A foolproof guide to disagreeing with your boss

"I wouldn't say the reason I refrained from speaking up is because I'm working hard to be liked. I just don't want to being viewed as disagreeable or difficult to work with. And that fear is interfering with how effective I am in my role."

My friend had just come out of a gruelling two weeks at work. A decision that had been made by the executive team, which she was a part of, had negatively impacted her department. While she was part of the discussion that had culminated in the aforementioned events, she had had reservations regarding the course of action but did not voice them.

The key in ensuring positive outcomes lies in disagreeing constructively. But what about when playing your role entails disagreeing with your boss or someone who ranks superior to you in the office? How do you decide whether to speak up or stay quiet? And if you decide to speak up, how do you reduce the chances of fallout especially if your organization puts a premium on deference?

There are two things that no one can argue with. The facts and the bigger picture. It is one thing to speak about a decision in abstract terms, but if you can support it with facts and figures, it changes the dynamic. The bigger picture refers to the overarching goals of the organisation. If, for example, the point of a certain decision is completing a project on time and you phrase your alternative view with reference to this, you are likely to get a more receptive audience. Connect your disagreement to a higher purpose and ensure you make this link as clear as possible.

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You are obviously part of a team because of the skills and expertise you bring to the table. However, If you are constantly playing the devil's advocate or disagreeing on all decisions, it could earn you the title of being a negative team member and result in your workmates avoiding you. The key to having your insights taken seriously is in being selective about when to agitate for a different perspective and when to let things slide.  

Think about the long term impact of the decision being considered, and whether it is an easily reversible decision with little or no consequences. If the latter applies, then refrain from pushing your views if you can tell that you are alienating your team members.  

Benjamin Franklin described tact as "remembering not to only say the right thing in the right place, but far more difficult still, to leave unsaid the wrong thing at the tempting moment." How you 'correct' your superior will make all the difference between being regarded as a valuable resource and your insights backfiring on you. James Richman, an organisational specialist based in Boston recommends being sensitive to timing and tact. Do not correct your boss in a public forum, and especially not in the presence of his juniors or his bosses. Instead, approach him or her privately and explain your thinking in light of the end goals the department is trying to achieve.

In particular, do not make the correction or alternative view about how smart you are or how uninformed your boss is. This will just make the conversation defensive and most likely backfire on you.

If your organisation has a culture of deference or your boss expects overt respect, before you voice a contrary opinion, ask for permission. While this may seem like the trait a 1920s workplace, giving power to your boss by asking their permission gives them control and ensures they feel less threatened by your standing up for a perspective.