However, at some point, a business gets too big (hopefully) for one person to do it all. Choices have to be made about starting to delegate tasks to other people. Which areas of responsibility should an entrepreneur hand over to others, and at what point in their business’s growth? Those can be hard calls to make.

I’m currently at the point of having to make some of those decisions myself. My business, which up until recently I’ve been running basically by myself, has grown exponentially in the past 12 months. I have come to the reluctant conclusion that I need help, but I’ve been struggling with how to best go about getting it.

I did make one recent change, which means I’m not doing absolutely everything myself. I brought a contributing writer onto my web site to help me produce content. But that decision was more the result of happening upon the perfect opportunity than of strategic planning, and now I need to figure out how to move forward with more delegating of responsibilities.

As I’ve weighed how to go about this, I’ve come to the conclusion that there are several prime factors to consider in deciding what tasks to offload and how to do it.

• Know your value. Remember to focus on what your true value is to the company. In my company’s case, my personal brand is closely tied to the brand of my company. Readers equate me with Scrapbook Update. It would be counter-productive to the success of the company for me to hire writers to be the visible face of the company while retiring into a behind-the-scenes editorial role. (The writer I recently added expanded the site’s offerings rather than taking burden off of me.)
• Know the true cost. Some types of help will cost more to bring in than others. But these costs must be weighed in relation to how much time will be freed up for you to expend on income-producing activities. Help that seems expensive but which provides you a lot more income-producing time that you are able to take full advantage of may actually be very cost-effective. Also, don’t forget that paying for an expert to take on certain responsibilities could lead to those tasks being done in a way that saves the company money (for instance, an accountant might be able to find tax savings for the company that would offset the costs of accounting services).
• Know your abilities. As our businesses grow, some of our company’s functions may get complex enough that we really have no choice as a smart business person but to call in experts to perform them. There might be other tasks that you could more cost-effectively outsource, but if your needs in a certain area are getting too complex for your DIY skills, then you need to make getting help in that area a priority. Experts that you may need to hand off responsibilities to might include accountants, lawyers, web designers and sales people.

Don’t forget to factor personal tasks in your evaluation as well. There are only 24 hours in a day. Since time spent on non-work related tasks can’t be spent elsewhere, examine everywhere that you are spending your time and consider whether responsibilities can be delegated. Perhaps it would be cost-effective to outsource cleaning your house, or mowing your lawn. (And I’ll bet you wouldn’t miss doing those tasks, either.)

At some point, we have to admit we can’t run every function of our business ourselves. Even a control freak like Steve Jobs has help. Admit you need help, then go about getting the right help for you and your company.

What responsibilities would it be a good idea for you to delegate?

Photo by Flickr user ralphbijker, licensed under Creative Commons Attribution 2.0.

In this post I’m going to discuss deadline management. Successfully managing deadlines is part knowing why specific deadlines exist in the first place, part knowing which are soft and which are firm, and a big part relationship management. Striking the right balance depends on the situation at hand, but generally speaking, deadlines fall into one of three categories and should be managed accordingly.

First Type: The Faildate

Depending on the institution you’re dealing with, and the level of consultant or employee they’re used to working with, a deadline might actually be a test to see if your work is up to their standards. As a consultant taking on a first contract with a high profile client, for example, a deadline could be the point at which you’re no longer considered for future work. And that’s if you meet them, not exceed them.

To beat these kinds of deadlines, you actually have to beat them. Coming in early is the real key to success, but of course your product can’t suffer as a result. You’ll know when these kinds of deadlines are in play if you do adequate research before signing on with a new client or employer in order to find out about their corporate climate.

Sometimes these types of clients will also want frequent, regular status updates, either weekly or bi-weekly, but even if they don’t, it’s a good idea to micro-manage these deadlines by breaking them down into sub-tasks on a fairly small scale. Hourly goal setting might even be appropriate. Good tools for this kind of work include GTD apps that send you notifications on a schedule you set (Things or Remember the Milk are recommended).

Second Type: Firm, But Flexible

This sounds contradictory, but it isn’t. This will cover the vast majority of deadlines you’ll encounter. These are deadlines that are set as firm, and that should be met if at all possible, but that are susceptible to change depending on circumstances and when in conflict with other deadlines.

The key to successfully negotiating these deadlines is finding out why they exist in the first place. If, for example, a deadline exists for the group you’re working with because without that piece of work, another group is just sitting around waiting, then that deadline takes priority. If it exists because it’s based on a reasonable, pre-project estimate of how much time a task should take, then consider it flexible and move on.

Zen is a nice tool to use to track these kinds of deadlines, because it allows you to create custom groups for your different tasks, so you can make your own priority categories depending on the deadline source.

