Be like water: The martial artist’s guide to empathy in enterprise product


Many product-oriented people focus on “what should we build” when in reality the far more important question is “why should we build this?” The role of a product leader is to be the voice of the customer, which means finding pain points that are fundamentally hindering the customer’s progress, and that said customers are willing to pay you good money to solve. This is described well in the “Vitamins vs. Painkillers” discussion. There are several great articles on this, but TL;DR if you aren’t building a product that solves a vital issue for a customer, you aren’t likely to build a scalable business. Whether you are attempting to get your first customer or to get an investor to write a check, no one is going to part with their money until you can convince them you’ve found a pain point truly worth solving.

There is no better way to identify and build painkillers then by feeling your customers’ pains yourself. This is where empathy comes in. According to Wikipedia, empathy is “the capacity to understand or feel what another person is experiencing from within their frame of reference, that is, the capacity to place oneself in another’s position.” If you’ve spent any amount of time in product or reading about product, then you probably know about the importance of empathy. Again, many articles have been written on this topic, though not as often in the specific context of the enterprise.

The challenges of empathy in enterprise

Gaining an intimate understanding of your customer is often difficult in enterprise organizations, where product development teams can be disconnected from their end-users for a variety of reasons:

One common reason is lack of commonality of experience. In the consumer world, a Facebook employee probably uses social media and knows others who do too. On the other hand, it’s not as often you’ll find an enterprise developer or product manager who runs, say, employee payroll systems on a day-to-day basis. This problem gets exacerbated when product managers communicate more with buyers of their product rather than the actual end-users, which is a common phenomenon in the enterprise world.

Another is falsely equating different personas. For example, in the infrastructure world, there are many who equate Silicon Valley developers as being similar to developers in other parts of the world (in terms of mindset, ability, to adapt new technologies and workflows, etc.). Even more damning, there are those who believe developers and IT operations folks have similar workflows and concerns. You might be surprised how many developer and IT tools startups stumble because they build tools for themselves instead of their erstwhile customers.

Regardless of the source, these are the sort of problems that can result in everything from poor feature design to fundamental lack of product-market fit--in turn, the sort of disconnects that can stagnate a large company, or kill a growing startup.

Be like your customer

So how do you go about gaining empathy in the enterprise? Let’s finally turn to the title of this blog post. As it turns out, martial arts and product have a lot in common--discipline is a critical skill, knowing the world around you requires you to first know yourself, and sometimes it takes deft and unexpected maneuvering to get the job done . Earlier in my life I studied the martial art Jeet Kune Do, founded by Bruce Lee. If you don’t know who Bruce Lee is, stop reading this and go watch some of his genre-defining martial arts movies. Once you have, you too will agree that Bruce Lee would’ve made a great product manager, as evidenced by the following famous quote:


“Be shapeless, formless, like water. When you pour water in a cup, it becomes the cup. When you pour water in a bottle, it becomes the bottle. When you pour water in a teapot, it becomes the teapot. Water can drip and it can crash. 
Be like water, my friend.”

Technically Bruce Lee was talking about being adaptive in martial arts, but the metaphor applies to product just as well. Everyone advocates having your PMs meet with customers in order to gain empathy with them, but you can do one better. Want to gain empathy for your enterprise customer? Then be like your customer, my friend. Engage in the same workflows as your customer so you can viscerally feel their pain.

Train like your customers with live fire exercises

So exactly do you go about engaging in customer workflows? Many martial arts stress the concept of “liveness”--focusing less on repetitive exercises and more on fighting real, breathing opponents on a regular basis. The belief is that the more closely you can simulate the conditions of a real fight during training, the more likely you will succeed in the real fight itself. In a similar manner, one powerful way to gain empathy for your customer is to train your team to run the exact same processes as your customers do out in the real world. To be clear, this is is not just dogfooding--this is going through the full process of end-to-end deployment, management, and troubleshooting, as a customer would have to do themselves.

One way to accomplish this in the enterprise product world is through a live fire exercise. At VMware, we had a training program known as “Livefire” in which employees went through a grueling multi-day bootcamp of deploying a complex IT infrastructure system and solving various “s*** hit the fan” emergencies that the instructors would throw at them. This was a powerful tool for helping VMware development teams to understand the lives of an IT ops administrator, as there is no better way to understand the terror of a “customer down” situation then actually seeing your own carefully-constructed deployment fall apart in your face, and frantically trying to solve the problem. 

I’ve seen live fire exercises used successfully in both infrastructure and SaaS apps companies across multiple company lifecycle stages. Early in your company’s lifecycle, as a founder see if you can invest time working at customer (or prospective customer) site and actually run their workflows. There’s a reason many of the most valuable startups had founders who lived the pain points themselves. As your company grows, you can expand this empathy to your team through live-fire exercises, but you don’t need to invest a lot to make this training happen. Fundamentally, you create a running deployment of your software, train everyone on your development team to actually deploy and manage it, and then find ways to simulate breaking the product. Chaos Engineering solutions might be helpful here, or perhaps roping in savvy white-hat friends who like watching the (software) world burn. If your company is already at a decent size and you have budget to spend, take a look at comprehensive training programs like Livefire and see what it would take to make that happen in your organization.

Empathy is the most critical skill you can build in order to be a successful product leader. Live-fire exercises are all about putting the “pain” in “pain points,” and are a great way of institutionalizing empathy within your team. So be like your customer, and this will help build understanding and respect for what your customer goes through.

Image Citation: The Unpublished Musings of Bruce Lee

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