The WorkingPoint Community is made up of small business owners, like yourself, and we want you to get to know each other. We’d like to introduce you to Cileia Vieira at Cileia’s Cleaning Service:

Cileia specializes in residential and commercial cleaning, with over 10 years of experience,

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Over the past year, the Enterprise 2.0 space has started seeing some momentum that its evangelists have been waiting years to experience. And it’s for one basic, underlying reason: Enterprise 2.0 is about collaboration, and collaboration is a profoundly difficult and expensive business problem, particularly in a down economy.  Technology and society have started catching up, so world of corporate collaboration saw a big jump this year.

But what about small teams and organizations?  What collaboration challenges do they face? (In reality, since person-to-person communication has limited scalability, small businesses or small teams in larger businesses often face precisely the same challenges.)

What Is So Hard About It?
Collaboration is at the heart of knowledge workers lives: everyone has a different specialty, and in order to accomplish a project’s objectives, several people must each bring what they are good at, and work together to deliver an end result that is superior to what any one individual is capable of doing alone.

As inherently social creatures, it would seem that collaboration should be far easier for people than it often is. But, as FreelanceSwitch notes in their recent article on collaboration failures, the single biggest obstacle to collaboration is almost always communication. Whether the problem is schedules, geography, technology, language or ego, how well a team communicates is directly related to how well a team collaborates.

According to the Project Management Institute, 90% of project management is about communication (which is usually the biggest reason it’s a bad idea to have your technical lead function as a project manager on most large or complex projects: you need them spending their time building technology, not communicating with stakeholders). As a result, I’ve had to learn a lot over the years about how to make the flow of communication work during collaborative engagements. After a decade of doing this, I now live by five rules when it comes to getting work done with teams:

1. Ask for preferences
I hate the telephone. Really. I can’t stand it. I almost never answer it unless I know who is calling and why, so when it comes to work, I will typically schedule phone calls. However, I am lightening fast on both email and text messages. But not everyone is the same. How do you know until you ask? (And, for those like me: check out Google Voice. They convert voicemail to text and sent it to you via email. It’s almost as good as not having to deal with the phone at all.)

I recently started collaborating with a an entrepreneur who is much more of a traditional telephone guy, and he was constantly asking me to get on the phone and call our client to ask questions or get information. At first, I made the mistake of assuming that he knew they prefered to communicate by phone. After about a week I recognized a familiar pattern (because it’s what I do also): I’d leave a voicemail, and then I’d get an email in response, often with the answer to my question.

The next time I was on the phone with the client (during a scheduled call), I asked her what her prefered method of communication was. As I expected, her answer was: Email.

Lesson: Never assume that second-hand information is accurate (or applicable in your case). Check with the source.

2. Define groundrules — and get agreement
In the world of project management, large projects will often create a Communications Plan. This lays out the groundrules for the communications process everyone is expected to follow. The problem that I’ve most commonly encountered with these, however, is that the document is frequently created in a vacuum and reflects what the project manager wants, instead of what is native to the team.

Some things that I’ve commonly encountered in enterprise environments:

• Weekly team meetings will be in person only. No dial-in.
• All status reports & meeting materials will be posted on the intranet.
• No laptops or smartphones allowed in meetings.
• Presentation decks must be limited to 10 slides or less.
• Any meeting without a distributed agenda 60 minutes prior to start time will be canceled.
• Meeting facilitator will designate a note taker at the beginning of each meeting.

In more laid back environments, some of the ground rules I’ve experienced are:

• All notes and agendas are posted on team wiki.
• Anyone more than five minutes late to a meeting pays a dollar.
• Only one person speaks at a time; violators are fined a dollar.
• Food allowed in meetings only when you bring enough to share.
• No meetings during lunchtime unless food is provided.

And these are just the things that are focused on actual meetings. There are plenty of other groundrules to get in place: do you use video conferencing? What Instant Messanger client does everyone use? Is email the preference? And what about the ever-annoying and always-growing “Reply All” habit in email? At what point do email conversations escalate to a conference call or an in-face meeting? Is trouble-shooting a technical problem with the team a priority that warrants an emergency meeting, or should it wait?