Third Type: Staledate

The final type of deadline isn’t really a deadline at all. It’s the date at which something ceases to really be a concern, and passes into a client or employer’s distant memory. Be careful, because no one you work for will likely admit that these kinds of deadlines exist, so identifying them won’t be easy.

The best way to go about finding your staledate deadlines is by watching ones from the second category you’ve flagged as low priority. Other signs a deadline may actually indicate when you can drop something entirely include a lack of ability to quantify what would result from meeting said deadline, a lack of client stakeholders associated with it, and lax reporting requirements.

Keep tabs on these as you normally would other dates in your usual PM tools, but don’t worry too much about following through until someone important starts asking questions.

Deadlines don’t have to be the movie monsters we make them out to be. Sometimes they’re just a way of saying “we would like this done within a reasonable period of time,” or even “we don’t care about this at all, but we have to pretend to until time X because the policy says so.” If you listen to your deadlines and monitor them properly, the won’t loom so much as pass uneventfully.

How do you manage deadlines?

Image by Flickr user wili_hybrid.

In the meantime, I still need to use databases on occasion. When I do, I generally turn to the inelegant and probably inappropriate solution that is Microsoft Excel. I’ve even been known to use tables created in Word. What can I say, I have a deep-seated mistrust of numbers and their attendant programs. As I do to solve most problems, I turned to the web for a better answer. That’s where I ran into Grubba.

Besides having a moniker that sounds like an Aussie nickname for something or other, and a disarmingly eccentric front-end layout, Grubba offers online database services and is meant to operate as a viable alternative to desktop-based solutions like Access. It offers a number of support services for people like me who aren’t necessarily database experts to begin with, too, which is what made it such an appealing choice to begin with. Those services include a selection of one-minute tutorials, a quick start guide, and even a form design service (which incurs a fee, of course).

Using Templates

For me, since I’m too cheap to pay someone to design a form for me, and not experienced enough to know how to create one from scratch, the best way to put Grubba to use was to dive into the ready-made templates offered by the site. It was easy for me to figure out how to get started with a template thanks to the one-minute screencast tutorial provided on the subject. Best of all, I didn’t have to worry about any audio instructions, a pet peeve of mine when dealing with online web app tutuorials.

Grubba doesn’t offer a huge selection of templates, so don’t go expecting anywhere near the depth of choice available in many desktop apps. But those on offer will suit the needs of most casual/light web working end users, especially as each template is fully customizable once created, so you can use one to get started, then change things around as needed.

Form Designer

I set up a recipe book, because I want to keep one for personal use, and because friends of mine are thinking about opening up a bakery/confectioner’s business via our local flea market and the web, and could use a database storage tool for recipes. Using the form designer, you can customize each field by changing its name, making it searchable, changing the input type, deciding whether Grubba should check the input on exit for a specific format, and making it required or not. You can also set row color and add help text, which is great if you’re creating a database for use by others.

During the database creation process, you can preview entry fields or your final database entry form at any time, and the results are impressive. Even users with absolutely no prior form creation experience in any medium should have very little trouble creating completely customized entry forms with very little ramp-up time. And for end-users, the little “i” boxes provide a fairly intuitive way to deliver helpful tips without having to leave the page or open a new window.

Additional Features

For users who are already working with other database programs, and who don’t want to start again from scratch when trying out Grubba, the site offers a data import tool. The tool uses industry standard .csv formatted information to import your data, and you can preview the output before completing the operation. Any major database software supports .csv exporting, so transitioning should be relatively easy. Importantly, you can also export your database as a .csv file if you want to transfer it somewhere else, so it’s not stuck inside Grubba.

You can create new users, and set their access level, although it doesn’t seem as though you can customize user level abilities. You just get read-only, read/write and administrator options, but that really should cover all your needs for basic database applications. There’s also a shared to-do list app built-in, which gives you some basic Getting Things Done (GTD) features you can use in combination with your Grubba databases.

Final Thoughts

If you want a simple and lightweight app to help you create and manage databases, and you aren’t keen on installing yet another system-resource eating standalone app, Grubba is an excellent choice. Not only is it user-friendly and well-designed, it also has a free version that supports most conceivable uses. The free version supports unlimited users, but limits you to a maximum of three forms and 10,000 records. If you need more than that, for $7.95/month you get eight forms maximum, and 25,000 records, plus improved support.

Have you tried Grubba? How does it compare to Access for lightweight database applications?

But as Paisano wrote recently, current conditions won’t last forever. Many sites will eventually become fee-based; others will shut down when their funding runs out, or when their owners decide to move in a different direction.

