How I Built Up My “Asking” Muscles…

Adventures in Asking…

My first real job, where I had any kind of authority, was for a small real estate firm that hired me to be its office manager. I was 25 years-old, and quickly learned I was not nearly as smart as I thought I was. Though my title suggested some semblance of clout, all the agents were in fact independent contractors, so implementing any kind of company policy was challenging. When push came to shove (though it never came to that), as long as they were bringing in business, they could basically do (or not do) whatever they wanted. I watched my predecessor struggle with these dynamics. To the brokers, she would accommodate pretty much anything. Behind the scenes, she was resentful and frustrated that so much was put on her plate. Not wanting to end up like her, I decided to try something she hadn’t: Asking for things.

I started slowly by looking for openings and requesting things that would have been hard to say no to. For instance, I learned that there was money set aside for professional development that no one was using. When I received a flyer in the mail for a seminar for first-time supervisors, I asked my boss if they would pay for the seminar and two “professional” days, so I could attend the 2-day workshop. They said yes, and at my next annual review, I asked for four paid “professional” days to attend more seminars.

After that went so well, I ventured into more dicey territory. One problem my predecessor dealt with was constant interruptions from agents. It was especially disruptive when I was working on the firm’s weekly newspaper advertisements. The distractions often led to typos and mistakes, which all of us could agree was a problem. So, I requested a limited number of hours of uninterrupted time when agents would cover the phones and leave me alone. I taped a pen cap upside down to the side of my computer monitor, and whenever I needed quiet time, I would place a small Canadian flag (I lived in Canada before moving to Nantucket) in the cap as a signal to the office that I was temporarily unavailable. Admittedly, the whispers of “Is her flag up?” and “I think her flag is still up” was still a little distracting, but I appreciated the support.

This led to a non-negotiable lunch break away from my desk, while agents took turns covering the phones and welcoming walk-ins. Brokers grew to respect my boundaries and make sure I had what I needed to do my job well. We wouldn’t have reached that point if I hadn’t been willing to just ask.

In 2010, I gave noticed and moved on having learned the following:

• Asking for what I need teaches others to respect me

• Getting buy-in from others makes asking easier

• Asking is a habit that takes practice

Is It Always That Easy? No….

In the scenario above asking for things came quite easily to me, but there have been other times when I struggled to ask for things from others. It has come up most frequently in personal relationships, but in professional settings as well.

I can be a bit of people pleaser and a fixer. With the benefit of hindsight, I look back on many circumstances and see how I might have handled it more gracefully, or at least more quickly, if I had been willing to just ask for what I needed.

Here are some lessons and insights, I’ve learned from many mistakes. Full disclosure, I made the same mistakes over and over and over again before I actually learned the lessons I’m about to share. So, try and try again. Each applies to professional, personal and romantic relationships.

#1 Do a reality check before asking.

People love to catastrophize. They love to come up with worst-case scenarios and/or rationalize why asking just isn’t that important. Unfortunately, many people experience the same aversion to risk regardless of what they are asking for. Asking for more money from an employer or a rain check from a friend should not evoke the same fear and anxiety as asking for something that might end a career or dissolve a marriage.

When I started my pet sitting business, I was so worried about losing clients and failing that I bent over backwards to accommodate every request. For some reason, it seemed rude to ask for people to work with my schedule. Finally, I reached my breaking point and got up the nerve to ask a client if I could walk their dog at 10:30am instead of 10am. “Of course!” she responded. “You can come any time between 10am and noon.” *DOH!! Why didn’t I ask sooner?!? It was such a small thing to ask for!

If you are avoiding asking for something, be honest with yourself, what do you really have to lose? What is really at stake? It’s likely the more dire result is they say no.

#2 Ask even if it is inconvenient.

A big reason people don’t ask for what they need in a relationship is that it might rock the boat and mess up a situation that is otherwise quite pleasant. If you describe your relationship as “fine” this should be a red flag.

How long are you willing to go without what you need to keep the peace? What is it costing you to deny yourself? Is it really in your best interest to keep a mediocre connection intact? What are you sacrificing for this convenience?

There have been several times when I’ve gone outside my comfortable zone and risked convenience to ask for what I wanted or needed, and I have seen it go both ways: my needs are met and the relationship remains or my needs are not met and the relationship falls apart. Either way, when the dust was settled, I’ve accepted that convenience is not enough of a reason to not ask for what I need.

#3 Ask even if the answer could be no.

Most people are fearful of asking for things because they might not get it. Which makes sense. To make yourself vulnerable only to be rejected is a universally uncomfortable concept. What most people don’t consider is that avoiding the “no” is also denying you the “yes” you are looking for. There are moments when you must be willing to ask and get a “no”, which will free you up for someone or something else that will give you a “yes”.

I remember just before having “the talk” with someone I was dating, I spoke to a fellow coach, and he helped me come to the realization that if I didn’t get the answer I wanted, I would at least get the answer I needed. I got the answer I need and moved on. Looking back on that time three years later, it was also the answer I wanted, I just didn’t know it yet.

Value yourself enough to ask. You deserve it.