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Anticipate What the Boss Wants or Needs

Most bosses set the organizational success bar to the desired height, and their expectation is that the rank and file will reach whatever that might be. That can lead to mission accomplishment, which is fine unless the boss is demanding and expects more than what has been asked for.

One way to achieve expectations or, better yet, to exceed them is to anticipate what the boss wants or needs. If your boss is not particularly demanding, he or she may ask for little or nothing. However, if expectations and demands are high, you need to be thinking ahead.

Having worked for many bosses with high standards, I became accustomed to anticipating what needed to be done. Not thinking ahead is what derails the train of progress.

Too often in our work life we suffer from a failure of imagination; in other words, we do not think the unthinkable. Let your imagination wander so that you think of all the things that could possibly go wrong on a project or with a plan. Map them, analyze them, and determine how to deal with them. Even if missteps never happen, you have anticipated the worst and probably can achieve the best.

Provide imaginative, creative thinking to the boss before decisions are made or actions are taken. This can elicit what the boss expects you or others to do to work through the issue. Always provide more detail or information than the boss may be expecting. Your thoughts cost nothing and may save money down the road.

You can also be an effective buffer or go-between for those things the boss either doesn’t want to or doesn’t have time to deal with. If the boss allows it, take charge of a project or a process that reflects favorably on the boss and at the same time is important for a successful outcome.

In the preparations for the first Gulf War, which began in January 1991, there were endless decisions that had to be made to get ready for the largest military operation since the Vietnam conflict. Generals Powell and Schwarzkopf had much to consider to get things right.

One consideration that gained their attention was the need to explain our military intentions and operational decisions to the various stakeholders involved. Both veterans of Vietnam, they understood well the critical importance of gaining and maintaining public approval for our actions, something we had failed to do in Vietnam. They chose not to repeat that calamitous error.

The late Arthur Page was the vice president of public relations for AT&T for 19 years in the 1930s and 1940s. Known today as the dean of the public relations profession, he earned that title for many principles that are hallmarks in the profession today. One thing Page said that fit the Gulf War requirements was, “All business in a democratic society begins with public approval.” How true.

Public approval was what we sought. As chairman of the Joint Chiefs of Staff, General Powell had overall responsibility for the conduct of the war. As central command commander, General Schwarzkopf had operational responsibilities. Those responsibilities had to match.

After they had a powwow, General Powell summoned me to his office in December 1990. He told me that when the war commenced there would be a series of daily press conferences: one in the morning in Saudi Arabia and the other in the afternoon in Washington. He said, “Secretary Cheney and I will do some of the lifting, but I intend to ask Tom Kelly and Mike McConnell to do the bulk of it here in the Pentagon.” Kelly was the three-star J3 operations officer for the Joint Staff; McConnell was the one-star J2 intelligence officer. Together they would know as much as if not more about friendly and enemy forces on the ground than anyone else.

By the time the war began on January 17, 1991, we had a plan in place. The next morning, Secretary of Defense Cheney and General Powell conducted the initial press conference in a Pentagon briefing room full of reporters. They did a masterful job. Our mission was under way to keep the many key stakeholders informed. They included the American people, Congress, the heads of state of international partners, the men and women in uniform, and, perhaps the most important of all, Saddam Hussein. A coalition of some 34 countries had been cobbled together to participate in the allied operation. It was crucial to keep them in the game with operational information.

Powell had directed me to work with Kelly and McConnell to develop both the style and the substance of the daily press conferences once the operation began. They were easy to support and eager to do what I recommended.

Since the daily press conference in Riyadh was going to be held at 10:00 a.m. EST, I recommended that ours be at 3:30 p.m. in the Pentagon. I told them I would prepare a list of anticipated questions each day by noon. We agreed to meet at 1:30 p.m. to war-game their answers.

Upon arrival at my Pentagon office each morning, I began to assemble likely questions. They were based on news reports over the last 24 hours, and I would add questions curious reporters would ask me in my office that day before noon. My crack staff helped me with that process. I would stop to watch the press conference from Riyadh, courtesy of CNN.

Typically, I’d have the 35 or more questions delivered to Kelly and McConnell by noon. They were educated guesses, but for the most part they resembled what was to come. At the appointed hour, I’d meet the general and the admiral in Kelly’s office. They would assemble experts from their respective staffs to provide them with as much detail as necessary.

This process had been coordinated in advance with the assistant secretary of defense for public affairs for Secretary Cheney, Pete Williams. An exceptionally sharp professional, Pete would convene the press conference and provide details of his own to reporters after the two officers gave the briefing.

By day 3 of the war, a horde of reporters had assembled for the daily ritual. They grew in number to more than 200. Many were from international news organizations. Kiddingly, we used to describe many of them as the equivalent of food editors. Some knew little or nothing about national security. That made the challenge even greater for the briefers.

The war lasted 43 days. The air campaign accounted for the bulk of the operation; the ground phase lasted only 100 hours. Throughout the war, we held 38 press conferences in the Pentagon. We managed to gain and maintain public approval as Arthur Page had advocated. Only once, when I felt it start to falter, did I recommend that the chairman step in along with Mr. Cheney to get us back on track, and they did.

It was a memorable lesson of life: anticipate, assess, plan, and execute. Staying a step ahead of Colin Powell and others I worked with was indeed a challenge, but I vowed to never let them down. You won’t get paid any more for anticipating what the boss may need, but you will be richer knowing that you did everything you could and should have to get the job done.

Anticipating for someone who already is your boss is hard enough. Anticipating for a new boss and someone you don’t know yet is even more challenging. Rather than waiting until the new boss arrives to set that bar, reach out to the boss’s current staff or colleagues. Ask the right questions of a chief of staff or a special assistant for the boss-to-be.

My new assistant-to-be as I transitioned from government to academia did her research well. She investigated everything down to the simple things such as my liking and using No. 2 pencils. What is he like as a person? What are his management routines? What are his customs and habits? What can I anticipate him wanting or needing? Voilà! She had it down by the time I got there. It was seamless. It probably lowered her temperature to know in advance, and it certainly raised my spirits when I got there.