How to Get Your Boss to Say Yes

You have this really wonderful idea but:

A.) It's a little bit out of the ordinary, so the traditional way you go about getting approvals is not going to work.B.) Your boss has previously shown signs of being "risk adverse."

How do you get the go-ahead?

The first answer is don't ask — at least not at first.

Are we advocating the old adage that it is always easier to ask for forgiveness than for permission? Sort of. What we're saying is that your first series of actions should not create a situation where you have anything to apologize for — even if you're not acting with the boss's permission.

The way to make that happen?

1. Your initial steps should have you acting like an entrepreneur. You want to act quickly with the means at hand. (That's right — before you ask for approval.) What's right around you that you can employ?

You have to be the judge of the size of those steps. Executing it must carry no negative consequences for anyone, especially you and your boss. Then, keep taking those tiny steps for as long as you can. You are building evidence! And as Scott Cook, the founder of Intuit, says, evidence is better than anyone's intuition. Even your boss's.

As you are taking your small steps, under the radar screen, get other respected people's help and fingerprints all over it. That will do a few things for you, all of them good. You will: gain additional perspectives ("Hey, did you ever think about this?"); have access to additional resources ("Sure, we have a lot of X that we aren't using); and be introduced to other like-minded people that, quite frankly, might give you a bit of protection should you be discovered at this early stage. Again, only you know how far you can go with this. The politics of every organization are different, and you don't want to do anything that could be taken to mean you are trying an end-run around your boss.

2. At some point (again, you have to be the judge) you'll want to let your boss know what you're doing. Even then, avoid asking for approval if you can. The conversation might go something like this:

"Hey, boss. I have this idea that fits in with what the company is trying to accomplish and could make some money. I haven't a clue if it is going to work, so I'm just spending a little time during off-hours or during downtime on it. I just wanted to give you a heads-up."

This conversation:

• Keeps your boss from being surprised. (That's always a good thing.)
• Buys you time to see if the idea is actually doable. If it's not, you don't have anything to ask your boss for later.
• Gives you information. You might learn the idea is doable, but you don't want to do it. And that is a good thing to know, before you offer up the idea for formal approval. (You can suggest people who would be perfect to spearhead the initiative.)

The smart boss will appreciate your enthusiasm and initiative and maybe even try to help, or offer a suggestion or two. At the very least, she won't stop you at this point.

The dumb boss will say something like "if you have any time to spare, work on what I already assigned you to do." If this happens more than once, you probably want to transfer to another boss or job. Research has shown that a prime determinant of workplace satisfaction and performance is a supportive boss who respects you and your ideas. For a detailed look at other ways to handle your supervisor, read the classic HBR article Managing Your Boss by John J. Gabarro and John P. Kotter. It's one of our favorites.

Okay, you've taken some more steps. The idea is a good one and you want to be involved in it going forward and it's going to require your boss to not only sign off, but also provide some resources. What do you do?

3. Make your best prediction of what the acceptable loss is for other key players, especially your boss. You already know the first couple of steps to take. You position the idea in the context of her hot buttons, whatever they may be.

"Hey boss, you know how you are always talking about how our department has to be more innovative. Well, the thing I have been working on seems to fit with that perfectly."From there, you want to make sure you keep your requests (at least at first) within her realm of acceptable loss. How much is she likely to be willing to risk and write off if the idea fails? How can you do everything humanly possible to keep the number at risk below that?

Implicit in this is that the next step is going to be relatively small. That's a good thing. When you are facing the unknown — and starting something new certainly qualifies — you always want to begin by taking small steps. In fact, when you have been acting on your own, and even when you are acting with the approval of your boss, you are preceding just as successful serial entrepreneurs do:

• They take a small step toward their goal.
• They pause to see what they learned from taking that step. ("Yes, it looks like it is worth continuing for now.")
• They build off of what they learned.
• The process repeats until they (and you) achieve their goal — the project is a success — or they realize it cannot be done, or they find something more appealing.

Who knows? Telling your boss that she's acting like one of the most successful entrepreneurs in history might get things to go in your favor.