#product org

I've spent the last year meeting with entrepreneurs at varying stages. I've been struck by how frequently a company's product practices and product organization are lacking - and how they're in complete shambles more often than you'd think.

It's a boring position to take, but I am proud of and thankful for my experience as a PM at Microsoft. I learned a great deal about software development practices as a whole... and how to develop, articulate, and shepherd a product vision. Sure, Microsoft takes it too far and slows down development, but there's a ton of good in knowing how to lead rigorous product exploration and development.

The lean startup movement combined with lower costs of development has been fantastic, but it has come at the cost of best practices. Whether it's poorly written code or poorly considered product road maps, many of today's companies are cutting corners across the board. Taken as a whole, this is fine because the ecosystem lets a thousand flowers blossom and we celebrate the few that survive. My point isn't that these companies should be judged, but I've observed that these companies face serious challenges as they mature.

We are all familiar with the concept of technical debt. I believe startups have debt across every discipline and product debt poses as great a risk as technical debt.

Like a movie with an interesting premise but no real story (Hot Tub Time Machine), many startups shoot out of the gate with early, but limited traction and raise money. As these companies begin to scale, they can quickly find that their product isn't as appealing as broadly as they had imagined. Their story starts to fall apart. There are an infinite number of challenges with an equally large universe of solutions. Although founders brought the initial inspiration to the table, many often lack the skills to understand their customers' competing needs, maintain the big vision, and balance this tension to prioritize development efforts to refine and grow a product. What’s more, product problems typically arise at the same time teams have just scaled. With an elevated burn rate, it’s extremely important to make the right product decisions.

While I've been surprised by how many companies have these problems, I've been equally encouraged by how many founders openly acknowledge them. In almost every case, hiring “a great VP Product" is the solution they've identified. Unfortunately, this also presents enormous risks.

Given today's startup environment, truly great product leaders are either starting their own company or being chased by top tier companies. If you want to hire one of these people, good luck. Get in line. Presuming you have the tenacity to prevail, a few words of advice...

There are two gaps you need to fill: product management and product vision. It's important you understand what your organization lacks and how a candidate fits in.

Many startup founders believe they're the visionary and only want help with product management. As the engineering team grows and is capable of completing more tasks, a startup will say, "we need someone to manage the list!" This comes with its own risks. The problem with lists is that they put things in an order. The problem with inexperienced people taking over the list is that they become a target for other employees to get their pet projects prioritized. Before you know it, you've handed over prioritization to someone else and the politics are out of control. If you do go this route, it's extremely important to maintain a leading role in prioritizing tasks and maintaining your position within the company as the setter of the road map.

Fewer founders admit they need help with Vision than ought to. Putting YOUR talents aside, I would argue that most people are not capable of defining a winning vision in a hyper competitive market AND managing a company's operations and strategic relationships/opportunities. Some founders (ie David Karp at Tumblr) offload operations to focus exclusively on product. Others remove themselves from day to day product to focus on operations and high level strategy, interfacing with the product team by setting strategic milestones. As a founding CEO, you need to be great at one of these disciplines and should relinquish the other. At any startup, someone needs to have the entire product in their head. If it was you, but you've become too busy and can no longer do it, it's time to supplement yourself and hire for operations or vision.

Hiring for vision is one of the hardest things you'll ever do. First and foremost, it's incredibly important that the person isn't just a project manager who wants the VP Product role. Domain expertise is a must, but I believe curiosity and fearlessness are most important. A good VP Product will research the hell out of your business and your competitors. They will know your customers intimately. They will be bold in their recommendations. One of the most dangerous mistakes a startup can make is to hire someone for vision that is too timid or too focused on project management. In these scenarios, the founder will relinquish vision and task prioritization and the new VP Product won't grasp the baton. The company will seem to be making progress, but they’ll be working off a task list that fails to advance the company strategically.

Any healthy product organization should be able to answer three questions:

Who are you building your product for and what is their pain?

What would address your customers’ pain and improve their lives?

What will you actually build?

Unfortunately, many startups can answer the last question, but fall apart on the first two. Their task list is a poorly considered jumble based only on gut instinct. At the earliest stages, it can be great to throw a half-formed concept against the market to see what sticks. But this will only take you so far.

Big companies teach employees to think about their products in terms of a Market Requirements Document, Product Requirements Document, and Technical Specification. By no means am I advocating that a startup should be this rigorous, but they should understand why these documents are written in this order. They’re a tool for understanding your customer’s needs, coming up with ideas to meet them, and then planning a release to get there. Working in the other direction is foolish.