Get Out of Your Own Way

Self-advocacy is difficult for many of us, especially in professional situations. Whether it is “selling” yourself or your business, asking for a raise or a new position, negotiating or resolving conflict, or standing up for yourself and speaking up, when it comes to professional advocacy, many people stall and struggle. It’s difficult to sell without seeming like you’re selling, asking for a raise without demanding or backing down. When it comes to negotiating your worth, professional situations often make it harder because of the degree of professionalism that needs to be maintained. When you’re advocating yourself in personal situations, often you can go hard and not worry as much about the reactions and effects. In professional situations, you worry about the audience and the people the audience know, and the people they know . . . .

Many times it all comes down to you and how much you get in your own way. At all stages of improv education, people get in their own way. This might look like a lack of confidence, a nervous energy, self-deprecation, or not standing up for yourself. It might come from a lack of preparation, lack of listening, missing focus, or missing presence. It’s “easier” to play things safe a lot of the time. If you’re constantly trying not to fail, you’ll never succeed.

Let’s get out of our own way.

PITCHING A BUSINESS

Personal elevator pitches have been covered, but what about business pitches? Generally speaking, when you’re pitching your business, no matter what size, you have to think about your audience first. I’ve seen some horrific business pitches before (and if you’ve watched Shark Tank, so have you), and I’ve seen some that knocked it out of the park. The winning pitches have something in common I bet you can guess by now: they attend to the audience.

Think about who you’re talking to and what you want your audience to do. Talking to customers is different than talking to investors, which is different than talking to a potential board. Every audience needs to be handled very differently. Let’s compare pitching to customers versus pitching to investors. A customer needs to know what the product or service does for them, while an investor needs to know the business’s capability. The investor cares about the customer, but they also care about the bottom line, customer acquisition cost, marketing cost, distribution, and potential, among others. In efforts to not dive too far into the rabbit hole, it suffices to say that the customer and investor want two very different things to buy in to the product or service and will spend two very different amounts of money.

Aside from thinking about the general audience, since you’re pitching to a specific audience, you need to think about what’s in it for them. Since the purpose of most pitches is to get buy-in, you want to think about what the person you’re talking to can gain. Once an investor told me that businesses are either painkillers or vitamins. That makes so much sense to me. Is my business solving a problem as a painkiller, or is it making life better for someone as a vitamin? The key to this? You’re thinking about the result with them, whoever they are. You’re not thinking about anything else. You often want to start using those influence techniques when you are showing worth to whoever your specific audience is, and they most likely want very different things!

Pitching your company is much like going on a job interview for your business. Before you even walk in the door, you should think about potential questions and answers and how could you adjust if necessary. You’ve got to get straight to the point in job interviews; you have to actually be at the point before it even begins with pitches. We shouldn’t be left wondering why you’re here.

Employ a strong sense of excitement. If you have to use Viewpoints and see what your body and voice look like when you’re excited talking about your business idea, go for it. If you can’t excite your listeners in a pitch, you’ve lost before it even started. Again, control the room by walking in with the right energy for the audience. Once you’ve got the ideas of the pitch out, do that 90-second, 60-second, and 30-second version. Get it sharp, tight, and clear. In an interview, the interviewer is usually looking to meet a need and wants to hire someone. In a pitch session, investors don’t necessarily need to spend their money on someone. They want to or are interested in the possibility of it. Your product or service is the candidate they want to hire, whether it’s a room full of investors or a room full of customers.

You need to start your presentation with a bang. If you’re going in front of customers or investors, they need to be impressed in the beginning. Having a tight first line or two is critical in getting your audience’s immediate buy-in on your concept. Storytelling is critical: bring back Sit-Prob-Sol—the situation is the market, the problem is the problem, and the solution is your product or service. Finally, end with what makes you special. Why are you the best person and company for this particular group’s problem? “Show, don’t tell” is another improv strategy critical to pitching. By showing the effectiveness of your idea, product, service, and how your customers or investors can benefit from you specifically versus telling them, you’re connecting back with the storytelling component of how we learn and process information. Finally, make sure they know what you want, and be clear with it yourself. If you can’t describe what you want in one or very few sentences, you’ll never be able to connect your audience with what you want them to do. Easy, right?

Now is a great time to take a moment and step back—this sounds remarkably like a job interview, doesn’t it? That’s the trick—they are so very similar. Conversations, too. If you understand who you are talking to, what they want, what you want, and how you can provide it, you’ve got so much in the bag. Listening and responding make up everything in verbal and nonverbal communication, no matter if it’s a conversation in the office in front of the bathroom or a meeting with a potential multimillion-dollar investor. At the core, it’s all listening and responding; which means it is all improv.

Tying pitching back to interviewing, when you are practicing your pitch, make sure you know it forward, backward, left, and right, because most of the time, unless you are giving a pitch for a competition, you’ll be stopped and interrupted. Remember, if you are memorizing something word for word, you’ll memorize the word order. If you memorize the word order and get interrupted by a question or five, you won’t be able to restart that confidence that got you in the room in the first place.

THE UGLY: IMPOSTER SYNDROME

Ah, that confidence. Quick, check in: Have you ever felt like a fraud? Thought you don’t belong in the room? It’s all luck and will come crashing down when someone discovers you? I feel you. Both of my businesses are successful. I don’t work another job, I don’t worry about finances . . . and even writing that sentence, I almost wrote “knock on wood” because of that little nagging voice inside my head.

For most of this book, I’ve used student examples and have saved my own personal examples for very key moments. This is one of them.

I had left New York City after a long tenure, ready to move along to a life that was cheaper and calmer in Winston Salem. I still had that New York City hustle, so one of my big goals in the first few months of my new city was to meet as many people as possible and try to get EE off the ground. Getting the meetings were easy. Showing up with confidence wasn’t. There was one meeting in particular that I will never forget. It was the meeting that changed everything about how I introduced myself and my business.

In my move, I sent out dozens of emails for meetings and set one up with the woman who was in charge of one of the artistic entrepreneur organizations in town. Being the City of Arts and Innovation, Winston had a few organizations that helped art-based businesses succeed. This particular organization was one I had heard so much about; it was one everyone told me to talk to because what we did with EE was such a fit. Seriously, we used a dramatic art—improv—and focused on professional development for businesses. I still remember how excited I was to meet with the executive director.

As for the who, where, what, and how—you’ve got me (who), this executive director (who), me sweating from a non-air-conditioned Jeep in the South and into the historic house turned office (where). I wanted to be welcomed into the arts scene here (what), and I felt excited, nervous, and uncertain (how). I had notoriously bad imposter syndrome. Whenever it would come time to introduce myself or my business, I would downplay, say I wasn’t sure how it happened, act as if I didn’t know what I was doing, or just wave off any successful things people may have heard about me. Internally, I felt like a fraud: all of this was luck, and I got here because . . . who really knows? This meeting was no exception: it could not have gone worse.

Well, it could have. She asked me to introduce my company and I could have frozen, broke into tears, walked out, or threw up. I totally could have done one of those things. Didn’t do any of those things . . . the things I could forgive myself for or give myself grace about.

