Entrepreneurship – Can It Be Taught to Operational Managers?

November 23, 2016

“Marrying Entrepreneurship with Design, and combining it with what we are good at today, Engineering” is a product of my thoughts on how to bring the organization to the next level and prepare it for what some are calling the “Fourth Industrial Revolution.”

The idea comes from a video on Lean Startup meets Design Thinking, where Eric Reis (Lean Startup), Tim Brown (IDEO), and Google Ventures Design Partner Jake Knapp are invited into a conversation by Google.

Marrying Lean Startup and Design Thinking

Listening to these great minds, the question of how one concept fits into the other comes into play, and it becomes really difficult to pinpoint which is the bigger idea and at what point do they intersect. So as not to try and compartmentalize ideas, they go into an analogy of whether a prototype is the equivalent of the MVP in Lean Startup, or if it is the first or second iteration in Design Thinking.

Guilty as I might be of trying to compartmentalize these great ideas, I frame them to be able to understand better whether they are joined at the head, or the hip, and how they might be used to work in tandem.  

At this level, Design Thinking is the process of defining the product design and implementing the design using engineering practices. And after watching the video, my own take is that at a corporate level, Lean Startup is the entrepreneurial discipline. It guides people through the process of marrying new product design and product engineering to understand customer needs.

At any rate, we at Pointwest are engineers by profession. Given a problem, we design and implement the solution within the definition of what the problem is.

Bringing Entrepreneurship into the Fold

After watching Eric Reis and Tim Brown, my thoughts return to the need to bring back the sense of entrepreneurship in the organization, especially for the leaders. The three skills I tried to bundle were entrepreneurship, design and engineering.

This is the type of leadership you need for companies in their 3rd and 4th stage (see image below).

The Corporate Life Cycle and Four Work Types (Diagram)

What we have bred in the company is the engineering skill, which resulted in leaders always thinking scalability and reusability or repeatability.

But, if we are looking for our second (and third) S-curve, then the challenge is not solved using engineering skills. We need the entrepreneurial and Design Thinking skills that help companies look for customer pain points and provide them the gains to address these.

The question begs: “Can you teach IT leaders to be entrepreneurs?”

My response is that I think people grow into it. It is sparked in those who see opportunity and move quickly to explore the opportunity.

“Does it work the other way around?” Can entrepreneurs become IT leaders? The answer in one of the talks is that the founder is kicked out by the funder, more often than not. That is because at 2nd and 3rd growth stages, the owners are looking for people who stabilize and operationalize the firm. And, most founders are as Steve Jobs termed “the crazy ones.”

In fact, Steve Blank (a serial entrepreneur, watch: How to Build a Great Company, Step by Step) says:

“You have more chances of becoming a successful entrepreneur if you are dysfunctional. That is the one single time – you might have an advantage over calm cool people with stable upbringing – because dysfunctional people (not a requirement, just a plus) know how to survive and thread through the unknown.”

What Leaders Think About Entrepreneurship

So, what I have here is more of a question: “Can we really institutionalize an entrepreneurial mindset into our existing leaders?”

I posed them this question and there were varying ideas:

Mike Togle, our Lead for UX and Digital Marketing, feels that entrepreneurship cannot be taught; it has to be inculcated and indoctrinated into the leaders – a cultural change. He felt that people have to gradually grow into the entrepreneurial mindset.

For Mike, entrepreneurs have that “first-to-market” mentality, failing fast, failing hard, fail often, and pivot often until they find that perfect model for their business. Making IT leaders feel the need to shift into this mindset, and how they can approach it is not impossible; just difficult. Teaching them the tools is just part of the equation.

In the end, he felt that not all leaders can be entrepreneurs.

Steve Blank, in the video, shared that there are more chances of being a successful entrepreneur if you are dysfunctional. Mike believes that it is more of eccentricity, and the “imperative need to survive.”

“Operational Leaders will try not to rock the boat; they will stick to their comfort zones. Entrepreneurs, on the other hand, are always on the look out for the next opportunity to attack, beat, and then lead… because they have to, and can’t afford not to.” Mike Togle, Lead for UX and Digital Marketing.

On the other hand, Sherwin Pelayo, Digital Capability Development Head, expressed that he believes that although entrepreneurship can be taught and learned, the culture and operational mindset of leaders in project delivery has to be changed, or overcome.

“One of the main root causes I see that prevents us from building a nationwide entrepreneurial spirit is our own Filipino culture: an overpowering sense of responsibility to our families and our fear of failure.” Sherwin Pelayo, Head of Pointwest Labs and Digital Capability Development

In terms of culture, that sense of responsibility for the welfare of families may deter people from jumping into new waters, lessen their sense of adventure, and cling to something that is certain.

He also shared that the fear of failure, or the lack of appetite for risk, also prevent existing leaders from the notion of accepting help from angel investors for their business ideas. The mantra “Fail fast, fail hard, fail often,” may not be enticing for people that have managed risks for the longest time.

Is Entrepreneurship the Catalyst for Continued Success?

I am adding a short video clip on the business canvas model – a tool we have used to encapsulate the business plan for a new product/service offering.

business model canvas

Business Model Canvas (from https://espriex.co/business-model-canvas)


As I shared earlier, we have created a handful of seed product arms out of these through Pointwest Labs, and we have seen the assigned leaders grow into the entrepreneurial role.

The question of whether it is sustainable, and if the mindset can catch on and flourish into the projects remains to be seen.

In your organizations, have you tried shifting your leaders to a more entrepreneurial mindset? Do share your journey as I’m interested in the story of how you are getting there.


Rene B. Quizon
Senior Executive for Business Development


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