Startups: How to Plan with Too Many Options

Plans are worthless, but planning is everything.
– Dwight Eisenhower

One common difficulty startup founders face is how to avoid being overwhelmed by the sheer amount of stuff to do.  In a typical startup, you need to know your market well, execute on building a product, acquire lots of customers, raise money, hire great talent, build a strong company culture, and manage your cash flow.  Our brains simply don’t have the power to wrap themselves around all these areas in all their details all the time.

I faced this difficulty myself in running HitPlay, and I see this issue all the time in companies I mentor.  From my own experience — and the experience of various other people I respect — I’ve outlined an approach I think is helpful.

The trick is to wrap your head around one area at the right level of detail, and to be smart about how you move this focus around.

Here’s the process:

  • Figure out which aspect of your business is the most important to address right now.
  • Focus like a laser on this area until it’s no longer what’s most important.
  • Rinse and repeat.

Great, thanks, but how do I do that?

Start with awareness.  You (as the founder) will be in the best position to make the right call.  What’s most important is that you actually follow this process, and refine your instincts as you go.

You should cultivate a habit of asking yourself “what’s the most important thing to be thinking about right now?”.  The answer may be high-level and strategic.  Or it may involve low-level implementation details.  Whatever the answer, once you identify it, you can use this awareness as a tool to cut down on wandering thoughts.

Seek advice.  More experienced entrepreneurs can give valuable perspective, especially on high level “what’s the most important thing to focus on” kinds of questions.  Often, when you’re deep in the operational trenches, you don’t see the forest for the trees.  You feel like you’re in the middle of a sprint, when really running a company is a marathon.

As for how to find mentors, a little flattery goes a long way.  Find someone you’d like as an advisor, and send them a note as to why they in particular would be helpful to you.  Ask to schedule a quick phone call, and be respectful of their time.

Embrace Constraints

You’ll never get a handle on complexity without ways to reduce your search space.  Some techniques:

Say no a lot.  Say no to random requests to “grab coffee”.  Say no to most prospective business deals.  What you say no to is more important than what you say yes to.

Suppress thinking about something until a certain condition is met.  A couple examples:

  • You have a site and are considering throwing up ads for revenue.  Before devoting resources to this task, do a little math.  Let’s say you can sell ads for $1 CPMs, and anything less than $1000 / month of revenue is immaterial.  That means you should wait until you’re getting 1 million page views per month before you think further about this task.
  • You know your code needs to be refactored to allow horizontal scalability.  But there’s a high likelihood that you’ll never have enough concurrent users to require this scalability.   So you could use a trigger like “don’t worry about refactoring until my server load is greater than 1”.

Group tasks into milestones. By milestone, I mean:

  • A measurable deliverable at the granularity of “a few weeks of work”.
  • What you learn by achieving the milestone will improve your subsequent planning.

The second point is the key.  Because of the expected knowledge to gain, there’s no point planning beyond the milestone (other than the rough planning to determine that the milestone is comparatively more important than other things to do).  The milestone acts as a horizon that limits the scope of your planning.

And once your identify a milestone, switch into execution mode where you drop down to the low levels of detail you need to do the work.

Let me walk you through an example.  Let’s say you and a friend have an idea for a startup, but don’t have anything built yet.  A good milestone could be “create a landing page that expresses the value proposition of your product, and collect 300 email addresses of interested people”.

This milestone is small enough that you should be able to wrap your head around all the necessary steps.  And consider how much you learn upon achieving it:

  • You’re forced to clearly articulate your value proposition.
  • You gain knowledge on how to acquire customers.
  • You validate your interest in the company, as well as compatibility in working style with your partner.
  • You have lots of people’s contact info to reach out to for feedback.

I’d like to end with a few anti patterns to be aware of:

  • The founders cannot agree on what’s the most important issue.  Founder disagreements are a big deal.  If you find yourself unable to agree on what’s the most important issue, then your most important issue is this inability to agree.
  • I’m fighting too many fires all the time to do much planning.  You need to make time for non-urgent / important tasks.  If you find yourself in reaction mode all the time, your most important issue is to get ahead of the chaos so you can be proactive.
  • We know what we need to do and we’re too busy to spend much time in planning.  This situation is almost never true for a startup, but is a common sentiment since it’s easy to get caught up in the details.  It takes discipline to operate at multiple layers of perspective.  When you’re executing toward a milestone, you shouldn’t be spending a lot of time planning.  But between milestones, you should give yourself (and the entire team) lots of time (several days, if necessary) to focus just on planning.  You should have a healthy ratio of time spent thinking vs. doing, or else you will slowly drift off course.

How about everyone else?  What approaches to planning and prioritization have worked best for you?

3 thoughts on “Startups: How to Plan with Too Many Options

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