She asked me to introduce myself and my company, and I did what I always did: I downplayed. I’m pretty sure I said I was just along for the ride to see where it went.

And she tore me apart. Aside from telling me that what I was doing didn’t sound very innovative, she pointed out a few different organizations that were doing similar things (they weren’t, but I did a terrible job of explaining what I did). She suggested I could work for these companies because what I was doing and trying to do in Winston wasn’t something that would “make it.” On top of that, she said no one cared where I was, that people care where I’m going and what I’m changing now, so the fact I was an actor wasn’t a big deal—and didn’t matter in the end.

I slunk out of that meeting, sat in the hot car, and cried. I got home and kept crying. I texted my New York friends and cried more. I started looking for jobs, applying to schools for teaching positions, used my time to look for a job, and went along with being something that wasn’t very special, angry that whatever luck happened to me in New York City wasn’t worth anything in Winston Salem. A few weeks passed by, and I realized this woman wasn’t a horrible human being who was just trying to smash my soul in a million pieces and get me to conform. She based her understanding of me on my awful, self-deprecating, and insecure introductions. The qualifiers! The awkward apathy! The “oh I don’t know how I got here!” I knew how my business became successful: I worked so damn hard, slept very little, and pushed myself and my limits. We had been working with major clients, and we were successful because of the work I put in.

Yet I showed none of it. I didn’t own the success of my business, didn’t show how much I cared about it, and didn’t speak up about what it really was: I spent so much time trying to be friendly and cool in that moment, hoping for her to “just see” how successful I was, and maybe my luck or whatever everyone else saw in me would work out again. Ironic, right? I help people speak up about their own professional accomplishments and worth. It’s not always easy to see the forest when you’re stuck in the trees, no matter who you are.

I did a hard stop on all introductions and job applications. I took a moment and wrote out my introduction for both myself and my business. I knew how to introduce myself, but clearly not in a professional way that incorporated my business in a confident manner. Then I started to introduce myself again and kept working. I would be lying if I said it was the only time someone had doubted my worth or I introduced myself in a terrible manner. It was far from it—but this time, I knew how to quiet my imposter syndrome in the moment.

A few years after that moment that changed everything, I ran into the same woman at an arts event. As small as Winston is, it was definitely the first time I had seen her since we had our meeting. I walked up to her, and while I’m not entirely sure she remembered our meeting, I thanked her for it. Specifically, I thanked her for making me feel so awful that I realized my introductions completely did not represent who I really was and how great my business actually was. She looked a little caught off guard (I mean, I came up to her at an event and basically said thanks for making me feel terrible), but I felt I really needed her to know how much she changed how I viewed myself. It was that moment when I knew my imposter syndrome was holding me back.

Imposter syndrome is no joke. It’s a psychological phenomenon that is categorized by the belief that you are inadequate despite evidence that you are actually quite successful. According to Dr. Valerie Young, an expert on imposter syndrome, there are five types of imposter syndrome.¹ Certain activities can help combat each of those types.

The first is the perfectionist. Control freak, anyone? This type always feels like they can do better and success is never achieved, especially not in a situation where people are assisting with the final project. It could always be better if you did it, and you could have always done it better, so the vicious cycle continues. The second is the superwoman/man. This type is the one constantly trying to prove their worth despite their success. They work longer than everyone else, pushing their own physical limits to prove to themselves and the world that they are worth it, even when no one questions their worth. The third is the natural genius. Irritated when you don’t get something immediately? Feel like you should have understood something by now and beat yourself up if you don’t? This is you. The fourth is the soloist. Need to do it yourself? Does asking for help sound like a failure? You might be a soloist. The final is the expert. You fall into this type if you’re measuring yourself on what or how much you know, feel like you’ll never know enough to be competent, and fear you’ll be uncovered as a fraud because you don’t know enough.

The cure for all of these? Know the phrase “eat, sleep, breathe x”? Well, do, think, and live improv and go back to the basics. Remember Zip, Zap, Zop from Chapter 4? You stand in a circle, one person points to another and says Zip, that person looks at another and says Zap, that person looks at another and says Zop, and the game begins again. When one person makes a mistake, everyone makes that mistake, puts their hands on their hips and says, “AaahhhOOOgah” while doing a hip thrust. Failure becomes funny. You’re practicing failure and training yourself to accept that yes, you fail, and not only is it not as bad as you think, it’s always OK. This is true in all of improv as well as in taking initiative. You might not have something ready but you have enough to move forward and figure it out while you are listening and responding. While you’re listening and responding, think: Did anyone question your worth? No? Then you probably are proving it. Yes, someone is asking? Like, literally asking for your receipts? What does it look like? Why are they asking you to prove your worth? Is it real, or something you are imagining? What is true and provable in this moment?

This takes time and effort. Remaining present with yourself isn’t easy. Ask what is real. What do you know to be true about your abilities and worth? Are you questioning or is someone else? If this is hard, don’t worry, you aren’t alone. Think of all the people who suffer from imposter syndrome. According to a 2011 article from the International Journal of Behavioral Science, some 70 percent of people suffer from imposter syndrome.² Ask three people in the next day if they have ever felt like a fraud, or if their successes are simply luck. The unfortunate truth is that many of us feel this way, and often that’s what makes advocating for ourselves professionally difficult at the very least. Sure, talking about your business, idea, or personal accomplishments might be easy if you stick to the facts and present them in an unbiased manner, but you are much, much more than that. Furthermore, when you are pitching a business idea or yourself, you need to have the confidence that you’re the best person for whatever you’re pitching. If you don’t believe that, why should anyone else?

Confidence is one of those funny side effects of improv, mainly because you can’t necessarily pinpoint specific activities that help with confidence. Yet at the same time, I can say without hesitation that they all help. The secret sauce once again? “Yes, and.” When I’m talking about improv, there are so many times I bring everything back to “Yes, and.” It’s one of those lessons that I really believe is a game changer. Since you already know “Yes, and” is great for conversation (affirm and equalize) and ideation (affirm and elevate), as well as listening (recap and confirmation), you already know how it can easily be brought into all areas of your life—not limited to professional.

Confidence in professional life often comes from understanding that you can indeed handle whatever comes along. You are prepared for anything and you can roll with whatever the world and work throw at you. Those blips? Simply that—a blip that you deal with.

Building Confidence with the Power of “Yes, And”

When you have confidence in your own abilities to handle anything that happens or could happen, no matter how unexpected it might be, you start simply absorbing and reacting to all of the other stuff around you as part of life. Remember the yes in “Yes, and” isn’t agreeing. It’s affirming a reality. If you start to yes to the reality around you and affirm that “Yes, this is all happening and I have to deal with it,” things simply become a small part of the larger picture of your life. Also, when you are attending to things happening around you, you can incorporate them into your life instead of fighting it, pretending it’s not happening, or worse, resenting that this is “always happening” to you.

We have quite a few clients who are small business owners. It’s interesting to see the ones who take things in stride and incorporate bumps into their every day, and those who build resentment when things aren’t happening in the specific way they planned. It shows up in improv conversations, and those conversations are indicative of how they are in life. One workshop for start-up founders brought a group of people together that were all starting new businesses with grant monies. Each business idea was their own, and each of them was part of the cohort that was supposed to launch at the same time. We taught a few improv for confidence classes and got to know quite a few of the founders through our partnership with the organization. Some of them really wanted the polish for their public speaking: they believed that if they presented well enough, they would be completely fine in securing more funds for their business. Others wanted to develop presence and confidence—they felt like they were fine presenters, and knew they wanted to really do well with how they walked into a room and worked the people in the room.

