Too hard a project? What do you do? [closed]

Question

This is a situation that everyone has to deal with on a regular basis simply due to the nature of work. (Typically, if you know everything you need to know to complete a job, you've already completed the job and don't need to do it again. :) )

1. Be honest with your boss about your anxiety. Your manager needs to understand your assessment of the project's risk profile. Odds are good that you'll be doing it anyway. That's OK! This is your chance to shine! :)

2. Break the problem down into tasks you understand and tasks you don't understand, then start tackling issues one at a time. I, personally, like to alternate between easy tasks and hard tasks. Completing easy tasks helps me feel like I'm making real progress on a gut level, which is important for my personal motivation. Completing hard tasks addresses potential problem areas earlier in the schedule. This mitigates the tail-end risk of the project by evaluating unknowns earlier, rather than letting them fester and explode when you've got 2 days left and no more planning/wiggle room. It also helps your stress level because you know you've gotten the ball rolling on the project's scary bits. Remember-- your unknown areas are where you don't understand the problem domain, so that's where the real risk of schedule/budget slips lie. You need to mitigate those risks early and often. Get the ball rolling with colleagues that you can consult to learn how to do these things.

3. The one month goal is probably a target. I don't believe it's reasonable to expect person A to realistically estimate person B's scheduled completion of a task in the general case. To track your progress against the target, set up milestones, none longer than 16 hours/2 days, and track your completion rate against them. This goes hand-in-hand with your list of easy/hard tasks.

4. The simple fact is that, sometimes, you'll just get dumped in over your head. In that case, you may have to make the best of an overwhelming situation. My very first task at my first job out of college was to design a reliable, transaction-oriented, peer-to-peer n-way server synchronization system for high-volume, high-rate data. I told my boss up front that I did not have the expertise for this, and at the time I didn't have enough experience to understand that I needed to push back on the requirements. (In retrospect, given the political environment, I don't know if pushing back on the requirements would really have helped anyway). That was simply a case of a poorly managed project that took about 18 months to ultimately collapse under its own weight. I still leveraged the opportunity to learn a lot and take some knowledge about the way my particular organization worked, though, and that can be very valuable no matter what. :)

Good luck! :)

Edit after question update

Ok, if I understand your update correctly, we're definitely in #4 territory here. There's nothing realistic about creating a competitor for Ning in one man-month. I assumed in my prior answer that you were dealing with someone who had a base understanding of software development. Based on that:

1. Ask your boss to clarify the requirements more. Perhaps (cross your fingers!) you simply misunderstood what you were being asked to do, or the scope of the project. Always assume competence until absolutely proven otherwise for social reasons. Maybe you were only being asked to come up with an overall design and some very simple proof of concept?

2. If your boss is truly this out of touch with reality, put together a sensible, 15-minute back-of-the-envelope estimate with him/her on a whiteboard or a shared piece of paper. It shouldn't be hard at all to blow all kinds of holes in this one month to completion. Perhaps your boss thinks you'll be able to reuse some internal code that you're not aware of? This will bring any faulty assumptions your manager is making re: project scope to light.

3. If your boss is absolutely unreasonable (this doesn't happen often, but it occasionally does-- perhaps the company needs a killer app by the end of the month to sell to avoid going under), prep your resume for an intra- or extra-organizational move (depending on how big the place you work is). Unrealistic expectations on that order can be a sign of organizational desperation or malfunction, and your position may simply not exist 3 months from now.

1. Don't panic. You may have misinterpreted the goal your boss has. It sounds like he was not very clear if he said only "Ning-like."

2. Research Ning. What are all the things Ning can do? On Ning's Resources link, they list at least 21 major social network features.

3. Write up a high-level statement of the goal for this project. Include all the features Ning lists. Also include an objective for how many users this app should serve. Don't try to think about how to solve these goals objectives, or how many programmers it'll take or how long it'll take. Just list them. Keep this write-up to one or two pages.

4. Present the list to your boss. Ask him, "does this sound like what you had in mind?" Ask a few direct questions to ensure he has looked at your write-up:

   • "Who are the target users for this application?"
   • "How many new users per month do you expect to sign up?"
   • "What level of uptime do we need to support?"
   • "What's our budget for hosting this service?"
   • "Do you need this application to support international users?"
   • "What is the end-user license agreement (EULA) for this application?"

5. It may become clear at this point that your boss has more modest goals than you assumed. Perhaps he does not intend to duplicate all the capabilities and scale of Ning. So then it becomes a task of getting your boss to articulate more clearly what subset of Ning features or capacity he needs.

6. Install Drupal, Joomla, or Wordpress, download some plugins, and design a custom site for your boss. That'll probably give him 99% of what he wants, and it's the only way you'll be able to do it in one month.

Don't start by saying "No" or "It can't be done" or "Its too hard" or any of the other things you said in your post. Most managers in a company do not even begin to understand the effort level involved in a programming project and need a little education with their software planning estimates.

I would suggest a conversation which includes the following steps.

• Estimates: review the effort level you believe is required for this project to be a success. Make sure that you have thought out tasks in enough detail so that you can answer questions.
• Education: if your boss doesn't understand why something will take a certain amount of time, explain as clearly as you can (good analogies tend to help, bad ones can be devastating).
• Alternatives: if you believe there is some middle ground or some set of sub features which will fulfill the project needs discuss these alternatives. Managers hate when an employee says something is hard or difficult, they want workable options.
• Alignment: are you sure that you and your boss are on the same page about this project? Perhaps you see it as a piece of mission critical software and your boss sees it as a minor enhancement to your existing tools. Be sure that you both have the same expectations; otherwise, you may be planning more complex software than what is being requested.

The most important thing I ever learned in software was how to "push back."

It doesn't always mean saying no. What it means is providing your best estimate of what the impact of new work is. Whether you're saying "yes" or "no", you say, "we can do that, but it will require (x, y and z resource). I think it will take (n days for me, n*a for person b) to understand problem b), but I know how to handle (c, d and e). I've never had to solve problem b before, so I don't know if my estimate for that is realistic."

The difference between "yes" and "no" is whether the cost equation is acceptable.

Any good manager will respect your analysis, question some of your assumptions, expect a round of rethinking, and then, either accept the risks, find additional resources, or abandon the project.

If they say "I see what you're saying, but you're going to have to accomplish the impossible anyway," start looking for another job.

Would your boss not understand the truth? Just talk to him about the requirements of the project, and mention what can and can't be done.