LIKE A BOSS: 5 Ways to Unlearn Female Politeness & Fast-Track Your Career

Diana Adams
6 min readApr 18, 2019

Like many women, I grew up learning to make other people happy, to avoid complaining or seeming emotional or needy. I was praised for the skills that would make me a good wife and mom — self-sacrificing and easy-going. I wasn’t taught how to deal with money or take charge.

As I founded my own law firm and became a business owner and supervisor, I realized that many of the ways I was socialized as a woman were holding me back. I wasn’t advocating for myself. I didn’t want to ask for too much or seem aggressive. I definitely avoided any conversation that involved disagreement or potential awkwardness.

I’ve been on a decades-long journey to unlearn some of the harmful cultural lessons I absorbed, and to replace them with emotional practices and communication techniques that have bolstered my professional success as an entrepreneur as well as helped me to create a partnership and family of my dreams.

These are some of the core principles I share when I mentor and train other women:

  1. Ask for what you really want & Say No to the rest

Before you can develop the communication techniques to ask for what you want, you have to figure out: “what do I want?” You need to get clear on your goals, needs, and desires before you can ask for them.

When it comes to work, I recommend this thought process:

What’s the career you want in 5–10 years? What do you need to do now to get there? Choose three-to-five aspects of your work that you want to prioritize over the next year, as part of your long-term goal setting.

I spent years stretched too thin, because I said yes to way too much, and ended up making my decisions about how I spent my time based on who wanted and asked for it, rather than on what I really wanted. Sound familiar?

I decided to choose which projects I wanted to say YES to according to my specific list of priorities, and realized they were very different than how I was spending my time before:

· Highly paid legal gigs that would pay my bills to allow me to pursue my other passions

· Chances to expand myself as a writer and public speaker

· Opportunities for leadership and activism for marginalized LGBTQI communities

· Large-scale promotion of my work to my target audiences

I compared every request to those priorities to strengthen my NO muscle, and to give myself a rubric as to whether a YES was serving my own goals.

Unpaid MC night to a small crowd of female comics? Tough to say no, but it’s not targeted enough to my current goals, so NO thank you!

Interview on a popular LGBTQ podcast? That meets my need for promotion to my target audience! YES!

Speak for free to lawyers? NO thanks!

This process got easier until I felt clear in my goals. Eventually I found it easy to offer an appreciative NO — and pass those opportunities on to someone else for whom the opportunity would be more in-line with their own pursuits.

2. Ask for MONEY! Believe you deserve to get PAID

As a justice-minded activist who grew up poor, the only thing I was taught about money was that it’s for bad people. Rich people in movies were the selfish bad guys. I disdained materialistic consumer culture and those whose primary goal was to make money. The money part of any job was the awkward, crass part that I had to get through before getting back to my ideals.

That’s the short version of how I ended up with seven years of Ivy League education and fantastic ideas . . . and on Medicaid, in debt, and worried about paying rent.

Disdain for money is self-defeating. For me, part of my guilt and discomfort with money was my female socialization. I was taught to not have needs, to give to others, and to be proud of my selflessness. But I can’t make big change in the world if I have to redirect my energy from activism to anxious scrambling to pay my bills. I can serve the world better if I am grounded and confident about providing for my rent, health-care, and family.

You deserve to be paid your industry standard. That means as much as white men are paid to do the same job.

Learn your industry standard fees, and then BELIEVE you deserve it before asking for it. Ask for that big number and avoid immediately hedging with ‘but that’s negotiable.’ If you don’t believe you deserve it, no one will.

Before a call or meeting in which you offer a price quote for your services, decide your high-low range, including the lowest you would accept on the spot. Ask for your high number and let THEM tell you if its too much before you offer anything less.

Overcome any fear or avoidance of money and make learning about it a practice. Listen to podcasts about money and business management, get resources, and make money part of your vocabulary. If you want to take a deep dive into your finances, consider a course, such as this online workshop with Manisha Thakor, Financial Well-Being: Gaining Wisdom, Balance & Joy, or a fantastic women’s finance resource such as

3. Ask for More: Negotiate

When it comes to salary and other payment for your work, a first offer from a potential employer isn’t a final offer. Negotiate for more. One major factor in salary disparity for professional women is the prevalence for men to negotiate harder for themselves over initial salary and benefit packages, for promotions, and for their own interests in professional contracts, such as proportions of intellectual property.

I challenge myself in these moments to silence the thoughts about seeming pushy or ungrateful. I push myself to advocate for myself, ask for more, and get all agreements in writing. Advocate for yourself like you would advocate for your mother or your child.

4. Ask for Mentors

How will you know the range of how much other colleagues are paid if you don’t have others to ask?

I seek out those whom I admire, particularly more senior women, and develop relationships. Particularly if you work in a team office environment, seek out positive supervisors and develop rapport, so that they are in your corner if you need to advocate for yourself at work.

If you’re cold-calling a person you admire, avoid this key mistake when soliciting mentorship: Be aware of the mentor’s own needs and time limitations. I receive many emails per week from well-meaning people asking for personalized career plans and advice (without payment). Providing such personal support to each person certainly wouldn’t be sustainable. Instead, I offer mentoring and support through regular trainings, articles, workshops, internship programs, and paid coaching. Look for opportunities your potential mentor is already offering.

Also, think about whether you have something to offer the mentor, and perhaps offer to volunteer in exchange for some targeted mentoring.

Find male allies, as well, who can share their insights into industry standard fees, including how much men in your position are being paid. If you know that the other two men in your position negotiated hard before accepting their salary and benefits package, you’ll feel more assured in doing the same.

5. Ask for the Awkward Conversations

The underlying principle in all of these suggestions is to embrace bold, potentially challenging conversations. The conversations we feel social pressure to avoid are those that are essential for self-advocacy and advocacy of others, such as those about money, setting limits, and asking for more.

You need to be able to give critical feedback to those who work for you in order to become a great supervisor and boss. You need to be able to ask for the support you need to collaborate effectively. You need to be able to honor your own limits and celebrate saying NO.

The crucial ‘soft skills’ of communication and emotional awareness aren’t taught in schools because they’re feminized and devalued. Our whole culture is suffering from lack of them. Social courage and communication savvy aren’t innate character traits. They’re learnable and need to be taught, especially to women, to people of color, and to LGBTQI people, who all receive even more damaging social pressure to shut up and smile, rather than speak up.

In teaching these skills for thirteen years, I remain inspired that developing ourselves as communicators has the power to dramatically improve our lives at work, at home, and beyond. As a broke young woman, I gradually found the wonderful audacity to ask, with confidence, for big opportunities and higher pay. By acting like a boss, I got paid and treated like one.



Diana Adams

Speaker/policy activist/mom. Lawyer/Mediator for LGBTQIA/non-nuclear family: Communication educator: http://CourageousConversations.Work