Priorities:  Since my job gives me the flexibility to work on lots of things, lately I’ve been concentrating on two of the things that are most important to our business as a whole: sales, and more sales.  Although I have some insights and funny anecdotes about my conversations (Q: “May I speak to Mona?” A: ”Last I heard, she choked on a chicken bone and died”), they’re not generally appropriate for this blog.

Progress:  As a whole, we’ve been concentrating on JobTracker, which means that there’s little or no change to what’s going on in the Skedsheet world.  This is frustrating to all of us, but at the end of the day, we need to spend a good chunk of our development effort on what brings us money.  This is the classic trap that  Clayton Christensen describes in the Innovator’s Dilemma.

We need to keep serving our existing customers, and we continue to bring them a higher level of service, but we’re possibly leaving ourselves open to competition from the “low end” – Skedsheet could provide a solution to companies like our customers who don’t see the value of our relatively “high end” products in the JobTracker family.

Writing on a daily or weekly basis takes focus and concentration.  When there’s not much progress to talk about, and your priorities are shifted temporarily, it’s hard to come up with good ideas on a regular basis.  Because of the priorities, it’s also hard enough to justify the time you need to spend to do it well.

Enough excuses…I’ve got a stack of half-written posts with ideas, so hopefully I’ll get back on the writing wagon.

One of the main reasons that we’re excited about Skedsheet is that we want to eliminate “implementation” altogether by having a software utility that’s easy enough to just get going.  But, it’s still on my mind…frequently.  Any time you decide to change something in your life or business, the process requires effort, and maybe a little pain. 

There are some steps you can take to make sure that when you’re making a change (buying software, using new equipment, changing pricing, or introducing new products), it goes smoothly.

1. Get everyone on board early.  If your coworkers and employees don’t know what kind of change is coming, they will revolt. The earlier they’re involved in the process, the better.
2. Be ready to break things.  Making a change to your business means breaking the way you do things today – even if it’s already broken.  This is scary, but it’s necessary because you can’t just add to what you’re already doing – that doesn’t fix things.
3. Set deadlines.  If you don’t have a deadline for getting software implemented, it’s really easy to put it off another day. Setting hard deadlines and sharing it with your coworkers is a good way to make sure you’re accountable.
4. Uninterrupted time.  This is probably one of the hardest, especially if you’ve got the responsibility for changing your business and the authority to actually do it… your time is in short supply.
5. Remember the goal. Every so often you need to take a deep breath and remember why you’re making a change.  It’s to fix the problems you had before or allow you to do something new.

It’s not foolproof, because there are always going to be unexpected problems that come up in a software implementation, but having a little planning and perspective will help.

Let’s say that the cost of doing the beta version of skedsheet is around $100K – that’s development time, graphic design, and the direct costs of setting up a website, getting trademarks, and all of the other administrative parts of setting up a new product.  I think that’s the right ballpark. 

After that, there are the ongoing costs of running skedsheet.  We’ll need servers, which will probably start around $500/month, and grow as we’re successful.  I’m sure we won’t have all of the features right in the first version, so there’s going to be ongoing development, and I’m sure that  we’ll have to spend time on customer support, too.  Let’s say that adds up to $2000/month for each. 

Even if we’re willing to toss out the initial investment, that means around $5000 per month just to break even.   And if we want to recoup the original outlay in the first year, it looks more like trying to get $14000/month.  Zoiks! maybe instead we want to break even on the original investment in 2 years, which makes it closer to $10K/month.

While we haven’t thought about price in detail, there are a couple of strategies we can take.  We’ve ruled out having expensive software.  Even if we choose a number as low as $100/month, chances are that we’ll need a sales process, and a sales guy to convince people to part with their money.

We can’t be totally free either.  That could get lots of users, but there’s not a chance of making money for just giving away our service.  So the answer is Free + Cheap.

Is a $10/month cheap?  $1?  I think that the right model for us is to have a small group of our hardcore users pay for the costs, and allow us to give away our software to 95% of the people who want to use Skedsheet.  So if the numbers I just pulled out of the air would work out, it’d be something like:

(Paid Users) x $10 = $10000, so we’d need a thousand paid users.  And if

(Paid Users) = (All Users) x 5%, we’d need twenty thousand people using Skedsheet before it makes financial sense.

So, the next  question should be “Does Skedsheet solve a problem for tens of thousands of people?”

Schedules!  Who’d of thought that could be controversial?

