The pros and cons of "Shadow IT" in software development [closed] - user-defined-functions

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Recently we’ve seen the emergence of so-called “Shadow IT” within many organisations. If you’re not already familiar with the term, it refers to those who manage to dodge the usual IT governance by means such as using thumb drives to share files or “unapproved” software products to achieve business tasks. Shadow IT can emerge from within technology groups but in many cases is sourced from non-tech areas such as the marketing or sales department.
What I’m really interested in is examples you have of Shadow IT within software development. Products like Excel and Access are often the culprits as their commonality means they’re easily accessible to the broader organisation. In many cases this is driven by someone who has just enough knowledge to make the software perform a business function but not quite enough to be aware of all the usual considerations required when building software for an enterprise.
What sort of cases of Shadow IT have you witnessed in the software development space? What processes have you seen unofficially addressed by this practice and just how important have these tools become? An example would be the use of a single Access database on a folder share becoming common practice for tracking promotions across the marketing department. Remember this cuts both ways; it can be extremely risky (lack of security, disaster recovery, etc) but it can result in innovation from a totally unexpected source.

Why does IT assume they should own and control all technology in the business?
The very fact that we have a name for technology that IT does not control (Shadow IT) suggests that we'd like IT to have control over all technology in an organization.
The only real reason I can think of for IT to have control is security (even then, I'd be very weary of trusting the most sensitive data to IT). Most other reasons given against business user-developed solutions are completely false. Take the reasons above: "software produced may not be well designed...", "the software may not be well supported...". Who are we kidding here? IT's track record on these fronts is simply not good enough to claim the high ground here.
Savvy business users solve their own information problems - they have been doing so long before IT existed. Anyone remember triplicate forms? Fax machines? Photocopiers? These things didn't need IT departments to govern them and they worked very well. If IT cannot solve the problem, or IT's track record has been sufficiently poor that business users have lost faith in IT, then business users will solve their own problems, using whatever means are available to them. Access, Excel, and shared drives are frequently used very successfully by business users. If IT is to stay relevant to an organization, it needs to support it's business users needs and deliver technology that people actually want to use, not just technology people use because they have to.
I have seen an organization where a multimillion dollar portal implementation promised to solve many business technology and information sharing problems. Years later, still not in production, business users gave up, and in despair developed their own solutions by outsourcing the development of a data centric web application. Guess what? It worked brilliantly and other departments are now bypassing IT and doing the same, on their own departmental budgets.
IT is a support organization for business users. This may offend some who believe IT's place to be somewhere alongside executive management in terms of its importance to the business, but IT has to deliver what the business needs, otherwise its just justifying its own existence.

The advantage is that users get exactly what they want and need, when they want and need it. Getting a request through a largish IT shop is a trying experience for a user. IT rarely has the business knowledge to let them give the business owners exactly what they are asking for, and when requests are denied or requirements amended, an explanation in plain English (or whatever language) is rarely forthcoming.
The disadvantages outweigh the benefits. Societe Generale lost billions due in part to "Shadow IT". It can cause support nightmares when an Access application, for example, becomes essential and outgrows the capabilities of the person who created it, or that person leaves. Even a poorly written Crystal Report can become so popular and widely used that it starts to drag down the database it is accessing when reporting times comes around. And if the person who wrote that report did not fully understand relational databases, it could produce bad data in some situations; data that causes bad business decisions to be made. Using a commercial (outsourced) application guarantees that the users will not get exactly what they want; there will always be compromises, and no explanation of why they were made.
The previous poster was right. Shadow IT exists because IT does not do its job well enough. There is not enough business knowledge, not enough responsiveness, and especially not enough communication. These things are why "Shadow IT" exists. The business owners paid for the machines, the admins, the dbas, and the programmers. It frustrates them when IT loses sight of that.

At the end of the day, the primary driver for most businesses is results i.e. making money. If the business sees that it can achieve the desired outputs necessary for the operation without spending thousands on software but through "shadow IT", then I can only see it being encouraged. I feel that that it is part of our job as developers to point out the pitfalls in operating in this fashion.
The pros of "shadow IT" could be
cost - less expensive
whilst the people writing the software may not be software experts, they are likely to be domain experts and have an intrinsic knowledge of how a piece of software should function.
depending on how the IT is organized, "shadow IT" may be able to respond faster to changes and business needs than the core IT can.
And the cons
software produced may not be well designed to be extensible, handle errors correctly a d all other aspects that come from experience in software development.
the software may not be well supported or, due to the way in which it has been produced, there may be no support at all.

