organizing code and how to hit deadlines in a programming deadline [closed] - project-management

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I know this may not be exactly a coder question, but I feel it is still related to programming because I'm sure many developers have come across this before and might have some insight on how to resolve this or have advice. There is an actually programming question though.
My issue as a developer.
I work in a small company, roughly 15 people, 5 of which are developers include myself, the rest are tech support and management. Problem I'm having is, when we get a SOW (Statement of Work), our clients give us a rough description of the project they are requesting, which usually is a 1-3 page brief description, usually including a Visio document, now as a programming, I'm responsible for going over the document and relaying a time-line on how long it should take me to complete the project.
Unfortunately, there have been times, not only me, where we under-estimate the project because we didn't fully get into it till we actually developed it, which ends up slapping ourselves in the face, because my boss is upset because he is being hounded by the client, who is now upset because we missed our promised deadline.
My question is, how do you guys handle organizing basic project description when you need to give deadlines on more concept, and do you have any ideas on how to organize it.
I'm thinking of going to my boss and suggesting, instead of always pushing a estimated deadline to our clients which expect us to hit that, we should write up a detailed document that is more step-by-step (more like what to do) on how to develop the application they want, it may take a lot more time, but least if the project is moved to someone else it is laid out for them, and when I usually get back to it 4 months later, I don't have to refresh up again, I can just follow the steps I wrote.
What do you guys think? Ideas? Or better ways to handle this?

If you switch your development to using an iterative methodology (Agile, XP, Scrum, etc), then the customer will see results much earlier than any deadline you feel you have to promise - usually every 1 or 2 weeks.
The moment they see what you've developed, I can pretty much guarantee that they'll make changes to their initial requirements as they now have a visual representation of the product and it may not be quite what they were thinking of. Some of their changes might be quite radical, so best to get the feedback as early as possible.
In all the projects where i've insisted we do this, the customer was delighted - they saw the results early, could influence the project outcome, and we hit their end deadline. Unexpectedly, a whole load of features got left behind and - guess what - the customer did not mind at all as they got the top features they wanted and put the project/product straight into production as they'd had lots of time to refine it to suit their business, so they were already familiar with it.
It takes a lot of effort to get management, sales, creative, etc, to all buy-in to an iterative style, so you may need to implement a hybrid solution int he mean time, but in my experience, it is well worth it.
If a complete shift to iterative is not possible, split your project into tangible milestones and deliver on those milestones. As others have said, inflate your estimates. My previous manager doubled my estimates and the sales team doubled his too.

Inflate your project deadlines. It's something that most programmers should do (and I quote the VP of Freeverse, the company that I work at):
It is a well-known fact among people
who work in the software industry that
the last 5% of development always takes the longest.

If possible try to divide the higher level tasks as much as possible so that you can get a better approximation of how many man hours that sub-task would take.
Also, adding hidden buffers to your task execution helps in covering some of the unseen contingencies.
cheers

If you mock up (balsamiq or whatever) with your customer, you will get more details. Armed with those details and some experience, your estimates will be more accurate. And then double it and add 4 (hours,days,weeks,months)

First, unless you systematically under-estimate, your boss should not get upset. It's his job to answer to the client, and he should know that by definition, an estimate is NOT the future. Statistically, sometimes you should deliver earlier, sometimes later.
Personally, I think that the frame of "how long will it take" is not exactly the right discussion to have. Software development is a risky business, and change/surprises happen all the time. One approach which helps is to focus less on the "right" number, and more on the volatility. Look at the project, and consider the places where you are pretty clear on how long it will take (you have done it before and understand it well), and look at the places where you have uncertainty (unclear requirements, new technology), and for these, think about how bad it could go, and why. That will help you get not one number, but rather boundaries: what you think is reasonable, a worst-case scenario, maybe a best case scenario (which the client should never see :) ) - and convey that information to your boss, so that he can manage accordingly.
Additionally, this will allow you to identify the danger points of the project, and you can then prototype accordingly - look into the uncertainty points as early as possible, so that you can tighten up the timeline fast, and have early warnings for your boss and the client.

