Seven Steps to Respectfully Disagree With a Boss

A difference of opinion is inevitable.

talking in meeting
Chris Ryan/KOTO/

Even if your boss keeps on encouraging team participation and speaking up, there is often a strange power dynamic when it comes to disagreeing with a person who has more authority than you do. Of course, it all depends on personalities, and organizational and cultural differences — there are a lot of leaders who welcome greater candor and radically honest feedback. Even if they do, you may not have the training on how to speak truth to their power.

Start From Day One

A difference of opinion is inevitable. I cannot imagine smart people in a room seeing eye to eye all the time. If they did, that would be a group-thinking bias and not an effective working environment. Therefore, it's important to predict challenges and invite open communication and honesty. Proactively ask your superior, "What if we disagree?" Find out how and when they want to hear your counterproposals.

Evaluate the Risks

Unfortunately, there is a good chance that you have not done that and the issue just happened. Evaluate if it is worth it to speak up and do a risk assessment of what the consequences will be if you do. Many employees assume they have two choices: confrontation or avoidance. However, these are not the only options available. Power is more dynamic than you think, and it is not only associated with a position. It stems from charisma, expertise, network and sometimes having powerful stakeholders. Good preparation, reframing drawbacks, and understanding how to persuade others can give you some advantage in the process.


Preparing for disagreement has nothing to do with making an exhaustive list of benefits your idea will create. When people dispute your claim, the first step to consensus is being neutral, not excited. List your manager's objections. Be extremely frank and look for all the holes and issues they might find in your counterproposal. The longer the list the better. The next step is to come up with contingency plans for all the challenges that might show up. Eventually, you can look at the benefits your idea provides and connect them with your leaders' objectives.

Open With Your Intentions Then Focus On Solutions

Your boss wants to believe that your ideas will not jeopardize their goals. Make it clear that your main intention is to meet their goals and satisfy their concerns. It often comes down to more listening than speaking. A lot of people use monologues as a persuasion tool. I find it off-putting. In my experience, those who ask questions and listen are more likely to be effective negotiators.

Be Respectful

Stay calm and show respect by listening to what they want to say and expressing your desire to help them make a decision that will work the best for the whole organization.

Be Affirmative Yet Reframe

"Yes, and..." is an improv technique that can pay off when it comes to persuasion. However, it seems to be commonly misunderstood, because some think it equals agreeing with others and following their agenda. "Yes, and..." is a relationship-building tool that allows you to collaborate on the best solution possible as it connects your boss's idea with your proposal. Some examples of this in practice:

"Yes, I loved what you just said, and it reminds me of: the thing... the solution... this concept..." (redirecting their thinking toward your idea).

"Yes, and in theory, this could work. Can we explore what it might look like in practice?" (Talking about practical implications might show that your leader's concept is not the best one to follow. What is more, this will help them recognize the gaps in their own understanding.)

"Yes, and I'd like to execute it like that as well. Is it okay if we think about obstacles that might show up?" (An open conversation about obstacles might show weaknesses of their plan and create an opportunity for you to present how you want to tackle them.)

"Yes, and if we had the access to [technology x], we could [thing y]. What is the likelihood that we will have that access?"

"Yes, and this functionality has been very popular for quite a while. Do we want to stay with an old favorite, or do we need to be more innovative here?"

Demonstrate Your Collaborative Skills

Asking higher-ups follow-up questions is a great opportunity to fully understand their objectives. Listening to your boss proves as well that you are willing to collaborate on what works best for the organization. Another thing that shows you the superpowers of cooperation is the ability to leave some autonomy for them. You provide your leadership with necessary data by outlining 2-3 options with their consequences. Share which one works the best for you but leave room for them to choose. This signals your flexible approach. Moreover, it works well with people who like to control situations — as many executives do.

Between a Rock and a Hard Place

Sometimes, however, you might find yourself in a complex situation of disagreeing with your boss and agreeing with your skip-level. The obvious suggestion is to avoid taking sides. Let's be honest, it might be easier to say than execute. You might have your own preferences when it comes to their personality, experience, and approach to the problem discussed. Whatever they are, try not to create a challenging situation for your boss. Communicate how awkward you feel if you are pressured by a skip-level to take sides or actions your leader disagrees with. Be honest and ask them to decide together on the course of action. Remember, you are hired to do your job — not be a mediator.

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