3 Questions You Should Always Ask Your Boss, No Matter How Awkward They Are

These 3 questions may seem awkward, but they'll start important talks between you and your boss.

Boss and employee at coffee


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Taylor Tobin1.84k
July 14, 2024 at 4:12PM UTC

Even if you have an enviably-open relationship with your boss, you’ve likely experienced hesitation when approaching particularly “awkward” topics with her. We all want to present the very best versions of ourselves to our supervisors. And when a situation arises that you don’t know how to navigate, it can feel uncomfortable to bring that to your boss’s attention. However, it’s important to remember that your boss — assuming that she’s good at her job — wants to stay in the loop on your progress and to be aware of your comfort level in your position. 

Even though these 3 questions may seem tricky to navigate, they all open up streams of dialogue that will solidify your relationship with your boss, and also address important work-related concerns.

1. “Is my position in jeopardy?”

We’ll start with the most awkward boss-employee conversation possible. If you notice your project load dwindling, your responsibilities becoming less and less crucial, and your face time with your boss shrinking in an unprecedented manner, it makes sense to conclude that something not-so-great may be afoot for your career trajectory. Many employees assume that their only course of action involves waiting around until their boss chooses to terminate their employment. But in actuality, you can and should have a direct conversation with your boss about your suspicions.

If you ask your supervisor for a sit-down meeting to discuss your job stability, a responsible manager will not only acquiesce, but will provide you with the necessary information on your prospects, what’s weakening your employment status, and — if relevant — a plan for improvement. 

2. “What can I do to improve?”

This question relates to employment-related conversations with your boss, but can also be utilized in the aftermath of a project that didn’t work out quite as you hoped. Asking your boss for guidance on how to support her goals more effectively proves your initiative — and taking ownership of your past errors while still looking for ways to actively fix them in the future — reveals impressive and valuable levels of self-awareness. 

3. “Can we sit down to discuss these new responsibilities?”

Most jobs include a fluctuating scale of responsibilities, with busy periods requiring more of you than the more quiet spells. But if you suddenly find yourself taking on far more work than you anticipated (perhaps due to lay-offs or company restructuring), it’s in your best interest and the best interest of the company to ask your boss for a meeting to discuss your expanded role and what you’ll need in exchange for this increased workload. Staying silent and resentful during this process won’t help the situation, and your sense of discontentment will only continue to grow. Talking your new responsibilities through with your boss will give you a better sense of the scale (is this a temporary increase or a permanent one?), and will also provide you with the opportunity to advocate for yourself, potentially leading to a higher pay rate or increased benefits

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