Both are correct, really. To be a confident speaker—and not an arrogant speaker—you need to constantly have your finger on the pulse of your audience. Yes, the polish is incredibly important. It’s also the secret sauce that some people think can’t be taught.

We discussed really digging into what made someone confident when they were pitching their ideas and business, and how was it different from someone who thought their business was unshakable. No one wanted to seem cocky, but at the same time, the balance between the two is difficult for many people to understand. One of the things that came up consistently was the acceptance that it could fail—someone could make a bigger and faster version of it. The reason why it wouldn’t? Because of the person behind it and the work they themselves were putting into it. They discussed that attending to reality and everything that goes with it, like competition, market, cost, and more, made their business stronger. They were planning on hitting reality head-on, taking it in, digesting it, and using it. That awareness is developed by the “Yes,” and dealing with it is the “and.”

The sneaky side effect of applying “Yes, and” to the world around you? You start to “Yes, and” your own ideas, thoughts, concerns, and dreams. When is the last time you were around a table discussing something you had a stake in, and you got a glimmer of an idea of what to say that was very much yours? And instead of saying it and owning it, you shut it down and let the moment pass only to have the reaction of, “I wish I would have said that!” Or worse, someone else says the exact same thing and at this point, you have nothing to add. By using “Yes, and” to your own thoughts, even if you start in your head, you will notice you’ve probably put limits on ideas and inspiration.

“Yes, and” makes you think about what the possibilities beyond your original idea could be—you are yes-ing the possibility. You are saying there is a possibility and chance it could happen, and it’s a path. One of the guys in my start-up group I mentioned earlier had the idea of a brunch food truck. So we discussed late-night food, specifically bar food, as well as straight breakfast. Then we selected one alternative possibility: brunch and late-night food on the weekends at bar time. After that decision, we thought about being at the same location in the morning for brunch and pairing with the bar for a brunch drink special, as well as in the evening for patrons who needed to grab some late-night food. Then what if he also had a deal with the bar where if they brought a receipt from the bar, they could get a brunch upgrade from the truck for free—which would make the bar more than happy to promote the truck because it was a win-win.

Nowhere in this scenario did we start to think, “Well, what if the bar doesn’t want the truck outside?” or “What if the bar already serves food, wouldn’t they think that’s competition?” or “Am I even good enough to make this crazy idea happen?” None of those issues, or really any of the issues that come up with a lack of confidence in your own abilities or the ugly imposter syndrome voice, have any place in “Yes, and.” That’s not to say you won’t deal with problems or that nasty self-doubt if you start to “Yes, and” things—you’ll still have issues, no matter what! If you use those issues when you’re using “Yes, and” to some creativity within yourself, you stop the idea much like you stop a conversation with the word but. You don’t need it right now, so don’t use it or bring it out.

Often, I have to tell small business owners to rein it in. When we say this, it is not to limit the “Yes, and”—it’s to focus it, like a beam of light. If you have some highly dispersed light, sure you’ll light everything just a little bit. If you have a focused beam, you shine all the light on a specific point. Same for business: if you have 10 ideas and are trying to “Yes, and” all of them, you’ll have 10 wildly creative paths you could follow. Take one idea and “Yes, and” that idea first—then finesse it, go back, recalibrate it, and “Yes, and” it again. If that idea doesn’t work, then your job is to “Yes, and” another one of your points. By focusing your light on one thing when you’re opening up a possibility, you build a sustainable structure for your business. And there’s less possibility for you to get overwhelmed—if you’re not overwhelmed by options, you can monitor the imposter syndrome and handle it with that focus.

On the same token, if you start to “Yes, and” yourself often, both in professional ideas and in settings where you are offering ideas, you make speaking up a regular thing. The more you speak up, the more you’re either going to get told “Brilliant!” or get ignored because someone won’t like your idea—or almost always the more likely response, something in between the two. The more you experience all of those things, the easier speaking up will be. You’re lowering your bar for speaking up. It quickly becomes a very normal thing; so you do it, embracing each outcome as the norm. If the outcome is good, you digest it instead of basking in it, and simply deal with it. If it’s negative, you digest it instead of basking in it, and simply deal with it. It no longer becomes a big deal. It’s simply part of a normal day. Now when your imposter syndrome acts up, you can shut it down with a simple, “Well, sometimes people don’t like ideas, but yesterday they did, so maybe tomorrow, someone else will again.” There’s more empirical data to draw from to shut that negative voice down.

Yet another win with “Yes, and” comes with being in the moment. You absolutely cannot be thinking 10 steps ahead when you are actively using “Yes, and.” If you are constantly overthinking everything you say, you cannot “Yes, and.” “Yes, and” keeps you connected to your thoughts—and you own each and every one of them. Sounds a lot like assertive communication as well, doesn’t it? You’re taking little steps to become assertive, and you’re following and owning your own thoughts along the way. On top of that, you have to pay attention, so you’ve checked in to your own moment and the people around you, to correctly “Yes, and.” If you’re in the moment, you also can’t catastrophize situations, a common side effect of imposter syndrome. You’re too busy attending to the present to dive into the “What if?”.

ASKING FOR A RAISE, PROMOTION, AND NEGOTIATING

Before starting this section, I’d like to take a moment to tell you that you absolutely deserve a raise or promotion. Maybe this moment isn’t the best moment or the “right” moment, but you deserve one because you’ve worked really hard, you’ve gone above and beyond, and you deserve to be paid your worth.

If you thought about applying improv’s core structure of who, where, what, and how here, you’re absolutely correct on the place to start. We’ll dive a little deeper into each of those when it comes to asking for a raise or promotion, and then take a bit of a turn when discussing negotiation.

The who is you, and the you that is the best version of yourself at work. When you’re thinking about asking for a raise, take a moment to review recent accomplishments or guideposts. For example, I’ve been working with a social media manager who was looking for a raise and didn’t know where to start. She came in telling me that everyone who had coached her prior said she needed to ask for a raise after a big accomplishment. But as many of you might know about social media, there isn’t an outpouring of viral content in the everyday life of one person. So if you aren’t causing a terrible social media issue, you’re probably doing it right, but there won’t be a big shining moment that can be referred to as an accomplishment. So she didn’t know what she could pinpoint as her reason for a raise and was looking for something that didn’t exist. Because of this, she had probably gone a little too far between raises, and thus that vicious cycle of feeling like you’re not being valued, to looking for value, to not finding it and knowing you’re working hard.

This who is not just the who you are right now—it’s who you’ve become at work. What changes have happened? In the case of the social media manager, we looked at the additional followers, average engagement, and analytics for all of the accounts when she first started to present. The increase? That’s an accomplishment. Seems easy for something that already measures analytics. Understanding the changes you directly influenced at your job is an excellent place to start when you don’t have multiple points of accomplishments. Essentially what you’re doing is making a résumé of your work for your work. This is something you should prepare for. Have it ready, even if you don’t have an annual review. It’s crucial to have this information at the ready before you ask, before you make an appointment to talk, before you even think of making that appointment. Take a step back and understand that who.

