In Leadership

A version of this article was originally published on Forbes, and is reprinted here with new content with the author’s permission.

Years ago, in my first sales role, a coworker pointed out to me that I was driving almost 80% of our company’s overall revenue. I should have been thrilled but was frustrated instead. I still hadn’t received the promotion I had asked for and knew was deserved. My colleague’s comment only added gasoline to my already burning fire: I loved my job but knew that staying wouldn’t be possible if I didn’t muster the courage to talk to my boss about the things that would help me thrive in my role.

Preparing for the conversation wasn’t easy.

I agonized for days about the best approach and was given a lot of well-meaning but unhelpful advice from friends and family, who encouraged me to throw around ultimatums and refuse to take no for an answer. Ultimately, I decided to be positive and strategic in presenting my asks. The conversation I had been avoiding for months resulted in an immediate promotion to team lead: and a year later, to Head of Sales.

Asking for what we need at work can feel intimidating and risky, especially if you are a woman, a person of color or LGBTQ. But the danger in avoiding these important conversations is that we eventually become less engaged and productive at work, and inevitably begin looking around for the next best thing. Addressing these issues head-on, and verbalizing the things we need to grow as professionals, are the keys to being successful (important) and happy (even more important). It’s not easy, but over the course of my career, I’ve continued to work on making my voice heard and speaking up for myself.

Here are some tactics that have helped me gain the confidence I need to prepare for any hard conversation:

Understand The Ask And Your Boundaries

You have to know exactly what you want to get out of the conversation, how far you are willing to go and where you’re willing to compromise. Figure out ahead of time what your priorities are and make them clear. Are you looking for more responsibility? Be ready to show you can handle it and point to examples of leadership that you’re already exhibiting. A raise? Demonstrate how you’ve earned it and how you came up with the number. A promotion? Don’t just ask for the title change: show that you understand the responsibility that comes with the new role. Flexible hours? Prove you can manage your workload. Only you know what you need, but you can’t be afraid to put it all on the table.

Know Your Audience

Often when we are having tough conversations or negotiating, it’s easy to only think about ourselves. By taking time to think about what the person on the other end of the table needs, you’ll be better prepared to have a more productive conversation and negotiate successfully. (In the legal world, they call this “interest-based negotiating,” and it applies to workplace conversations as well.) Perspective is everything. Your goal should be to have everyone feel like they are winning without letting the things that are important to you slip away.

Check Certain Emotions At The Door

Everyone gets worked up and emotional at the office at some point, and that’s natural. But there’s a time and place to vent, and it’s usually not at the negotiation table or when you’re asking for something important. Data and facts should be the foundation on which you approach these conversations. This doesn’t mean you shouldn’t bring your full self into the room or express emotion. It means that you should try to keep yourself in check to ensure you don’t put the other person on the defensive: this will likely never result in the outcome you’re looking for. Focus on being solution-oriented, and be careful not to weaken your position by expressing frustration or complaining.

Use your network

It’s sometimes easy to forget that other people genuinely want to help you. A desire to be helpful is part of our human nature, but oftentimes the only way to get that help is to ask. Seek out the guidance of your network for a fresh perspective on your situation, rooted in personal experience. Mentors and coaches can help you prepare for the conversation (try role playing!), and they can answer questions you wouldn’t feel comfortable asking someone within your company. They can also provide a necessary reality check that’ll help you remain accountable, self-aware, and able to advocate for yourself.

Be Positive

Talking about what you appreciate or love about your job right out of the gate immediately demonstrates your commitment, and will likely make it easier to ask for more. If you start by making demands or pointing out how you’ve been underappreciated and wronged, it’s easy to immediately create a negative dynamic. Attempting to establish a positive vibe and create a sense of cooperation will make other people feel it is in their best interest to support you.

There will be times when you do everything right and still don’t get what you want or feel you deserve. At this point, you must assess whether or not you can continue to stay engaged at a level that feels fulfilling to you. Sometimes, the answer may be to move on. The good news is that it’s often much easier to make this decision after you’ve had the tough conversations: and by figuring out how to take this first step, you’re already halfway there.

About the Author

Sarah Sheehan is the co-founder of Bravely, a platform that connects employees with professional coaches for confidential conversations about whatever they’re dealing with at work. 

She began her career in HR at companies like SiriusXM, Coach, and the Gilt Groupe. While at Gilt, she pivoted into a sales role at Gilt City, the company’s luxury experiences platform, where she led a 65-person team and saw firsthand how relationships impacted not just company culture, but the bottom line. She is passionate about providing women and underrepresented employees with the access they need to succeed.


Recommended Posts

Start typing and press Enter to search

person in blue sweater using black laptop computer