Top Tips for Having a Tough Conversation with Your Boss

Top Tips for Having a Tough Conversation with Your Boss

Top Tips for Having a Tough Conversation with Your Boss 1080 675 VP Legacies

Just like managers need to have tough conversations with their employees, employees need to have tough conversations with their bosses. Whether it’s a raise, a promotion, or an office conflict, employees need to feel like they can have tough conversations with their bosses without backlash.

As an employee, you want to feel empowered and confident to be able to speak to your boss. You want to build a relationship with your boss where they can be your mentor and advocate. Not only do you want to have that professional relationship, but you also want to have a personal relationship too. This relationship allows you to bring problems to their attention freely and openly.

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Difficult Conversations with Your Boss

“Your Management Style Doesn’t Work for Me”

As Sun Tzu wrote in The Art of War, “If you know the enemy and know yourself, you need not fear the result of a hundred battles.” That is not to say treat your boss as your enemy, but you should know what your boss’ management style is and know why it does not work for you. Maybe their demands are unrealistic, or their tone is very abrasive; let them know whatever it is that is bothering you. This discussion is not the time for you to vent all your frustrations, but you will want to take this opportunity to discuss how you can both learn and grow. If you can show your boss that you want to help them become a better leader to you, the message will be much better received and seen as constructive rather than combative.

“I’ve Made a Mistake”

It is difficult to admit that you have done something wrong in general, much more so when it happens at work. However, making mistakes is just a part of life. If you are open and honest about your mistake, you are looked upon much more favorably than someone who does not take responsibility for the error and seeks to blame others. There is an adage, “The first time is a mistake; the second time is a choice” As long as you can take the opportunity to show how you can grow and not make the same mistake, but more importantly, how you can fix it, it will go a long way towards showing that you are a team player.

“I Want a Raise”

Asking for a raise is never an easy subject, but you are only hurting yourself by not asking for it, especially if you really feel like you deserve a raise. If you have self-doubt and do not feel like you deserve it, there are ways to overcome that self-doubt and make your bosses aware of how much you contribute. Keep track of your accomplishments, both big and small. That way, when it comes time to discuss why you deserve a raise, you can show what you have achieved in your time with the company. Being prepared with that information further solidifies your justification for asking for that raise. Additionally, if you are motivated by something outside the company that makes you go into work with a positive attitude, it makes difficult conversations such as this less daunting. 

“I Need Help”

As hard as it is to ask for a raise, asking for help is also a struggle for many people. We have this thought that asking for help means that we are weak. That is the opposite of reality. Asking for help means having the strength to realize your limitations. Also, asking for help does not only have to be when you are in trouble. If you want help to become better at what you do, your boss will appreciate you asking for help. Alternatively, maybe you are unclear about how your success will be measured. Ask for feedback, and be proactive about reaching your goals. 

Those are all difficult situations. However, they all end with a positive outcome, despite the initial difficulty. Remember, all those conversations will help both the company and you. A happy employee is a better employee. The main thing is to start the conversation. How do I go about starting the conversation, you ask?

Without further ado, here are six tips we have for having a tough conversation with your boss.


Explain the situation and context

One of the first steps when approaching your boss with a situation is to state your issue explicitly and give context around the issue. Your boss isn’t going to know what you’re thinking or feeling so you need to explain it to them. You also need to help them understand why you’re feeling a certain way and what prompted that.

Don’t waste time beating around the bush, just go straight into your issue. This doesn’t mean you’re being aggressive; you are just sharing facts from your point of view. By explaining your situation with “I” statements, you can explain your feelings to better explain your situation without coming off as aggressive.


Be honest and truthful

Though this may be a no-brainer, it’s a lot harder than you think to be honest and truthful when approaching your boss. While you want to exhibit candor, you don’t want to do so in a way that comes off as obnoxious. Be graceful and respectful when approaching your boss, choosing your words carefully. Don’t throw people under the bus or play the blame game. Make the conversation about you, not everyone else.

That being said, if something is bothering you, bring it up with your boss sooner rather than later. You don’t want to reach your tipping point before going to your boss with an issue. If you a non-confrontation person, this may be difficult for you because you anticipate the worst-case scenario if you do say something. However, it’s quite the opposite; it might be the best-case scenario if you have the courage to speak up.