Over time, the average person is becoming more IT savvy. Younger marketeers and finance people know that Excel and Access make them vastly more efficient. Working without them would make them feel handicapped.
I expect this trend to continue, and Corporate IT becoming more of an enabling organization. Where you make available data, help users troubleshoot their workflow, and limit them to a specific compartment for security.
What was called software development 10 years ago, will be everyman's tool 10 years from now!

There is no such thing. There are dinosaurs, and there are people who need to get work done.
If something like 'Shadow IT' happens, it is because 'Official IT' is not doing its job.
Software developers have hundreds of little and not so little applications they need to get their work done. The IT governance organisation should learn how to handle tens of updates a day, and switch to releasing daily (and patching a few times a day). Development has learned how to do that, they are next.

Sometimes I use Amazon EC2 and/or RDS when my company's resources are not enough or would take too long to provision. I pay for this out of my own pocket but do get to achieve my goals faster. All this without having to spend painful hours in meetings, trying to convince superiors or the SA-s that I really do need to do some thing or other.
In my mind, EC2 is the ultimate shadow IT. It's super easy to get going and provides me with the ultimate control.

Well, I suppose these things are everywhere. Not a big deal if it not threatens the company operation in any way.

Ya it's a big problem where I work. Architects and DBA's try to make a centralized system but these little "Shadow IT" departments make these small apps that have their own security or duplicated data... Personally, if I was the head of IT I would fire anyone who started such a project without IT support. Kinda harsh but it's important to keep the system healthy.

Most software developers have "unapproved" software on their computers. Just expect it. I'm not sure how much I have, but I'm sure I have dozens, if not hundreds of utilities that corp. IT has never even heard of on my work laptop.

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Protection of code from its own developers [closed]

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Perhaps the most obvious way of protecting a company's intellectual property from its own developers seems to be an NDA - Non Disclosure Agreement. Effectiveness of this approach may vary, depending on many factors, and sometimes or somewhere it may not work as expected.
What other approaches, apart from this purely legal one, exist for protecting software code from the people who develop it? Do they exist at all? Does it make sense in practice?
Maybe, for example, Team Edition of Visual Studio already contains some features related to this problem (for example, levels of access to parts of code, depending of role inside a development team or something like that)?
Reference on the topic:
As statistics says, on average, programmers tend to change their job every three - four years.
Try to build a team you can trust.
The first approach is to force programmers to only know interfaces of other components, so that each one can only steal a small part of the whole software. This approach can be borrowed from footwear production. One transnational corporation, to prevent stealing by employees, arranged its factories so that each factory produced only left or only right shoes. You could do the same with your code: some programmers only write lines with odd numbers, and the others--those with even numbers; provided that they can't see the work of each other! That's sometimes referred to as "pair programming".
Some organizations force employees to sign a non-compete agreement. That's the kind of agreement that prevents programmers to work for competitors. This technique is best combined with job postings like "Looking for senior programmer with 5 years of experience in the similar field".
To prevent your programmers from stealing, you can do harm to them as soon as they finish the software. The method proved itself as the most efficient, and has been used for centuries. For example, Russian Tzar Ivan The Terrible burned eyes of the architect that designed a beautiful church at the Red Square, so the one designed remains the most beautiful ever. You can do something like this to your architect. I heard, latest Visual Studio contains some features...
Nowadays, however, it's more humanistic to hire already blind and already dumb people that lost their hands, so that they can't look at your code to memorize it, can't tell anyone about your code and can't type it again. The advantage is that this will help you dealing with labor agency in your country, which watches for balance that your employees are not discriminated.
