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Startup Conversations With Myself: What Should I Work On?

Entrepreneurs (particularly bootstrapped ones) have a tough life.  In the early days, things can get lonely.  So many decisions, so many challenges, so much to do — and very little by way of clear answers.

This is a somewhat light-hearted episode in perhaps a series of articles that I’m calling “Conversations With Myself”.  I’d like to think that I’m not alone in my strangeness in that I actually have these kinds of debates going on inside my head (often after 3:00 a.m.).  My guess is that some of you have variations of these kinds of conversations yourself.  If not, then I guess I’m just weird.

Conversations With Myself:  What Should I Work On?

Me:  Self, I’ve been thinking a bit about things.

My Self:  Are you you sure you’re not just procrastinating?  Don’t you have bugs to fix in the product or some other real work to do?  Thinking is for smart people.  Get back to work.

Me:  That’s just it, there’s just way too much work, and the list of things to get done seems to get bigger every day — even though I’m staying up later and working harder.

My Self:  So, what’s your point?  It’s a startup, that’s the way it’s supposed to be.  If you don’t have 10X as many ideas as you have time to do them, you don’t have enough ideas.  Quit being a whiny-assed pansy.  Nobody said it would be easy.

Me:  Yes, yes, I get that.  I know startups are hard with the 80–hour weeks and all that.  What I’m saying is that there are several items in the backlog that must get done.  And, as the product gets bigger and more users come on board, more and more time is taken up keeping the system running, responding to user issues and a bunch of other stuff.  When will the new stuff ever get done?

My Self:  Ok, so define “MUST get done”.  What happens if you don’t do some of those things?  The planet stops spinning?  You lose some users?  Your ego gets bruised?  You watch one more episode of “The Office”?

Me:  Ok, fair point.  I guess not all of those things are technically “must-dos”.

My Self:  Well, it actually goes beyond that.  Not only are most of the things on your list not “must-dos”, a lot of them are probably “shouldn’t dos” .

Me:  So, how do I go about figuring out what I should get done? 

My Self:  That’s a great question.  Unfortunately, we share the same brain, so I don’t have a great answer.  But, here are some things to consider.

Simple Tips For Deciding What To Work On

1.  Are you tracking all of the bugs and enhancement ideas (however crazy) somewhere?  If not, that’s step 1.  You need a central list.  Not this list and that list, but THE list  The One True List.

2.  Decide on a simple and semi-objective approach to classifying each item on the list.  Scales of 1–10 work reasonably well.  Some high level dimensions could be: 

a) This will help make customers happy (0–10)

b) This will help me sell more customers (0–10)

c) This will reduce costs of keeping customers happy (0–10)

d) This will give me and my team joy and happiness (0–10)

e) How much effort will this take (0=Several lifetimes.  10=Hardly any work at all.)

Of course you don’t need to have those specific attributes, but you get the idea.  Here’s why this is more useful than simply trying to assign a “priority” to an item.  First off, many items in the backlog often have more or less the same priority.  It’s hard to decide between them.  Second, priorities change as things happen.  You might wake up one month and need to focus as much as possible on getting new customers.  Another month the priority might be to take your existing customers and make them happier (so they stay customers).  By assigning the above attributes to each backlog item, you can “sub-sort”.  The key is to remain flexible, while remaining mindful of the costs of task-switching  when you change your mind.  Maintain a steady velocity and keep cranking away at the items that are important.

Item (d) above is interesting.  Why should you care whether a given task on the backlog will create internal joy and happiness.  Shouldn’t we all be maniacally focused on customers and make money?  Sure.  But, startups are hard work and trying to continuously perfectly optimize is sub-optimal.  Every now and then, you need to do some things that might not make sense, but might delight users or delight yourself or just plain allow you to sleep better at night.  It’s worth the investment simply to keep spirits and energy up.

3.  Try to build a rhythm for getting stuff done.  It’s a great feeling when you can “feel” the forward progress (however small).  If you get stuck on some project, put it aside and crank some of the other ones out.  Don’t go too far down the rabbit hole for any particular project or task.

4.  You should try to balance the kinds of tasks and projects that you select.  Don’t work just on new features that will help sell the product.  Or just work on things that make the UI/UX better.  Or just work on system optimizations that make your costs lower.  It’s important to pick a variety of tasks (with emphasis on whatever seems to be the bottleneck in the business right now).

So, what are your clever little tips and tricks to make sure you’re working on the right things?  Do you struggle with trying to decide what to do?

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Posted by Dharmesh Shah on Mon, Mar 23, 2009