So when I evaluate a product that I’d like to incorporate into my company’s workflow — especially a product that will be visible to clients — I try to consider the product’s feature set, along with the issues raised in Judi’s 2007 WWD post. I also ask the following questions:

• Is the product open? Like a lot of people, I prefer open source projects. But I will consider proprietary systems if I am comfortable with how my data is stored and backed up, and whether the product allows me to do my own backups.
• Does it use standard formats that are easy to import and export? If the product will interface with my existing data, I need to evaluate how much work it will be to prepare the data for use by the new product.
• Can I host the product or software myself? Because my company does web hosting, we have easy access to web servers, bandwidth and backup systems. Therefore, I tend to prefer software that we can host ourselves. Maintaining a web server isn’t everyone’s cup of tea, although most of the major hosting companies make it really easy, as long as you’re willing to keep up with security patches and so on.
• If I can’t host the software myself, how reliable and robust are the product’s servers? Of course, even major services (like Gmail) have occasional outages. Here in Seattle, a fire caused a significant outage for many web sites just a couple of weeks ago. So I need to decide how my company will deal with such outages if we adopt the software.
• How will using this product affect my bottom line? Managing any new product requires investing time and resources to install, set up, maintain and troubleshoot. Proprietary services are priced many different ways, and may require an up-front cost, plus continued license fees or service contracts. And while open source products don’t require license fees, many open source software companies offer service contracts. I need to decide whether I want to invest in such a contract, or whether I think I can rely on the user community. Whether open source or not, it’s always a good idea to look at the complexity and maturity of the product, how likely it is to need support, and how active the user base is.
• What is my exit strategy should the product no longer be available? I need to decide how I will get my data, and plan for alternatives, if the product goes away.
• How likely is it that the service provider will be available in the long run? This one’s tricky, since as a small businessperson, I’m hardly in a position to see, much less analyze, the business plans and financial statements of every producer I consider. But there is a fair amount of public information available, so I need to do what due diligence I can.

It’s never possible to plan for every contingency. I had to scramble to replace my Sunrocket VoIP service when that company ceased operation, and I still have some SyQuest backup disk cartridges somewhere for which no players are now available. But with a little common sense, it’s possible to avoid putting all of our technological eggs in one basket and becoming too dependent on any one service.

How do you evaluate what new services to include in your workflow?

Image by stock.xchng user CraigPJ

Several upcoming products (Google Wave, for example) want to make every communication channel available in one place in real time and should, in theory, help to make all these communications easier to manage. But will these apps actually make it harder to separate business and personal lives? Will real-time access to all electronic messages make it more difficult for us to provide effective customer service while maintaining personal lives? As Mashable asks: are we ready for the walls between email, messaging and related technologies to come a-tumbling down?

These products appear to be the next-generation “universal inbox,” although as Sam points out, such services have been tried before, with limited success. I wrote about a couple of message aggregators a few weeks ago, although the services I profiled aren’t real-time. At first glance, these next-generation universal inboxes appear to be good ideas — messages of any sort, using whatever channel, will go to one place, and important people can have priority visibility.

Some companies with significant clout are pushing the next-generation universal inbox. Google Wave has been extensively covered, and will be more widely available in September. Google Wave is expected to have additional capabilities, but its real-time communication features are key. Real-time communication is also included in Shareflow, which Darrell reviewed recently.

In addition, the cellphone maker HTC (previously known as manufacturer of such phones as the Android G1) is planning a major consumer push, with its own Android-based “people-centric” software and interfaces. In its software, you will prioritize your contacts, and the interface will display all communications from that person (whether email, SMS, IM or Facebook) in one place.

All of these products (none of which I have yet used) seem to assume that we will go to the trouble of assigning each of our contacts to one or more groups, which can then be given an appropriate level of access. This is an old idea that’s been a feature of every operating system that I know of.

But frankly, users like me, with over a thousand contacts in my address book, won’t want to individually assign people to groups. It’s much easier to give clients one email address, and friends and family another. The same is true of IM accounts and phone numbers. Similarly, some people don’t “friend” business connections on their Facebook accounts, preferring to use a site like LinkedIn instead.

I worry that the next-generation universal inbox services will require a lot of setup and maintenance, and ultimately, make it harder to carve out personal time. People are already feeling the need to check email, text and tweet at concerts and baseball games. Maybe it’s time to bring back pagers.

How will you prioritize electronic communication in the approaching era?

Kukoo is a web app that’s specifically geared at helping you maintain what many would argue are healthier email practices. I found that emails were far less pressing than I thought they were when I used it to limit myself to checking, replying and generally managing my accounts only twice during the day.

