Five Questions to Ask Your Boss When You’re Ready for More

You’re sitting at work and you’re bored. You’ve been doing the same work for a while now and you’re ready for a new challenge, but you don’t think that challenge involves leaving a company you love, or a team you’re vibing with.

You feel stuck and you want to ask for more responsibility, but approaching your boss is daunting as hell. You don’t know how to ask for what you want without sounding ungrateful for the opportunities you’ve had thus far.

Hands up if you’ve been there, sisters. I know I have.

It’s a rickety rope bridge to walk. As working women, we constantly feel we need to prove our worth. Which means when the time comes and we’re asking to be trusted with a challenge, we do this awkward dance between wanting to be straight forward and ask for what we want, and trying to not sound like we’re unhappy with our current position.

There are other factors too. Maybe we’re relatively new to a company with long established processes. We want more but don’t know how to go about asking for it without stepping over some imaginary corporate culture borderline.

If you’re ready to start the conversations with your boss, we’ve got a couple thought starters for you to ask to get the ball rolling.


What is the typical career path for someone in my position?

This is a good one to use if you’re still new to a company culture or if you’re interested in staying within your particular line of business (i.e. marketing) that has multiple branches (i.e. digital marketing, media spend, graphic design).

When you ask this, you’re essentially looking for archives. If your company has been around a while and you’re looking to identify the next logical step, it’s best to look at where the people who used to have your job have gone to after vacating your position.

You can use this information to either follow a similar path as those people or recognize that your career trajectory isn’t aligned with your ultimate goals.


Over the next calendar/fiscal year, how can I best contribute to our company’s key results in my current role?

This question can reveal a couple things:

1.)   You’re asking your boss what they believe to be the most valuable functions of your role; the things you do that drive defined business results. Knowing this information can give you a good tell of what is most worthy of your time at work and help you evaluate whether or not you’re currently performing those functions to the best of your ability.

2.)   Your boss could provide you with a large scope of work that you’re not currently doing, providing you a new outlet to pursue and combat your boredom.

3.)   You could learn that the function your boss believes to be the most important task of your job is your least favorite thing about it. With that information, you can start to evaluate whether or not you want to continue down that path for some time.


What skills do you recommend I focus my development on to have a lasting career in (FIELD) and/or with (COMPANY)?

This question allows your leader to share with you the cultural values they believe to be the most valuable within your current field and within your company. You’re essentially asking about opportunities you have to better melt with the culture of your particular area.

Say you’re in marketing and your leader says that most successful marketers in your company have a strong understanding of how Facebook store visits and dollars spent on those ads translate to estimated profit, and you don’t understand jack shit about that, take that as an opportunity to learn and ask questions.

If your leader responds by letting you know you should “keep doing what you’re doing,” you’re probably reaching the end of what that person can teach you. Time to branch out – seek out a new mentor or look for opportunities above where you’re currently at.


What strengths and opportunities can you see as helpful or hinderance to progressing my career into a position of leadership?

Ladies we all want to be boss bitches. It’s my lifetime goal to be a in a while pantsuit, commanding a boardroom of a company I created. But the most important thing about leadership is feedback.

You need to constantly ask what your higher ups, peers and direct reports have to say about you and your work, and you have to be willing to actually listen.

The thing about this question is that it will provide you with potentially harsh feedback about your performance in your current role. 

If you’re bored at work and dragging your feet to get the simplest tasks done and your leader tells you your work ethic needs help, wake up and fix yourself.

If you’re asking for more responsibility and your boss tells you that they are totally happy with what you’re doing right now and don’t want anything to change, decide whether or not you’re going to be comfortable being bored, or start seeking out opportunities to push yourself.


What additional responsibilities can I take on?

This is the hardest question to ask but it’s the most important. If you want more responsibilities, ask what you can take on. 

More often than not, your boss is going to turn this one around on you. And you better come prepared. Do your research, look within your scope of work or within your department for needs that you can meet and offer them up. If you see a peer struggling with a project you’re interested in, offer to be an extra set of hands on it. 

There are other options here. Your leader could tell you that one function of your job is too important to divert your attention to other projects that aren’t a priority to you.

What if you love that super important task?

Make yourself the master of that task. Maybe that task your bitch. Make sure you understand every single function of that task. All it’s ins and outs. You have its social security number and a list of all its fears. Evaluate ways to make it more efficient. Consider ways to merge that stream into existing ones in your department to make the work you do more effective. Offer to present on the topic as often as you can. Show your leader and your department that you are the absolute best and this important task isn’t even a challenge. That will speak volumes about your work ethic, tenacity and desire to build a long career at that company.  

What if you hate that super important task?

Well, you have a decision to make. If you’re honest with your leader and telling them you don’t like this thing about your job and they think that’s the best thing you do, you need to decide if you stay and be complacent, stay and try and solve the problem to make it less terrible, or move on. And we can shower you with advice on feeling ambivalent about your job, but the decision whether or not to leave is ultimately yours.

If you’re at the stage of having these conversations with your boss, remember the most important thing: This is a conversation. Be honest about your feelings and have an idea of what would make you feel better about the job if you’re interested in staying.

Go into any discussion with clear goals for yourself, and be prepared to not hear everything you want to. If you are truly ready and reaching for something new to challenge you, and you leave your conversation feeling like the things you want are increasingly out of reach, decide if you can live with that or not.

Be confident. You are the only thing standing in between you and all the things you want. Have courage and go for it!