Many of these things start off as assumptions — some people like Skype, while others like GTalk. Some people want a voicemail, while others prefer an email. Some people avoid formal documentation, while others consider anything less unacceptable.

Teams that don’t define what their standards and expectations are, will inevitabley run into a problem. The best way to avoid it is to define what the principle methods are going to be, make sure that meets everyone’s needs, and then revisit the question as challenges or concerns come up. Keep it fluid, and evolve it as necessary, but never, ever, ever assume that everyone is starting off on the same page.

Lesson: Communication is a two-way street.  One person’s preference cannot dominate.  Unless the team defines what is expected, each individual will do what makes sense for them.  Remember, there is no ‘i’ in ‘team.’

3. Don’t get tech crazy
In my tech-centric universe, this one is always hard to battle because geeks tend to like gadgets. So if you find that your communication groundrules are getting bogged down in religious battles (Mac vs. PC!) between evangelists of different solutions, then stop and ask the question: do we need synchonous (phone, instant messanger, meetings, etc.) communication, or will asynchronous suffice (email, blogging, etc.)?

Don’t let the conversation be about technology until you are crystal clear about whether a discussion needs to happen in real time, or if it can occur at a more leisurely pace. One of the biggest time wasters any project can experience is endless emails that go on for days, instead of someone just putting a stake in the ground and getting everyone on the phone at once. Often times a week’s worth of email can get resolved in 30 minutes worth of phone call.

Lesson: Communication comes in different flavors. Pick the right one for the right job.

4. Pay attention to communication styles
This is especially important for managers and project leaders — and it’s often particularly difficult for us extroverted types to keep in mind — but some people are just shy and have trouble speaking up. This problem can also be complicated by cultural factors, where people are raised in societies where being direct is considered rude or where the “boss” is considered an authority not to be contradicted.

Collaborative team environments only work when everyone participates. But it’s vital for the leaders on the team to recognize that quiet people are not always quiet because they don’t have anything to say. Sometimes they just need to be solicited directly for their feedback.

Lesson: If someone is staying quiet, meet with them privately to try to understand why. Don’t assume everyone is going to speak up in a crowded meeting.

5. Bad news doesn’t get better with age
This is the mother of all lessons for projects. No one likes being the bearer of bad news. No one likes disappointing people, and no one likes to be considered the Grim Reaper, out to kill someone’s hopes and dreams. But the fact is, bad news isn’t going to go away. And you always stand a much better chance of finding a solution to work your way through it by addressing it early than if you wait.

Consider this: waiting until the last minute to give bad news says two really negative things about you, either you didn’t know until now, or you are not showing the recipeint of the news the respect of treating them like an adult. Of course, not everyone is going to take it well. But that’s not the point.

Lesson: Don’t ambush people. Bad news is easier to digest when you have some time to do it. It’s empowering to know as early as possible. The longer you wait to share it, the more options you eliminate.

No doubt about it. Collaboration is hard work. FreelanceSwitch covers a few other great reasons that collaboration commonly fails, not the least of which is ego (one of the most difficult challenges to handle), and is worth a read.

In the meantime, though, remember: people communicate all the time. Often times, we don’t even realize we’re doing it. So pay attention to what is native to your team members, and build your formal communication structure around what your team is already doing naturally. But more than anything else, once you figure out how you want to manage communications, make sure everyone agrees and then make sure you continue to evolve as your team, your projects and technology continues to change.

Alora Chistiakoff is an entrepreneur, blogger, content strategist and project manager who has been developing online business and technology for startups for more than a decade.  She co-owns The Indigo Heron Group, Inc., a content strategy firm in Austin, Texas.

Filing your sales tax report in the state of California has never been easier. With WorkingPoint and the California’s Board of Equalization (BOE) move to electronic filing, you can complete your sales tax report and pay all online in no time at all.

As a yearly sales tax reporter in California, my sales tax return is due on January 31, 2010, so I took a few minutes this last week to file my return and it took me literally minutes.  Here are the simple steps I took:

Prepwork
Back in October, the BOE sent out a notice announcing that they were transitioning to efiling, so I would not be receiving a paper return starting this year and that I can prepare for efiling now by completing some easy steps:

1. Read the brochure
2. Register as an eClient
3. Record your eClient login information on the back of the brochure
4. Begin efiling

But, why do today what you can put off til tomorrow? So I put it aside until this week. This week, I read the brochure and found the initial letter I got which included my Account number, Express Login Code.  From here it was really easy to complete the return.