Chris Schoenfeld, who runs StationStops, created an iPhone application which provides the Metro-North train schedule.  The whole idea was that he didn’t like the paper schedules that were available because they were hard to sort through and read.  And, the MTA’s website and ways of publishing their schedule to an iPhone didn’t work for Chris, because they relied on a live internet connection – something you don’t always have  when you’re in a subway in New York. 

So, he did what any good nerd would do – he fixed the problem for himself, realized that it might be useful to other people, and built a product around it.  Since then, he’s gotten cease-and-desist orders from the MTA and requests for licensing revenue.

It shocks me that the MTA would do this – what possible good can come from this kind of action?  Even if originally they thought that they might be able to get a few thousand dollars in licensing money from Chris, wouldn’t they realize that they’re burning much more goodwill? 

And most likely, the outcome will be that hundreds of apps or sites like this pop up just to spite the bureaucrats.  Here’s more coverage of the story:

• Greater Greater Washington
• Techdirt
• WTNH Channel 8
• Slashdot

I’m not even worried about spam – between the filters on our mail server and the Bayesian filter on my client, things that are spammy disappear before I can see them, or end up a folder for junk suspects.  Of course, you shouldn’t make email that looks like spam, but I think most of the emails that bug me are well-intentioned.  Here are 5 rules for writing a clear, readable email.

1. Just rehash.  Don’t introduce a new concept in an email.  It’s hard enough for me to read an email when I understand the point…but trying to teach me something new, sell me something, or proposing a new venture just doesn’t work well in email.  Email is best when it’s the follow-up to a live or phone conversation.
2. Short & sweet.  There are probably 20-30 emails that I want to read and act on every day, but I don’t want to kill my whole day to do it.  I’m a pretty fast reader, but there’s a huge difference between spending 1-2 minutes on an email versus 5 minutes – in the worst case, that means almost 3 hours per day.  Just reading… and trying to understand.  Usually, if I see more than one long paragraph, I’ll just make a phone call.
3. No emotion.  Nuance, sarcasm, anger, and sympathy are really hard to convey in an email.  Even if you think your smileys give the right emotional cues, they could easily be missed.  Controversial subjects can spiral out of control too easily, so it’s much better to leave the tough stuff to live conversations.
4. Bullets won’t hurt you.  I love enumerated lists, and I think the world would be a better place if that’s the only way people communicated.  Having numbered bullet points in an email allows you to reference specific parts of a message, makes it a little more readable, and can convey priority without much effort.
5. Contact info.  It surprises me how often I get emails without contact information.  “blah blah blah… from John”.  For work, most folks are somewhere in our customer database, and I can look it up with some effort based on context, but even that occasionally fails – for example, if someone’s sending an email from a hotmail account with an unrecognizable name.  It’s really easy to add a signature to your emails, so add a useful one.

Just following these 5 tips won’t make your emails great, but at least it’s a step in the right direction.  Personally, there’s  a much better chance that I will read an email and care if it’s short, concise, organized, and isn’t blindsiding me.

“Even if it’s free, how do we sell this puppy?”

I know you don’t need to “sell” free stuff – at least not in the traditional sense.  It’s much more about providing something in exchange for your time.  Since we’re giving something valuable, and making it easy to share…each of our “free” customers should become an advocate for our software.

But, we still need a Unique Selling Proposition:  What’s the reason to even look at us?

I expect people to compare the cost (in time and effort) of Skedsheet to using Outlook and Excel.  I’d argue that Outlook and Excel are both effectively free – I bet you didn’t pay for them and you already know how to use them. 

Here’s what I’d want to say:

With the system you have today, you’re re-typing some details from your spreadsheet onto the calendar, and figuring out how to show it to other people. 

Of course, there’s the chance of making mistakes that cost big bucks, as well as time wasted looking in more than one place for information. 

I think we’ve another unique concept in Skedsheet that I haven’t seen touted other places – the idea of multiple dates being tied together as one “job”.  I don’t know how to describe this well – but that’s what ended up being the defining feature for our JobTracker software, and it seems like it will apply more generally through Skedsheet.

But, because it’s free, there won’t be a salesperson telling you any of this.  Instead, I assume the sales pitch will be:

1. Right here, with us writing about our software on this blog.
2. An demo video that will explain everything clearly.
3. Stories and examples of how other people use Skedsheet.
4. Skedsheets that you see because a friend shared them with you.

Part of the problem with the software is that it’s ugly, and there’s some minimum level of attractiveness that needs to be there so our future users don’t run away with bleeding eyeballs.

We’ve been working with a designer to help fix the ugliness.  To start, we needed a logo, website, and some design in the software, itself.  I was trying to wait until we could actually update our website with the new design, but I’m too excited.  Voila, the logo!