Related

Result Only Work Environment [closed]

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I would like to set up a ROWE for my dev team: Result Only Work Environment.
Basically, people work how they want, when they want, as long as the work gets done.
This environment has been a huge success for Best Buy: increasing productivity and reducing turnover.
Does anyone have any advice for making this work for a dev team?
Edit:
More details: I will be leading a team of 3 other fairly experienced developers. I plan on standardizing the basic processes, such as version control, bug tracking, code review, planning, testing, etc. "How they want to work" more refers to how they manage their time: i.e. scheduling meetings, pair programming.
If you have other departments in your org., consider managing their expectations as well. It will be difficult to convince them that their project is going to take longer (throw in all the technical jargon you can think of) than you thought when they notice your team is never around (in their eyes).
You'll still have to have realistic expectations in your planning. Are you really allowing for flex time when they have 10 hrs of work to do that is due in 10 hours? How are you going to handle trouble-shooting issues that get escalated to the dev team?
One developer could be consistently better than the rest/take less time, but the team may feel this person has a lighter workload. Get ready to crush some egos.
I guess pair-programming is out?
The answer to this question is going to vary depending on the size and culture of the organization. Some would also argue that the process can matter, and you don't want your people taking any approach to achieve a result at the expense of something which they do not feel as as important.
Can you provide more info on the size of the organization and what working there is like today?
Make sure you hire the right people, you might find they work more than they WANT to admit X-).
Programming is more than a job, its a passion, and if you find the right person to fit your environment, performance measures go out the door, as the do it for the love of it.
WHEN they want will be easiear than HOW they want. I wouldn't give that much freedom to devs. IMHO, this would lead to a total mess of code.
There's very few very good developers out there today and those that are good enough should be made development leads and make the global decisions. Others should just follow the instructions or all hell can break loose.
You need to define what the results they're meant to achieve are clearly and completely unambiguously so they understand what they can control (essentially how they work, the order they develop things in and so on) and what they can't (usually what they're expected to deliver - both in terms of actual product and supporting materials such as progress reports - and when it's all meant to be delivered). You also need to let them know what resources they have - can they order high spec machines or order new software for instance or is that all decided?
I'd also ensure that one of their early deliverables was a schedule of completed milestones against which you could measure progress and agree with them what happens if they start missing milestones.
But I am slightly dubious about the idea that you're going to define version control, bug tracking and so on. Surely these are things you should let them decide? After all they're part of the process. Personally I'd state that they must have version control, centralised defect logging and so on but the mechanisms, tools and processes should be up to them.
It feels a little like you say you want to create a results only work environment but you don't quite trust them. If you're saying what you're going to do is create a ROWE then you need to make sure it's just that otherwise you're really only doing half the process and those situations rarely deliver the benefits people are hoping for.
After all, either you trust them or you don't but if you can't trust them to work out how to do version control which is frankly second nature to developers, you probably shouldn't be trusting them with the schedule which is normally a far less straightforward matter.
Results oriented means that you must trust your developers to make the best decisions. Some people love this freedom. They cheer when they have the freedom to use a wrench as a hammer if it meant quicker results, rather than switching tools just to nail a picture on the wall.
But sometimes it could be damaging. Processes are designed for maximum productivity, efficiency, and effectiveness, with all kinds of safety measures. With the wrong subversion tool, a developer could easily slip and delete all history of all work done by the team, thus eliminating the magical "undo" feature.
In another case, most fresh grads (that I know) don't have the knowledge or capacity to make decisions on their own. They may not produce as fast as they would be able to with someone barking orders at him/her. One of the most distinguishable characteristics of a fresh grad is when he is stumped or doesn't know what's going on, he doesn't ask for help.
Your developers must have the right set of mind in order to achieve goals. Freedom is good, but monitor and make sure it's the correct way to go.

