One of the most significant challenges any of us ever face in the workplace to telling our boss that he/she is wrong. How do you walk that fine line between potentially angering the person that controls your career food, air, and water versus sanding up for what you believe is right.  Because this tightrope is so difficult to navigate, most individuals choose the least risky choice of simply nodding and saying nothing.

Any boss that is satisfied with his/her teammates being “bobbleheads” and never voicing a dissenting opinion is one with either a very low self-esteem or an extreme love of power or both. However, these bosses frequently get less than acceptable results because of group-think or that feeling of “go along to get along” perpetuated by that boss.

I do believe, and witnessed it in my own career, that we gain courage as our career advances. The “filter” that might have pushed us into bobblehead-mode early in our career seems to dissipate as we gain confidence and career success.  However, there are times throughout our career that we need or must generate the courage to simply communicate to our boss, “You are wrong.”  How do we do that without completely ruining our relationship with our boss?  How can we do it without embarrassing our boss?  How can we do it most positively and productively?

Here are a few suggestions on how you can approach your boss when he/she might be wrong. Some of these are most appropriate when you need to speak up in a public setting, while some might be more effective in a private, one-on-one meeting.  In any event, these approaches may help you cross the line without ruining the relationship:

1. Have you ruled out any other possibilities? – This is a low risk question to simply encourage a dialogue on other alternatives. If your boss does agree to articulate other possibilities considered, it might allow you the opportunity to inject your thoughts on why his/her approach may not be the proper choice.
2. Would it be OK if we discussed some of the risks of this approach along with ways to mitigate them? – Most leaders welcome an opportunity to discuss risks and their mitigation. Thus, when you ask your question in terms of risk, you open the door to a discussion on why other alternatives might pose fewer risks.
3. Could you talk about some of the factors you considered and how you came to this decision? – This approach solicits the wisdom of the leader that gets him/her talking about the factors considered and the rationale behind the decision. In the ensuing discussion, you might be able to discuss the risks posed by this approach.
4. There are some factors that you might not be aware of. Can we talk about those and how they might affect where we are headed? – This approach seeks to provide new or additional information for the boss to consider. This “new” information might give the leader a way to reconsider without appearing to vacillate on the decision.
5. Would it be OK to discuss a similar situation we had (or that I experienced) in the past and what we learned from that? – This approach seeks to provide a new perspective from someone that has experienced a similar situation – again, new information that might give an opportunity for reconsideration.
6. Could we tabulate the pros and cons of this approach, so we could better visualize how to communicate this to others? – This approach does two things: it creates a very visual way to better assess the decision and it facilitates a discussion on communication that can lead to a “what if” or “why” dialogue.
7. Would you be open to a discussion on why another approach might be better? – This is the direct approach that seeks to elicit an open discussion. This direction is preferred when the boss is confident and has demonstrated trust in your opinion in the past.

To achieve success, we cannot afford group-think that takes us down the wrong road. We need to have the courage to speak up when a decision or direction is not right or when it could be improved.  Think about how the approaches outlined above might be helpful in these situations and during critical conversations.

Have a terrific and successful day!