Spotlight: Alexandra Dickinson

Alexandra Dickinson

CEO and Co-Founder, Ask For It – New York, NY

Do you know what you’re worth, but have a hard time asking for it? Feel like you need to develop or improve your negotiation skills? Then you have to read the advice from Ask For It Co-Founder Alexandra Dickinson. Alexandra graduated from New York University with a B.S. and Master’s in Media, Culture and Communication. After working in both the corporate and nonprofit worlds, she saw the need to help others learn to negotiate. Keep reading to hear her advice on building a business, what class she wished she paid more attention to in school, and ultimately her tips on asking for what you deserve.

What Helped Her Become An Entrepreneur And Why She Started Ask For It:

A few years ago, I started a Lean In Circle that met once a month after work. They’re based on Sheryl Sandberg’s book, Lean In: Women, Work and the Will to Lead. They are small groups that meet regularly to talk about professional development and leadership issues in the workplace. As the organizer, I chose the members and facilitated our  group discussions. That made a big impact on me. It made me realize, “hey, I started something. It may be small, but I’m making a difference in my life and in the lives of the women in my circle, and this is really exciting to me.”

I love teaching negotiation because  the skills are so learnable. If you didn’t go to business school, chances are you were never formally taught how to negotiate. The good news is, it’s never too late to learn.  You can practice, get better, and then use your new skills and make an impact in your life right away. You don’t have to get another degree to be a better negotiator. All you have to do is learn the basics and then practice to develop your confidence, which is amazing.


On The Benefits of Working For Yourself:

I have always valued autonomy and self achievement. Growing up and even when I was in college, I felt sort of constrained. I thought to myself, “when I get to be an adult, I can do whatever I want.” Then I got a full time job and realized I still had to show up to work every day, go to meetings I was expected to attend and do the projects I was assigned. I’m a rule follower by nature, so it’s not that I really acted against these things, but I did think about it.

One of the best things about working for myself is having control of my schedule. It’s really nice to have that flexibility. Plus, I love being able to take my dog, Margaret, for a walk during the day.


On The Problems of Working For Yourself:

One of my strengths is productivity: I’ve trained over 300 people and put on eight events just in the last five months. I built and maintain our website and our research wiki; I plan and execute our events; I design our training decks; I do the social media; I invoice our clients, along with many, many other tasks big and small.

The flip side is that I can focus too much on the task level when it would be beneficial to consider the bigger picture. Because I don’t have a boss to report back to, I have to make time to stop and assess my own performance and whether everything I’m doing aligns with my strategic goals. For this reason, I have some trusted advisors who I can turn to for an external perspective from time to time.

What Skill Should Entrepreneurs-To-Be Learn:

Math. 100% math.

When I took the GRE to get into graduate school, my husband had to re-teach me all the math, which was pretty stressful for both of us. Now as a small business owner, I do my own basic bookkeeping and I wish that I had taken an accounting class. I realize it’s not too late, but it’s hard to make the time for it once you’re busy building a business. I wish I had a stronger foundation in math.


Alexandra’s Top Negotiation Tips:

  • Ask for small things all the time - even things that you know that you are not going to get. You’ll get used to small-stakes rejection so eventually it won’t seem scary to ask for bigger things.

  • When you’re asking for something, frame it in a way that makes sense from the other person’s point of view. Be sure to think about what that person wants as well as what you want.

  • Practice makes perfect. Tell a friend or family member the objections you think you might face. Then ask them to role play with you so when the time comes, you’ll already know how to respond to pushback.


Photography by Guarionex Rodriguez, Jr.