6 Ways to Prepare to Ask the Hard Questions at Work 

Have you ever felt nervous asking your boss a question? If so, you're not alone! Many young people go through this–and for some, the nerves never go away–and only learn through failure and success in their professional journey. 

I remember my first and only job interview with my current job, and the overload of information that was shared with me. Mentors advised that I be attentive, and ask questions surrounding my benefits as a contractor with the organization, but when it came time to it I shied away.

Don't be like me. You'll most likely want to learn to ask questions as early as possible, instead of wasting time building up the courage to do so a few months down the road. 

Questions that you may find yourself needing an answer to at work that you don't usually think about right away may involve paid time-off, salary adjustments, clarity on job description, unfair treatment and more. While this can seem overwhelming and scary for most, asking the hard questions is doable no matter where you work or who you work for. Here are six tips for preparing to initiative difficult discussions about your job. 

1. Be your own advocate

woman posing in business casual blazer Pexels / Emmy E The first step in being your own advocate is to believe that you have the power to use your voice to raise a concern or to ask a question. It's past the times of having your mom or mentor stand in front of you asking your question. Now, it's time to stand up for yourself. 

Ayah Ziyadeh, a graduate of Metropolitan State University, is working on learning when she should be standing up for herself. “I’m pretty obedient and disciplined, so I often get taken advantage of...but ever since I got my job at the Colorado legislature, I'm realizing I need to advocate for myself more–especially, when I realize that I’m not the only one being affected by a policy,” she says. “I’ve noticed my boss stands up for me and due to the wrong policy there has been a collective of us fighting for a common goal and that helps me feel like I do have the authority to use my courage and find the confidence I need to stand up for myself.” 

You know your situation better than anyone else, and even with nerves, you're the best person for the job.

2. Build your confidence

Strong Arms Girl Her Campus Media In order to advocate for yourself, you may need to build courage within you. To find confidence, you have to believe that things will work out in the end, because you have the power within you to make a difference for yourself. Finding confidence is easier said than done, but once you have confidence in what exactly you're going to ask, the task at hand will start to feel easier. If you’re struggling to do so, think about people you look up to and emulate the ways that they used their own courage to stand up for what they believed in. If you're desperate enough to make a change for yourself in the workplace, you may be able to draw up the confidence without really thinking about it, but if not, picture yourself as your idol. Know that you have friends and colleagues to lean on, and that you're not on your own.

A. Mayleen Mermea, a graduate of the University of Illinois Chicago, was always scared to ask questions at her first job out of college. "Sometimes I did get in trouble and it only validated the fear I had," she says. "But now, I’ve grown confident enough to ask, no matter how scary it is, because if I’m not asking then the only person I’m hurting is myself. I’ve learned that no matter my role or my credentials, I will always deserve respect just as much as I’m giving it. I’m also thankful I unpacked the underlying systems that created a toxic work environment, which now prepares me for current and new jobs that may have the same culture.” 

Alexia Martin, a graduate of St. Catherine University, chimes in on courage and self-advocacy. "Through a triggering and traumatic experience from leadership, I advocated for there to be more trainings on cultural sensitivity with hopes that no one would have to experience what I experienced," she says. "Although it felt like a challenging time for me, I always remind myself I have a team of people supporting me."

3. Practice, practice, practice

Unsplash Start practicing your ‘ask’ a few nights before your meeting. You definitely don't want to be too rehearsed, but you do want to know exactly what you need to say, how to say it, and to prepare for any counterpoints you may need to respond to.

Peace Sinyigaya, a graduate of St. Catherine University, uses her mentors and older friends who have navigated the system before to bring in their expertise. "I typically run what I'm going to ask by someone else who has been in the industry longer," she says, "to make sure I'm approaching the question appropriately, and so I can also receive feedback on how I can improve my language or manner of asking."

You will also want to consider alternative options, in case your manager doesn't give you the response you wanted to hear. Brianna Kempema, a graduate of North Dakota State University, has had to deal with difficulty with scheduling at work. “I’ve had to just find my voice, make compromises, and really just have the confidence to ask,” she says. “I reminded myself that if I didn't ask, then I would be unhappy with the outcome that I didn't try advocating for, and then I told myself that the worst thing that could happen if I ask is that my boss says no. If it didn't work out the first time I asked, then I'd try again another time and prepare a different way to persuade my boss the next time.”

4. Be direct from the start

a woman in business casual stands in front of a white board, writing with a marker in an office space Christina Morillo | Pexels You don't want to beat around the bush when asking for something so important. Not only are you wasting your time and your boss’s, but you’re giving them an opportunity to think that you aren’t ready for whatever you are about to ask them. 

Fatumastar Aden, a graduate of St. Catherine University, recently asked for a salary raise. “I was really nervous about this question, because I’ve never asked for salary negotiations and didn’t want to lose this job,” she says. “To prepare myself, I researched the earnings of others who do the same work as I do and how my values correlated with what the earnings I deserved. This made asking the hard question easier, because I was prepared and knew exactly what I was asking for. At the end, we did go back and forth trying to figure out a compromise, and we walked away both content.” 

If you're looking to discuss renegotiate your salary or discuss your current role, for example, you'll want to do your research and prepare your case.

5. Manage up 

two women having an interview mentatdgt Hard questions are not a one-end deal; they come up quite often. Managing up (the act of effectively working with a manager/supervisor), is a way for you to create a relationship with your boss and build trust for further questions that you may have in the future. One way to do this is to schedule a weekly time to connect with your boss, and check-in on what is going well and what needs to be worked on (on both ends). 

Mirna Serrano-Barahona, a graduate of St. Catherine University, knew she had to put her foot down when her boss started assigning her tasks far outside her job description. “I knew I needed to grow in my shoes at the law firm,” she says, “I decided to immediately communicate with him on my priorities and our work’s priorities. He understood and saw that he was not doing his job as a boss. While I recall this experience being scary, I know that after that my boss respected me even more because I stood up to them and asked clearly what needs were not being met.” 

6. Ask for help with someone you trust

Wiktor Karkocha | Unsplash I’m very timid, so the best thing I can do is find a coworker that I trust and have a conversation with them about my struggle with asking my boss a question. If they’ve been there longer and know your boss better, they might have a better idea as to how to go about asking your question. And that’s what happened exactly! I felt reassured that my questions and concerns were valid, and my coworker felt appreciated and honored for going to them for help. They gave me tips on the best ways to go about asking my questions and it all turned out just fine.  

While you may fumble a few times in getting it right, just understand that you and many fresh employees are dealing with this exact fear. At some point, you'll become an expert in getting what you need at your workplace, and soon people will be looking to you for help.