Register as an eClient with the BOE
Following the BOE’s insturctions, I logged onto www.boe.gov and clicked on eServices and signed up for an account, using my account number and Express Login Code. After I received my confirmation email, I logged as an eClient and was ready to file my return.

Log in to WorkingPoint
Next, I logged into my WorkingPoint account and pulled up my Sales Tax Report for 2009 by going to Reports > Sales Tax Report.  All the cities I sold products in were listed and broken out into taxable and non-taxable sales, and included how much tax I charged.

Complete the BOE Sales Tax Return
Using the data from my Sales Tax Report in WorkingPoint, I entered my Total Gross Sales, my Deductions and broke out the sales by District. The BOE calculated my tax due for me.

Pay the Sales Tax Due
The California BOE lets you pay by e-check, credit card or paper check. I chose e-check. It was easy to complete the information by entering my banking information and I even got to choose the any day up til the due date to process the payment.

Record the Payment in WorkingPoint
Lastly, I recorded the payment in WorkingPoint. From the home page, I clicked Record Expense, then chose Paid from a Bank Account and entered the BOE as my contact, the date as the date I set the payment to process, I chose check as my payment method and entered the check number I used. Then I chose Sales Tax Payable as the Bookkeeping account and entered the amount of tax due and clicked Save.

Who said filing taxes has to be hard? It was super easy to do this year! I saved time and money on stamps.

Notes: Your filing requirements will vary if you are not a California business or if you are, you may have a different filing schedule and requirements. The Sales Tax Report in WorkingPoint is a Premium feature and available only on Premium accounts. To upgrade to Premium, go to Settings > Manage Accounts and click Change Account Plan.

Estimates taxes for the Sept. 1 – Dec. 31 period are due January 15.

Use WorkingPoint’s Estimates Tax Report to help you calculate you what to pay. The estimated amount it based on the data you have in WorkingPoint,  so if you are new to WorkingPoint, be sure to figure in any sales or expenses not included in your WorkingPoint account. In addition, be sure to subtract out any payments you have already made for the 2009 year from the Total Estimated Federal Taxes Owed for 2009 to get an estimate of the balance.

The Estimated Tax Report is a premium feature and only available on the Premium account plan. Not on the Premium plan? Upgrade today!

Let me describe a common scenario that I recently relived for the 1000th time in my career:

1. Agree to scope of project and set out to get it done by the due date.
2. Encounter problems that put the date in jeopardy.
3. Deal with stakeholder upset at the prospect of a late delivery date.
4. Someone comes up with a brilliant idea that simplifies something and buy back some time.

Of course, whether or not Step 4 buys back enough time keep the project on target varies from project to project, but the part that interests me is the first half of Step 4. When I was first starting out in my career, I would typically find myself surprised when it would seem to happen at the darkest hour of a project. Over time, I came to expect that it would (and I still often get frustrated if it doesn’t).

This phenomenon was what was on my mind when I read the blog post on 37signals‘ blog, Signal vs. Noise, called “You can always do less.” The recent VentureBeat post I wrote about asked a similar question in a different way: “What initiatives could be done half-assed without significant impact?”

To me this is a point worth considering for a number of reasons.

Too Attached to the Original Point of View
As noted in the 37signals’ post, often times the problem is rooted in becoming too attached to our original plan, and not adapting accordingly. (This is something I am often guilty of doing.) All the work goes into planning, and the last thing anyone wants to do is feel that time was wasted — so we will often stick to a plan, even if updated information reveals that plan to be outdated.

In the world of software development, this issue is at the heart of the Agile Development methodology. Traditional Waterfall Development approaches were originally borrowed from the world of manufacturing, where extensive planning was a must due to the investment of time and resources that went into building a factory. The world of software proved to have trouble with this model, though, because technology shifts too quickly, and business needs are too fluid. So if you spend two years planning and building a product, chances are, by the time you launch it, the business conditions that led you to build it in the first place have changed, rendering the whole thing (or at least large parts of it) a wasted effort.

