CHAPTER 16 The Role of Leadership

The primary job of leadership in any technology organization is to recruit, to develop, and to retain strong talent. However, in a product company, the role goes beyond people development and into what we call holistic view of product.


One of the big challenges of growth is knowing how the whole product hangs together. Some people like to think of holistic view as connecting the dots between the teams.


For a startup, there's typically just one or two product teams, so it's not too hard for everyone to keep in their heads a holistic view of the product. However, this quickly becomes much tougher as the company grows—first to a larger product and soon to many product teams.

One of the big challenges of growth is knowing how the whole product hangs together. Some people like to think of holistic view as connecting the dots between the teams.

The three distinct but critical elements to the holistic view of product are described next.

Leaders of Product Management

To ensure a holistic view of how the entire system fits together from a business point of view (product vision, strategy, functionality, business rules, and business logic), we need either the leaders of the product management organization (VP product, directors of product), or a principal product manager.

This person should regularly review the work of the various product managers and product teams, identifying and helping to resolve conflicts.

For large‐scale organizations, some companies prefer this to be an individual contributor role (e.g., a principal product manager), but let me be clear that this is a very senior role (usually equivalent to a director‐level manager). Since the head of product is first and foremost responsible for building the skills of the product managers, a dedicated principal product manager is able to focus on the product itself and is readily accessible as a critical resource to all the product managers, product designers, engineers, and test automation staff.

If you use a principal product manager for this, he or she should be a direct report to the head of product so that everyone understands the importance of the role and the responsibilities of that person.

Whether this role is covered by the head of product or a principal product manager, this is a critically essential role for companies with large and complex business systems, especially with many legacy systems.

Leaders of Product Design

One of the most important roles in a company is the person or people responsible for the holistic user experience. These leaders must ensure a consistent and effective user experience systemwide. This is sometimes the leader of the product design team, sometimes one of the managers or directors of design, and sometimes a principal designer reports to this leader. In any case, it must be someone very strong in holistic product design.

There are so many interactions and interdependencies—and so much necessary institutional knowledge of the business and the users and the customer journey—that at least one person must review everything going on with the product that is going to be visible to the user. You can't expect any individual product manager or designer to be able to have this all in their head.

Leaders of Technology Organization

Finally, to ensure a holistic view of how the entire system fits together from a technology point of view, we have a technology organization leader (often titled CTO or VP engineering). In practice, that person is often helped by a group of engineering managers and directors and/or software architects.

The CTO, managers, and architects are responsible for the holistic view of the system implementation. They should be reviewing the architecture and systems design of all the software—both systems developed by your own staff, as well as any systems designed by vendors. They should also have a clear strategy for managing technical debt.

Again, this is a critically essential role for companies with large and complex business systems, especially with many legacy systems, and should be placed in the organization somewhere that makes these people visible and available to the entire technology organization (this is usually a direct report to the head of technology).

Holistic View Leadership Roles

The larger the company gets, the more critical these three roles are, and their absence is usually all too obvious. If the product or site looks like it was created by half a dozen different outside design agencies, with conflicting user models and poor usability, you're probably missing a head of design or principal designer.

If projects are constantly getting stuck because product managers don't understand the implications of their decisions or product managers are constantly asking developers to look at the code to tell them how the system really works, then you're probably missing a principal product manager.

And if your software is a big mess of spaghetti and it takes forever to make even simple changes, you're probably suffering from significant technical debt.

You might ask what happens if one of these people gets hit by a bus or leaves the company? First and foremost, don't lose these people! Take care of them and don't give them any reason to want to leave or feel like they need to become a manager to make more money.

Second, you should always be trying to develop more of these people, and each of them should have at least one person they're working to develop into a strong second. But they are a rare and incredibly valuable commodity, as this learning does not happen overnight.

Some companies think the answer to this is to try to document the system to the degree that everything is captured somehow in a way that members of the organization can all go to get the same sorts of answers for which they use the principal designer, principal product manager, and software architect.

I know a few organizations that have tried hard to achieve this, but I have never seen this succeed. The systems always seem to grow in complexity and size much faster than anyone can document, and with software, the definitive answer always lives in the source code itself (at least the current answer—not usually the rationale or the history).

One final note: These three holistic‐view leaders—the head of product, the head of design, and the head of technology—are obviously very valuable individually, but in combination you can see their real power. This is why my personal preference is to have these three people sit very close to one another, sometimes in the same physical office.