And yes, this post is a sarcastic joke, which criticizes the idea of any code-stealing-prevention measures. Sorry, couldn't help posting it.
How do you protect a power plant from sabotage by an employee? How do you prevent a boxer from throwing the fight? How do you prevent a brothel from distributing the clap?
Your concern, while valid, is one that can only be properly addressed by personal responsibility and accountability within your team. Any options you employ to secure the code against theft is likely do more harm than good. If you feel a team member is not trustworthy, get rid of them.
If really necessary you can split the application in subapplications.
Each team works in a single application and sees all others as "black boxes". Maybe SOA helps here.
It's highly unlikely that your code is the real intellectual property - that is your company's business knowledge and process.
SVN has the ability to limit different users to different folders, so you could split your code up into seperate libraries, and allow only certain people Read / Write access.
The file for this is under conf\authz
Here is a sample
[aliases]
# joe = /C=XZ/ST=Dessert/L=Snake City/O=Snake Oil, Ltd./OU=Research Institute/CN=Joe Average
[groups]
# harry_and_sally = harry,sally
# harry_sally_and_joe = harry,sally,&joe
[/
# [/foo/bar]
# harry = rw
# &joe = r
# * =
# [repository:/baz/fuz]
# #harry_and_sally = rw
# * = r
Some documentation can be found here
Under 'Per-directory access control'
Either build a team of developers that you can trust, or entirely lock their system down so they can't access the USB ports, the CD drive, or web mail clients. The only thing they could do is work on the code and possibly browse the web. Also only give them access to the code that they are in charge of.
But with all these security measures chances are your developers will hate working with you and quit their job
There's no straightforward way to do this if your code is within the same project (i.e. you want to allow access to some parts of the code and not others). However, if you have seperate projects that require different security levels, it's possible to allow developers to only have code access to certain projects, and then pull builds from a common build server.
Keep in mind that decompiling of frameworks that work against IL like .NET is relatively straightforward, so preventing access to the code files is not necessarily a silver bullet to protect IP.
I know you said aside from the purely legal one, but I'd just like to add that in addition to the legal one you mentioned, there is also the Non-Compete. Basically says that once you leave your job, you won't be able to compete in any way against your former employer. Stealing code is not as appealing if you won't be able to put it to use for a year or two.
You could make them develop a module that would be seperate from the rest of the application. If you had a plugin/module type system going this would suit well. You could release APIs for the developers to develop against and have them integrate with your DLLs and not the source code.
People seem to be very critical of this but there are legitimate reasons for doing this i.e. partnering with a potential competitor if you gave them all your source you would be shooting yourself in the foot.
It might be worthwhile to spend some brain cell activity on the business model you want to follow. If the core value is embodied in the code, the core value can be stolen by stealing the code. If, however, the core value of your business is embodied in a group of employees, some of them engineers, others sales people, yet others customer support people, and when the software is only the net that keeps these peoples business going, then there's no easy way of stealing the value of your business. And if the software does get stolen, the thieves won't be able to make much use of it.
So, in addition to what cherouvim said, build a team that you can not just trust, but a team that is the core value of your business.
Develop your software in modules.
Have one common module that contains objects that pass back and forth, and utility classes that act on those objects.
Have each group build modules on top of that, without much need to know about other modules.
Have one trusted team of developers do the planning of what goes in each module, and have that team also do the integration of all of the modules into the whole.
Also have a lot of trust in whoever runs your version control server. While it's stable, no one developer can do all that much harm; they can't delete everything, for example, and you'll know exactly what they did and when if that ever becomes an issue.

