Skillful Improvisation: The essential arts of venturing

Three venture craft skills detailed in my book Spinning Into Control: Improvising the sustainable startup  (Palgrave Macmillan) collectively define the art of entrepreneurship, without which no amount of management science can deliver startup success. At the heart of each core skill lies improvisation, the real-time fusion of thought and action, design and execution. Improvisation — by embracing chance events and uncertainty — steadies and accelerates hypothesis-based methods relying on adaptive, so-called “lean” planning.

Explorers at heart, venture craftsmen recognize the sense-making power of wandering. Letting go of assumptions and unlearning past notions and skills frees these entrepreneurs of the tyranny of legacy. Questioning their biases and inviting critique from collaborators helps them avoid cognitive traps. 

By giving free rein to their wanderlust, they gain control over what counts the most, namely, their destiny, while giving up control over the path that may lead them there. The starting point? Tim Brown of design agency IDEO in Palo Alto, California, points to “the power of asking the right questions.” 

This sets the stage for opportunity identification and creative problem-solving enabled by conversation and tinkering, the two other key startup incubation skills.

The art of conversing underpins what Professor Richard Sennett, sociologist and New York-based author of The Craftsman, calls the “craft of cooperation.” It mobilizes resources and talent. While estimates vary, surely less than 1% of startups are accepted into venture accelerators or receive funding from professional investors. 

The bootstrapping majority must master active listening and open dialogue to accumulate and fully leverage social capital. Achieving productive relationships with early customers, partners, employees and other stakeholders ensures that founders maximize the return on sweat equity invested during incubation. 

Whereas storytelling, very fashionable these days among marketers and management coaches, is about advocacy and persuasion, the art of conversing requires above all a refined ability to listen to and dialogue with others.

Finally, the underappreciated art of tinkering (see detailed article here) helps handcraft products or services of enduring value as well as programs to market and sell those offerings effectively. Through tinkering, entrepreneurs engage in a dialogue, not with people but with resources, tools and prototypes. They prize proficiency in learning as much as furthering their startup’s mission. 

They accumulate resources without clear plans for their deployment; ceaselessly disassemble and study competing products and joyfully recombine product components—whether their own or those of others—into a menagerie of exotic prototypes. Tinkerers spin towards excellence by hacking a succession of rough prototypes that embody individual elements of form and function. 

They break “out of the box” of the past by challenging themselves and their teams to bust constraints and orthodoxies viewed by others in their businesses and industries as ineluctable.

Mastering these loose, on-the-fly improvisational arts—wandering, conversing and tinkering—requires practice and discipline. But investing in their development will provide guard rails against chaos in fast-changing environments rife with inchoate ideas, ill-defined products and projects destined for failure more often than success.  Perfecting improvisational skills will not guarantee venture craftsmen a one-in-a-million blockbuster, but it will move more startups from the loser to the winner side of the economy’s scorecard.

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