Have you experienced any of these issues with your boss?

  • Your boss tells you to do something that is completely the opposite, or in contradiction to what he/she told you to do earlier
  • Your boss forgets what he/she asks, and repeats things you already know, or doesn’t seem to be organized with communications generally
  • It seems impossible to get your boss to pay attention to things that matter to you and to your team, unless it’s an emergency
  • You suspect your boss has a hidden agenda you are supposed to figure out, but when you ask directly about it, you can’t get an answer
  • You desperately need resources, tools or an answer to something but your boss won’t make a decision on it
  • Your boss tells you to explain something at a meeting and later berates you because you didn’t say it the way he or she would have said it

If you have experienced any or even all of these issues, you are not alone. I’m going to give you some tips on how to handle these workplace communication dilemmas, but first let’s look at it from your boss’s perspective: reversing the roles can be quite helpful in making sure your message, method of delivery and strategy are going to work.

Step 1: Get to know your boss’s preferences and priorities

The foundational rule is to work at understanding your boss. What are the specific goals and concerns of your boss? Pain points, sensitivities? What makes your boss happy?

Everyone has their own take on what they are responsible for and what really matters personally to them. Find out what your boss’s goals are and why they are so important to your boss. Then work in reverse order to phrase your requests to meet that goal. For example if your boss is concerned about cutting costs, then your request to buy new tools or machinery will not be met with any interest. But if you explain how the new equipment will save money and cut unnecessary costs, your request will be seen as a solution to a problem rather than an extra expense.

Sometimes the concern of your boss is not the business goal, but rather having him or herself look good on some upcoming project. You may not agree with that motivation, but explaining how your proposal will help your boss meet part of that goal may be just what is needed to get some attention for your idea.

To find out more about your boss, here are some questions you can ask:

  • “What’s your management style?”
  • “How do you like to receive information – email, phone, text, at a meeting, paper?”
  • “What challenge do you have that I can help you meet and how?”
  • “What would make you most satisfied with my work?”

Step 2: Negotiate

Once you know what your boss prefers, be ready to negotiate:

  • If your boss says, “I’m very hands off” and you need more feedback, ask, “Would you be alright with weekly 15 minute meetings so I can check that your expectations are being met?”
  • If your boss says, “ I just want you to take initiative,” ask, “What does initiative look like to you? Can you provide me with an example?”
  • If your boss says, “I want things done in a very specific way and I have to check everything,” consider saying, “Can you provide me with a checklist or should I create a checklist that you can add on to?”

Many supervisors have inner dilemmas about negotiating. We seem to think that when a boss tells us to do something we should just do it without asking questions, elaborating or trying to negotiate. In fact, your boss NEEDS you to do those things. That is how the job will get done with the least amount of rework or lost productivity.

Step 3: Be solution focused

No matter which communication issue you might be having with your boss, considering a possible solution and coming to your boss with an idea in mind is always likely to get a more receptive ear. The way you communicate your solution will depend on your boss’s preferences. That is why if you aren’t getting good results, you may need to go back to step one and make sure you really do understand your boss’s management style and goals. But it will also depend on how you strategize, which leads us to the next section of this article.

Step 4: Be a strategic communicator

A helpful way to consider which kind of communication strategy to use with your boss is to think in terms of: “DO,” “SOMETIMES” AND “NEVER.” First let’s look at the short list for these strategies and then we’ll add detail:

Category #1: DO communicate like this

  • Engage
  • Collaborate
  • Show loyalty

Category #2: SOMETIMES communicate like this

  • Challenge
  • Advise
  • Object

Category #3: NEVER communicate like this

  • Override
  • Criticize
  • Undermine

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Category #1: DO communicate like this

In the “DO” category consider that the way you approach or respond to your boss should engage your boss. This means you want to make sure you have your boss’s ear and are speaking in a way he or she will listen. It also means you will respond in a way your boss is likely to want to continue communicating with you.  Show a collaborative attitude by offering possible solutions and asking for more ideas or input from your boss. If your boss is too busy to listen, ask when would be a better time. Consider that your boss also has to respond to someone or some group and needs to be able to focus on you and your requests during a time where this is possible.

All of these have the effect of demonstrating loyalty, but you can add in the occasional comment about being loyal to the company as it seems appropriate. Because most managers are hoping for loyalty and many employees are hoping for opportunity, the two goals don’t always meet. Remembering that loyalty is a big win from the company perspective can help you phrase you comments in ways that are reassuring rather than provocative.

Which brings me to the next category: “SOMETIMES.”

Category #2: SOMETIMES communicate like this

If you never challenge your boss, you will not only never stand out, your credibility will suffer. There have been a number of interesting research articles about why provocative employees were more likely to get results than those who always agreed with their bosses. You don’t want to go too far on this end – challenging your boss has to be done carefully and certainly respectfully. But when you do, you may be surprised to find out your boss found it helpful.  I have appreciated it whenever my employees challenge me; they have frequently offered a perspective that helped me make a more balanced decision.