The same is true of business: being agile is at the heart of entreprenurial survival. I wrote a post last year about the importance of agility in business, as well as technology development. Truth be told, agility is also the biggest advantage that startups and small businesses can potentially have — assuming they have the right attitude and organizational structure to support dynamic and fluid change.

Not Being a Good Groundhog
I like the Groundhog metaphor when it comes to building anything from a website to a business: you can burrow away for months, but if you don’t pop your head out every once in a while and look around, you have no idea where you’ll really end up. Part of being too committed to early planning is a deluded sense of faith in where you end up. If you don’t take the time to stop and look around, it’s hard to correct course when you discover that your terrain has changed.

Necessity is the Mother of Invention
This I truly believe with all my heart. The human brain is a wonderous, mysterious and fascinating thing. And it is capable of immense creativity and adaptability when properly sparked. For many of us, though, those sparks usually have to come from outside sources. So no matter how much rigerous planning you may go through, it’s always a distinct possibility that it’s not until the team is feeling pressure that the creative juices really start flowing enough to come up with creative solutions.

The Gulf Between Assumed and Real Value
Again, one of the core tennants of the Agile Software development movement is the idea that, if you plan everything too far out, you are making assumptions about what is really going to be of the most value. Whereas, if you give people a little bit at a time, let them absorb it, give you feedback and then move on to the next piece, it’s very easy to see what has true value to your stakeholders and focus your efforts there, instead of on bright-and-shiny objects that sound cool, but which provide little in the way of real value.

Of course, there are conflict in things like this all the time. What has the “higher value”: spending billable time on a client request that you know they are never going to do anything with, or spending that same time on non-billable activities within your own business? Starving entrepreneurs struggle with conflicting needs like these all the time. Some times you need to do client busy work; other times you need to push back on the client and focus on your work. It all depends, and only you can make that call.

But when faced with the a task — any task — always try to ask yourself two questions:

• Is there a quick-and-dirty version of this I can do, instead of the time-consuming one?
• What are the consequences if I take the short-cut?

For some things, the price is too high (especially for things like taxes, legal documents, cooking chicken or buying your wife’s birthday present). But for some things, what you get out of the long version simply isn’t worth the investment. How do you decide which is which?

Alora Chistiakoff is an entrepreneur, blogger, content strategist and project manager who has been developing online business and technology for startups for more than a decade.  She co-owns The Indigo Heron Group, Inc., a content strategy firm in Austin, Texas.

I was speaking to two different small business owners recently. One owns a drive through coffee kiosk and has 400+ friends on Facebook and hundreds of Twitter followers who are alerted whenever he gets a new product. The other owner has a cleaning service with no online presence and no idea of where to start. If you are like the coffee kiosk owner and very web savvy — this article isn’t for you. If, like the cleaning company owner, you have no idea where to start on the internet read on.

The internet is truly a huge place. It’s even more huge than most of us can imagine. Luckily, to increase your small business web presence you don’t have to take it all on yourself. You can also have a positive impact without a great deal of effort or money. Let’s talk about how to get started.

Google your business/self. Go on. Go to a browser and type in your business name in the search bar. Do you come up? Is anyone writing about you? Do you like what you see? Can your customers find you? Probably not. So let’s start the process of correcting that. First, have a quick read of this article that explains why you should have a google profile. Or I can summarize for you that it’s because the profiles show up nicely in google searches. Then go and set up a google profile for your business (you can create one for yourself at the same time). If you don’t have an email address now would be a good time to set up a free one using gmail. Here’s a list of ten things to keep in mind as you create your profile.

Next, let’s get you set up on a review site. Many small businesses have a local trade area only. If most of your clientele or customers are local then the first place you should start out your web odyssey is with Yelp. If you haven’t heard of it, Yelp is an online directory and rating site for businesses. Your customers can use it to rate your business and describe their pleasure (or not) with your establishment. As a business owner, you can take over your business profile, add details and respond to and communicate with your customers via Yelp. Get started here.

