Given that entrepreneurship is nigh by-definition fuzzily defined, what is the core skill all entrepreneurs are practicing? “The Ask,” argue the authors.
In our search for such an activity conducive to purposeful and deliberate practice in entrepreneurship, we observed one in which entrepreneurs engage across all types of ventures, geographies, and times. We call this activity “The Ask.” In building a venture, entrepreneurs continually and iteratively interact with other people. Almost all of these interactions involve Asks. Asks can cover a variety of inputs necessary to creating a new venture that may include both intangibles (advice, introductions to network contacts) and tangibles (resources such as customer orders, supplier materials, labor, and money). While the “what” of The Ask differs across stages of the venture and particular stakeholders and situations, our observation is that the “how” of The Ask has repeatable common elements capable of continual practice and improvement. Likewise, while the “who” of The Ask differs (the identity of The Askee, from family, close friends, and network contacts to complete strangers), the activity of asking remains comparable.
This led us to posit “The Ask” as one of the most important activities on which purposeful practice may be applied to improving entrepreneurship. Most importantly, asking is intrinsic to the early stages of the entrepreneurial process. Whether they like doing it or not, entrepreneurs have to engage in The Ask on multiple occasions each day in the course of launching a new venture. Hence repeated practice of The Ask is an inevitable feature of the startup environment (Ericsson & Smith, 1991).
The Ask itself may not be inherently motivating for an entrepreneur but the larger objective is motivating, e.g. of successfully establishing a new venture. This provides the entrepreneur with powerful incentives for getting better at asking. Furthermore, an Ask typically creates spontaneous natural feedback for an entrepreneur, whether verbal or non-verbal, from The Askee or from surrounding observers. Immediate feedback in the form of rejection, acceptance (with the provision of new resources), or the introduction of new alternatives (perhaps an introduction to another person) provides the sort of feedback necessary for diagnosing failures and identifying improvement opportunities (Ericsson, 2004, p. S77). Lastly, The Ask may be tailored to the skill level of the entrepreneur. Indeed, we can precisely conceptualize a natural progression from apprentice to higher proficiency levels of asking.
Here I’m again inclined to offer Patrick McKenzie as a concrete example. I can think of nothing that betters exemplifies “the Ask” than his approach to developing Appointment Reminder:
Three years ago, I had had the idea for Appointment Reminder, and wanted to discover whether businesses had a large enough no-show problem to justify paying $30 a month for it. I don’t have great access to non-technical small business owners, so I just decided to pretend I was an extrovert for a day, and interview people door to door in Chicago.
Here was my pitch, which I made to every massage therapist and hair salon owner I could find just doing a breadth-first search down Michigan Avenue:
Hiya, do you take walk-ins? Are you the owner? Great, can I book the thirty minute option for name-a-service? Great, actually, I’ve got a request. More than the name-a-service, I am really interested in the business of name-industry-here and want to talk to you about it a bit. I’m happy to pay for your time. Does that work for you?
I lost my notebook where I kept the interview results (d’oh), but my recollection was that only one person out of a dozen plus actually took my money for this. Most were happy to talk, since unscheduled time for them in the early afternoon had a predicted value of zero anyhow. (n.b. That was, in itself, a useful lesson.)
Did you catch how he was surprised to discover how friendly everyone was? This segues perfectly into my favorite bit of this post:
It turns out that these perceptions significantly affect an individual’s performance in the activity of asking in a strongly negative way, i.e. help seekers underestimate the likelihood that others will help them by as much as 50 percent. Non-expert askers appear to systematically believe that others will say no, even when they have no hard evidence on which to base such an assumption. Expert entrepreneurs, however, achieve better calibration through the actual practice of asking.
People tend to underestimate how willing others are to help them by a staggering 50%, except for seasoned entrepreneurs who, with practice, have learned the monstrous truth of it: people are secretly fantastic, want you to succeed, and are willing to help you get there. (!!!!)