Has Crashing or Fast-Tracking a project schedule ever worked? [closed]

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I posted this question on Reddit Programming and did not get a single response. So I am hoping that Stack Overflow community will have an opinion.
Have any of you ever been on a software project that had fallen behind, where 'Crashing' or 'Fast-Tracking' the project schedule actually brought the project schedule back on track? I have never seen either of these project management techniques actually work. And all the articles on software development that I have read all state that these 2 techniques do not work and actually pushing the project further behind (for example literature on the Mythical Man Month). So who has seen it work?
Thanks Bill.
I have only ever seen it work once. It was a three or four month long project that was projected to run an extra two months over the original delivery date. The project got fast-tracked and things ended up getting back on track for the release.
...keep in mind though, that was only once. I've been on many more projects where the PM tried to use one of those two methods and they failed miserably and dragged the project out for months beyond already extended date.
It can work. But there's a price to be paid: lower quality (more bugs, less testing) and turnover of burned-out programmers.
And in many cases, a fast-tracked project will both fail to deliver on time and will still pay the full negative price, for the reasons stated in Mythical man-month.
I've seen it work but it's not the norm.
Things I'd want to see before I thought it might be feasible:
1) Staff available with suitable skills and approach. By that I don't mean ".NET programmer", I mean detailed technical skills, business domain skills (so they understand the problem), personality fit and understand the tools and the approach (source control, methodology and so on). This can happen in large companies where there are common tools, standards and knowledge but you need to be sure that they're ticking pretty much all the boxes.
2) Tasks must be nicely divisible. The best situation is where there are whole modules, applications or tasks unstarted and you can put new people on that. It minimises upskilling, additional communication and so on. If you can't separate out what the new people will do you're likely to majorly disrupt the existing team.
3) The whole team must have bought into the approach. If the existing team don't agree that bringing people on board will be right they'll likely fight it and you're doomed.
4) You need to be sure you've addressed why it was running late in the first place. If it was just bad estimates then are you confident the new estimates are good? If it was scope creep have you got the scope and change control in hand now? If it was because the deadline moved, are you sure it won't move again?
If you can't tick all four of those off, it isn't going to work.
Crashing and Fast-Tracking are two very different things...
Fast Tracking is where you take something (tasks or work packages) out of sequence and do it early. This may because of hardware delivery lead times, availability of resources, risk or whatever. So you might do things in parallel where originally you had planned to do it sequentially. I've fast tracked a lot of projects.. and yes it works.
Crashing a project is different in that you typically throw more resources at a problem to get it done quicker... this can be tricky. If it's done as a crisis response it can be painful adding extra people as you are already under the pump. In some situations you just add more problems.
Another alternative to crashing is to reduce scope. This is not always possible, but it should be considered.
With fast tracking or crashing... the sooner you know when you need to make a schedule change the easier to manage. This is why early deadlines are so important, they indicate how the rest of the project will go.
Both of these project management techniques work well to maintain a schedule, but they should be used intelligently by judiciously analyzing the network diagram:
study the variance,
study lead and lags;
decide what suits to your project: ‘Crashing’ or ‘Fast-Tracking’.
There is a software management principle that says adding manpower to a late project makes it later.
That said, as long as the measures taken are sensible it should be ok. Don't expect too much of your staff and provide reasonable incentives and don't take short cuts. It won't make miracles happen but if you're practical and want to push things just that little bit faster it can definitely be done.
When people have a stake in the potential success of something it's amazing how much more effort they're willing to put in.
It depends on what you mean by "work". I don't think I've ever seen it make a way late project deliver on time, if that's what you are asking.
However, I have seen it make way late projects deliver only a bit late. From the fuzzy perspective of management, that might be called "working". I've also seen it significantly lower the customer-based pressure on the company. Some might also call that "working".
Of course the price is rather high. Employees burn out, develop health problems or big problems in their neglected personal lives, etc. All of that has large financial repurcussions to the company. So I doubt the company comes out ahead in the long run. Is that "working"?

