How to Cross the Boss, without making the Boss cross

Have you ever felt that you really wanted to disagree with your boss on some work-related matter but were too afraid that they might not receive your opposition very well? Most staff who report directly to a General Manager or influential member of the executive team see it as a career limiting move to disagree openly with their boss’s decisions. However it need not be so.

The same applies to junior members on a board of directors and their willingness to speak up in the face of a dominant Chairman.

When I held the post of Chief Executive Officer of a large organisation I certainly wanted to see my direct reports loyally supporting the direction I was setting for the organisation. At the same time however I never wanted them to be a band of yes-men/women or lapdogs.crossboss

I have seen both chief executives and board chairmen who are highly defensive of their roles and positions of authority, such that they do not encourage any argument contrary to their own views. Unfortunately such an approach has the effect of:

a. Suppressing even good and valuable ideas by discouraging freethinking;

b. Preventing important strategic intelligence coming forth because it might be seen as distasteful to the Boss and cause retribution upon the messenger;

c. Preventing the identification of weaknesses in strategies or decisions that could be remedied, strengthened or mitigated.

I chose my executive staff for their skills in delivering outcomes for the organisation and our community and I valued executives who demonstrated creative thinking, good analytical skills and problem-solving abilities. These qualities meant that they would have a good prospect of picking up on any gaps in my own strategic thinking. Consequently in order to get best value from their skills I had to be open to their ideas and views even if they didn’t directly align with my views in the first instance. I therefore encourage them to speak up and where necessary challenge my own views, provided always it was done respectfully and approached with positive and constructive intent.

Conversely, any subordinate wishing to exercise the freedom to cross the Boss, needs to observe a few simple strategies.

  • Get to know what the Boss will allow in terms of free expression and work within those bounds;
  • Serve an apprenticeship of only offering advice when asked or when the circumstances permit;
  • Listen to and observe how others successfully navigate the minefield of crossing the boss;
  • Build a reputation for reliable ideas and comments that come to the Boss’s attention indirectly;
  • Demonstrate a preparedness to analyse situations carefully before offering commentary or suggestions and then make sure they are based on sound logic and judgement;
  • Start slowly by offering comments in simple non-confrontational situations, gradually building your reputation for intelligent remarks and appropriate input;
  • Be careful to keep your input focused on the key objective the boss wants to achieve and ensure your contribution will help progress towards that achievement;
  • If you are not certain about the boss’s likely reaction, use questions rather than statements to clarify any non-negotiable aspects of the bosses view;
  • If the boss is known not to appreciate contrary advice, then try to use adroit questioning to get the boss to come to the conclusion from his own deductive reasoning;
  • Where possible enlist the aid of other influential advisers to the Boss who can support your point of view;
  • Demonstrate that you have thought the issue through thoroughly and addressed any risk factors;
  • Above all, maintain positive and constructive sentiment throughout and strictly refrain from aggressive or argumentative demeanour.

Generally, good  bosses don’t get cross when they are crossed, unless the crossing crosses the line of acceptable behaviour and respect for the boss’s legitimate authority.

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