1. What iteration means for your organization

    Mona Lisa Iteration

    "Iterative" is a regularly used term for those that follow the agile and lean development philosophy. The base meaning of iterative is to simply do repeatedly, over and over. Though iterative is a colloquial word in the Valley, the tactical application is often forgotten. Iterative tactically means to efficiently learn and make better decisions with a low cost when mistakes are made.

    To iterate means to learn faster.

    As iterations build, organizations learn faster and have a stronger foundation in data. Teams that don’t use data in making product decisions usually have two reasons: it requires more work and more introspection into an individual’s intuition (self-analysis).

    As Mark Suster writes, entrepreneurs have a habit of doing rather than thinking + doing. Ironically, teams that do not have an iterative mindset still value speed; they just don’t realize that they are their own worse enemy. Not using an iterative mindset causes the following problems:

    • Resource waste: no one wants what you are building; thus you miss company goals.
    • Energy waste: mentally, employees only have so many iterations in them before they lose hope. 
    • Time waste: it takes longer to build product that is not iterative (aka feature creep).
    • Overtly risky: large releases put too many eggs in one basket; thus it can be hard to tell why a product did not work.
    • Team bickering: Without small iterations, people see only a few opportunities to get their amazing ideas built; thus more energy is spent on political power maneuvering than focusing on real objectives.  

    When working in a team with a low coefficient of learning, the best strategy is to push the team to do more with instrumentation. By pushing for faster deployments, the organization will start breaking down projects into minimum builds. This will naturally result in a testing and data mindset. A team will start to ask themselves the right questions to scrub out unnecessary features. Feature creep is easier to spot. 

    Egos become less of a problem. Egos are deflated with two tactics based in an iterative mindset:

    1. "Our previous iterations did not/ did validate your {fill in the blank}." 
    2. "We can test {fill in the blank} in the next iteration." 

    The reality is that egos prefer not to ship. Shipping requires execution (which is hard) and exposure to failure (which feels uncomfortable). The riskiest thing to do as a team is to not ship. “Ship often. Ship lousy stuff, but ship. Ship constantly,” said Seth Godin.

    "Shipping" is a synonym of "iterative". Failures with a slow moving, data-less product are big. Failures with an iterative team are small and doesn’t hurt the underlying business. With each shipment/ iteration, a team can learn from successes and failures and apply them to the next round, which spans days not weeks. 

    Everyone is embarrassed by their first product. If you are not embarrassed, you are not doing something right. To be pixel perfect is for those who have market share and make millions in revenue a year. Being a quick and iterative team is the single greatest advantage every startup has over the establishment. 

    Own this advantage. Iterate. Otherwise, you will lose the battle and the war.  


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    “Iterative” is a regularly used term for those that follow the agile and lean development philosophy. The base meaning...
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