Welcome to our special interview series, Women Who Lead. In partnership with White House Black Market, we’re celebrating five women teaching us to think differently, speak louder, and live better. No career is the same, and that’s just how we like it. These women are leading by example and living by their own rules.
79 cents. Chances are that number sounds familiar to you. For working women, there are few things more frustrating than the very real existence of the wage gap and the fact that, on average, women make 79 cents to a man's dollar is a constant reminder that we still have much to fight for. Alex Dickinson is a woman at the forefront of that fight. As the founder and CEO of Ask For It, Dickinson has made it her life's mission to help women build confidence, speak up regularly and often, and fight for what they want and deserve. Whether that's landing a raise or negotiating an initial offer for a new position, Alex's one-on-one coaching and training sessions help them get there. Today, we're turning the tables to talk to her about her own work and how she embodies that "ask now, not later" philosophy on a daily basis, building her own career with conviction and daring. Here's Alex:
"My professional background is [in] communications and training. I always had jobs where I represented the organization I worked for, and over time I felt that I wanted more meaning and satisfaction from my career. I’ve always been passionate about women’s leadership, and had started studying negotiation while I was running a Lean In circle. I began planning a negotiation workshop series as a side hustle.
In the midst of this planning, I was unexpectedly laid off from my full-time job. I had interviews and offers from other places, but I realized my heart wasn’t in it. This was my chance to dedicate myself to something that I care deeply about. If not me, who? If not now, when?
When I decided to work on Ask For It full-time, my husband and I discussed the opportunity costs of me giving up a regular paycheck. We agreed that I would put my best effort into the business for a full year. At the end of a year, if I had made no money and didn’t have any opportunities, I would start looking for a job. Happily, I recently celebrated my second business birthday, so I’m proud to say that I’ve grown the company steadily from that first public event into something much bigger...
On Helping Others Help Themselves, Jerry Maguire-style
I do trainings at companies, coaching one-on-one with individuals, and I teach group workshops. I’m also a contributing writer for Women@Forbes, and I write about how to use a negotiation mindset to achieve your goals.
At companies, I’m typically working with sales or business development teams. I do a lot of work with agencies where folks negotiate with clients on project scope and budget on a daily basis. With individuals, I’m usually coaching people on how to ask for a raise, how to negotiate a new job offer, or even sometimes something trickier like severance. Most of us were never formally taught to negotiate, but it’s never too late—or too early!—to learn. I’ve worked with high school students, senior executives, and just about everyone in between.
On Going From First Event To Forbes
One big milestone for me was being invited to join Women@Forbes as a contributing writer. Being able to introduce myself as a writer for Forbes gives me instantly recognizable credibility. It’s been an incredible opportunity to meet lots of people and share their stories with a wide audience.
Another was making my first hire, and it’s a story that I love sharing. Lily, who now works for me part-time, originally heard me speak on a podcast. She loved my message and decided to reach out to me cold on LinkedIn. Her message was so thoughtful and specific that I knew I was interested in chatting with her. She originally wanted to volunteer for me. She wrote a few guest blog posts and was still hungry for more. She came with her own ideas and was so self-motivated that I realized I had better make her an offer quickly before I missed my opportunity! She’s been on my team for eight months now and she’s been a complete game-changer for the business.
On Empowering Other Women Entrepreneurs
I serve on the Junior Board of She's The First and volunteer as the City Manager for the NYC Chapter of the Lady Project. I’m also part of the Ellevate Network, and I’m a mentor with the Girl Scouts Leadership Institute. So yeah, you could say I’m part of a lot of organizations that support women! Lady Project was the first women’s organization I got involved in, and it’s not an exaggeration to say it completely changed my life.
It's so true that you can't be what you can't see. Without having met women who work hard every day to make their business dreams a reality, I would not have had the courage to start my own business when I got laid off. I believe in lifting as you climb, and women’s organizations provide space to do that.