What's most important when you need to establish a software development infrastructure in your company? [closed]

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Let's say you work for a huge company which suddenly decides to do custom in-house software development. Additionally, they want to be able to offer successful developments to their customers as well (if any).
Now you are in charge of it.
What would you see as most important to build a successful software development infrastructure?
flexible to future growth
flexible on used technologies (projects with c, java, .net, web, mobile, ...)
What kind of tools (source control, forge, ...), hardware (virtual, seperate dev & production, ..), processes (guidelines, code reviews, ...), etc.
UPDATE: Please don't answer that you need the right people and the right tools. This is exactly what i am looking for.. What are the right tools and what people of what type would you hire first to join your team? Think of it as you will be the lead of that development.
Set yourself up to pass the Joel Test with at least a score of 10.
I think having the right people is going to be the most important. Nothing else will matter if your programmers stink.
Someone in charge who knows what they're doing.
Obviously, there are lots of factors, but here are the ones I'd say are crucial:
Hire smart people (and pay them what they're worth)
Select good tools appropriate for the kind of development (don't go for cheap tools)
Establish version control system and policies
Establish testing mechanisms and policies
Don't be afraid to outsource the stuff you don't know how to do
Get the best people for the job. If they aren't willing to pay for the best available, or give you a hard time over your personnel budget, you're off to a bad start.
Get the right tools for the job... software, hardware, support contracts from your vendors, etc.
Establish procedure early on for your development life cycle, and make sure that you have the people in place to make use of it. This is everything from how you evaluate Opportunity Assessments to Development, Testing, and post-production support. Make sure you have the people and the tools for each part of the life cycle.
Dont try to be flexible in technologies. First start by focusing on one technology (Java, .NET, whatever...) and then move to other if you need to. You will be able to solve problems using any technologies, but it is very hard to find people good in many technologies.
At the infrastructure level, Source Control is a must. Continuous integration is a plus. Take time to put in place a standard project layout that you will be able to evolve. It make it easier for developers to switch projects. Take time to put in place a good build process (Ant, Maven, in the Java world). Integrate your build process with your IDE so that developers dont have to wait 5 minutes to deploy their project every time they want to test a code change.
I agree with Guillaume: If you want to build a department from scratch, you need to focus. You need to build your team, have everybody grow into their new responsibilities, get to know each other etc. Trying to go into too many directions at once is the direction towards failure.
So, identify the technology you want to develop in. Since the primary goal in your example is in-house development, the in-house requirements will determine your decision. Build your team with that primary goal in mind.
For in-house development, you need at least two people who already know the company and its processes. (Two because one will definitely be ill or on holidays when the first major crisis hits you). On the other hand you need some outsiders, who are not entrenched by the "we have always done it like this" mindset, who can think out of the box. Those should also be at least two people, for the reason stated above. Your job as the team leader is to balance those two groups and integrate them into a team.
For future growth, always think in terms of organic growth.
Do not increase the team size by 200 %, hire one new guy here and another guy (or gal) there. Slowly build your team.
When you take on a new project, always think of expanding your teams expertise. Try something new with every project. That can be a new source repository, an automated daily build process, a new system to write specifications or documentation, or even a different technology (for example Java when you usually develop in .Net, Delphi or C++). Just make certain you never try to make a big leap in an important project. (I once worked for a company who decided to switch from VB 6.0 to .Net for the biggest project they had ever attempted before. They survived. Barely.)
That way your department will slowly but constantly expand its capabilities. Then when the opportunity presents itself to do development for an external customer, you will already have accumulated most of the knowledge you need in order to pull it off.
Oh yes, and smacl is right, too: You need solid QA/QM if you want your department to survive long term.
Start laying out (and follwing) your QA rules from day one. Keep them as short and flexible as possible. Add what you discover to be missing, and throw out what proves to be unnecessary or impractical.
Not sure this is what you wanted to know, but I felt the need to say it ;-)
Develop a strong QA strategy, including acceptance criteria and change control. Preferably keeping it lightweight to suit internal clients. In addition understand how to carry out requirements analysis, expectation management, and resource management.
Put another way, don't just wing it to create crappy solutions that waste more time than they save and are impossible to maintain. Take time to think about what you want and need, how you can achieve it, and what it is going to cost.
I will offer an answer more focused specifically on coding and the developers / architects role in addition to the previous answers on teams, version control, qa etc. which are of course all important.
Many of your decision is very dependant on your specific business and software structure (a single product code base, SOA, many projects etc.) But in general you should always spend significant time up front developing Core Software Infrastrcuture that will pay huge dividends during the SDLC.
Software infrastruture
Coding Naming Conventions Exception
Handling strategies Logging
Strategies Settings and Configuration
Base classes and Helper Classes
General Architecture and Layers
(Presentation, Facade, Domain
Entities, Data Stores etc.)
Design Tools such as UML 2.0
Requirements
Management / End user interaction
There are tons more, but these are certainly some basics to think about. All of the successful projects I have been involved with incorporated decent software infrastructure. I will also note that many of the project that fail have a common theme... lack of a common infrastructure in place. In most cases these failed projects are lead by a non-technical person that think they can simply throw a bunch of ideas at a few programmers and expect them to deliver in a few weeks.
Bottom line, you need to invest some up front planning and prototyping to ensure success in the long term!
Good luck.
Raiford
www.blacksaber.com
The first persons you should hire should be experienced senior level professionals. Then build up from them / with their input. Add the junior people later.

Build vs. Buy & Integrate - How do YOU make the decision? [closed]

