Read Time: 8 minutes

Ask These Two Questions to Create a Thriving Relationship With Your Boss

Shivani Berry


Many people think a poor relationship with their manager is the manager’s fault or can’t really be helped. But in my experience, the people who get promoted the fastest and most reliably are the people who have learned to manage up

Managing up means you establish and maintain trust with your manager, and you manage expectations with your manager and stakeholders. Your relationship with your boss can seem completely out of your control, but the good news is that it’s not. Influencing your boss is a skill you can learn.

Managing up means you establish and maintain trust with your manager, and you manage expectations with your manager and stakeholders. Your relationship with your boss can seem completely out of your control, but the good news is that it’s not. Influencing your boss is a skill you can learn. 

One of the best ways to start managing up is to ask two simple questions about your manager:

  • Do you believe your manager knows what matters to you? 
  • Do you know what matters to your manager? 

These two questions come from Julie Zhuo, former VP of Design at Facebook and author of the Wall Street Journal Bestseller The Making of a Manager. They can be powerful tools to help you reimagine one of the most important relationships in your day-to-day life.  

In her fireside chat with Shivani Berry, founder of Arise, Julie explains how these two simple questions about your manager will: 

  1. Help your manager become a better advocate on your behalf 
  2. Help your manager see you as somebody who’s critical to the company

Let’s start with the first question:

1. Do I believe my manager knows what matters to me?

Your manager needs to know:

  • Your career goals
  • What you think you’re good at
  • What you think you’re not so good at, but want to get better at
  • Your hopes and dreams for your career in the next five years
  • How you see your job and your work in the context of the life you want

If your manager doesn’t know these things about you, it’s time to sit down together. Julie admits she struggled with this in her own career. It can be scary to put yourself out there, especially if you feel disconnected from your manager. 

But, as Julie explains, “If your manager doesn’t know what you care about, how do you expect them to help you find opportunities or be able to pick the right kinds of projects or think about you when the right opportunities come up?”

The more your boss understands your goals, the more they can advocate on your behalf. 

And don’t be shy about upward mobility. If you want a promotion in six months or a year, say so.

Here’s a simple script from Julie you can use to start the conversation: 

In our next one-on-one, do you mind if we talk a little more about my career? I want to share with you my goals and how I see my role and my job in the next couple of years. I’d like your feedback on how I can get there. 

Why People Fail to Ask This Question

“Do you know what matters to me?” can be the hardest question for people to ask. The reason is that it requires you to advocate for yourself. 

In my time coaching women 1:1 and in our Arise Leadership Accelerator, I’ve found that we often tend to fear advocacy because we’re afraid it will make us seem “braggy” or “self-centered.” 

The truth is that knowing and confidently communicating your value helps the entire team and company reach its goals.

Being able to advocate for yourself in this way also helps your boss see that you take ownership of your career development, and will continue to put in the work to improve and eventually excel at what you do. 

Helping your boss understand what you care about is vital, but it’s equally important to ask yourself the second question:

2. Do I know what my manager cares about?

This question helps you think strategically about your future and the future of your company and team. 

Julie says, “If your manager is up late at night thinking about something, worrying about something on the team, do you know what that is?”

Julie explains that this question forces you to put yourself in the shoes of your manager. 

You want to understand: 

  • What is success for your manager? 
  • What should your team be thinking about or doing that would help your group, your manager, and your company? 

Answering these questions gives you a window into what problems you can proactively help with, and as Julie says, “I guarantee you it’s just much easier for a manager to see you as somebody who’s critical to the team, who’s exhibiting a lot of leadership.” 

Here are some sample questions you can ask your manager to get this information: 

  • What does success look like for you? 
  • What are your biggest challenges? 
  • What, if any, pressures are you currently facing at work? 
  • What’s the best way for us to work together? 

Pro tip: before you ask these questions, reflect on what you expect the answers will be, and be prepared to share your ideas and thoughts on how you can help your manager succeed and take things off their plate. 

Don’t fail to ask these questions! When you don’t ask them, you risk: 

  • Being micromanaged by a boss who can’t understand your value. 
  • Losing your manager’s trust altogether. 
  • Missing out on important strategy updates or expectation changes from the top, because you don’t have healthy lines of communication with your boss. 

If you always come through for someone when it matters, that person will trust you. But if you don’t know what matters to the person, how can you make sure you’re there when they most need you? Don’t leave this up to chance. By knowing what matters to your manager, you can make sure to earn and keep their trust.

What happens when you have a thriving relationship with your boss?

An aligned relationship with your boss can be a turning point for your career. It will lead to:

  • Fewer surprises and problems 
  • You and your team being set up for success 
  • A sponsor and an ally in the form of your boss to help you get promoted

It’s worth making a plan to bring these two questions up in your next 1:1 with your manager. We’re cheering you on!