Along with challenging, providing helpful advice is also something you should do once in awhile. There is a story about a successful entrepreneur whose bookkeeper once asked him, “Could I show you how to read the financial report so it helps you meet your goals more effectively?” With his bookkeeper, the entrepreneur was able to come up with a much more numbers-specific strategy that aligned with his ultimate desired outcome. In fact, it helped him double  his profits. The entrepreneur thought he knew what he was doing, but when he looked at things from a bookkeeper perspective he saw things in a more comprehensive light.

There are also times when you should object to something your boss tells you. If you can see a train wreck coming from a decision or lack of one, objecting can be the wake-up call your boss needs. Bosses are human beings and they can only know what they know. If you don’t share your perspective, you are doing the boss a disservice AND failing to carry out your fiduciary responsibility to point out potential problems. I suggest documenting any objections and challenges as a way of looking at patterns of behaviour and examining decisions made around certain issues. This can be helpful in terms of collaboration and it is also good for you to show you did what was right.  After all, from a legal perspective this may come in handy as a protection for you at some point.

Category 3: NEVER communicate like this

If your boss makes a decision and you disagree with it, you can tell your boss why and offer an alternative. Or you can uphold it anyway because if there was an error, it will become obvious over time. Or you can also get a delegation together to explain how this could be a serious issue if you feel really strongly about it. But you cannot override the decision. That puts you in a position of being insubordinate: grounds for dismissal. It is also arrogant because it assumes you know more than your boss and are overriding the organizational structure, which is a serious offense. It causes everyone to lose face and you end up looking worse, not better.

Never criticize your boss either: not privately to his or her face, not in a meeting or publicly, and not in a backbiting, underhanded way. Criticizing your boss is mean spirited and shows poor professional judgment. Imagine yourself in your boss’s position. How would you like it if you were criticized for something you did or for who you are? Most of us would be angry. Instead, think of a way you can be helpful and do your part to solve the problem. If you must say something to your boss, do it in a way that is private, kind and allows your boss to have a way out without losing face, no matter how bad the issue is. It is never a good idea to cause anyone to lose face, especially your boss.

To recap, let’s revisit the initial list of problem scenarios and add some solutions to them based on the three categories I just described. First we’ll identify the workplace communication issue, name a strategy to tackle it, then see how that strategy looks in action.

Communication issue #1: Crossing wires

  • Your boss tells you to do something that is completely the opposite, or in contradiction to what he/she told you to do earlier.

Your strategy: Engage and advise

  • Explain that you are confused about how to prioritize and ask for clarification. If there are still contradictions suggest a potential course of action and say why. Then wait for your boss to decide.

Communication issue #2: Have we gone over this before?

  • Your boss forgets what he/she asks, and repeats things you already know, or doesn’t seem to be organized with communications generally.

Your strategy: Collaborate

  • Suggest a way you can track your boss’s communications/decisions that involve you and a way to check on current priorities. Ask how your boss would like to approach this so you are both able to get to the goal.

Communication issue #3: Getting heard

  • It seems impossible to get your boss to pay attention to things that matter to you and to your team, unless it’s an emergency.

Your strategy: Show loyalty and challenge

  • Explain that you believe in the company and want to do your best. Show how lack of attention to the team will cause your boss to lose out on what he/she wants. Challenge your boss to come up with a consistent way to deal with this.

Communication issue #4: Things aren’t what they seem

  • You suspect your boss has a hidden agenda you are supposed to figure out, but when you ask directly about it, you can’t get an answer.

Your strategy: Engage and challenge

  • Say what you think your boss wants and ask if that is actually the case. Name the issue, the potential consequences and challenge your boss to be upfront with you so you can better get to the end goal.

Communication issue #5: Waiting…and waiting some more

  • You desperately need resources, tools or an answer to something but your boss won’t make a decision on it.

Your strategy: Object and Collaborate

  • Ask to meet with your boss, schedule a time and be prepared with your facts. Explain to your boss how the lack of decision making on the resource issue is causing – or will cause – a problem for the boss (not you or your team). Invite your boss to help you find a solution that will meet both needs, or suggest that the decision be handed off to someone else if that is possible. Listen carefully to the response.

Communication issue #6: You happen not to be a parrot

  • Your boss tells you to explain something at a meeting and later berates you because you didn’t say it the way he or she would have said it.

Your strategy: Show loyalty and challenge

  • Make sure you have allies in the team or company. If you don’t, consider seeking another job. If you do have allies, set up a private time to speak with your boss when you are calm and have a strong plan in place. Explain your loyalty to the company and to your boss. Then explain the effects of his/her behaviour on you and your work and ask if that is what your boss wants. Do not criticize or make reference to your boss’s character or personality. If your boss wants to stop doing this, you can suggest a way for that to happen without being critical. If not, consider leaving.

The key to resolving workplace communication issues is to start from a place of respect (especially when it seems that others may not deserve it), always allow people to retain their dignity, and you should expect that treatment yourself.  As you practice the above strategies, you will begin to feel more confident, the words will come more easily to you, and you will better understand how you need to act and what you need to say not just to your boss, but to everyone around you.

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“Communicate unto the other person that which you would want him to communicate unto you if your positions were reversed.”

Aaron Goldman