Kukoo works by setting you up with a custom email address based on your existing one. Emails sent to that address are governed by rules of your choosing, and senders are notified according to these rules about when to expect a reply. As a sender, you get more piece of mind because you don’t have to wonder whether or not you’re being ignored. On the receiving end, you’re free to let things pile up a little bit without worrying about whether clients are getting impatient, and the pressure of replying will be somewhat alleviated. And if you feel like giving senders more info regarding your inbox habits, you can even include information regarding when you last checked your email.

There’s always a catch. In Kukoo’s case, it’s that anyone sending you emails has to add “.kukoo.com” to your existing email address in order to receive your auto-reply notifications. That’s a problem, because people are creatures of habit and as such, won’t change their address books. They’ll also figure out that emailing directly to your address bypasses the auto-reply function. Finally, if you’re concerned about branding, having “yourdomain.kukoo.com” as your go-to address might, er, water down your image somewhat.

If you aren’t able to stomach the idea of leaving senders hanging while you scramble to get a million more urgent things done before you reply to them, Kukoo might be the answer for you. If you haven’t been able to give singletasking a proper go, this could be the app to get you started.

Teleworking has been gaining traction for years and now more than 2.44 million people spend at least part of their work week at home.

But recently some major employers have been pulling telecommuters back into the office. The goal of any would-be teleworker is to show your boss how working from home will benefit him and the company.

If you’re having trouble getting your point across, here are some possible reasons he wants you in the office.

He Doesn’t Know What It Means

Don’t make the mistake of proposing telecommuting to a manager who has no real idea what teleworking is or how it works. Just because they can navigate around in Microsoft Outlook and can operate a blackberry doesn’t make managers tech savvy. Even at the risk of insulting their intelligence, it helps to provide a clear definition of what you’re asking for.

Of course that means figuring out what you want before you broach the subject. Do you want to work from home once a week, a few times a week, or full-time? Good negotiators know their end-points (what they want) and their breaking points (their bottom line).

In fact, avoid using the word “telecommute.” Even though I do it full-time, I almost always use the word telework, because it focuses on work, not my commute or lack thereof. It might be better to not use the words telecommute or telework at all, and instead just say in plain and simple terms exactly what you want.

For example:

“I get so bogged down here at the office that I end up working nights and weekends away from the office. I believe my productivity would increase if I could work from home for two days a week. I’ll still be readily accessible by phone, IM, and email during those times. Do you have any concerns with allowing me to work from home two days a week for the next three months?”

He Thinks You’re Getting Preferential Treatment

Some managers buy into the idea that everyone should be treated equally. It’s egalitarianism management and it stinks. Managers who buy into this concept care more about what their employees think about them than productivity or effectiveness.

I could give you a pep talk about changing corporate culture and management styles, but I won’t bother. Instead of wasting time trying to change management styles, it’s better to work within their framework. That means getting the approval of your coworkers and team members first, the people who will be most affected by your departure, before going to your manager. If teleworking will put additional burdens on your coworkers, they’ll let you know.

Approaching your coworkers first will also require you to take a realistic look at whether your job is a good fit for the teleworking. A production manager at an assembly plant has very little chance of telecommuting if 90 percent of his job duties require him to be on-site.

Approaching egalitarian managers with your coworkers full support tells them there’s no need to fear unpopularity or repercussions from the masses and that it’s okay to give you the green light.

He’s Old School

Many managers prefer “seeing” how hard you’re working. That includes a lot of managing by walking around, which is pretty ineffective management. Good managers know that managing by results is better for the company, employees, and ultimately themselves.

If your manager doesn’t focus on results, it’s up to you to help him start. Start reporting simple management numbers that focus on your productivity. Productivity numbers don’t just show how much you’ve completed, but shows how quickly or efficiently you tackled them. That generally means including a time component to your statistics such as tasks competed per hour, income generated per day, or product per week.

When it comes time to propose teleworking, you’ll already have management measures in place for him to ensure that you’re working hard.

He Just Loves Your Pretty Face

Some managers could forget all about you if you’re not in the office. If your manager fits this description you’ll need to retrain him or her to show that even if you’re not in the office, you’re still accessible. These managers are also less likely to allow you to work from home even on a trial basis.

For those employees, I suggest finding a reason to work from home, even if that means using a vacation day, to show just how accessible you can be. Send emails, make phone calls, or ping your coworkers and manager with instant messages. Do whatever it takes to show your boss that he’s not missing much by you not being right there with him. Most importantly, be more productive outside of the office than inside!

He Doesn’t Trust You

Stop now. You’re in trouble. If your boss doesn’t trust you then forget it. Whether the mistrust is warranted or not is unimportant because you can’t make someone trust you. Without trust you’re left with two options: build or rebuild the trust that is missing or go work somewhere else. The latter is usually easier.

Justin Draeger has been teleworking full-time since March 2008.