On Charting—And Owning—Your Career Goals (And Yes, Ya Gotta Ask For It)
The most successful executives I’ve worked with are crystal clear on their goals and the next steps in their careers. They’re thoughtful and thorough in their work and genuinely invested in their team’s success.
If you don’t already have a professional development plan, that’s a great place to start. I don’t mean one that your boss hands down to you, but one that speaks to your priorities and interests. If you don’t love your role now, be honest about that and work toward something that’s a better fit. You have to know what you want before you can go out and get it!
Alex is wearing White House Black Market’s Ponte Fit and Flare Dress in Berry, Silk Floral Oblong Scarf (similar style here) and Suede Kitten Heels in Black.
We know no day’s typical, but we’d love to hear an example of what a day might look like for you and Ask For It.
7:45am: My alarm goes off. I’m not one of those people who jumps right out of bed to exercise… I’m more of a roll over and hit the snooze button. To be honest, I have the snooze built into my wakeup time.
8:02am (because snooze button!): I brush my teeth and throw on a cotton sundress to take my dog Margaret out for her morning walk.
8:25am: Time for breakfast! I make my own cold brew coffee—it’s dead simple in a French press—and I have giant 20oz. glasses that I serve it in. I also have metal straws that feel extra special. I usually have a piece of toast, a piece of fruit, and either two scrambled eggs or yogurt with berries. I catch up on Instagram stories and read The New York Times while I eat.
9am: I work from home, so my “commute” is walking from the kitchen to my home office. I’m usually at my desk by 9, working my way through my inbox.
9:30am-10am: My daily round of calls begins. First up is a call with a fellow female founder to discuss partnership opportunities.
10am-10:30am: Next is a business development opportunity to do a negotiation training for a large group. This one is really promising since it would be with an awesome organization, and I’d get to do some fun travel, too.
10:30am-11:15am: I have 45 minutes to get some tasks accomplished before my next call. I’m efficient under pressure, so I write the first draft of my next article for Women@Forbes.
11:15am-11:30am: If I’m doing an intro call with a potential client or partner, I’ll often suggest a window of 15 minutes. I’m open to the call going long, but having a short time frame helps us move forward quickly. This call is with a prospective corporate client who is interested in bringing a negotiation training to their company’s women’s group.
11:30am-12pm: I like to have tranquil mornings, and that usually means that I don’t put on full makeup or a real outfit right away. Working from home gives me that flexibility, and I like it. Today, I’m meeting with a one-on-one coaching client at a co-working space, so I’ve got to get properly dressed: hair, makeup, outfit, plus packing up my computer and the other things I’ll need for the rest of the day, including high heels. Commuting on the subway in heels doesn’t work for me, so I usually wear sandals and switch when I arrive at my destination.
12pm-12:45pm: Transit time from home to the co-working space where I’ll meet my client. I usually read The New Yorker when I’m underground and can’t respond to emails or scroll Facebook.
1pm-2pm: One-on-one coaching session with a client. I’ve met with this client several times and I’m excited about his opportunities.
2pm-2:25pm: I head out to grab a quick late lunch—I’m starving by this point! My go-to when I’m at my co-working space in midtown is a Pret a Manger chicken avocado salad.
2:30pm-5pm: I can finally get some work done. Right now I’m finalizing content for my new online class, Secrets To Negotiation Success, and polishing up the PDF downloads that accompany it.
5pm-5:30pm: Call with my new graphic designer. She’s helping us up-level our email templates and making improvements to my client workbook, and we’re talking through some details.
5:30pm-8pm: I head up to Madison Square Garden to cover a WIN Summit event for Women@Forbes. WIN stands for Women’s Insights into the art of Negotiation, and I attended their conference earlier in the year. This event is a lecture from a Columbia University professor and expert in negotiation and conflict resolution, in partnership with the WNBA. Bonus: great seats to the New York Liberty game after the event!