Last but not least, you should set your business up with a WorkingPoint account AND create a free small business web profile. They’re both free and quick to do. Once you have a public profile in WorkingPoint your customers can find and communicate with you and other like-minded businesses can as well. Here is a good example of a WorkingPoint profile: Island Planet Sails. We work hard to make sure the WorkingPoint profiles show up well in Google searches.

Remember this is only a starting point. Maintaining your business’s web presence could have a huge impact on your marketing and sales efforts and bring you new customers you can’t get any other way. It takes time and effort but will pay off handsomely in the long run.

The WorkingPoint Online Help Center is filled with valuable information that can help make managing your business with WorkingPoint easier. While you don’t need to read the whole thing to start working in WorkingPoint – a lot of questions you may have about a field or a section in WorkingPoint can be answered by clicking on a help bubbles  throughout the application – the Online Help Center is an excellent resource when you have a question or want more information.

The Online Help Center home page offers quick links to step-by-step instruction for how to perform common tasks under How do I…?, as well as Table of Contents organized by feature. Our Other Resources section gives you links to our feedback forum and the Accounting Basics section that offers insights into the accounting principles behind WorkingPoint. Use the Search feature to cruise the help and find all the topics by keep word or phrase. Or use the Index to get to topics quickly.

Access the Online Help Center from within your account by clicking the Help link in the upper right hand corner of your account or going to our new Help Center page on our website.

If your questions isn’t answered in our Online Help Center, contact Support and we’ll see you get your question answered.

Today Gartner released findings for a new 2010 technology survey (see here for the press release with the highlights, or here for the full detailed report). While nothing it lists is shocking, there is an interesting statistic that I think is worth discussing:

By 2012, 20 percent of businesses will own no IT assets

Of course, in the world of small businesses and entrepreneurs, this is already true, but the fact that Gartner is predicting this for the enterprise space as well, is good news for those of us who run smaller businesses.

For starters, the enterprise market continues to be a huge driver. And it’s not as much that enterprises are driving cutting edge innovation themselves, but that the prospect of landing enterprise contracts and clients is driving small startups to innovate in an attempt to secure that business.

This has potentially immeasurable value to smaller organizations. Since one of the most common sales models for cloud-based applications is a ‘freemium’ model (such as WorkingPoint), in which small organizations or teams can use basic functionality for an extremely low price, this provides endless opportunities for small business.

Cloud-based solutions, such as SuccessFactors and SalesForce, started off with a focused market target of small to mid-sized businesses. And then when enterprise clients start signing on, it was a major win. With enormous new client contracts and fresh rounds of funding, these companies (and others like them) have continued to grow and evolve their product offering — and the small businesses who use their solutions continue to benefit. (This report from Interwest discusses how SaaS providers often start at the SMB market, and then work their way upstream.)

The other place this is great news is for those of us who work in the technology industry: not only does this potentially help spur an entire new generation of technology startups, but it also raises the need for specialized consulting service. Migrating data from legacy systemst to hosted ones is a big and highly lucrative business. And, as more environments have to manage more data across more disparate systems, more complicated challenges about security, access and operational efficiency will continue to surface.

So, while the downside to some of Gartner’s predictions mean that more technical people are going to be laid off from enterprise IT organizations, there are always going to be technical needs that have to be met in any large business environment. And whether an entrepreneur is building a startup that provides web-based products, or developing out a suite of professional services to help business leverage their distributed technology assets, in the end, there are going to continue to be exciting opportunities for entrepreneurs with experience in this space.

Alora Chistiakoff is an entrepreneur, content strategist and project manager who has been developing online business and technology for startups for more than a decade.  She co-owns The Indigo Heron Group, Inc., a content strategy firm in Austin, Texas

Of all the words people frequently use to describe me, “optimist” rarely makes the cut. And while I would argue that the reverse is definitely not true, the term I have self-applied over the years is actually “pragmatist” (even in the name of my own blog).

However, when it comes to the world of entrepreneurship, I am an optimist — and, more importantly, I think that entrepreneurs innately inclined towards optimism. Even more than that, however: I think that optimism is at the heart of entrepreneurial power and success.

