4 Ways to Tell Your Boss the Truth Without Getting Fired

Dear Employee,

It's strategy season and what your organization most needs now is the truth. Here's the bad news: the truth is usually in hiding.

You and your teammates know things about what's going on with the business that your boss can't hope to know. You live closer to the customer, the competition, the code, the supplier base and the staff than she does. You hear the rumblings in the cubicles. She may have a better handle on the big picture, but you see what's happening at ground level.

Now you're headed into the planning cycle, often the most elaborate game of charades on the planet. You will spend countless hours examining the past, analyzing the present, and trying to divine the future. You'll scrub numbers. You'll scratch your head. But will it be worth it?

It's easy to blame your boss for the futility of this process. She's temperamental and strong-willed. He's aloof, Spock-like. She's dictatorial. He's tightly wound.

Okay, that's fine. But sit in the boss' chair for a moment. He's between a rock and hard place. The "rock" is his boss -- or worse yet, the board. The "hard place" is you.

First, the "rock": Bosses and boards have no senses of humor about missed numbers. No matter how nonsensical it is, they lay the successes and failures of your company at the boss' feet. Yes, this gives the boss both too much credit when things go well and too much blame when they go poorly. But it's the world your boss lives in.

Next, the "hard place": That's you and your colleagues. The boss often feels lonely, like she's the only one rowing in this boat. Yes, she causes a lot of that loneliness because she grabs the oar right out your hands. But feelings, while not always reasonable, are always forces to be reckoned with. Don't let anyone fool you. Feelings dictate a lot more of how the boss acts than anyone guesses.

You'll be tempted to try all sorts of tactics to handle the truth during this planning cycle. Most stink. But that doesn't stop us from trying them. See if you recognize any of these:

• The Duck and Cover: It's easy to play defense when your boss is on a tear. Keep your head down. Don't say too much. Peek over the edge of the bunker tentatively to see what it's like out there, then hunker back down. Let's call it what it is: self-preservation. It's understandable, but truths will go unspoken that could alter the future of your organization for good.
• The Bank Shot: When the boss isn't listening well, it's tempting to try to bank the truth off someone else. So in a meeting, you talk at someone else hoping that the boss, perhaps with the shields down, will let your message sneak through. But what if the bank shot hits the rim and falls away harmlessly? What then?
• Turning Up the Volume: Maybe you've tried to be subtle and clever, but the message isn't getting through. Maybe you've tried a bank shot or three and haven't yet scored. Now you're tempted to amp it up with the boss. If she's not listening, should you speak LOUDER and S-L-O-W-E-R? In reality, she might just think you're treating her like an idiot.

1. Put yourself in the boss' shoes. Think about what he's trying to accomplish. When it's time to tell him a truth, help him see how ignoring this truth will actually prevent him from achieving his goals. Can he accomplish his goals despite ignoring this truth? Okay, then show him how he'll achieve his goals but at a significant personal cost. Either way, your attitude is that of a friend trying to help someone get important stuff done.
2. Pick your spots. Even the most self-aware boss has a limit on the difficult truths she can face at any one time. Maybe you have 10 Truths to share. On stone tablets. Pick the top two.
3. Choose your setting. Do you want to raise hell? Okay, push back against the boss in a big, public setting. But if you want to maximize your chances of a positive reception, perhaps a quiet word in private or on a break from the planning session would work better.
4. Choose your words. A friend told me of an executive who was hesitating to make a bold strategic acquisition. The executive could tell that one of his key team members was troubled by the situation. "What do you think?" the executive asked. "I think you're acting like a scared accountant," the team member said boldly. Those eight words of truth shook the executive into action.

While simple enough, none of these things are easy. It's easy to duck and cover or blow your top. But your organization needs the Truth. So gather your courage and give it to them.