Managers accountable for on-time delivery may deny that their projects have encountered difficulties - These are human tendencies, but they are very, very dangerous in the business context. The severity of technology-based problems is often greatly multiplied by this kind of denial. How catastrophic the consequences of technological uncertainty are depends on how quickly a developer or manager comes forward to say, 'This is going to be harder than I thought.'
When it comes to developing projects, not recognizing or admitting technology-based problems can easily spell disaster. It is the project manager's responsibility to find out about those problems as early as possible. IT professionals are often optimists, inclined to believe that what is possible will also be achievable. When things do not go according to plan, they sometimes deny the severity or existence of problems.
1. Set aggressive deadlines that are stretch goals for your staff. This one is counterintuitive. You might think that aggressive deadlines would increase time pressure on staff and thereby increase their likelihood of keeping problems hidden. In fact, making deadlines aggressive - so aggressive that it is unusual for people to actually hit them - makes missed deadlines unremarkable and unembarassing.
2. Separate deadlines from planning estimates. This one goes with #1. If you set deadlines so aggressively that you don't expect people to meet them, you obviously can't use those deadlines as planning estimates. Who ever said deadlines and planning estimates ought to be the same thing anyway? Make deadlines unrealistically tight; keep estimates realistic through principles of successive calculations.
3. Ask direct, concrete questions about progress. Listen for indirect answers and "tap dancing." A tap dancing answer is one that is interesting and entertaining enough that you might not realize that it doesn't answer your direct, concrete question. Realize it. The phrase "It's almost done" should always set off alarms.
4. Establish communication links to the front lines. Is there someone on you staff you think will tell you the straight scoop no matter what? Talk with them occasionally about the work. Is there a member of your management team who hangs out with the troops? Ask her or him how the troops think things are going (and believe what this person says -- you'll be tempted not to).
5. Know the technology. To the extent possible anyway. The best venture capitalists are not deep technologists, but they know something about it and they know when someone is trying to snow them with technological mumbo jumbo. Study the technology a little. Acquire this skill.
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