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262: Negotiation: Asking for a Raise & Managing Conflict - Ashley Fillingim

On Air with Ella podcast 262


Listener Question: "How can I be confident at work and ask for a raise?"


  • Collect praise and feedback about you before you go into the conversation

  • Be prepared with a track record of your recent accomplishments and past achievements

    • How has your company directly benefited from your work?

    • Did you play a role in increasing sales? By how much?

    • Did you bring in new clients?

    • Were you included in any important projects? What were the results?

  • If you’ve taken on work that extends beyond the scope of the job you were hired for, take your job description and list all of the key responsibilities beyond the scope of the original job description - this might not just be a $ conversation, but a role / job description evaluation, too.

  • What are their priorities? What does success look like for them? What's in it for them if they increase your compensation?

  • Do your due diligence!

    • How much would it cost them to hire (and train) a new you?

    • Look for comparable jobs and their pay ranges.

    • Talk to people. (We don’t do this enough!).

    • Add value for seniority and performance.



  • Ask for a "cost of living raise" or one to align with your increased expenses (e.g. kid in college) - that is not their problem

  • Leave without time-bound action and expectation. You might not get a yes, but don’t settle for less than the date of the next conversation and what is expected in the interim (from either or both of you).

  • Be tone deaf. If the company just had the worst quarter ever, maybe it's not your time. Read the room.


  • Outside of any standard review period, ask your Leader for one:one time to discuss your current and future priorities, expectations and compensation.

  • Have a real number in mind and be specific when you ask.

    • Don't forget to add ~10% to it - this is a negotiation, and you need wiggle room!

  • Practice the conversation out loud - preferably with a friend

  • Practice breathing in and out through your nose deeply. Yes, I'm serious. if you are super uncomfortable or even sometime emotional talking about money, this is a subtle way to get your nerves under control.

  • Approach this conversation like a journalist - just the facts. And remember, they're not doing you a FAVOR, you're asking for what you deserve.

  • Stop talking. Make your points, ask for what you want, and then stop talking.

  • Be prepared with your "back up ask."


  • Chances are good that your boss won’t be able to say yes or no right away. They’ll likely ask you for some time to discuss with others and/or review your information. Thank them for their time and give them some space, but make sure to touch base with them if you haven’t heard back after a 7-10 days or so.


Ashley Fillingim shares her fail-proof method for managing tough conversations.
  • Managing difficult conversations in business and life

  • What Ashley learned about conflict after 20+ years of high-profile, high-stakes litigation

  • War stories of negotiations that went … not so well.

  • When you "lose it," what do you lose? (money, time, respect, credibility, leverage...)

  • Perspective, preparation, strategy and integrity are at the core of a good negotiation

  • Ashley's Take a Beat formula:

    • Breathe: center yourself, own the moment

    • Evaluate: their motivation, your goals

    • Assess: your options, your pacing, your values

    • Talk: stay curious, state your position, end game


Managing Conflict - KickAshLaw Take a Beat Worksheet
Download PDF • 63KB


Ashley Fillingim is an attorney who helps entrepreneurs establish business and legal foundations so they can create, grow and scale. Ashley is a recovering “Big Law” attorney who spent two decades at a top-tier international law firm representing Fortune 500 clients. Recognizing that she could not fully understand the entrepreneur’s journey until she became an owner herself, she went all in.

She founded Sandstar Law, which provides legal services to entrepreneurs, and KickAshLaw for business consulting and education.

Ashley owns Mothers Wine Market in Panama City, Florida. She hosts the Beachpreneur Podcast (launching soon!). She is passionate about her children, travel, the beach, sunsets, and one very large dog.




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