terms that mattered to her boss.

3. Share your concern frankly.

Speak your truth. Share why you are concerned for the business. Have several supporting points. Listen carefully. Your boss has broader perspective and more context. Learn as much as you can. Hear him out completely and suspend judgment. Listen some more. Appreciate his point of view. He’s likely not a jerk. He has pressures too. Understand them. Learn all you can. Consider, deeply.

If you’re still convinced, bring on the data. Build graphs. Show correlations. Draw pictures. Find stories. Benchmark with the best. Engage your support team. For us, this usually means the finance person. She’s fantastic. Yours can be too. These folks are usually reasonable and thoughtful, and can help you clarify and support your position. Convince others to care about your point of view. Get a light murmur of whispers started to support your cause in other people’s words.

Of course, the other side of the side of the confidence-humility spectrum is humility: Know your vulnerabilities, admit mistakes, and invite challengers. As in all relationships, humility is vital when you work to improve your relationship with your boss.

Managing Up When Things Go Wrong

Perhaps the most important time to stay humble is when you’ve screwed up. The biggest mistake you can make with bad news is to wait too long. Your boss would rather know what’s going on, even if you don’t need his help. We recommend using our DARN method to guide your approach.

D—Disclose (explain the situation and root cause)

“I’ve had a bad day. We have a bit of a situation I need to fill you in on.” _____ happened and now we have _____.When I dug in deeper I learned it was caused by _____” (Identify a behavior or situation, not a person.)

A—Accountability (don’t be a blamer)

“I accept full responsibility. Here’s how I can prevent this next time _____.”

R—Response (share your solution)

“Here’s what I’ve already done _____.” (It’s important to have something to say here.)

N—Next Steps (share your plan and what you need)

“Here’s what I’m going to do next _____. I could use your help with _____.” (If needed.)

YOUR WINNING WELL ACTION PLAN