What’s cool about this is that since we’re starting with a blank slate, we were able to give minimal direction, and be happy with the outcome.  I’d say that the logo succeeds in meeting the few requirements that we had. 

This logo is very typographic, original, and has a simple icon that suggests a spreadsheet or a calendar.  It works on a black background, too:

So far, so good.  Hopefully we’ll be rolling out decent-looking website soon.  What we’re realizing is that this is an iterative process.  We’ll have the place-holders for the web pages and parts of the software that we imagine needing… after a few months, we’ll understand what we really need.

One of the missing ingredients is to figure out how we make money.  I still think we want a freemium model for skedsheet, so the question is

“What’s free and what do you pay for"? 

The dividing line all needs to be about value… what’s valuable enough to pay for?  And, can we build a product that’s free for lots of people, but have a small percentage of users cover the cost of development and infrastructure?

Even the free version needs to be valuable – otherwise nobody will care.  I want the free version to be useful for a single person working on a schedule, and maybe sharing it with a few other people.  But if it’s being used by lots of people at a Fortune 500 company, we should be charging.  The extreme cases are pretty easy to nail down, but we need to figure out where the dividing line should be.

Can we split up the features in a way to distinguish a casual user from a big company?

Which other features should be on this list?  Are there other dimensions for the free/pay boundary?

If you’re trying to manage a few schedules, but you care deeply about having your data secure, is that a feature worth paying for?  How many editors is “a lot”?  Would we really build a separate mobile version? 

How do we make sharing and using Skedsheet really easy and not have new users worried about paying until they really find value?

Getting out of the office is a good way to shake things up.  As time goes by, we are learning that we should actually plan to be out – doing something active really gets our creative thoughts working better.

A few years ago, when we had our sales meeting for JobTracker, we planned to have a little time off to go to the beach, boogie board, and hang out.  It was just half a day out of the whole time we had allotted to get together.

At the beach, while we were all floating in the water, we came up with a new product, new pricing, and talked about new approaches to selling our products.  We didn’t even realize it at the time, but I think we made some fundamental changes to the business – figuring out that we need to keep trying to  undercut our existing products with new ones that are cheaper and easier to use.

About a year ago, Ted and I were trying to hammer out some features – sitting in my office, getting bored and hungry, and not making any progress.  So, we decided that it’d be a good idea to walk to lunch and think about it when we got back. 

Instead, we kept talking through a problem that had been frustrating our customers and making support hard.  And, on that walk we came up with a different approach.  Looking back, we radically improved one of the hardest parts of our software.

Now we just came back from our strategy meeting – and we walked or hiked the whole time.  And once again, we planned some radical changes to our business, marketing and sales.  And once again, my to-do list has 15 new things on it.

Despite our whole marketing pitch, product, and general company philosophy of centralizing information, I’ve been secretly using a whiteboard to help me manage my job and schedule some of my activities.

Well, maybe it’s not so secret, since the board is about 5’x4’, so anyone who’s been in my office sees it takes up about a third of one wall.

Here’s a picture of it – yes, it’s a mess.  What works about it is that it’s a place I can easily go and have a daily reminder of what I need to do. 

What’s bad about using whiteboard is that it’s hard to move activities, I’ve accidentally erased parts, and since I like to doodle while I talk on the phone – it’s filled with little notes that are out of context or completely unreadable.

How is my whiteboard being used?

30%: Kid’s scribbling.  I work at home and I occasionally allow the kids into my office.  They need the part of the whiteboard they can reach in order to do their artwork. 

30%: To-do list.  There is a giant list of things that I should be doing, but they’re hard to get to on a day-to-day basis.  About once per month I get the satisfaction of erasing something from this list.  Of course, in that time I’ve added four more items.

5%: Sales pitch.  I have 4 sentences on my whiteboard that remind me that when I talk to customers my conversation should be centered around them: “What are you doing today?  What works about that?  What doesn’t? What’s the consequence if you don’t change what you’re doing?”

35%+ Unreadable.  I have no clue what most of this stuff is.  I know I wrote it because it’s in my handwriting, but beyond that there’s no information.  My favorites are the time “3:30” and the ominous number “2365”.

I don’t have any plans to get rid of my whiteboard – but the reason I can have it is that it’s not the only place I have my information.  At least 70% of what’s there has no value after I write it down, but since I’m a pretty visual person, I need to write as I talk or think.  It’s more of a doodle pad than a calendar or a spreadsheet.