Ask for your boss’s perspective

As an employee, you don’t have all the visibility into why your boss makes the decisions they do. You have no idea why they picked your co-worker for a project over you. That’s why it’s key to ask their perspective on the issue you bring to them. Don’t be afraid to ask them why they gave the project to your co-worker and ask what you can do next time, so you are at the top of the consideration list.

Go into the conversation with an open mind. Don’t think that your boss has it out for you because in most cases, they probably don’t. Finding out the reasoning behind their decisions can help you better understand their thought process. As a result, you might end up shifting your attitude and perspective to something more positive by the end of the conversation.


Make sure you reach a resolution and decide next steps

The worst thing you can do when talking to your boss is leaving the conversation unresolved. The whole purpose of meeting with your boss was to resolve the issue by the end of the conversation. You don’t want to leave anything unresolved. Use the time with your boss to bring up any and all issues to make sure you have answers for all of your concerns. Not only will laying everything out on the table will help with your conscious, but it will also help your boss’s too.

A way to do this is by assigning each party action items to complete. Maybe you need to follow up on something or your boss needs to talk to their supervisor. Whatever it is, make sure you decide what needs to get done before you end the conversation, so you have something to circle back on.


Ensure that you and your manager are in a trusting relationship

When talking with your manager, you want to make sure that you can trust them. Like a friend, you don’t want them to spread your conversation around as office gossip. You want to make sure they approach your conversation seriously and with full confidentiality.

In the case that you don’t trust your manager, reach out to another colleague in the company who you can trust and feel comfortable talking to. You want a good gut feeling about the person you’re talking to without questioning their level of trust. If employee-manager confidentiality becomes an issue, reach out to their supervisor to bring the issue to their attention.


Find a time to meet with your boss to make sure you have their full attention

Like many bosses, your boss is probably busy every day between meetings they have and work they need to get done. Set up your meeting with your boss at a time where you know you’ll have their full attention, so they can focus on the conversation with you without getting distracted by other work.

You also want to set up a meeting in person and in private. While a phone meeting is great, it doesn’t lend itself to emotion and body language, both of which convey how you are really feeling. Make sure your meeting is in a private room or your boss’s office to have full confidentiality without the office hearing what you have to say.

It’s no easy feat talking to your boss. For some, it’s the hardest thing to do. However, it’s necessary to not only address conflict but build a relationship with your boss. With these tips, you’re sure to feel comfortable talking to your boss the next time a conflict comes up.

Templates for Difficult Conversations with Your Boss

Your Management Style Doesn’t Work for Me

I have thought about how you are managing my work, and it is not a style that makes me comfortable. I am uncomfortable with your management style because [insert reasons why it makes you uncomfortable]. I realize that your style might work with other employees, but maybe we can try [insert suggested alternative] when it comes to managing how I work. I have been working with your management style so far, but I would like for us to work together to help each other become both a better boss and a better employee. If we can agree on how to best work together, we can both learn and grow.

I’ve Made A Mistake

I have made a mistake. It is not easy for me to admit that I [insert mistake committed], but I want to be transparent and assume full responsibility for my error. It is my hope and my desire never to make this mistake again. Since it was my mistake, I will also be the one to fix it by [insert how to fix mistake]. I would appreciate any assistance in instructing me in what I did wrong and how best to avoid making this mistake. I will take this as a learning experience and use it to become a better employee.

I Want A Raise

I would like a raise. I believe I deserve a raise due to my hard work and contributions to this company. I have been here for [insert amount of time with the company]. During that time, I have achieved the following for this company: [insert list of accomplishments, big and small, that you have personally contributed to the company]. With those accomplishments, I believe I have earned a proportionate increase in my compensation. Other workers with the same job title in this area make [insert amount made by similar workers in your area if it is higher]. I do enjoy working with this company; I would just like my work to be appreciated appropriately.

Personal Connection and Tough Conversations

It goes without saying that tough conversations with your boss are virtually unavoidable. Don’t be caught off-guard if you ever find yourself in such a situation. Instead, prepare yourself to make sure you have a level head and clear goals. These strategies will help you engage and connect with your boss in meaningful ways so you get as much out of your meeting as possible, no matter the circumstances.

Employees’ relationships with their direct reports are some of the most important ones at work, and cultivating strong professional relationships over time can help you collaborate better when conflict occurs.

We are here to help prepare you for success in your career for all challenging conversations. In week 7 of our 8-week intensive Personal Connection Boot Camp we solidify an actionable plan with you on how to create career fulfillment. To learn more schedule a time to chat with one of our co-founders. We look forward to speaking with you.