Should You Disagree with the Boss?

When teaching, I often used to observe that your boss works much harder than you do and, more often than not, is smarter than you. Nothing riled up the class more than this, but such provocations are extremely important. The role of a professor is not to tell students “what to think”, but instead “to make them think” and provide frameworks on “how to think”.

After listening to their disagreements to my provocation, I would pick on an individual, and ask: well, if they aren’t working as hard as you and are not as smart, how have they managed to become your boss? What are you missing?

Often, this discussion led to the realization that people tend to take one aspect where they have more expertise, knowledge, or skill, and generalize that to the capabilities needed to be the boss. But, technical skills matter less as one goes higher up the organization ladder. It is the price of admission. What matters more is the experience that one brings to the job, as reflected in the wisdom, emotional intelligence, and social capital of the individual. In addition, everyone believes they are smarter, better looking, and more personable than reality. Both misjudging the criteria and overestimating our capabilities leads to the erroneous conclusion that we are smarter than our boss.

This is not to say that there aren’t poor bosses. Rather, my contention is that for reasons given above, it is seldom true, and always better to assume it is not. If by chance, one does have an unworthy superior, it can be used as an opportunity to learn from their weaknesses. Learn fast, because they are not going to last in their position. In the long run, rationality prevails and cream rises to the top.

Now there is a big difference between having a healthy respect for the superior to having an unhealthy slavish mentality. Returning to India after 30 years, I was taken aback by how hierarchical managerial structures are. You could see this in how people behaved in the presence of their superiors as well as the absolute power that bosses demanded and commanded. For example, it took more than a year to get everyone on my floor on a first name basis.

Watching people in meetings with the Chairman would have been amusing, but for the detrimental effects on the organization from this subservient behaviour. I recall a strategy discussion where the CEO remarks to the Chairman: My instinct is to always agree with you! Despite the presence of several junior executives, I could not resist smiling.

After a few months, I began to see meetings as races between people trying to guess what the Chairman believes so as to express it before he could. This behaviour led me to ask the Chairman to hold back from revealing his stand on any matter until closer to the end of the meeting. Once his opinion was known, it effectively concluded any substantive discussion on the topic.

The challenge is to encourage people to disagree and voice their opinions. This helps make better decisions by unveiling the best arguments on both sides of any issue. Yet, how to disagree with the boss is an art. While readers will have their own views and I encourage you to share these, may I start us thinking on how to disagree with the boss:

  1. Disagree only if your boss is convinced that you respect him / her. If you believe that you are smarter than the chief, it will taint how you express yourself and how it is perceived by the superior. In these conditions, I suggest don’t disagree, but find another job.
  2. Disagree selectively. Choose when to disagree, as from the organization’s perspective, everything is not worth fighting for. In addition, on some issues, if the CEO has taken a strong public stand, then it may be best to disagree only one on one, and not in front of others. There are some executives who dislike any disagreement in public forums from their underlings. However, they are open, and may even enjoy, debate in private conversations.
  3. Disagree without undermining authority. It should be clear that after you have been heard and a decision is made, even if against your opinion, you are 110% behind it and will work to make it a success. This means you accept that you may be wrong, and in any case, it is ultimately the boss’s prerogative / responsibility to make the decision.
  4. Disagree without being disagreeable. Make an argument, but don’t have an argument. The moment it is perceived as interpersonal, one loses the argument and the fight. To appear constructive rather than condescending, it is often better to pose the disagreement as a question. As professors, when teaching a case, we often play this trick. By asking the right question, you can get students to give the answer you seek, while making them feel it is their insight.
  5. Disagree without personal agenda. The intent of any disagreement with one’s superior must be in service of the organization. It cannot be self-serving, as once that is transparent, it reduces you to a joke.

Unfortunately, strategy is often seen as a document rather than a conversation between the CEO, the Board, and top executives. It is through these conversations that a joint view is developed on what are the opportunities and threats as well as what is the firm’s advantage and competitive set. Strategy is the outcome of these conversations, with a consensus on where the firm should be heading and how to get there. However, strategy is continuously evolving as the future unfolds in unpredictable ways.

It should be apparent that without encouraging active disagreement and debate, the thoughtfulness behind any strategy will be shallow.



Magic Dust

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