What should I do? let this product branch in two, or keep it unified [closed]

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I am a first time intern at a large corporation and I created a GUI tool that lets my coworkers visualize the log file that their product produces. The tool, known as MRI, is nearing completion and I face a conflict.
One party, (Two ambitious Indian guys that live in California) want me to adapt MRI to a new format and to display much more detailed information. The current version of MRI is built around the idiosyncrasies of the 20 year old log file format. In my opinion it is a bad idea to attempt to grow a more powerful, more universal tool out of a less powerful and idiosyncratic one (Better to start from scratch; something I probably don't have time to do).
The other party is composed of several marketing types and my father. They are drooling over the shiny new GUI that I slapped on top of their crazy old log file, and every one of them wants some feature that would help them with their day to day work.
Whom should I please? I just want to code. Which path will lead to less dumb conflicts like this?
Sounds like you are getting your first taste of the world of a manager! I'm doing exactly the same thing 10 years later, with a much bigger budget and head count. So it never really ends.
I love the answer about doing some time estimates for each requested addition, and then sitting down all parties and working on a negotiation that gets the greatest degree of satisfication. I'm betting that since you are an intern, and many of the people you mention have seniority, that they will be able sort out amongst themselves who has the biggest stake and most power in the situation. But if not, don't hesitate to act as moderator -- after all, this is your project.
Other things to think about:
Types of stake holders:
Customers - the person who controls the budget is often the most powerful of stakeholders, after all, they control your ability to do the work by controlling your funding. For an internal tool, this is probably an internal stakeholder, but it may be someone from a non-engineering group, if this tool is for a non-engineering purpose.
Users - in the long run, users often make or break a tool. They definitely determine the tool's longetivity. It's not unusual, though, for users to lack advocates. And in a big internal project, it's entirely possible that users are not the customers.
Technical Management - particularly when you are an intern and when you are working on an internal project, technical management is the group that's most important for you (as an individual) to please. They may have their own stake in the feature set, as they may be looking for a certain feature path for the product that fits a long term technological end game. Ideally, they should be on your side, and helping to figure out the best feature set.
In a big company, hopefully these roles are really well defined. Probably with an org chart. But not necessarily. And in a group that's used to working together, they may not make it really clear to a new comer exactly what the official roles are. As the guy doing the work, you're job should be to accurately and honestly tell them your best guess on what effort it will take to get the feature done. And to be open to ideas for making it cheaper/easier.
Negotiation:
The best negotiation advice I've ever gotten was "A good negotiation is one where everyone thinks they won". Sadly, the frequent outcome is that everyone feels equally screwed. The trick between every stakeholder leaving happy and every stakeholder feeling beaten down is to see the big picture and be innovative about getting everyone's needs met. In the end, no one really cares how you do it, if you can make their jobs easier, they will be happy. So finding features that serves everyone well can be the key to resolving the conflict.
Being able to do this well will really make a positive impact on your bosses. This is an extremely rare skill, and this type of finesse does get noticed.
Not having it does not mark you as a pariah, however, not many engineers enjoy negotiation. And it's never worth making every engineer be good at it. It's far better to find an engineering manager who is good at negotiating and to let them be the "speaker for the geeks", so the rest of the engineers can do their work in peace. :)
Sit the two parties down in the same room. Show them a list of the features each has asked for and how long you think each will take. Then explain that all of it is possible but all of it takes time, and ask them to come to agreement on what they would like when. Note down what is agreed and mail it to everyone afterwards so there is a record. Don't forget to pad your estimates to allow for testing and debugging time.
Alternatively, work out who the person directly responsible for managing you is, implement what they tell you (feeding back estimates of how long each thing will take) and tell anyone else who asks you to implement anything to go talk to that person to get it on your schedule; then doing the above management work becomes their problem.
Explain, if doing one of the above does not cause the matter does not resolve itself, that the Californians' features would require a refactor, and if you are going to do that you would rather hold off implementing any features for the other party until that is complete since doing the same work twice is wasteful.

