You might get through a lifetime of working and never criticize your boss, either because your bosses are that good or (more likely) because they’re bad enough that it just isn’t worth the risk of retribution.

But what if your boss is a basically decent person who’s got some habits that wreak havoc on you or your team? That’s when some well-thought-out, judicious feedback is called for.

Step One: Before You Criticize Your Boss, Take a Reality Check

It’s all too easy to get swept up by our emotions and misjudge reality on the ground. So before you decide to criticize your boss, take the time you need to engage with these questions:

1. What, exactly, is my boss doing that seems off to me? Describe the precise behavior you’d like them to change. Are they micromanaging? Judging people unfairly? Causing people to miss deadlines because of disorganization or perfectionism?
2. What is the impact of this behavior? Again, be specific about the damage being done: Is the primary impact on morale? On relationships? On productivity? On the bottom line?
3. Do I think that my boss will be able to hear this feedback? If your boss thinks he’s a kind and sympathetic person, it may not be easy to get him to realize that people are, in fact, terrified of him.
4. Are the consequences worse if I don’t speak up? Is this really as urgent as it seems, or should you try managing your own reaction first?

If you can answer questions 1 & 2 with specific details, and answer questions 3 & 4 with at least a qualified yes, it’s worth proceeding.

Step Two: Choose Your Time, Place, and Method

Let’s assume that you know your boss’s communication preferences (and if you don’t, now’s a good time to start figuring them out!),

Would she rather have a difficult conversation face-to-face at 8am while the office is relatively quiet? Would he prefer hearing from you by email at 9pm when he’s finished putting his kids to bed? Is it better to talk at a coffee shop? In a conference room or private corner? Or is your best bet to just stick your head in your boss’s office, gauge her mood, and then say, “Hey, can we talk for a minute?”

Whatever the answer, choose a time, place, and communication method that makes your boss comfortable and sets you up for success.

Step Three: Start Your Communication By Showing Empathy and Good Will

A client of mine (we’ll call her Layla) is in charge of creative for a global corporation, and she recently decided to speak up to a boss who she felt was depressing her team’s morale.

Layla did everything right in this encounter.

• First she spoke to her boss in person, keeping her feedback focused, clear, and unemotional.
• Then she followed up with an email that starts off with empathy:

I can really understand the pressure you must be feeling, given where things are from a business perspective. And I can imagine that what upper management is asking of you is effecting your stress levels.

Rest assured that my team and I want to support you, and we are excited to do so.

I have a couple of requests for when you’re working with my team and me, and I want to have an open conversation about broader patterns that I’m seeing and my team is experiencing.

Let me tell you what is showing up…

Clearly, Layla’s boss needed to be carefully prepped, and Layla took her time laying out the big picture by saying:

• I know you’re under stress.
• My team and I are here for you.
• We are, however, experiencing some issues in working with you.
• Let’s have an open conversation about this. (Notice that Layla says “what is showing up” instead of “what you’re doing”; this sets the stage in a non-blaming way.)

Whether you use your own version of Layla’s words, or address the underlying points in a shorter or more casual way, this is a great model for calming someone down before you get to your actual critique.

And however you approach this set-up, make sure you don’t do what someone recently did to a different client of mine, which was to walk into her office and blurt out, “Why are you acting like everything is my fault?”

Believe me, that approach will not produce the desired effect.

Step Four: When You Criticize Your Boss, Make a Case that Isn’t Personal

Nobody likes being called out. That’s why it’s best to avoid “you” language, as well as any comment that sounds inflammatory.

If you’re trying, for example, to ask your boss for more positive reinforcement, you don’t want to say things like:

• Morale is dropping off a cliff since you took over.
• You don’t seem to realize that creative teams need support.
• Are you aware that you always talk like you know how to do our jobs better than we do?
• Sometimes, you sound really condescending.

What’s a better way to make your case for more positive reinforcement of your team’s work? Let’s go back to Layla’s email:

My team is feeling that every time they present, they get what you don’t like about the work versus what you love about the creative.

We understand that you were once on the creative side, and we respect that. But our experience is different from yours and we need to bring our experience to the table.

My request:  Can I ask that when you are with my team to please start with what you like about the creative and keep the feedback strategic? I find that gratitude builds energy and excitement.

Again, this is a textbook example of excellence. Layla tells her boss:

• Here is what my people are experiencing.
• We understand where you’re coming from, but we don’t feel heard by you.
• Here’s how we can collaborate more effectively.

Step Five: Organize, Prioritize, and Choose Your Battles

OK, this actually happens before The Conversation, but I wanted to give you a sense of what that conversation sounds like first.

In her talk with her boss (and her follow-up email), Layla actually made several requests:

• More positive reinforcement,
• Fewer details (in other words, don’t nitpick in someone else’s area of expertise), and
• Recognize systemic issues (if input doesn’t reach Layla’s team in time, they can’t provide their deliverables in time).

There were plenty of other things that Layla could have added to this list, but it’s important when you criticize your boss — or anyone — to pick your battles. Not all problem behaviors are created equal, and it’s wise to tackle the ones that are having the most negative impact first.

What’s the Bottom Line When You Criticize Your Boss?

The better your motives, and the better prepared you are, the better this important conversation will go.

So if you’re having trouble at work, and know that other are, too, don’t just sit back and wait for someone else to speak truth to power.

It may turn out that you’re the best, wisest, and calmest person to make that leap and criticize your boss.