Assertiveness Training 101: 3 Steps to Getting What You Want

In my late 20’s I created an amazing career opportunity for myself, making more money than I dreamed possible following a frustrating experience of hitting an unexpected glass ceiling. I have found people are gracious in guiding and advising, but it is up to me to make the life I choose. From deep down within me, I found my own well of determination. I learned in that moment, what I call Assertiveness Training 101, which is: Determine the life you want, take calculated risks and ask for what you want.

Determine the Life You Want

At this pivotal “Assertiveness Training” moment, I wanted to live a bi-coastal life- one that allowed me to live in both New York City and San Francisco. The circumstances seemed prime: I had built relationships within the firm I was working and understood how all the departments operated because I helped with the start-up. I knew the systems- everything from how the departments were ran to how to leverage the service needs and how to rebuild them. The relationships I built were strong because I was trusted, collaborative and would follow through.

I knew I had the skill set and my co-workers knew I had a strong work ethic and proven success. I knew what I wanted, so I decided to take a risk.

Step one: Determine what you want and know what you know.

Take Calculated Risks

Along with my skills and relationships, I knew the company would hurt if they had to go through another transition of leadership. I also knew I had built the trust of my leadership team and required minimal supervision. I also knew it was well within my means to ask for more money and a relocation package to New York because I had seen them do it for others. In that moment, I was able to use what I knew to become assertive.

Step two: Consider the risks around making the change or not.

You Don’t Know Until You Ask

There is always the possibility of hearing ‘No’. But there is also the opportunity to hear ‘Yes’. So often we talk ourselves out of something because we believe the story we are telling ourselves rather than hearing directly from the other person or people in that story. By asking with purpose and clear intentions, while not being afraid of the ‘no’, (what do we have to lose anyway?), we give ourselves tremendous opportunities.

We have no idea what is possible if we don’t ask, and sometimes the best answer we can get is ‘no’ because it allows us to check in and see exactly where we stand. It allows us to learn our values and if there is potential for growth in the specific situation.

Step 3: Ask!

This mini-lesson in assertiveness training is then: get some determination behind what you want, understand the risk of both taking and not taking action could create, and then ask. In my situation, I did receive a ‘yes’ and created an opportunity that allowed me more freedom and experience. In other situations, I received a ‘no’ and it really helped me to see my priorities more clear than ever before. So, be assertive and ask, because there is no way to lose!


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