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

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What do you do when you get assigned a project that is just way too hard to do:
Say it's a mammoth project and your boss thinks you alone can handle it
You have knowledge to do somethings, but some other things are a little beyond your expertise at this point in time
Your boss probably thinks it's something that can be done by one person in probably one month
SO users, I would love realistic answers here. This is a real world situation and I am trying to figure out my response to my boss tomorrow on how to approach him delicately.
I just wanted to add an update to my note here. The app in question that my boss is targeting is a "NING like" web app. My hesitation is mostly being the only person being assigned to it for such a complicated app in such a short time period.
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. :) )
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! :)
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.
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.
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:
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?
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.
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.
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."
Research Ning. What are all the things Ning can do? On Ning's Resources link, they list at least 21 major social network features.
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.
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?"
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.
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.
Here's how I would plan it out:
Don't panic and to react - tell your boss that you would like to review the request and will get back to him shortly with questions and concerns
Go through the spec (or if there is no spec, the email or write down the request somewhere) and create a work breakdown structure for each delivery. This should be done to a level where each item is understandable (User Login, Message Entry, etc.)
For each item, est. the amount of work and +/- % amt. based on your knowledge, questions, risks, etc.
Create a list as you're going through the spec of any major/important questions (how many people is this targeted for? does this include the ability for users to IM, etc.)
You now have a rough timeline, risk assessment and list of questions to review with your boss. He'll see that you put some effort into it, may open his eyes to the complexity and provide him with confidence that you are not knee-jerking reacting. He might demand you do it in the timeframe he provided anyway....look for another job, you have at least a month.
What you say is that your perception of the task scope and complexity differs greatly from the perception your boss has. Great.
Most likely you're both wrong: you have misunderstood the requirements and the boss underestimated the task or fell into the trap of wishful thinking.
It's best to go through the requirements with your boss once again, work out together that deliverables are required, try to guestimate amount of time and resource needed to deliver these. If there are blind spots in implementation that you feel you lack skills or expirience for, make this clear and work on the assumption that you'll have spend cash to source these externally (that will at least give you an idea of a market price).
I am sure, the longer you and your boss spend discussing and researching the project, the more detailed the dissussions will become and the better idea of what is feasible will emerge.
The worst thing you can do is to keep quiet. Any good boss relies on developers to give some assessment of a project: either affirmative or hear more questions.
You don't have to say "no", that's not your job to decide whether to go ahead, but you have to be asking good questions.
It really depends on the relationship you have with your boss. If you can, I would just be open and honest with them. Tell them a few things are beyond your level of expertise and you would have to do some research, lengthening the project time. And stress the point that you don't believe you can get it done in a month and you're requesting a team to help.
It's possible your boss doesn't really understand the full scope of the project. If you can break it down into a list of tasks or sections to show how much work really has to go into it, they might see where you're coming from.
In the end, if your boss still wants you to go through with it, just keep stressing that you will do your best but you cannot make any promises about the deadline.
You need to be realistic with your boss. You will come out much better having over-delivered on the project rather than under-delivering on an aggressive timeline.
You have to be honest and tell the boss that there's a problem. However you need to show how much exactly of a problem it is so that you don't sound like an incompetent person waiting for a pink slip.
You need to carefully analyze what is to be done and break it into small parts and see which of them you can do and which you can't. It's normal to have parts in the project which look possible but hard to do - every normal boss usderstands that.
This way you show that the problem is not imaginary and it's not your desire to get nice salary for trivial job.
The truth of course is always the right answer, which your boss will find out eventually, better to fail early.
But with that said, is it something you just don't want to be involved in. Make sure you explain to your boss that you don't want to commit to something that you're sure to fail at but let him know that it could be a learning experience and at least be involved at some level, even if it's to look at the solution after it's done.
Create a realistic schedule and present it to your boss. Ask your boss for his input regarding the schedule. Maintain a positive attitude and let him know that you are both working toward the same end goal. Tell him that this is your best professional estimation of the amount of effort needed to meet all the requirements. Point out where the complexities are if challenged. Be firm and clear and above all else give him an opportunity to speak his concerns. Demonstrate good listening skills and address each of the issues he presents in a language that he feels comfortable with. I wish you all possible success in your project.
If estimations are not yet there then your first task is to do a realistic project estimation. Second task would be to check what technologies are required for the project and check if the knowledge is already available. If not then estimate for the training and gaining the knowledge. I understand boss is boss but you do your part and rest is up-to him. If the boss appreciate others opinion then he will understand but if he is like "I am always right" then you do whatever you can(work as best you can and also look for a new job).
Its a bit on the side of all the good advice I've seen here, but I'll say it anyway: most managers are actually quite smart. Senior managers I've met have all been very smart. The problem is that, as Eric Raymond puts it, they are "differently optimised". So they may need some education. If you assume that they will be reasonable once they know all the facts then you will almost always be correct.
Of course you do occasionally get people who behave unreasonably, or think that saying "make it so" like Captain Picard is Leadership. But they are rare, and do not last long.
Go fight club on him? Get free monies and airfare!