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I've seen a lot of questions and discussions about build vs. buy, but most stick with the simplistic approach that you can simply do one or the other. Most of the time you have to either buy and integrate or build yourself. Either way you're in for some work.
In the next 30-60 days I NEED to implement a couple managerial projects to keep everyone from ripping their hair out and killing each other. The largest of which is a ticketing system (emails, support requests, self service, etc.).
There is no shortage of options but at the end of the day we'll have to buy whatever we decide to use, add all our clients and their users and make sure we keep things in sync over time. We'll also have to provide a single sign-on and do some design work to make it all look like we built it from scratch.
If we build we get to skip the integration pain points, albeit with a limited (but focused) feature set.
What do you typically analyze while making a decision like this? If it better to have 4-5 systems that do a very specific job well, or one monolithic system that does everything?
You've identified a key issue - when you buy you still have work to do, and potentially lots of it. Having said that my overall leaning every time is towards buy. Writing code is hard, debugging code is much harder - when you buy, you're not just buying the code/application you're buying the fact that it works - the latter is 90% of the benefit.
However, as your needs are pretty common, why not go with open source. This has two stand out benefits.
1) As you have access to the source, you can bend it to your will - ie no need to lash single sign on over the top of an existing system. Tailor the login modules to use your already existing infrastructure, therefore no need to keep things in sync, time savings, clean approach etc etc. Much open source acknowledges the real world by componentising (?) those aspects which are environement specific anyway. They're often DB/Identity agnostic.
2) If you choose wisely you will have a ready band of top tech staff who already understand the system ready to help - the only problem is they don't work for you (yet!).
My advice would be pick one of your easy targets - the ticketing system seems like the one, analyse whats out there that in the open source world that meets most/all of your needs. Evaluate and put out a request on Rent A Coder for any changes that are required. Sit back and await the results, which are hopefully excellent. You've lost a little time, and gained a lot of experience.
Open source does not equal Linux/Unix - lots of good stuff for .Net out there too.
One system is better for the following:
One data repository(i.e. the Database)
Easy way to link each system together, do cross referencing. No need to build intermediate importer/exporters/sync-ers
Allows for single log in. This is very useful in businesses to make sure everyone know where to find the right information. So more "what was the site for the bug tracking again..." Not everyone will use all the tools the majority of the time, and they will forget how to access and even use.
Everything has the same look and feel
Saves on training
Maintenance is cheaper. Everything is the same to update. Admins dont have to specialize in hear separate system.
But... obviously you're stuck with what you buy. Make sure to get a system if you can that you can build your own addins for, to match it to your busienss' model.
Obviously "it depends." My general rule is that if it's internal we buy it and integrate if required. Our corporate sys admin has a support line to someone external to our organization if she has issues and it isn't a huge project burdening our developers.
If it's part of a product I'm shipping, I build it or take bits of source as needed from open source libraries. There's nothing worse than someone else's black box code breaking your product. The fewer the dependencies in a shipping product the better, IMHO.
I'd lean toward buy for a support product like you mention. The good ones offer great integration points to shared authentication systems, user facing theming, and probably a boatload of features your customer service team hasn't realized they want/need yet.
But, what to analyze. The biggest thing for me when it comes to 'managerial' projects like this is opportunity cost. What else could my team be working on that will make our company significantly more money, get us more customers, etc? Of course these projects have some positive impact on the bottom line, but nothing compared to new products, improved products, etc. How long over time, including maintenance, will developers/pm's/testers spend on this managerial project? If you buy, integration points don't change often, but if you build, your customers (in house people) will be asking for new features constantly and you'll be in the position to maintain this project for the rest of your tenure.
Buy? What is this buy of which you speak, stranger?
Seriously, I haven't had to buy a piece of software for my own projects for a long long time. All my development tools are free, all my third-party libraries are free (not GPL). Even my OS is free. I have to pay for Windows for testing purposes but the majority of work uses tools that are cross-platform.
Anything that requires code not immediately available from free tools or libraries, I either write from scratch (all the algorithms are available for free on the web) or use my (huge since I'm so old) snippet library which I've been adding source code to for many years.
It's almost always quicker to buy ("obtain") than build unless the bought stuff is so crappy that integration is a nightmare. This can be mitigated by avoiding the latest whizz-bang stuff from suppliers that have little track record.
The more 'standard' your requirements, the better buying fits (Or to put it another way, don't reinvent the wheel). Conversely, the more unique your requirements the more you might consider building.
You quite rightly point out that even when buying there tends to be some customisation. Bear in mind that any customisation will cost you at each upgrade/patching time. I suggest that if your requirements are close to the business model supported by one of the tools you might buy that you serious consider realigning the business process to the vendors standard. If this is not possible ask if you are buying the correct tool.
I would suggest that if someone suggests building it for cost reasons run screaming. In my experience the cost of buying is well known and the cost of build is well hidden. Remember that you will be making a decision to keep coding for the life of the App (average of 7 years for a business app) but may be considering only the initial development cost when deciding between buy and build.
I have a strong preference for a single monolithic database but sometimes this is not workable. More important is to have a 'single source of the truth'; if you have multiple databases holding like data, pick one as the authoritative source of a given piece of data and have a process to maintain all others in agreement with that source. Preferable this will be automatic.
The monolithic system that does everything is the the Raison d'être for so many Enterprise applications. What I've found, however, is that if you're not willing to pay a buttload of money, you're going to have integration issues.
The 'best' solution is quite subjective, and any answer is as right as it is wrong, but if I were king, I'd probably go with the entrenched open source solution where it fit, and wrap web services around the items that needed to talk to each other. If I were king.
As a tangential point, there are free ticketing systems like RT (et. al.) that you need not worry about buying.

