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When you know you’re right, and your boss is wrong, deciding whether to speak up is often difficult. You may feel that to be respectful you have to tone down your disagreement. And if you are to be honest, you’re going to hurt her feelings.

You don’t want to make things worse, but not voicing your concerns feels like you are agreeing. Right?

This dilemma comes up often in my coaching practice, and we have found a way of tackling it. Here’s what works:


Step one: Understand your motivation

Why do you have the feelings you do? Is it only about the issue, or does it also bring up other issues you are not happy about?

Take an example of your boss deciding to introduce a way too optimistic schedule for a new client. Are you angry because you don’t want to disappoint the client, or is it because it’s another in a long list of decisions that she hasn’t consulted you on and it’s you, not her, who has to work late at night and over weekends?

Step two: Create the right environment

Unsurprisingly, most bosses don’t welcome public challenge, such as in large meetings and in front of their bosses, stakeholders or clients. It’s far better to find a time to talk privately to her, and when both your and her emotions won’t get in the way of listening to each other.

Step three: Align your interests

Begin the conversation by stating your commitment to an overarching goal. Explain that it’s because of your commitment to this goal that you would like to raise this topic. This shows that you respect your boss and her position. You will now have created the best possible platform for the conversation.

Using the example of the way too optimistic schedule, you could say: “I’m really excited to be working on the new client. It will help us meet our Department objective of limiting costs by replicating our systems with new clients. I have asked to talk to you because I want to make sure we do this integration onto our systems flawlessly and in the best way possible.”

Step four: Create engagement

Now we get to the crux of what differentiates an effective disagreement that to leads to change, and an ineffective disagreement that leads to irritation, polarisation and no change.

Make the crucial decision as to whether you want to get your feelings off your chest, or if want to be heard. Understand that to be successful, you need to decide which is most important to you. Trying to do both together is very tricky.

If it’s more important to say how you are feeling in order to get it off your chest, then do so: “This is a really silly idea!” …….. “You never consider me in your decisions” ……….. “It’s me, not you, that will have to work crazy hours!” …… “Don’t you ever think about me?”

It will probably be a relief to say how you feel, but it’s unlikely to set the foundation for good listening from your boss!

On the other hand, if you want to be heard, that requires a different approach. The most effective way is to express your concerns or disagreement in the form of questions that get your boss thinking the way you are. For example:

·         “Is there some reason that I don’t know about that led to the tight deadline for the delivery to this client?”, or

·         “With the previous client I worked late nights and on weekends for several weeks to meet the delivery date. Given how touch and go it was to meet that deadline, have you got some ideas on how we can be more certain to meet the deadline with the new client?”

Step five: Make proposals

If you want to get your boss to change her thinking, it will really help your case if you have at least one alternative suggestion to make. Do this by linking your suggestion to the achievement of the overarching goal, and show how it will also address the concern you have.

For example: “I was thinking that the best way to ensure that we meet the deadline for this new client is for me to train up someone as I roll out this project. This will mean that we will have greater capacity to replicate our systems on a larger scale in the future.”

At the end of the conversation, whatever the outcome of your conversation, tell your boss that you are committed to make the decision work. Good leaders respect their team members who express views different to their own, and nevertheless do their best to achieve the overall goal.

If your boss is a good leader, she will respect you for expressing your views using these five steps. If you fail, at least you will know that you have expressed yourself constructively and probably nothing much else would have worked.

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