It doesn’t matter what you say or ask

(1) I don’t answer yes-no questions.

Ellsworth’s reply: Is your name Dwayne?

(2) It is not probable.

Ellsworth’s reply: Good, you agree it’s possible.

(3) We can deliver a subset of the software by that date.

Ellsworth’s reply: Greeeeaaaaattt! I’ll expect it to do everything we need.

(4) I respect you too much to answer a question that might mislead you.

Ellsworth’s reply: I can take care of myself. Answer the question.

The problem for Ellsworth is someone who he believes must be obeyed has spoken. He has been told that a failure to meet the deadline means less revenue. Ellsworth’s experience is that less revenue impacts the company’s budget, which may mean cuts in the payroll budget, which may mean a layoff.

I think managers like Ellsworth want everyone to believe it’s possible to meet the deadline, regardless of whether achievement requires a miracle. If you tell him it’s not possible, he won’t believe you and he may label you a heretic.

He might come around to your way of thinking if have thought of an constraint that is impossible to satisfy by the milestone deadline. But don’t expect him to give up, which he shouldn’t and won’t. He may rob Peter to pay Paul to eliminate the constraint by juggling the schedules for other milestones so that your milestone has the possibility of success. Or he may find another way to solve the constraint.

Ellsworth has the role of middle manager, which, in my opinion, is the toughest role in a company. I think the upwardly mobile middle manager is simultaneously trying to delight upper management and satisfy you and the other people at the bottom.

I don’t know a response to “But is it possible?” that will satisfy an obedient middle manager. If middle managers have reached the point where they need to ask that question, it’s already too late.

When reality interferes with the construction of the required story, reality loses.

Some answers:

(1) I don’t answer yes-no questions.

(2) It is not probable.

(3) We can deliver a subset of the software by that date.

(4) I respect you too much to answer a question that might mislead you.