Just think about it for a moment. In order to be an entrepreneur, the following is (almost always) true:

• You believe you can defy the odds.
• You beieve that you have something special to offer.
• You believe that you are capable.
• You believe that the hard work and sacrifice is worthwhile.
• You believe that your product or service provides a value to your customers.

No matter how you slice it, those are all extremely optimistic notions. And though a bad day may make an entrepreneur question one or two of those premises, part of being an entrepreneur is coming back again the next day, and starting over.

I was thinking about this as I was reading Jeff Cornwall’s article on MyVenturePad called, “Seeing Things “Half Full” is More Important Than Ever!” He talks about a technique I routinely employ (originally inspired by Tim Ferriss’ book, “The 4-Hour Work Week” and his advocacy of a ‘low information diet’): refusing to be taken in by the bad news, and going out of our way to look at good news.

In his book, Be The Solution, author Michael Strong also points out that with all of the media’s tendancy to focus on the negative, it’s easy to forget that society can and does actually make promising, positive progress on solving problems more than many of us realize.

One of the reasons I go out of my way to surround myself with entrepreneurs is for this reason: I need that energy and optimism, particularly on frustrating days or during complicated projects. As social animals, we are subject to the emotional tides of those around us. And, as an entrepreneur, I can’t afford the luxury of being brought down by endlessly bad news that I can’t do anything about. Instead, I make a choice to be optimistic, and that often means putting a filter on constantly negative news.

In a business seminar last year, a facilitator recounted a story of a fishing trip with his best friend, a wealthy real estate investor. In response to the endless news coverage about the recession, the man said: “Recession! Ha! I chose not to participate!”

Scoff away, but there is something defiantly optimistic in that sentiment — and it helped carry me through 2009. So chin up, and remember: entrepreneurs lead the way, and the best way to do that is to remember that we have plenty of reasons to stay optimistic.

Alora Chistiakoff is an entrepreneur, content strategist and project manager who has been developing online business and technology for startups for more than a decade.  She co-owns The Indigo Heron Group, Inc., a content strategy firm in Austin, Texas

One of my recent posts was about asking the right questions at different stages of your business maturation — there are some questions that you should ask when you’re getting started, and others that you ask several years in. But as many of us are focusing on getting 2010 off to a solid start, what questions matter for today?

Jason Cohen of Smart Bear Software posted a follow-up to his previous article on VentureBeat in which he asked several new questions, and this time the theme was around managing an entrepreneurs time and priorities.

“If you were forced to hire someone today, how would you define her job such that she would contribute enough revenue to cover her expense?”
This is a great question, because it removes the knee-jerk, “I can’t afford to hire anyone” excuse. Instead, it requires really considering what it would take to make an employees role pay for itself. It may not be possible just yet, but defining what this would look like is a huge step to getting your business to a position where it’s possible.

“Which of your business operations do you hate?”
I particularly like this one because it’s an important reminder that some things we spend time on are such energy drains that they actually will bring down our overall productivity, even on tasks we enjoy. One of the things that entrepreneurs need to understand is how to manage their own energy levels in order to effectively manage my time.

“What initiatives could be done half-assed without significant impact?”
This is a great question because it’s the type of thing that no one ever wants to admit they consider. And yet, to Jason’s point, it’s something that we always need to keep in mind. Every task has a ‘point of diminishing returns,’ where the time and effort you put into it starts to exceed the value that you will get out of it. It is always important to be mindful of that threshold, because otherwise it’s easy to get caught in the cycle of perfectionism that will consume your time with no return.

“If you could get one solid hour of advice from a guru you respect, what would you discuss and what would be the goal of the meeting?”
This question is well-worded because, again, it is forcing you to consider how you are spending your time. It’s not, “If you could ask them anything, what would it be?” It is specifically, “If you could get one solid hour…” Period. Prioritize.

No one has endless time and resources. The people who are most successful are the ones who figure out how to maximize what they have, and work around what they don’t. And one of the hardest things for entrepreneurs to remember is that the single most scarce resource you have, is usually you.

Alora Chistiakoff is an entrepreneur, content strategist and project manager who has been developing online business and technology for startups for more than a decade.  She co-owns The Indigo Heron Group, Inc., a content strategy firm in Austin, Texas