This is part of my series on How To Be A Good Person.

My friend, Bruce, struggles with his boss and asked, “How do I push back without coming across as someone who is hard to work with? I don’t want to be a jerk!”

Sound familiar?

Every day, people pleasers want to push back on demanding bosses but fear they’ll be branded as a whiner and hard to work with. They wonder if it’s just them that struggle with this. (It’s not.) They lament that it shouldn’t be so hard to talk to their boss. (But it is.)

That’s the bad news.

The good news is that you can talk to your boss and get your needs met without being characterized as a complainer. It begins with identifying what you want, why you want it, and then knowing how to bring it to your boss—all without coming across as a jerk.


What exactly is the problem?

You need to get clear about the actual problem. Some examples:

  • Your job cuts into your free time and family time.
  • You have no idea what your boss expects.
  • You lack tools, e.g., machinery, office supplies, or software.

(Note: getting specific about problems doesn’t make you a jerk, but is the first step to solving them.)

How long?

Ask yourself:

  1. How long have these problems gone on?
  2. How long do you expect them to persist?

Answer these questions in terms of days, weeks, months, and years. For example, the late nights at work have gone on for several weeks, and I expect they will go on for many months.

It may not be worth talking to your boss if the problem will be solved soon.

What do you want to change?

This sounds easy, but it’s actually difficult.

It’s simple to say “I don’t want X thing to happen anymore.” But most folks struggle to understand what they want to materially happen (this is called Positive Action Language1). For example, let’s say I meet a friend for lunch and feel annoyed because he keeps checking his phone. My first inclination is to say, “Stop looking at your damn phone!” But that doesn’t tell him what I want him to do instead of staring at his phone. Alternatively, I might say, “I don’t get to see you often and would like to catch up without any distractions.” This gently communicates, “I want your attention.”

It feels scary to open up about what you do want because the other person may say, “No”. And that hurts. So, people protect themselves by not specifying what they want from the other person. But if you never verbalize what you want, you’ll never get it.

Let’s look at some examples that start with a problem and translate that into what you want:

  • Your job cuts into your free time and family time. →
    You want to leave work at 5 pm each day.
  • You have no idea what your boss expects. →
    You wish to meet with your boss and determine what success looks like, materially, for the current project.
  • You lack tools. →
    You need the latest version of OmniGraffle (software).

Why do you need it to change?

It’s crucial to understand why you need the change. Knowing why and articulating why, will help you speak with conviction (when you talk to your boss). When you specify what you want, add the word “because” followed by an explanation, which will help convince your boss (adding the word because is a persuasive maneuver2). It also keeps you from looking like a jerk (‘cuz you have a legitimate reason!).

Let’s run through some examples that start with what you want and include a reason why:

  • You want to leave work at 5 pm each day because you wish to have dinner with your kids, check their homework, and play board games with them before bedtime.
  • You want to meet with your boss and lay out what success looks like, materially, for the current project, because unclear expectations raise your blood pressure and increase your fear of wasting time on wrong priorities.
  • You need the latest version of OmniGraffle (software) because you’ll make those flow charts in half the time.

Keep in mind that this is a numbers game: the more justifications, the better. Each reason adds emotional weight to your request. Your boss will have a much harder time saying, No, when you have more than one.

Pick one thing to change

You may have a laundry list of issues to discuss with your boss. You may have a lengthy catalog of all the changes you want to see. And you may feel the temptation to talk about them, all at once.


Instead, pick one item to discuss. Here’s why: your boss is an emotional creature, and you need to manage their emotional state. (This sounds dehumanizing, I know, but your boss has more power than you and may not act in good faith. You need to be strategic in how you negotiate with them.)

Unloading all your grievances at once may overwhelm your boss and push them into a negative state where they become irrational, unpredictable, and focused on themselves. In this state, your boss will think, “How do I protect myself?” And your needs will be forgotten.

So, don’t overload your boss with a dozen headache-inducing problems. Just pick one and prevent their emotional state from free falling into a well of negativity.

You’ll have the most success when you choose the easiest one for your boss to solve. Go for the quick win, which will strengthen your relationship. And that bond will help you undertake the next issue. And the one after that.


How to talk to your boss

Pick a time. When is your boss in the best mood? For example, the best time to ask me for something is first thing in the morning. The worst time is right after I eat a big lunch and feel lethargic.

Act as if your boss is a reasonable human being. Your attitude influences their emotional state. Your body language and tone should project the idea that you are both rational adults3.

Feel the fear and do it anyway4. Talking to your boss is scary. Asking for what you want is frightening. But don’t let the fear stop you.

Use “I” statements. Don’t say “You better let me…” Instead, say, “I need…” Keep the focus on your needs and away from their ego.

Be comfortable with silence. After you make your request, there may be a period of awkward silence. This doesn’t mean your boss is angry — they may need time to process what you said. You will feel uncomfortable and feel tempted to speak up and soften your request. Don’t. Keep still and embrace the silence5.

When your boss objects, use calibrating questions6. Frame the problem in terms of what you need and invite your boss to empathize with you. These questions nearly always begin with “How do I…” For example, “How do I get home for family dinner and check on the kids’ homework if I don’t leave at 5 pm?” But be warned, your boss will use these against you, e.g., “How will we get the work done if you leave at 5 pm?”


It’s a challenge to talk to your boss without feeling like a jerk. But a few things can help. First, figure out what you want to change and why it must change (the more reasons, the better). And avoid the temptation to call out all your grievances at once: just pick one thing!

Lastly, pick a time when they’re a good mood (or less grouchy!) and act as if they’re a reasonable person. Employ “I” statements. And after you ask for what you need, there will be an awkward silence. Embrace it.


  1. Nonviolent Communication by Marshall Rosenberg discusses Positive Action Language and numerous other tools to improve relationships. 

  2. Influence: The Psychology of Persuasion by Robert Cialdini explains that people are far more likely to comply with our requests if we include the word because, and follow it with a reason. 

  3. Games People Play by Eric Berne details the three modes we can assume when talking to others: the adult, the child, and the parent. Each mode has a complementary mode, e.g., parent and child, child and parent, and adult and adult. For example, if you talk to your boss like a child would (child mode), they’ll respond as a parent would (parent mode is the complement to the child mode). 

  4. Feel The Fear And Do It Anyway by Susan Jeffers offers tools and insights to overcome fear. 

  5. Start with No by Jim Camp outlines numerous negotiating strategies ina business setting. One of the simplest and yet most effective methods is to embrace the silence. 

  6. Never Split the Difference by Chris Voss is about the subtle art of negotiating. It shows you how to employ calibrating questions to generate empathy in others. As an FBI hostage negotiator, Chris used a variety of these questions when negotiating with kidnappers, e.g., “How do I know they’re still alive?” “How do I get that kind of money when I only have $371 in my checking account?”