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How to know when you’re ready to ask for what you want


When we are asking for something we want, we know how it will help us as individuals. But those reasons are likely not the reasons that will get your boss to jump up and down exclaiming a loud, Yes! Go for it!

Instead, we need to think about the request as our boss would see it. This doesn’t mean just thinking of the right phrase or way to frame the request. It means actually putting yourself in your boss’s position, and asking, how could granting this request feel good / like the right decision? What would make granting this request a no-brainer for the boss?

By answering those questions, you will see how what you want doesn’t need to be just about what you want – it can also be about how it can help the company.

Because it never needs to feel like an us vs. them request.

Situations – such as requests we want to make – are always neutral. And it’s only how we interpret that request that determines if it’s good or bad. So what this means is that if we can help show our boss how the request is in fact a blessing – for them, for the company, for the team, for the client, etc., we can help them to see it as good.

Often what I find is people are so focused on the negative of what their boss may think when they ask for the request, that they themselves don’t even see how it could be a good thing for the boss – so they never identify or present it that way. Their too stuck in scarcity us vs. them thinking to realize that a request could be good or bad – not by what the request itself is, but by what we make that request mean.

As the requester, it’s your job to show how that request is good. For all involved.

To check that you yourself actually see it that way – ask yourself:

1. How do I think my boss will actually feel about the request?

2. Why do I think my boss will feel that way?

Whatever answers you provide yourself, those will be the points to start with. Those are the thoughts and perspectives to undo in yourself if they don’t create the feeling you want your boss to have about the request.

Now, ask yourself:

3. What feeling do I want my boss to have about the request?

4. What would allow my boss to feel that way?

The gap between the first two questions and the last two questions is where your work lies. Once you can come from the place where #3 and #4 is what you think your boss will think by default, you’re ready to make the request.