When you’re making this résumé of milestones for your work, keep it as quantitative as possible. Stick with measurable outcomes versus feelings or qualitative issues. If you can measure it, whether it’s in people, money, or time, it should go on the list. Right now, do not worry about making it too long. Start it with the ones that immediately come to mind, and then keep going. You’re looking to get it out there, not to debate it in your head. This brain dump of information is important: you don’t want to edit yourself. If you get stuck, there’s a pretty great stream-of-consciousness activity that we do for creativity.

After you feel comfortable with the process, look at your accomplishments again, and try it with an accomplishment. This is going to be infinitely harder. Start with one accomplishment and move from there. I’m going to use another client example, a woman in human resources (HR) who was looking for a raise:

Accomplishment: Less turnover

First thing: Happy

First thing: Relaxed

First thing: Easy

First thing: Calm

First thing: Yoga

First thing: Stretching

In this example, you’ve got a few pathways to take. One, think about employee satisfaction: were there any surveys or internal reviews that talk about the happiness of employees? Another: how are the management teams? If you think about work in HR, you might be working with professional development or leadership training, which might be making work easier. On the same note: Do you have any health initiatives? Have you added any or enhanced something that was already there? This exercise helps you examine the work you’ve done, as well as the work you might want to do with this raise or promotion.

This activity leads to the you that you could be with this raise. What are your plans for your position? What do you want to accomplish? You can use this stream of consciousness or “Yes, and” to brainstorm the possibility. Sure, you don’t necessarily want to admit you’ll work harder, stronger, or faster with a raise or promotion. Real talk though: we work harder when we are appreciated. Money, specifically a raise, is a way employers often show appreciation.

When you have the you part of who worked out, think about that person you’re asking. How do they work? Do they need a dossier of why you should get this raise or promotion? Are they the decision maker? What style of communicator are they? Have you asked for a raise in the past, or has there been any conversation about a raise? What is your relationship with this person like?

One client was an associate dean for a college in New York City. She was overworked, underpaid, and exhausted. So much to the point that if she didn’t get a raise, she was looking for another job. This had gone so very far that before even thinking about asking for a raise, she had started looking for another job and came to us more for interview skills than anything else. After a few conversations, she admitted she used to love her job and wanted to stay, but she didn’t think her health, both mental and physical, could handle it. We started to help her asking, and it came out that she never once told her supervisor she was feeling this way, and never once (in five years) asked for a raise. They had minor pay increases but no annual review or official increase based on merit.

Since I didn’t know what we were dealing with, we halted some prep, and her new homework was to go into his office and set up an appointment to talk about the possibility of a raise. Since it never came up, we didn’t know if he was even open to an increase that was outside of the yearly (minor) increase. She made the appointment, and he accepted it. Her ask was simple: she was looking to have a conversation with the person who would be responsible for a possible raise or promotion in the department.

He gave her a raise that day. Now this is a magical situation: also a terrible one. He said, and I quote (from her): “You never asked for more money, so I thought you were fine.” This is one of the most frustrating things I can think of but also incredibly telling. They never once had a conversation about who would be the person in charge of granting a pay raise. Our client didn’t actually know who she needed to ask, and a lot of the appointment was based on the idea of figuring out who she needed to talk to and what the process was for asking for a raise. Her situation was really one of the best- or worst-case scenarios. Because she didn’t ask, she didn’t know he was in charge of raises. Because she chose that moment to ask, he either realized they had never talked about it, or it simply took that ask to make the raise happen. This is why both whos are important in this situation. You and the person responsible for that raise. Do a bit of digging and figure out what you need to make your case.

Once you understand both your accomplishments as well as the person you’ll be talking to, it’s time to think about where. The where this time around encompasses a when. There may never be a perfect time to ask for a raise. Some times are better than others. For example, if you did just accomplish something major, you can “Yes, and” to ask for a raise or promotion. If you have a review policy at your work, figure out how that fits your plan. Did it just happen? Is it coming up? When you think about timeliness, you don’t want to go too far from said accomplishment; otherwise, that momentum is hard to replicate.

If you don’t know, ask around. Talk to people who have been there longer or people who have gotten raises or promotions. The where is also on your terms. Don’t surprise someone with a raise conversation if they think they are just having a status meeting, because you’re going to end up with a potentially annoyed raise-giver. On the same note, do your planning before you ask.

We were working with a museum professional who had been at his job for about three years with no raise aside from the yearly inflation increase, and we decided to do a lot of the planning before any whispers of an ask happened. He figured out who he was now compared to who he was before he started the position, and from there, what he had accomplished. Once he had that information together, he decided to ask for a meeting with the person who was responsible for any raise requests: the executive director. That executive director took the request, scheduled a meeting, and then a week before the actual meeting, requested they meet in the building—not in his office, but in the auditorium down the hall from all of the offices.

Shake your head, it’s fine. I did too. This was an interesting situation. On one hand, I have to give the director credit. He was trying to throw the museum professional off his game, potentially getting him in a place where it could be refuted, or in a place where the museum professional didn’t do enough research or prep for the raise. This is a strategy by people who are interested in power plays, as well as status plays. Set a meeting to discuss something, then throw them for a loop by asking them to meet early and in a place that was less formal. Lucky for the professional but not lucky for the director, we prepped prior to the ask, with notes and everything, so the change was not something that tossed him off guard. On the contrary, it threw the director off that the professional came in with so much information and ready to ask for the raise.

This is why I recommend preparing in advance, even if you are interested in setting up a meeting. On top of the advance meeting, the director in this particular example decided to select a location that was a little more casual and less private than an office, which hosts an entirely new set of things that might throw a person off their plan. By preparing in advance, all of the changes and alterations are simply noise, because your focus remains the same.

When it comes to the where, be ready to have this conversation anywhere and at any time. Sure, it’s highly unlikely you’re going to ask for a meeting and then on the spot, someone says, “Oh, I have time now!” but it could happen. So hold off on your asking until you have an understanding of who you are.

Patience is also important here. Please don’t wait years to ask for a raise, but don’t ask for it a few months into the job. A good rule of thumb is a year, if you haven’t gotten an increase—and I’m talking about an increase that only you get, not an increase that everyone gets because life is expensive—then it’s time to start thinking about it. If you took a job at too low of a salary and realize it a week into the job, then you might be stuck a bit until the timing is right to ask again. You also can’t get a raise every time you hit a new goal. As amazing as that would be, patience pays off in this situation.

In the same area as where, please do the asking in person. You can definitely set the appointment in an email, but when it comes to the actual asking for a raise, be sure to sit in front of that person. If you work remotely, ask for a video chat. At the very least, be on the phone with that person. Too much gets lost in written communication, and you want to be sure to keep that connection in person as much as possible.