Software project manager: what is the best amount and quality of purely technical background? [closed]

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We are looking at hiring a software development project manager. His job is going to be concerned with running multiple dedicated project teams focused on delivery of software for external customers. He will also need to provide support to our business development unit and oversee post-implementations support of the aforementioned software. What level of hands on development experience should we expect from the applicants? Successful candidate is not expected to do any coding.
Not important. We should be focused on proven project management experience in software area.
None.
Some experience, exact technology does not matter.
Heavy experience, exact technology does not matter.
Some experience involving same acronyms as we use daily over here.
Heavy experience involving same acronyms as we use daily over here.
Some experience, mostly with technologies we do not use.
Heavy experience, mostly with technologies we do not use.
This question is regarding the best level and quality of required technical experience and is not concerned with any other skills and qualifications of a software project manager. Many thanks.
As with any position, you need to assess first and foremost what skills and experience you need on the team for you to be successful. Then hire to fill the gap for the skills that you do not already have on your team.
If you already have a team with strong technical and technical leadership skills then you don't need to hire someone who is likely to compete with the people you already have. If you are missing this, you probably want to hire a technical manager with some project planning and tracking skills.
Great project managers are those that are multidisciplinary - they are most successful where they can bridge the divide between the various stakeholders and team. The primary role of the project manager is to manage risk and facilitate communication and collaboration. As a minimum, you should look for someone that has proven experience in either your industry or with the technology space that you are playing in, otherwise they will be unable to gain the respect of the rest of the team and perform their primary role.
Which brings me to something else you should consider carefully - what is your culture? For example in a previous job, we had development leads that were very strong technically and wilful. Project managers were always relegated to second chair, and pretty much ended up as glorified MS Project admin. assistants. Anyone good did not stay long. What do you need to do to allow the type of skills you want to acquire for the team to flourish?
Most of our project managers have zero technical experience, so I'm guessing the skill sets are different enough that it's not necessary. However, they have to be bright enough to grasp/learn the concepts involved in development -- just not the implementation.
That's not to say that a technical background would be a bad thing -- it could be a "nice to have". Then again, it could possibly get in the way and they could try to control the implementation.
In my experience the very best technical managers I've had had very strong technical backgrounds (and usually were a little reluctant to trade herding code for herding coders). The worst were the the ones that were merely average programmers at best and had more of a management background.
The tentative conclusion I've drawn from this is that while not all programmers are management material, all good technical managers started out as good programmers.
Note that this answer is coming more from the perspective of hiring an engineering lead. For a project manager - someone whose job is to interface between the technical people and the customer - technical acuity is probably less of a requirement.
Some technical skill would be nice, but far more important is that they understand the functional area your company exists in. So if you sell an OS, then you probably want stronger technical skills than if you're writing banking software, for example.
Go with point 1. "Not important. We should be focused on proven project management experience in software area."
Edit: (after re-reading your intro-para) Seems what you want is a product-manager, and in support you need team-leaders on the diverse teams to handle and report on the technical issues. (Also since customer-contact is involved: a little marketing experience won't hurt!)
As an aside:
You are focusing on the wrong skill-set. You want proven administrative skill; proven organizational skill; and above all: proven people skills - (s)he must be able to communicate without antagonizing or patronizing the audience. The technical staff and programming staff will have all the necessary experience in development. (S)He must be able to manage and control these staff members effectitively.
The manager has to be able to communicate with developers. This either requires a decent technical background, although not necessarily with the same technology, or enough humility to know when the developers know more about something than the manager. I've seen both work well.
I think what I'm saying is that having respect for the developers is important, and there's two paths to it: understanding what they do, or understanding that you don't understand what they do.
Answer is "4".
Heavy experience with some technology is critical. I know the mindset is "project manager does not have to understand technology, he just manages people".
Well no, PM does not manage people: he manages project that is supposed to produce some deliverable that is acceptable at least across some desired aspects (capability, performance, reliability, security, maintainability, etc). If he can't understand technology, he's lost. Of course, he does not have to be an expert in peculiar technologies used in a project: but he has to be able to filter BS away, to question programmer's estimates (we know how those go), to feel at least technical risk here or there, to be able to formulate business ramifications of particular technologies.
In some ways I think that PM's challenges re technology are even bigger than those of programmer: he has to be genuinely interested in technology, yet he can't / should not have any technology bigotry, to be actually fair towards them (what they are actually good for and what they are actually not good for).
Read "In search of stupidity" for evidence how non-technical managers drove many tech companies into the ground.
This is excellent summary by Spolsky: http://www.joelonsoftware.com/articles/Stupidity.html
Now, the small print #1: not every programmer will make a good PM, of course. In short, control freaks, toxic personalities, egomaniacs, people who are good at coding but not at negotiating, people who are good at coding but yield to pressure too easily -- will FUBR their projects.
Small print #2: It might be possible that people with very good analytical skills might make up for lack of experience with technology. I've worked with people who were excellent business process and procedure designers, who instinctively understood how UI should be organized and what the software should be doing in this particular place and why and who could detect BS quickly even when served by domain experts but who could not program if their life depended on it.
Most has been answered already, but I'll add this:
Keep the same mindset that you would have when hiring an office manager. While the technology knowledge is important, you'll find that ambition, a will to learn, coupled with a team leader attitude will get you a better manager than looking at mostly technology knowledge. Most projects have some company/industry-specific skills that are involved and a quick learner / great leader will bridge that gap quickly.