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I find way too many projects to get involved in, way to many languages to play with (and way too many cool features within those languages), and way too many books to read...
How do you guys stay focused and actually get anything done, rather than leaving a trail of partially complete "experiments?"
Seems like there are two types of developers: Tinkerers and Entrepreneurs.
Tinkerers want to know how every little thing works. Once they get the hang of something, they're distracted by everything they don't know. The tech world is brutal for a Tinkerer because there's so much to learn and each new year creates more. Tinkerers are proud of their knowledge.
Entrepreneurs want to know enough to build something really great. They think in terms of features and end-user experiences. You never hear them argue about Python over .NET over Java over C because they just don't care. They're more interested in the result of a language versus the language itself. Entrepreneurs are proud of their user-base.
Sounds like you're struggling with your Tinkerer tendencies. I've got the same problem and have found only one thing that helps - find an Entrepreneur developer that you thoroughly respect. When you put the two together, it's unbeatable. The Tinkerer plumbs the depth of every technical nuance. They keep the Entrepreneur technically honest. In turn, the Entrepreneur creates focus and opportunity for the Tinkerer. When they catch you browsing the Scala site (assuming you're not a Scala developer), they reveal a new challenge in your existing project. Not only that, they're much better at understanding what non-Tinkerers want.
Money, and the feeling of accomplishment that goes along with actually finishing something. When I first thought about working for myself I started coming up with ideas of software that I would develop and then later sell. Of course, I really didn't know if what I was making would actually sell, so it was easy to get distracted and jump at new ideas.
So I decided to go with being a contractor/consultant. When you know that there is a buyer for what you're making, and that somebody is waiting on it, it gives you motivation. If it's an interesting or challenging project, there's a rush associated with finishing it. So that adds extra motivation because you want that rush more and more.
Once I got a fairly steady flow of work-for-hire projects, I found that I can stay focused on my side projects better because I have incentive to practice good time management. I give myself a certain amount of time every day or week to work on my side projects, and it helps me stay focused when I take that time.
Of course, I still go off on tangents occasionally and start new side projects as well, but the ones that I am most interested in I have been able to stick with.
Also, after you finish some projects, then you get a better feel for what it actually takes to go from conception to completion, and it makes it a lot easier to do it again and again.
I think a good programmer may well have lots of unfinished "experiments" hanging around, this is a good thing.
Usually with a good manager, you will be held accountable if your work is simply not getting done. If you're a student, though, it's tougher. I realized that it is impossible to learn everything you want to.
I limit myself to only learning 1 or 2 new languages per year, and only 1 book per month. That seems to be a nice balance between programming chaos and getting my job done well.
Kudos for having a great learning attitude :)
Probably the best motivator (for a team or an individual) is to set goals early and often.
One of the best methods I've observed in project management was the introduction of "feature themed weeks" - where the team (or an individual) was set goals or deliverables which aligned under a general flavour, e.g "Customer Features", "Reporting and Metrics" etc. This kept the team/person focused on one area of delivery/effort. It also made it easy to communicate to the customer where progress was being made.
Also.. Try to make your (or your team's) progress visible. If you can establish an automated build process (or some other mechanism) and "publish" incremental implementation of work over a short period of time you can often gain traction and early by-in which can drive results faster (and help aid in early course correction).
1) I leave a utterly MASIVE trail of unfinished stuff, all side projects of course.
2) When I need motivation to work I open my wallet... That usually does it for me.
I'm building an app I plan on selling and see it as a way of making extra money or reducing the amount of time I spend working for other people.
My wife likes this idea and her encouragement has managed to keep me focused longer than normal as it's now "work" rather than "play"
I find that getting involved with the "business" side of the equation helps tremendously. When you see how much benefit the actual users of your program can get out of your creative solutions to their problems - it's an extreme motivation to provide those solutions to them. :-)

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