Another thing to consider in the where is what else is happening in the company culture. Did something stressful just happen? Has there been a lot of turnover, or did a key position just leave? Read the room, and see if it’s an appropriate time to ask. Your chances are not going to be the best if you ask when everyone and everything are stressed. Look into what the other person’s schedule looks like as well. If they have their yearly review coming up, you definitely don’t want to dive into that moment, because how they currently feel is going to affect you and your chances. Stack the deck whenever possible.

Into the what you want: you might have to use some persuasive tactics to get what you want. Sure, you want a raise! Have you thought about how to get that raise? Your first step with this should have already happened—that list of quantitative things you’ve accomplished. That’s a big part of persuasion—you have facts. The more specifics you can provide, the better. Often, you’re going to be talking to a person who doesn’t have the final say in your raise or promotion. This is why you have to show and not just tell. If you aren’t making a clear case for yourself, you can’t expect someone to make a case for you. You need to relay that information in the best way possible so they can take it up with the actual decision-maker if they aren’t. That list? Make it look clear and clean, and print an extra one out or email it after the meeting. By giving them those resources before or after the conversation, you’re giving them the prep for what they have to do next.

The Don’ts in Asking for a Raise

Something to avoid in conversations about raises: don’t make it personal. By keeping it business focused, as well as merit focused, you up your chances. Yes, more money would make many lives easier, but you deserve a raise for your hard work and the things you’ve accomplished, not because your rent is going up. Keep your who as that best version of you at work—not the real-life person who pays bills. Also, when you’re digging into conversations about money, keep the reason for your want focused on yourself. There is no reason to bring up colleagues’ salaries, because this is between you and your raise and should have nothing to do with the other people in the office. Remember the idea of talking to the person in front of you and not about people who aren’t in the room or conversation? You want to focus on your own experience and keep communication assertive. You’re owning your ask as well as your accomplishments. Bringing in other people and what they make doesn’t help.

When you’re thinking about your influencers, you want to be very careful. If you aren’t ready to lose your job, stay very far away from ultimatums or threats. Even if you are planning to leave if you don’t get a raise, it’s often not a good idea to use that to get what you want, because in the case that your bluff is called, you might end up looking for a job faster than you’re ready to. Emotional influencers aren’t a good idea either. Guilt trips and the like aren’t professional and are not suited for a professional environment. Keeping it fact-based is best. If you’ve done the work in outlining your accomplishments and the changes you’ve contributed or caused, then you’ll be able to make your case without needing to pull out threats or emotions. If you are prepared to lose your job, then go right ahead and do it.

The next two examples are of people who did it, and one worked, and the other didn’t. Both were improv students of ours; both were looking to negotiate a raise. The first was an arts-based professional in New York City. He was frustrated being the lowest-paid employee who seemed to do the most work. While everyone feels like this at some point or another, he seemed to make a pretty decent case for it. Since it was an arts-based organization (read: nonprofit,) he was getting a yearly increase, but no actual raises, even though he had a new title that was essentially a promotion and more work.

We started with all of the homework, picked the right time, looked at the organization as a whole, and then he met with the executive director—and nothing. The director agreed he was a great employee and highly valued, but each time after they met, he would give another excuse as to why he couldn’t make the raise happen yet. This went on for over a year—which in my opinion, is way too long for someone to wait on something like this. Some kind of answer was necessary, even if it was an answer that led to a “no.” At this point, he had tried several influencers and was clearly expressing his wants. More than anything, he wanted to know if a raise was even a possibility because otherwise, he was planning on leaving the position and starting the very long process to find another comparable position. He started to apply for other jobs and got a few calls and interviews, and then asked me if he should pull that card in the next meeting.

We discussed it, and he understood that by doing that, he was playing a very dangerous game. If the director valued him, he would work harder to figure out this raise situation. We were both under the impression that the director was more passive than he needed to be because he didn’t seem to think my client would leave. If the director didn’t value him, the response could be anything from inaction all the way to letting him go. The problem in this situation was that the odds of either situation happening were equal. The client was valued: he brought a lot to the table and he had done a lot of good at the institution. At the same time, these negotiations had been going on for a year, which is incredibly frustrating, to say the least. He decided to go for it.

The other client worked for a sales organization. She had been there for four years, with no real raise aside from her commission. She had a meeting with HR and got a very small raise, only to find out that a new employee was making more than she was and another person with similar experience was making more as well and had recently gotten a larger raise than she did. It had been about a year since that raise, so she was ready to ask for a larger one, and if not, find another job. She was pretty set on that decision to get more money or go somewhere else and felt as though she could find a job if necessary. Since she had been looking, she knew the market was fine for her kind of position, and she wasn’t hurting financially to take a few lean months if something were to happen. We prepared in the same way. She asked if she should give the semi-ultimatum that she would be leaving and looking for another position if she didn’t get an appropriate raise. She wasn’t planning on mentioning her knowledge of colleagues’ pay (bad idea, remember) but was planning on leveraging her experience and the general pay in the market for her position.

We discussed it, and it was going to be less of a threat (“I’m going to leave if I don’t get this raise!”) and more of an ultimatum (“I’m sorry to hear that, I will have to start looking for another job”) and she was going to pull it out only if she needed to. Again, she was valued, got affirmation from her boss and coworkers, had performance reviews, and knew this information about her counterparts. She knew they were similar in experience if not less experienced than her and making a considerable amount more than she was. One even got that raise the same time she did. She decided to go for it.

What do you think happened? Before I get to that, as the coach, I can safely say both had the same chance of getting a raise as they did getting let go. That’s the improv part. You can put anything you want into the world in an interview, negotiation, conversation, and you have no idea what someone is going to do back to you. Things might go in the expected direction, and they might not. All of that is up to chance. You can only change how you respond to the situation. You can’t change how someone communicates.

Because you’re surely waiting with bated breath to hear what happened, I’ll tell you. The art professional got his raise and the woman in sales was told to find another job. The art professional asked for the raise and was told, “I’m working on it,” for the seventh time. He told the director he was at the end of his waiting time, because it had been too long and he was going to start looking for other positions. He said that he would keep the director informed if any interviews came up and would put in a notice if necessary. Simple, transparent, and direct. The director quietly took the information, told my client that he would “do what he could,” which is what he said every single time, and the meeting ended. The client did exactly what he said he would do, but two weeks after the last meeting, the director called him into his office, letting him know that he got a smaller raise than what he was asking for, but it was enough for the arts professional to stay in the position. He’s still there.

The woman in sales had another experience. She went in, asked for the raise, and made her case. Her supervisor took in the information and told her that he would see what he could do. She followed up in two weeks (a nice amount of follow-up time) to see where things were at, and he said he didn’t think it was possible this year but he would try. She told her supervisor she was disappointed and was planning to start looking for other options. This was buttoned with, “I really don’t want to and appreciate working here, but I believe that my work is worth more.” He took that information quietly and spoke with her the next day, telling her he didn’t think she was in a position for a raise anytime soon and she should look for other options. Not a firing, per se—just a definitive no. She found another job that paid her what she was looking for and life went on.

Why did each of these situations turn out so very differently? Who knows! Both were set up in the same way—two people who each deserved a raise. They were overdue, and while I only know what the clients tell me, I didn’t get any ideas that either of them were making up any of the experiences we discussed, which ultimately meant that they were in a fine place asking for the raise. By using a threat or ultimatum, they made a choice to force a hand, which in both situations resulted in an answer. The key here is knowing the potential outcomes and being comfortable if you get a “negative” one. Both people were ready to leave their job, regardless of the answer.

