15 Ways To Feel More Comfortable Negotiating With Your Boss

Forbes Coaches Council Members

May 3, 2022

Able (Find Your Voice Asia) helps individuals find their diamond within & grow beyond the ego in order to find peace within & with others.

When an employee feels they need or want more than what they’re receiving at work, they must address the issue with management and negotiate for a favorable outcome. However, many employees feel awkward negotiating with their boss for anything.


One should never remain quietly dissatisfied at work when it comes to asking for a well-deserved salary increase, promotion or more flexible schedule. Here, 15 members of Forbes Coaches Council share some mental tricks and specific types of language that employees can use to feel more comfortable and confident in negotiations with their direct support.




1. Model Honest Dialogue And Transparency


Courage, dialogue and transparency are keys to happiness anywhere in life, but the inherent power dynamics within organizations can stifle them. As a leader, I am far more interested in having conversations about these very things—how do we as a team enable courage, dialogue and transparency?—rather than trying to solve the areas for negotiations in isolation. Start by modeling honest dialogue. - Nick Bolton, Animas Centre for Coaching


2. Have A Clear Shared Intention And Trust


Successful negotiations are rooted in having a clear shared intention and trust. Consider what your boss values at work (their measure of your success) and prepare to communicate evidence of how you contribute to that intention through your skills, experiences, work ethic and so forth. By reflecting on your accomplishments and competencies, you will radiate more confidence and trust. - Vered Kogan, Momentum Institute


3. Use Affirmative Language With Yourself


The reason an employee, or anyone for that matter, feels awkward when negotiating for anything is because, internally, they don’t feel as if they deserve what it is they want. Reframing the language one uses about oneself is therefore key. Affirming yourself by saying, “I deserve this (whatever this may be), and I am worthy of it” is a surefire way to mentally prepare for that negotiation. - Dr. Rakish Rana, The Clear Coach


4. Pursue It From A Place Of Personal Power


I engage my coachees to pursue their negotiations from a place of personal power. Preparation is key. Know how valuable you are and start the conversation by showcasing key wins for the company that were a result of your work. Paint a picture of how much more can happen and how you will add even greater value by achieving it. Then, ask for what you want using words such as, “To reach our goal, can we consider...” -Arthi Rabikrisson, Prerna Advisory



5. Gamify Your Approach

One way to reduce the anxiety of such a difficult conversation is to approach it with humor as part of a game for the self. In gamification, a player treats overcoming obstacles as “quests,” and each one can be broken up into “mini objectives.” Hence, regardless of the intended outcome, one can lower the stakes by gamifying the experience and showing up armed with a smile. Then, the task will seem more manageable. - Thomas Lim, Singapore Public Service, SportSG

6. Consider Gender And Think About ‘We’ Instead Of ‘I’

Salary negotiation for women is very different because of socialization and social norms, so it is important that employees consider gender in their negotiation strategies. For women, one of the strategies that has been shown to work is thinking about “we” instead of “I” in any opportunities for negotiation. Most often, women are negotiating for their families, so keeping that in mind can help. - Susan Madsen, Jon M. Huntsman School of Business

7. Reflect On A Set Of Powerful Questions

Negotiating a salary increase, promotion or more flexible schedule can feel intimidating. Before approaching your boss with a request, reflect on these three powerful questions: What is the worst-case scenario? What is the best-case scenario? What is the most likely scenario? Hopefully, these questions will help you recognize that you are likely to get what you want at work. - Kyle Elliott, MPA, CHES, CaffeinatedKyle.com

8. Be Direct And Back It Up With Reasoning

In order to get more from your job, you must ask for more. Be direct with your ask and back it up with reasons why you deserve the promotion, bonus or salary adjustment. For instance, “I pride myself in bringing tremendous value to the organization. I would like to request a raise to X amount, and here are the reasons why I feel that I am deserving of this adjustment.” - Jarret Patton, DoctorJarret PLLC

9. Adjust Your Mentality And Approach

Adjusting the mentality and approach for negotiating with your boss can alleviate awkward feelings during the process. Approach the discussion with a mindset that the only way you know you won’t achieve the change (whether it be a salary increase, a promotion or schedule flexibility) is if you don’t ask. The only way you have a chance at positive change is to ask for it. - Luke Feldmeier, Online Leadership Training - Career and Leadership Accelerator for Engineers

10. See The Conversation As Your Project

Many employees feel uncomfortable with the idea of asking for something. Instead of thinking about the negotiation as an ask, reframe the conversation and think of the process as if it were a project you are running. Support your case and look for buy-in as you would with any other important project at work. - Michele Cohen, Lead to Growth Coaching

11. Know Your Value, Available Options

Know your value and that you have options. Organizations cannot afford to lose talented employees in today’s labor market. You have all of the leverage, so you don’t need to fear the conversation. Some things might be harder due to organizational constraints (such as a salary increase), but others such as scheduling flexibility (time and location of your work) should be on the table for everyone. - Jonathan H. Westover, Human Capital Innovations

12. Put Yourself Into Your Boss’s Shoes

Put yourself into your boss’s shoes because no boss wishes to lose an employee and take on the extra work of finding a replacement. Remember that you are equally valuable as a contributor to the company and no less of a human being than your boss is, even though they are in a higher position of power. Breathing deeply can help release tension and anxiety before heading into the meeting and speaking honestly through facts. - Able Wanamakok, Find Your Voice Asia

13. Learn To Harness The Power Of Anger

Anger can be polarizing because we associate angry energy with angry behavior. Anger is neither good nor bad, but it can be used for good. Many significant changes have been born out of anger. Leverage anger to identify what is happening and what is not happening. Base your points on reality so that you can state your points objectively. - Yvette Costa,Velocity Advisory Group

14. Consider The Costs Of Opportunity And Anxiety

What does it cost you and your loved ones if you do not ask for that promotion and miss out on that opportunity? How much are you going to drain yourself knowing that you deserve something, yet you are not asking for it? How would that affect how you interact with others? Add it all up and think about whether facing those outcomes or asking for a promotion is going to be more painful. - Csaba Toth, ICQ Global

15. Name The Point Of Tension For Clarity

It may feel awkward to negotiate, but it is far more awkward to move forward pretending that everything is okay. You will waste far more mental and emotional energy avoiding a potentially awkward conversation than you will by naming it and moving forward. Clarity will give you greater energy for navigating a path forward too. - Billy Williams, Archegos Want to ask questions or need guidance? Please email me at able@findyourvoice.asia.