How do you manage web developers remotely? [closed]

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I'm the leader of a small web development team, and I have a feeling that we will have a couple telecommuters joining the team pretty soon (either new employees, or existing employees that will begin telecommuting). Any idea how to effectively manage and collaborate with developers working remotely?
Most of the work we do is client-driven. We're doing agile development (or our version of it, anyway), but since it's mostly client work, we can't really assign a feature to a developer and set them lose for a week or two like we might be able to with a desktop app or something like that. The biggest problem we have when people occasionally work from home is collaborating - it's tough to work together without the benefit of a whiteboard and hand-waving.
It seems like software development is perfect for telecommuting, but I haven't been able to find many good resources about the practical aspects of working remotely within a development team. Has anyone else had any experience with this?
I freelance a lot and in doing so work remotely a lot of the time. These are the things that make my life as easy as possible (so might be things you want to "suggest"). I think they're mostly common-sense, but you never know...
[Everyone] Communicate well. When you're having a conversation face-to-face, you can be verbose and explain things in a round-a-bout way. When you're limited to email, IM and phone, all parties need to explain themselves fully but succinctly. I find that summarising long emails into request/action points goes a long way towards getting things done well.
[Everyone] Have a online project tracking space. Most tend to use a ticket system or some description, where action points can be assigned to members. It wouldn't hurt to use this same space for tracking emails and sharing whiteboard ideas. Most online project apps allow for that by default.
[Management] Don't pester devs. If you need something urgently, set the status of the ticket, give them a call and chase them up later on in the day. Half-hourly emails asking "is it done yet?" does more harm than good!
[Management] Make sure messages get passed along. If a dev says "somebody needs to do something", it's your job to make sure the message is passed along to the right person. There are few things more annoying than passing a message to a project manager for them to accidentally sit on it. I don't want to have to chase up things like that because it's, frankly, not what I'm being paid for.
[Management] Make sure people have something to do. If you send them home with nothing on their task list that they can immediately action, they're not going to put in the effort. It's a damned sight harder to keep yourself productive at home than it is in the office when you've little or nothing that you can do. You might have to juggle tasks if there's a blocker.
I work at home full time. Here are things that help in my small (6 people) team.
Set up rules for using IM. For example, allow remote workers to block off time not to be interrupted by email or IM. Require workers to keep status up-to-date somewhere (IM, Yammer, etc) which helps keep them accountable to stay on task. Stay in touch without being a distraction.
Meet in person occasionally if possible. Nothing can replace a face-to-face meeting. Skype is ok for group meetings, but not if whiteboards are involved.
Use SharedView or another screen sharing program for collaborating. Screenshots/screen captures are helpful as well to make sure both parties are on the same page.
"Any idea how to effectively manage and collaborate with developers working remotely?"
What does "effectively" mean? I can be negative and assume it means "with me, the project leader in control of everything". I can be positive and assume you want people to be as effective as possible.
Sometimes, "effective" is management-speak for "under my control". Or it means "not screwing around."
The question, then is "effectively doing what?" Effectively "working" is rather vague. Hence my leap to the dark side of project management. [Which, I admit, is probably wrong. But without specific team productivity problems, the question has no answer.]
"it's tough to work together without the benefit of a whiteboard and hand-waving" This is only sometimes true, there are lots of replacements. The "hand-waving" over the internet happens more slowly and more thoroughly.
The group-think around the whiteboard is fun -- it's a kind of party. However, for some of us, it's not very productive. I need hours to digest and consider and work out alternatives; I'm actually not effective in the group whiteboard environment.
I find it more effective to use the alternative "slow-motion" whiteboard technologies. I like to see a draft pitch for an idea. Comment on it. Refine it. A lot like a Wiki or Stackoverflow. I really like the internet RFC model -- here's my idea; comment on it. When there are no more improvements, that's as good as it's going to get.
I work in Mississippi and my home office is in Michigan. I spend several hours a day pair programming with my team with ease. The tools I use are:
SharedView
Remote Deskop Assistance
Live Meeting
Oovoo
