Never surprise the boss, particularly on potentially volatile issues that could affect your project’s timeline, budget, or performance.

Even good surprises can backfire. Many an example exists of employees bringing the boss what they believe were good news, only to realize later that that the surprises weren’t so good after all.

Consider the following example of a Boeing test pilot pulling off a shocking stunt on a prototype aircraft, much to the exasperation of his company’s leadership.

A Reckless Stunt That Created a Buzz

The Boeing 707 was America’s first passenger jet aircraft. Prior to the 707, which entered service in 1958, air travel was mostly limited to the affluent—and even they were hesitant about air travel’s safety. The 707’s in-service safety record and its economic characteristics quickly made travel more accessible and dependable. The 707 ushered in the Jet Age.

But for Boeing, today’s leading aircraft manufacturer, developing the 707 was a big gamble. The 707 had no orders, and Boeing embarked on its development entirely on the wager of its prospective commercial success. When the aircraft’s design commenced in 1951, Boeing’s estimated development costs were $16 million. That was roughly 20% of the company’s value, and more than twice its yearly profits—nearly all of which originated from military contracts.

The Demonstration That Was Far from What the Boss Had Authorized

Boeing built its first and only 707 prototype aircraft in 1955. The company’s leadership decided to show off the aircraft at Seattle’s Seafare Hydroplane races on August 7, 1955.

The display plan was to have Boeing’s Chief Test Pilot, Alvin “Tex” Johnston, do one low pass over the racecourse so that the airline executives, industry pundits, and government officials who attended the high-profile event could witness Boeing’s new undertaking.

Johnston had other plans. In his mind, the audience needed to be sold on the plane’s performance and safety. Seized by the impulse to flaunt the agility of the 707, Johnston had a little more in mind than just an unpretentious flyby.

During the in-air demonstration (see YouTube video,) with the aircraft soaring over Seattle’s Lake Washington, Johnston suddenly pulled back on the controls, and the plane started to climb at a speed of 400 miles per hour. Then, he did a complete 360-degree roll and flew the plane upside down for a moment. As the crowd watched in shock and amazement, Johnston did a second barrel role.

Overconfident Employee, Furious Boss

Alvin Melvin (Tex) Johnston, Boeing Test Pilot In the startled crowd was Boeing’s legendary president William “Bill” Allen. Allen, who had authorized no more than a simple flyby, thought that Johnston’s first barrel role was a mistake. When Allen witnessed the second barrel roll, he feared that either Johnston had lost his mind, or the aircraft was in grave trouble.

According to Robert J. Sterling’s Legend & Legacy: The Story of Boeing and Its People (1991,) Allen summoned Johnston into his office the next day. Allen demanded an explanation and inquired why Johnston had foolishly risked the company’s only prototype.

Pleased with his successful accomplishment, Johnston offered a simple explanation, “I was selling airplanes.” Johnston explained that he had previously tested barrel rolls on the prototype, and it was a safe maneuver. He hadn’t risked the aircraft at all.

Allen reproached Johnston and told him that he appreciated the efforts, but Johnston was never to do anything that had not been approved previously.

Never Let Your Boss Be Surprised by Bad News

If there is only one thing worse than delivering bad news, it’s not delivering bad news as soon as you know that some trouble is brewing.

No boss wants to hear about any looming issue from some third party—especially if it could be worrying—and put her on the spot with her peers and superiors.

When you fail to report any bad news, you are leaving your boss exposed to being blindsided with a potential problem, and the perception that your boss doesn’t have control of her organization.

Idea for Impact: A Good Employee is Predictably Excellent

The surest way to delight your boss is by setting the right expectations, discussing and coordinating on a plan of action, and delivering on her expectations of your performance.

When the status of important any project changes, make it a priority to bring your boss and other affected constituents up to date. If, right from the beginning, you’ve made the true picture clear, your boss may be less surprised with the bad and the good.

Never surprise your boss—just keep her clued-in on a regular basis.



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