By Kara Mason

Make Sure Your Work Matters: Communicating with your Boss About Goals


How to define and align to get the most out of your efforts.

The workplace looks different than it ever has before, and that can make defining success even more difficult.

A few years ago I left a job because I was frustrated with the organization and my boss. To be more exact, I was frustrated with how I felt like no matter how many hours I worked, how many questions I asked, or how many goals I met, I wasn’t living out the vision of my manager. It was maddening, especially because I really believed in our mission.

I tried sharing more of my own ideas. I tried to incorporate more of their ideas into my own work (even if it didn't always make sense). I sometimes even tried going rogue and doing my own thing, until one day the effort wasn’t worth it anymore. 

Looking back, there was a clear break in communication. While we were talking, we weren’t understanding each other. Some days we were two ships passing in the night and others we were colliding head-on because the direction was unclear and unorganized. Neither one was good.

Communication is a make-or-break point with your manager

If you’ve experienced something similar, you’re not alone. A 2017 Gallup poll found that about half of workers have quit a job because of their boss.

While I thought highly of my manager as a person, I can say with confidence their communication style — and most importantly, how I handled it — was the biggest factor in me quitting.

Now, I serve as a manager of a small team that has had to adapt to working almost completely remotely with the flip of a switch. In many ways, some of the fundamentals of teamwork have remained, but communicating is so much harder, and making sure we’re all on the same page about organizational goals feels like uncharted waters most days. 

There is no good way for anybody on my team to stop by my desk for a quick question or clarification. Instead, I encourage them to call or email — but of course, I can't control if they actually do. They have to be more proactive than they are used to, and so do I.

Now, in addition to weekly team meetings, I check in more often with each individual than I would have in person. I take extra time to make sure the communication that is happening is working for all of us, on both sides.

The Gallup poll of workers found that only about 21% of respondents think their work is “managed in a way that motivates them to do outstanding work.” While it’s surely much more difficult to communicate ideas and deadlines now, it’s not impossible. 

There are tons of tools to keep teams talking and coordinated, but truly staying aligned comes with some extra thought from managers and employees.

Establishing functional communication

Your success and the organization's success depends on functional communication. Functional being the keyword.

While I regularly talked with my former manager, we rarely ever got anywhere. That probably could have been resolved with the right questions and some deeper diving on my end, instead of internalizing everything and responding by just doing more of what wasn’t working. 

It can take a little trial and error to find a good way to communicate. 

Mary Abbajay, author of Managing Up: How to Move Up, Win at Work and Succeed with Any Type of Boss told the New York Times that good communication often involves two parts:

“You have to think about how you like to communicate,” she said, then “understand how your boss likes to communicate and assess the gap between and figure out what you can do differently.”

How to improve your communication with your manager

If you’re struggling with how to talk to a manager about your work, a good starting place is to write it all out for yourself first. I’ve often found that so many frustrations I have with people I’m working with (whether I’m acting as a manager or not) get so compounded or tied to other frustrations that eventually I end up in a maze of problems or confusion.

Journaling and writing lists can help you to sort out where the roots of miscommunications are. It can help you get to the heart of the matter, rather than getting caught up in emotions and details.

Even if you aren’t frustrated and just want a more transparent relationship with your manager about goals and work, coming to the conversation prepared and with your thoughts in order can’t hurt.

Take time to list big questions you have about the organization, including big goals and daily work. Sometimes a breakdown of communication happens because managers have their hands in many different conversations and projects, and don’t even think to clue their team in on a particular detail. 

Even a simple “Hey, how does this deadline fit in with the overall vision for ____?” goes a long way. 

It’s always a good idea to make time to check-in with a manager to follow up on concerns or how you’re fitting into the grand scheme or the organization. Do this regularly for a few reasons: 

  1. It keeps your motivation up. Even if you don’t really have any major frustrations with your manager or team, regular check-ins and understanding overall goals can make you excited about your work. 
  2. It prevents miscommunications from snowballing. You'll waste less time and make fewer mistakes when you're more in tune with the big picture.
  3. It shows initiative. Curiosity in the workplace is a good thing, and an open dialogue with your manager can sometimes inadvertently become a brainstorm session, which can be really helpful for both of you. 

Staying organized and on top of communication

The other half of communicating with your boss about organizational goals is actually being organized.

Good communication and organization go hand in hand, but with so many of us working remotely these days, it’s not easy balancing the two. A recent Asana survey found that working remotely during the pandemic has extended deadlines for about 43% of companies and about 47% of respondents said priorities in their organizations have changed. 

Likewise, the survey found that only about 16% of workers feel  “their company is effective at setting and communicating company goals.” 

In the long run, that could be a recipe for disaster and is why it’s really important that you keep your deadlines and goals in check. 

Even when you feel like communication is going well, a quick unsolicited update can be helpful to your boss. They might not always respond right away, but if it raises a red flag, they’re more likely to get back to you sooner rather than letting you continue on a project that no longer fits the organization’s goals. 

A manager’s top job should be communication, and so when that falls apart it can really be difficult for an employee. However, if you want to succeed, you need to take on that job and make communication work with your boss.

Even just asking for a few minutes each week can be a really helpful place to start.

When you’ve finally found a good way to communicate, keep at it. Staying aligned with the organization’s goals isn’t a destination. The target is always moving, so be prepared to ask new questions and be flexible if needed.