Skype
Depending on who and how many will depend on the tool I use.
"Use the right tool for the job and invest in a damn good headset." - Me.
I've generally used some time of community based software such as a wiki, blog, or forum to handle the documentation areas. We also have a Cisco phone system and use some capabilities of the system. I'd also recommend live meeting or webex to do frequent team meetings. Skype and IM clients such as Live Messenger are also good tools. For the short status updates, twitter does the trick.
Check out the Agile Scrum methodology with VSTS. Scrum forces us to have daily 15 minutes meeting and small mile stones , It makes sure the effective togetherness and tight communication. Make sure you use Task,Bug assignment etc through VSTS
I agree with John Sheehan's response. I am a consultant and manage other consultants - both on a project basis (as PM) and on a client basis across projects. I have worked with developers on a purely remote basis as well as telecommuting (meaning the majority of time we are co-located). Working remotely is a matter of trust and communication. Co-locating is best, but if you work remotely, simply create a culture of frequent communication. IM and phone are great for this, email less so. If you have a less than communicative co-worker, it is up to you as the manager to reach out. Ask for status. Force code-checkin on a frequent basis for review.
[EDIT] - Yes, don't pester and set expectations! Be clear and concise.
First of all use scrum (daily scrum calls, scrum board w/ burndown chart (wikis do a great job there), iteration in sprints etc). Next to that use tools that make it more easy to collaborate remotely like skype and VNC (maybe campfire?) and a wiki. I worked for 2 years on a project w/ people in 3 countries on 2 continents and various time zones and it worked quite well. The key is having tools and methodologies that make it more difficult for people to "hide", so that everything you and your team does is visible.
I find clear communication and staying on task are challenging with virtual teams. I try to use regular scheduled update meetings (over the phone or video conference) with a written agenda to help with these challenges.
At the front on the agenda list the major milestones and the near term milestones. The first item is always "check progress" each team member simply updates us on when they expect to finish the particular tasks involved. We try not to get involved in long stories here. It's simply "what are you going to do and when".
Once the progress check is done deal with any other issues raised in during the last week and any issues the team has that can be sorted out whilst you are in the meeting. Anything let over (such as new issues raised) needs to have the question asked "who is needs to sort this out and when".
Once you set a common format for the meeting you can do this weekly in 30-45 minutes with teams of 5-8 people. Keep it short and sweet so it isn't viewed as an imposition. Keep it focused on actions and schedule so it can be valuable.
I'm currently the PM of a smaller project that has two developers (myself and another developer that works out of the office). We are currently having daily SCRUM meetings, which last for about 15 minutes. We discuss what got done the previous day, what problems were encountered and what I can do to help with these problems, and what will be done tomorrow.
They're pretty quick and seemed to be very helpful.
Using a Time Tracking Software for your remote employees can greatly help you in managing the team.
While hiring a remote employee, you would be concerned about,
The amount of time spent in getting a task done.
The quality of the work done.
Collaboration based on the progress of the project.
The real time progress on a task.
Collaborating to solve bugs and logical errors.
I was in your situation a while ago and then I tried StaffTimerApp and it helped me in the following ways.
A Time Tracking Software gives crystal clear statistics about the time spent on getting a task done. StaffTimerApp captures screenshots and converts them into billable and non-billable hours. Hence, you would know if any time was wasted while getting the work done. You would also know the exact amount of time spent in getting the work done. If you pay your contractor by the hour, this application can help you tremendously.
If you use a time tracking software that captures screenshots, you can look at them to analyse the quality of work that is being delivered. I used this feature and was able to save some tasks from derailing.
A Time Tracking Software lets the employer know how far along the employee is with the task, hence the information extracted by Time Tracking will make collaboration easier. StaffTimerApp proved to be very helpful as I was able to collaborate with the other employees based on this information.
The screen sharing feature equipped me with the power of viewing my employee's laptop screen in real time. This way I would get to know about the progress on a task.
So you need a good Time Tracking Software with great productivity analytics and employee monitoring capabilities to feel comfortable with hiring a remote developer.

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