This wouldn’t be a good choice if you really needed your position and weren’t ready to lose it. Most people need their jobs (otherwise, why would we be working?), but some people are ready to take on another no matter what it is, have some savings, or have a plan B in case of emergencies. I personally would never advise someone to do this unless they were ready to be unemployed—even though sometimes it works out.

Improv-ing Your Negotiation Skills

Very few people like to negotiate. Like public speaking, it’s why people fear it: they try to avoid it, and then they never get better at it. It becomes this big scary thing that is often necessary for success in business—whether you own a business or work for one. The issue with negotiation for many people? They think it’s a competition of “winning” versus communication. Before diving into improv-based negotiation (because so much of getting what you want in improv is negotiation), let’s think about negotiation and what it actually is.

Negotiation is simply a discussion that seeks to reach a common goal. It’s a way to come together when there are differences and reach a compromise, all while avoiding an argument or dispute. When people disagree, so often they look for the outcome that is best for them, versus thinking of the greater good of both parties. Negotiation can’t be scripted, and using improv to help negotiation skills isn’t a new concept. Negotiation is very much listening and responding to finesse a solution that works for everyone. But you can only control your own responses, not the responses of anyone else. This is the very definition of improv.

Improv isn’t as simple as go with the flow. The best negotiators have plans A, B, C, and D in their heads. This means that following an improv mind-set lends itself to being a great negotiator. Specifically, one of the things that improv lends itself so well to in negotiation is taking the first step. Taking initiative is a nerve-racking experience for a lot of people. In classes and workshops, watching people take the first step in those three-line conversations previously mentioned in Chapter 2, an activity where success is possible 100 percent of the time, makes it incredibly clear that people don’t like to go first. During that activity, I usually have the group split in half. Half of the group is on one side of the room, and the other half of the group is on the other side. They often face one another, and I never pick a side to go first. I simply let them know they have to decide who is going first by someone simply starting, and if they say, “you go first,” that counts as a line.

It doesn’t matter how clear or how vague I am with my description, people will always get nervous and try to “indicate” who is going first. And no matter what, a lot of people will want another person to go first. When I ask why, the answers range from, “I don’t want to make the wrong choice,” to “I’m not a leader,” to “I can’t think of anything.”

In negotiation, making the first move shows confidence. Since this isn’t a competition, you’re helping the negotiation along to come from some place and give the person you’re talking to a place to jump off from. This is also why doing your homework in advance of the moment is incredibly important. You want to know what you’re looking to accomplish, what the other person wants as well, and what the “middle” looks like. It’s a win-win situation you’re working for. If you don’t understand what you want, or you don’t understand what the other person wants, you won’t understand what the win-win actually looks like.

Make the first offer, and make it the best case, win-win, in the middle situation. If you don’t know what the other person wants, transparency is confidence. Simply ask the person you’re negotiating with what they want, and figure out the middle. This is assertive, not aggressive. Understanding what you want and what they want is assertive. You’re owning what you want and understanding you’re going to have to work together to get as close as possible to what you both want. Aggressive would be demanding what you want without considering what the other person wants.

After you’ve made the first offer, be quiet. Remember those active listening skills? Put those in action and listen more than you speak. By listening, you can pivot and work through your original offer to get as close to win-win for both of you. If you have a question, ask it. Another element of keeping quiet and not filling space with chatter? You might find out more about what that other person wants by waiting. People chatter nervously. Silence is scary for many of us. We tend to fill the silence with information, so if you take a moment to stay silent, or ask a question and simply wait in silence versus following up with another question or an answer, you’re not only exhibiting calm, you’re letting the other person potentially fill that silence.

There was a period of time during workshops for sales teams when we would practice a silence activity. We’d partner up, and then I would instruct everyone to look into their partner’s eyes, take a deep breath, not to stare, and silently stand there while making eye contact for 60 to 90 seconds.

The room was so uncomfortable. Many people wanted to fill it with nervous laughter. I told them they didn’t need to maintain eye contact the whole time and should really take some time blinking and looking away. No matter what, a decent number of people always would start cracking up because silence is terrifying for some of us. Try to sit in a room with someone you’re talking to and just be silent in the middle of the conversation for one minute. You can look at each other, you can look away, you can’t do something else like read a book or hop on your phone or email. Just maintain silence for a prolonged period of time and see how you both feel.

What happened? Did you get nervous and want to fill the silence with chatter about everything or nothing? Was it simple? Try it the next time you ask someone a question, and they don’t immediately answer you. Take a few breaths and then rephrase or ask another question.

For the hundredth time in this book: you get the energy you put out. If you walk into a situation thinking the worst is going to happen, you might get that worst possible outcome. If you expect the best, with an understanding of the worst and negotiate to keep away from it, you’ll end up with a better outcome. Essentially, you want to “Yes, and” versus “Yes, but.” Keep the conversation as something that is continuously going versus something that is shot down because of someone not being able to work together.

“Yes” affirms the other person and how you are listening to them. Phrases like “Yes, I see what you mean,” and “Yes, I understand,” are excellent ways to show active listening skills in negotiation because you can then add your own thoughts and information with the “and.” Statements like “Yes, I understand that you’re looking to pay less for this, and I want to give you the best value for your money, how about $500?” are more effective than, “Yes, I know you want to pay less for this, but it’s worth more.” Again, saying “Yes” in “Yes, and” is never accepting blindly. It’s acknowledging the other person. You’re saying “Yes, I heard you,” not “Yes, you’re right!”

Another important tool to add to your negotiating toolbox is open-ended questions. Open-ended questions not only let the person you’re talking to think about their answer, it also gives you time to listen to their response and pivot while they are talking. An open-ended question is a question that has many possible answers versus a closed-ended question, which again is something like a yes or no question—only one or two answers. While questions aren’t always the best thing to use in improv, because they put the responsibility on the other person, and remove it from yourself, in negotiation an open-ended question gives the other person the illusion of control, because is it their control when you give it to them? Think about it like this: you know the other person likes to be the driver in conversations. You know what you want and what they want, and where the middle ground lies. So you ask an open-ended question to get more information from the other person and essentially give the decision to them to make. You’ve given them the control in the situation, but at the same time, you hold it, because it was yours to give. This is incredibly meta, so let’s consider it in a real example.

A client was working on a new position at a start-up. The company had been in business long enough that no one was actively worried about an implosion, so she decided to ask for a raise and a new position. She had been there since the beginning and wanted to stay and grow with the company. She came to her boss with a specific number (important), and a specific position (also important), and she was told the number was a bit too high and the position wouldn’t work for the structure of the company. A soft no, but a no still. So instead of taking it as a no, she thought about what to come back with. She dropped her number down a bit, added some responsibilities to her current position and came back to her boss, which is actually a great tactic because they didn’t outwardly tell her no! Essentially the response had been, “This was not quite right.” When she presented the new offer, her boss told her she was an incredible asset to the company, and they didn’t want her to leave, but this was a little too high and a few too many responsibilities. The frustrating part was that her boss wasn’t coming back with a counteroffer. He just simply negated her offer. A firm “no” would have been better than the “not quite.” We talked about it and decided that the best thing to do in this situation was to come back with an open-ended question that put a lot of the focus and power in her boss’s hands. We constructed a solid question that stated what she wanted and gave her boss the control to make the decision without deflecting.

