The Actual "Ask" is the Easiest Part

This post is in response to a reader’s request and is part one of two. If you have topics that you want to read about, you can always ask (get it?)! We love hearing from readers like you.

Asserting our needs and asking for what we want in our worklives can be really scary. It can feel so uncomfortable that we end up rarely even asking, which leads us to a place of pain and resentment. If you’re reading this, then you have asked for what you wanted at some point in your professional journey, whether it was for a job, a promotion, or a raise. We all ask, but receiving what we want is another matter, and there are ways to ask that increase the chances that we’ll hear a “yes” as a result; I want to share some of those ways with you in this post.

1. Sniff around your motivations. I love this quote from Clarissa Pinkola Estes: “Those who would develop consciousness pursue all that stands behind the readily observable: the unseen chirping...the lamenting door, the lip of light beneath a sill. They pursue these mysteries until the substance of the matter is laid open to them.” Oftentimes, we ask for things that we believe we want out of desperation - a desperate need to be validated, seen, heard, etc. Even if you’re not aware that your motivations stem from desperation, those on the receiving end can often sense it. Before asking for something you want, look behind the “thing” itself and ask yourself why you want it three times. By getting very clear about your motivations behind the asking, the asking becomes much easier.

2. Try it on. Imagine yourself getting what you want - let’s say it’s a promotion at work. What do your days look like? How do you feel arriving at the office? Do you feel excited to be there? Does your body feel light and awake when you’re imagining yourself in this new role, or does it feel heavy and tired? If the new role or opportunity feels good and your motivations are clear, then it’s probably something worth asking for; however, if you feel as though something’s not quite right when you’re trying it on, keep asking questions.

3. Do the work. On some days, I would like to ask for a job at an organizational think tank in Stockholm, but I haven’t done the work necessary to enable me to do that (yet). We have to do the work that manifests what we want. As Annie Dillard put it, “How we spend our days, of course, is how we spend our lives.” If there's a skill set, let’s say Excel mastery, that’s required for getting a promotion you want, you should probably invest in developing your Excel skills. If you avoid doing that because you hate working in Excel, then that new role may not be a good fit for you in the first place. Flashy jobs still require mundane, tedious work, and if you hate doing that particular flavor of tediousness, you may end up hating the job altogether. So do the work that nourishes you and that you enjoy even when it is mundane - that will enable you to ask for what you know you want.

4. Get in the head of the person you’re asking. Liz Ryan talks a lot about looking at the particular business pain facing an organization that you’d like to work for. Try to see the world from the hiring manager’s point of view and shape your asking in a way that focuses on alleviating that pain. If you’re asking for a mentorship or a nice favor, shape your asking in a way that acknowledges the sacrifice required of the person you’re asking and consider how doing so will ultimately benefit them. Speak their language, imagine what their days might be like, do anything you can to develop a better sense of how to ask for what you want in a way that they can hear.

5. Then, ask. In many ways, finally asking is the quickest and easiest part of this process. As one of my graduate school professors said, “You have to go slow to go fast.” Once you’ve become acquainted with your motivations and have ensured that they are the right ones...once you’ve tried the goal on to see how it feels...once you’ve done the work and considered the world from the others' eyes, then you should ask. Now you can ask standing tall and sure of what you want and why you want it. The person you’re asking will feel assuredness reverberating from you instead of a sense of desperation or neediness.

6. Then, let go. Trust that once you’ve asked, whatever forces you believe are at work in this realm will take care of the rest. The job search is so hard for many of us in part because we ride the emotional roller coaster of hope, rejection, hope, rejection, and we rely too much on a sense of external validation. If that mentor doesn’t want to work with you or if you don’t get that promotion, it’s because there’s something better waiting for you. I really believe that, and it’s hard to accept in the midst of being kicked down to the ground, but once you brush the dirt off, I think you’ll see that it’s true.

Next time, I'll be offering up some ideas for what to do once you actually get what you want.