How often have you tried to figure out what your boss wants?
The boss is the unseen participant at every meeting. The boss might not be there in person, but everyone wonders what her reaction will be to the decisions, initiatives or outcomes.
Most people want to make their boss happy, if for no other reason than their own survival. 
Yet what starts out as an effort to please the boss (proactive), frequently descends into reducing risk with the boss (reactive). People try to avoid upsetting the boss, versus trying to hit a home run.
For example, I was dealing with a training team who was considering a new initiative. They were fearful about approaching their boss with the project. I asked, “Why?” The lead trainer said, “Well, he chose the program we’re currently using when he had this job.” “How long ago was that?” I asked. “Five years ago,” they replied.
I investigated further, “Has he expressed an attachment to it since then?”
“No, he’s never brought it up.”
“Does he have a history of reacting badly to new ideas?”
“No, not really.”
In this instance, I knew their boss, and I knew he wanted his people to be more innovative. Yet all the team could envision was his potentially negative reaction if they suggested trying something new.
They had invited the smallest, most fearful version of their boss into the meeting.
It’s a common problem. Marketing guru Seth Godin says,
“One reason organizations slow and stumble is that teams of well-meaning people form committees and go to meetings, determined to please the boss.
What they do, instead, is assume that the boss is far more conservative than she actually is. They buff off the edges, dilute the goodness and quench their curiosity. They churn out another version of what’s already there, because they’re imagining the most risk-averse version of their boss is in the room with them.”
In the case of the training team, they were entirely driven by fear, which was largely unmerited. Their boss wasn’t a hot head. He was a guy with a million priorities, trying to turn around a struggling business, in a competitive market.
I have little patience with small thinking, so I called them on it, “Are you honestly telling me that your boss believes that a decision he made 5 years ago should stand forever?” I asked.. “Don’t you think he hired you to make the decisions for the future?”
Unfortunately, they remained fearful, and asked me to make the recommendations to their boss. I did, and ended up landing a consulting contract. The boss also hired me to coach his leaders to be less fearful. If the internal team had a little more guts, they could have been heroes. Instead, the company spent six figures on outside help.
There are two lessons here. If you’re an employee, don’t invite the worst version of your boss into meetings. Your boss wants the organization to win. He or she may not be perfect, they may not react favorably to every suggestion, but ultimately they want to win. You should act accordingly.
If you’re the boss, the answer is even easier. Tell your people point blank: “When you’re in meetings, or making decisions, I want you to imagine the biggest boldest version of me is right beside you cheering you on.”
Bringing the small version of the boss in your work benefits no one.