She came to him with this email: “I’m looking for a raise of [her original offer] and [this position]. I understand that my two previous asks were too much, and I do very much want to continue working with [company]. Since my asks were too much, I’m curious to hear what you are willing to do when it comes to a raise and promotion, because I feel like I’ve earned both. Can we follow up next week and discuss your offer further?”

This might seem like a terrifying thing to send to someone, and it’s because it’s incredibly assertive, powerful, and direct. Things she did well: she stated what she wanted, summarized the situation up to this point, placed no blame or emotion on the other person, and gave them all of the decision-making power. She told them she would like to discuss their offer while they had never made one. She was essentially telling them to do it without ordering or threatening them to do it. She gave a very finite timeline for follow-up and asked the open-ended question (What do you think I deserve when it comes to a raise and promotion?) even though she didn’t phrase it as such. She also used “Yes, and” in the situation. She affirmed the reality that the ask wasn’t acceptable on their end.

All in all, an effective message. Who held the status in this? You might think it’s the boss. He does have the ultimate say in this. But it could also be my client because she chose to give it to him, instead of coming back multiple more times with offers that might not go anywhere. The result: she got a decent raise, one that kept her in that job and additional responsibilities that echoed her first ask, the initial one she was told was “too much.”

Again, this is a best-case scenario: she threw the ball; they caught it and threw it back. Some clients have done exactly this, and it didn’t work out for them in whatever way. We learn from both though, and a lot of the “success” in this was simply chance. Her boss could have said, “I told you no twice before,” and that would have been the end of it. Because she thought about the situation, and read the room and her chances, she decided to go for it.

When you’re digging into the who, where, what, and how, be sure to eliminate as many emotional statements as possible. Often emotional statements are bullying tactics or a sign of insecurity. Stick to the facts, not the emotions behind them. The emotions only make the situation more difficult. Think of the previous example. She didn’t show a moment of her frustration, and I knew she was frustrated. Who wouldn’t be? She didn’t let anyone at work see that. I’ve watched other clients let that frustration get in the way when they’re negotiating for a raise or promotion. Letting those emotions into the conversation does nothing positive for anyone.

SPEAKING UP WHEN SOMETHING IS WRONG

When all else fails in good communication, you end up with a conflict. Workplace conflict is difficult, to say the least. It’s idealistic to think you will never have conflict in the workplace. If you are communicating, it’s a full-contact sport. You might try to avoid conflict, which is a terrible idea because you can’t escape it once you’re in it.

There are two major causes of conflict: communication and emotion. Think of the last conflict you had in the workplace. Was it because of poor communication? Low information? No information? Even if you got good information, and you had no idea how to handle it, you might end up with conflict. Emotion drives decision unless you consciously handle those emotions and remove them from the decision. When someone indulges in their emotions in the workplace, you usually end up with conflict. Out of all the points that guide the conversation, how you feel is often the most volatile one, mainly because emotions are so difficult for so many people and are often inappropriate for work situations.

But what happens when the communication fails or the emotions kick in, and you have to deal with the conflict? You need to develop conflict-resolution strategies, even if you are conflict avoidant. You can try to avoid it as much as you like, but you will have to deal with it at some point, so like all things in communication, preparation is key.

You’d be surprised (maybe not) how often improv conversations move to arguments and conflict. One of the biggest challenges for students is staying away from the argument in an improv moment. Whether it’s because we try not to argue in public in real life, or because it’s “easy” to have an argument (both things I really don’t like to consider either as truth), it’s a stretch to get people to not immediately go into a fight. Consider it though. You are finally firmly defining your who, where, what, and how, and if you don’t discuss it beforehand with your partner, which you shouldn’t, it’s probably going to be two different things. Conflict is bound to happen when two or more people are fighting for two (or more) different things.

Real life has the same issues. Often we’re looking for different experiences and things out of our professional life. On top of that, the competition that kicks in with career and work situations isn’t helpful to a conflict-free environment. One way to handle conflict in the workplace has to come from a larger place than just you—acceptable behavior needs to be defined. If a group doesn’t understand effective team communication or collaboration, there will constantly be conflict. Consider this strategy as more of a vitamin than a painkiller. You’re preventing conflict as much as possible with an understanding of good communication and how to work together for a common goal. The other thing that happens when you define acceptable behavior: you actually give a structure for how to handle conflict when it happens.

When that conflict happens, you need to understand that other person, and “Yes, and” and negotiation come into full play. As learned earlier, that “Yes” in “Yes, and” isn’t giving in and accepting what the other person wants—it’s affirming their words, thoughts, and beliefs. Even if someone is getting incredibly emotional in conflict and upset you haven’t done something or finished in time, and they haven’t said they are upset, yet you see it, you can easily say, “I see that you’re upset and I want to make this situation work.” You’re affirming how they feel—upset—and by that, you’re letting them be heard. With the and, you can add your thoughts or questions to that affirmation and move the discussion forward.

What happens when something is seriously wrong at work? What about an ethical issue, like someone stealing money, or constantly leaving early but leaving their coat to pretend they are still in, or doing work for Company B while on Company A’s time? Figuring out if it’s worth it to speak up, how to do it, and to whom and protecting yourself from consequences is complicated. Generally speaking, most of us aren’t in a life-or-death, jail-or-no jail situation if we speak up or not, but as we’ve both seen in the media and in high school, speaking up about even a small issue can have massive repercussions.

Mary Gentile, the author of Giving Voice to Values, believes that practice is the key to understanding how to both recognize and deal with these ethical issues that come up at work.³ When dealing with ethics, according to Gentile, we tap into our emotions, tying it to moral identity. Think about everything up to this point: when you’re dealing in the emotion space, we let those emotions drive—and considering we all share them in very different ways, we think that our emotions aren’t as valuable as fact-based information. Even if the ethical violation is based in fact and not feeling, that decision about “right” or “wrong” is often several shades of gray.

Gentile offers excellent advice when it comes to practice. If we never deal with these situations—really deal with them, digest, and not just sit and wait for it to resolve itself—we make them terrifying. This is just like public speaking—you do it once or twice, it doesn’t go perfectly the way you planned, and you deem yourself, “not a great public speaker.” This is one of those places where improv-based thinking has to come into play, by tapping into “Yes, and” and imagining those best-case and worst-case scenarios as well as exploring the possibilities.

Another great tip from Gentile includes assessing the risk, and in the same moment, asking what you want from this. Her question of, “What is the value that’s being violated here?” connects with what you want: what do you want out of this situation and why do you want it? Does it affect you if your coworker is doing another project for another company at work? If they are getting their work done, why does it matter? You’re digging into what you want to accomplish, and why you want to accomplish it. If you’re upset that they are doing two things at once, then maybe refocus that energy on to your work. If you’re getting all of their work because they don’t have time to finish it, that’s a very different story.

