Work Relationships

How to communicate honestly with your boss

Written by Eric Titner

Those of us who have spent any time in the workforce—from newcomers to seasoned veterans and across all industries and positions—have learned the value and importance of maintaining a positive and effective working relationship with our bosses. It just makes good intuitive sense—for most of us, our bosses are the professional gatekeepers, and we need to do our best to keep things going well with them if we want them to open the doors to promotions, new opportunities, greater responsibility, and more money. Like it or not, your relationship with your boss should be one you take seriously and put in the effort to cultivate.

In any healthy relationship, honesty is the cornerstone—it’s the foundation of trust, good communication, and mutual respect, all essential components of the boss-subordinate equation. If you want things with your boss to run like a well-oiled machine, which will help make your work life easier and hopefully open up the doors to new opportunities, you need to keep an open and honest line of communication.

Granted, this is sometimes easier said than done—all bosses are not created equal, and those of us who have had the misfortunate of working under the affectionately dubbed “challenging boss” know that these relationships often take a great deal of strategic finesse to manage properly. Also, not all situations present the opportunity for full disclosure and honesty in. While most of us don’t sweat taking our full and fair credit at moments of professional success and triumph, it’s not quite that easy to keep the floodgates of honesty wide open when things aren’t going so well. We get it—but it’s still important to make honesty your professional policy if you’re looking to climb up the career ladder and achieve your work goals.

If you’re looking to communicate more honestly with your boss, then consider using the following strategies for doing so effectively.

Know your boss

At a fundamental level, your relationship with your boss isn’t all that different from other relationships in your life. Yes, they may hold the key to the next step in your professional journey, but in terms of them being a person in your life whom you have to figure out how to deal with, you’ve been here before.

Difficult or easy, typically the best way to handle a boss is to first acknowledge the sort of person they are—including how best to effectively communicate with them. Then, use this information to your advantage. Do they like long meandering conversations or prefer you get straight to the point? Do they like talking over coffee or in conference rooms? Are they easier to pin down first thing in the morning or at the end of the day? Should you inject a little humor into things or is serious and buttoned up the best way to go?

Once you know your boss and are able to meet them on their own preferred terms, you’re setting up the groundwork and backdrop for an honest conversation that will go as pleasantly and positively as possible—and make sure you continue to adapt and modify this strategy as needed. With a little luck, your boss will actually look forward to communicating with you, which will make being honest in all sorts of situations that much easier.

Start small

Honesty doesn’t always come easy; in fact, for some of us who devote a great deal of time and effort to artfully spin reality into our preferred version of things, being honest can take some getting used to—especially with our bosses. If being honest is a challenge for you, we suggest you start small. Think of a relatively low-stakes conversation you need to have with your boss that requires some level of personal honesty (nothing too traumatic or anxiety inducing) and go for it. Practice it at first if need be, and do your best to remain sincere, humble, and likeable (once again, aim to meet them on their preferred terms). If this honest conversation goes well, then you’ve begun to lay a healthy groundwork for future honest conversations. Take this success and build from there.

Find a bright side

Most of us have been in a situation where things might not have gone according to plan and have to face our boss. This isn’t easy for anyone, regardless of tenure or level. When this happens and you’re planning out how to broach this with your boss, always remember that honesty is the best approach—and the one least likely to come back and bite you in unexpected ways. Don’t get defensive, don’t look to deflect blame, and don’t let negative emotions get the better of you. Instead, be humble, open, contrite, and sincere—and try to put a positive spin on the situation. Position it as a learning experience or an inflection point, and an opportunity to effect new and positive change and growth. Honesty isn’t always easy, and it might not always go smoothly, but trust us—it’s your best bet with your boss when confronted with a tough work situation.

Maintaining an honest flow of communication with your boss may not be easy at first, but it’s a worthwhile effort in order to bolster this essential work relationship—and hopefully it’ll get easier over time and come with a wealth of added professional benefits.

About the author

Eric Titner

Eric is a NYC-based editor and writer, with years of experience in career-focused content development across a wide range of industries.