8pm-8:30pm: Back on the subway to head home to see my husband and dog!
8:30pm-11pm: Luckily, my husband has a cocktail and dinner waiting for me when I get there. Tonight, we’re having seared chicken thighs with sautéed eggplant, bell peppers, and onions. We chat about our days together and talk about what’s going on tomorrow, plus plenty of playtime and snuggles with Margaret!
11:15pm: Lights out on another busy day!
We have to know—what’s your single best tip for negotiation?
Ask for it! If you don’t ask, you’re definitely not going to get what you want.
What’s your work uniform for working at home? What about when you’re in front of a crowd in your workshops?
My work uniform at home is a sundress with my hair in a clip. I don’t even bother to put makeup on. When I’m teaching a workshop or meeting with a client, that’s a different story! I always prefer dresses to skirts or pants, so I have a closet full of options. Full makeup, including liquid liner and my signature Jungle Red lipstick from NARS, and high heels.
Working from home often means a blurred line between work and life—how do you turn off?
Honestly, I don’t turn off. I’m on email all the time and it doesn’t bother me. I love the flexibility—if I have friends visiting, I can set my schedule so I can take the afternoon off to be with them, and get back to work later in the evening.
What’s your best productivity or time management tip?
I use an online appointment scheduling software called Acuity, and it’s the best thing ever. It syncs up with your calendar, so when you're trying to find a time to meet with someone, you can send them a link to your Acuity page and they can choose a time that works for them based on when you’re available. It’s cut way down on the time I spend emailing dates and times back and forth.
The most important woman in your life?
My best friend Carey. I’m an only child, so she is the closest thing to a sister that I can imagine. We know everything about each other and talk every day.
Your favorite part about being an entrepreneur?
My job is to help people achieve their goals. It’s an incredible privilege to be part of someone’s success story.
Best way to spend a Sunday morning?
Snuggling with my sweet dog, Margaret, with The New York Times and a cup of coffee.
Best kept secret in New York?
Oyster happy hour at the Mermaid Inn—it’s the absolute best deal in town.
The surprising app you can’t live without?
The one book every woman should read?
Gone With The Wind is my absolute favorite. Scarlett O’Hara is the OG feminist and she triumphs over every possible adversity.
Salary transparency is a growing trend—what do you hope to see in the next five years?
I hope all states adopt the ban on asking candidates for their salary history. Asking for salary history is a way to keep everyone’s wages down.
It’s 10 minutes before a big meeting or public speaking event. What do you do to get in the right headspace?
I put my phone away, mentally review what I’m going to be speaking about, and usually grab a glass of water.
You May Also Like
Consumer Goods
Our New Dream Job? Vice President of Social Consciousness & Innovation
"The truth is, having a more responsible supply chain or more responsible business is made up of lots of small actions. And one thing that I really love about my work is that nothing is black and white. It's all gray space."
Consumer Services
An Executive at Intuit on How to 'Send the Elevator Back Down'
"What I often tell engineers—especially women engineers—is that it’s good to be excellent, but you’ve got to make sure it’s not a well-guarded secret."
Consumer Services, Technology
A Top Lawyer Talks Leadership, Transparency, and a Music Empire's Goals for Diversity
As Chief Counsel at Pandora, Adelmise Warner has a few thoughts on leaning in.
Consumer Goods
Rising Tide Society's Founder on Why Not Everyone's Cut Out for Entrepreneurship
Natalie Franke on creative entrepreneurship and her journey with Rising Tide Society
Consumer Services, Technology
Here's How a Female V.P. at a Tech Startup Faces the Gender Gap
Nikki Pechet on writing your own maternity leave policy and taking a job for joy, not money.
Consumer Goods, Technology
A Sales V.P. on What It's Like to Work at Pandora
Casey Forbes is living an audiophile's dream career.
Get the Best Career Advice Delivered To Your Inbox
Join our newsletter to stay in the loop.