Shifting your perspective is something that improv lends a hand to and is a strategy for this kind of speaking up at work. This can be accomplished by thinking about what the other person wants out of a situation, remember emotional intelligence? If you’re looking at things from their risk and point of view, you might see why they are acting the way they are. Most people aren’t sociopaths or completely malicious in their actions, and often have a reason to do what they are doing, especially if there are emotions involved. Taking a moment to think about what the other person wants and why they want it will give you a better understanding of the situation. Look at their actions from a place of, “What’s their motivation of getting what they want?” instead of “Why do they want to do this terribly wrong thing?”

After you’ve spent some time weighing out those wants—both for you and them—it’s time to look at if it’s worth it to you or not. If you spoke up, what would happen? If you didn’t, would you care? Research by Thomas Gilovich and Victoria Husted Medvec shows that more people regret things they didn’t do over things that they did—even when those things have poor outcomes.⁴ The phrase, “Failure is never as bad as regret,” comes to mind when thinking about that if jump. A newer study by Gilovich and Shai Davidai show that people regret actions that let them become their ideal self—a staggering 76 percent regret an action not taken that would have led to this “ideal self” as their biggest life regret.⁵

The phrase “ideal self” is an interesting one, given the context of the kind of professional development in this book. Have you sat back to look at what that ideal self is? If you don’t have an idea, how can you get there? And placing this in perspective of this chapter, when you’re looking to speak up, will you get closer or farther away from your ideal self if you do or don’t decide to speak up? And on top of that, does achieving “ideal” matter to you?

At the same time, much like ultimatums in negotiation, it’s important to think about what you have to lose if things go badly. This is all a balancing act: if you don’t want something selfish, if what the other person is doing is because of a self-serving act, if it’s harming the company and your position as well and there is a small chance you’ll face repercussions, then you’ll want to say something. At the same time, if it’s something that’s affecting you, but there is a high probability you might lose your job or have another seriously negative consequence over speaking up, you’ll have to compromise something. Role-play these as Sit-Prob-Sol—specifically looking into various “solutions” and what could happen in the situation, and balancing that against the need to speak up. Spend time with a friend, partner, improv class—run through some of the points you’d like to bring up. Often, you don’t want to go immediately to HR or a boss; it’s better to go right to the person and give them the chance to explain it themselves before it escalates into something larger.

While you’re rehearsing your points, consider how you’re saying what you’re saying, taking care to keep it in a place of calm instead of a place of attack. Also, remember the power of questions. By asking those open-ended questions, you again are giving the control to them to justify their actions. They might not realize they are doing something wrong, and there might be things you don’t necessarily see. Planning to use open-ended questions gives the person you’re talking to the ability to explain and is a fairly safe way to see if they are open to having a conversation. If they respond to the questions in a negative way, they are probably not interested in having that conversation. If it’s a positive, “Thanks for helping me,” that’s your ultimate best outcome.

If the response is negative, consider escalating it by to talking to your boss or their boss. Again, look at the consequences, the new information from the conversation, rehearse some open-ended questions, and see this more as looking for information than an accusation. If that doesn’t work, consider your options. If it needs to be escalated further, think about that next step. If it’s not worth it, take a moment and recalibrate.

I was coaching a guy in tech for almost a year, and he was working for a toxic boss. This person wasn’t the person in charge of everyone. She had been there for about five years, and he was her direct report. She was in the process of getting her PhD and was writing her dissertation on company time. Like all on the company time. This client, since he was her direct report, got saddled with a lot of her responsibilities. She was using office time to write the dissertation and neglecting her other work, and when she did want things done, it was at times that were convenient for her with her schedule. When he couldn’t make a meeting because it was held outside of his normal work hours, or couldn’t make a strategy session she wanted to have on a Saturday afternoon, she would get upset with him and say he needed to care more about his job.

He started the conversation with her, asking her to think about his schedule and that he would be more than willing to meet during the day or to discuss things while he, and the rest of the staff, were in—Monday through Friday from 9 a.m. to 6 p.m. She got very upset about this, saying he wasn’t in charge and it wasn’t his job to determine when they met, it was hers. This particular conversation resulted in her saying he didn’t value his job, and they clearly had different priorities.

The next step was going to her boss because after that initial meeting, retaliation was a very real thing. Every time he would speak up in a meeting she would snap back, and the passive-aggressive comments would fly. She also sent an email to her boss (who was also my client’s boss) bringing in my client’s wife, and saying she heard his wife making disparaging comments about the company. Retaliation happens, especially when people are upset or threatened.

The main boss was fairly ineffective in this: he basically told my client’s boss to settle nonwork issues outside of work and everyone needed to act like adults. Funny story, adults often don’t act like adults. All of this escalated up to the point where she would accuse my client of trying to take her job (he wasn’t), and her passive-aggressive comments came to a head when she started to yell, then cry, then say, “Well, it’s a good thing no one is here to see this,” and then carry on with her work. And the cycle would continue. Since her boss was ineffective, we talked about going one higher, but for now, his job was to protect himself. He kept everything in writing, and after each interaction with his boss, he wrote an email to her boss, keeping as much emotion out of it as possible. Each email set up the situation, usually with an, “I am keeping documentation of this,” and then the problem—what happened, and then leaving the solution to her boss.

Unfortunately, not much happened. He logged every interaction with her boss, who was also his boss. It all kept happening and escalating. After a while, her boss removed him from her direct report, which caused another situation. Document, discuss, exist. Wash, rinse, repeat. He was accused of being smug and condescending when he used “Yes, and.” When he removed emotion from conversations with her, she told him he didn’t care about the job or company. And when he no longer answered to her, she would made passive-aggressive comments about how he “told on her.”

Occasionally, you’ll get in a situation where you do everything correctly—you identify the issues, you connect with your wants and their wants, you keep things assertive, you do everything that looks great on paper and would work in most improv-based conversations—and it still goes very poorly. You work on the confidence and initiative to speak up to someone in your office, in HR, or higher. Still, no progress and the situation is still awful and the conflict is still there. This happens.

So remember this: first, you aren’t pizza and not everyone will like you. Second, you cannot control how people respond to you. You can do everything “right,” and toxic environments are still toxic. Some people are simply toxic people. You can’t change that and the sooner you recognize those situations for what they are and leave, the better.

How did my client’s situation wrap up? The passive-aggressive PhD candidate got her PhD. Her boss ended up leaving. My client kept on track and started reporting the incidents to the interim. The interim suggested a reorg, and our PhD person quit. She “retired” officially because she could, but her exact comment was “I didn’t want to deal with the reorg,” and to my client, she said, “Now you can just take my job like you want to.” He’s still there, but working on his exit strategy.

Sometimes, speaking up doesn’t work out the way we want it to. As we learned in the previous example, “success” might have been the retiring. Is that really successful though? My client endured months of her bad behavior, and nothing was assertively done to help the situation: just a lot of Band-Aids. Success could be the idea of improving your current situation by speaking up. Using that improv mind-set, you affirm your situation—“Yes”—then add and improve it—“and.” Because in the end, you’re looking to improve your communication style and be that best version of you. So go get appreciated for it and speak up if it improves your life.