Why Companies Should Be Just as Worried About Cultural Debt as Technical Debt

Technology decisions that ignore cultural debt will involve more cycles and greater risk

Photo: Thomas Vogel/Getty Images

BBusinesses today are faced with myriad challenges to innovate and optimize. In doing so, we often need to make decisions that borrow against the future. This can come in a tangible form, such as taking money from investors to fund growth, or in more inconspicuous forms, such as making tradeoffs in technical decisions. When we make such tradeoffs, we expect them to come at the cost of additional technical work in the future; however, these decisions can also borrow against an externality that is often overlooked: culture.

What is technical debt?

Technical debt occurs in the development of software when the “easy path” is taken to solve a problem rather than using the best overall solution. The concept implies that the time saved now will need to be paid back later (with interest!) in the form of rework.

Ideally, technical debt is incurred knowingly — that is, a decision to take a shortcut is made deliberately to increase velocity, and it is flagged to be fixed before becoming a compound problem. In calling out technical debt as such, we can better analyze our decisions, considering their net present value and future opportunity costs. By documenting it, we gain better insight into the responsiveness and flexibility of the code base. Having a strategy around managing technical debt has, therefore, become an essential discipline in the management of software products.

Technical decisions also have an impact on the culture of a company, though, and this facet of technical management is often overlooked. “Cultural debt” can be taken on unknowingly, and the unmanageability that flows from it can be difficult to ascertain.

What is cultural debt?

Cultural debt happens when we make a technical decision that borrows against the culture of the organization. Such decisions can introduce divisions between teams, deteriorate communication, or even weaken the effectiveness of leadership.

These types of decisions need to be made regularly throughout the software development life cycle, and it is therefore critical that we begin to identify them, call them out, and manage them accordingly. If the interest goes unpaid we can end up with a toxic environment that is difficult and onerous to manage — we risk a paradox wherein attempts to innovate can stifle progress.

A closer look

Just as with technical debt, a business ideally will have a strategy for managing cultural debt rather than allowing it to accumulate and bog down the business. Typically, decisions that involve cultural debt will impact on areas such as:

  1. Mission: Ensuring connection to the company mission and that there is minimal variance in how the mission is understood by different teams and departments.
  2. Values: Effective and reliable transmission of company values, the ability to apply them consistently, and ensure that they are clear and tangible.
  3. Communication: Fostering openness and the ability to discuss, providing channels for communication, and using channels effectively with clarity of purpose and minimal “noise.”
  4. Visibility: Providing the ability for everyone to see up, down, and across their organization.
  5. Attitude: Happiness of employees, their effectiveness, and retention.
  6. Leadership: Ability for leaders to govern effectively, and influence across departments.

When making technical decisions, we need to think outside the box and consider how our decisions will affect these cultural dimensions of the business.

To reinforce the concept, let’s look at some current issues that the modern enterprise is being confronted with:

  1. Domain-Specific Tooling: As roles become increasingly specialized, a best-of-breed approach provides the tools needed to perform complex tasks. Unfortunately, tools create silos, and more tools means more fragmentation. Furthermore, in a world where tools are proxies for business processes, domain-specific tooling can cut off teams from processes, reducing visibility, and impeding communication. This means the business will need to devote cycles to meetings, emails, and other noisy distractions just to pay down the interest and get the visibility and coordination needed for cross-functional effective leadership. Paying down the debt requires tool integration, and without an infrastructure to reduce the cost of integrating, domain-specific tools can be a heavy debt to carry.
  2. Customization: Often we see the introduction of new tooling without the requisite investment to customize them to the business. Tools such as ServiceNow or Salesforce are highly valuable for being specialized to their use cases, but they still require customization to be effective. For example, when customer data is stored in notes fields rather than using structures data captured in the tool, visibility and reporting are gradually reduced and employee frustration abounds. The decision to introduce tooling should be made with the understanding that customization will be required and must be maintained over time to keep pace with the organization’s culture as it changes.
  3. Bimodal IT: One strategy for enabling cutting-edge technologies is the use of a “bimodal” structure with essentially two IT organizations that operate under different constraints—one optimized for velocity, the other for stability. While bimodal IT may be valuable for encouraging the adoption of new technologies, it also encourages confusion of responsibilities, cross-team rivalry, knowledge silos, and double work. The longer the structure remains, the deeper cultural divide and the more difficult an eventual transformation will be. The decision to introduce new technologies or practices using a bimodal structure should be done deliberately, cautiously, and with clear goals in mind.
  4. Technology Selection: Often we are presented with new technologies that promise to deliver great benefits. Let’s assume that the new technology passes a technical assessment and is found to deliver on the promises: For example, a language such as Clojure or Kotlin really will simplify development and increase velocity, or a new delivery tool does indeed remove a key bottleneck. Adopting such a technology invariably creates some cultural debt — developers unfamiliar with the new language may feel alienated, new silos will form around knowledge and expertise, and tribes could be forcibly broken apart. Technology decisions that ignore cultural debt will involve more cycles and greater risk, while those that recognize it will implement new technologies with those issues in mind, providing the cross-training and collaboration needed to ensure success.
  5. DevOps: The dirty secret about DevOps is that it involves the introduction of a number of technologies and technical practices that carry a large amount of cultural debt. This can actually tear an organization apart if that debt is not managed closely, and it is therefore why DevOps — despite being closely associated with technical practices such as automation, infrastructure-as-code, and CI/CD — is regarded as primarily a cultural movement. In the enterprise, DevOps technologies threaten roles, responsibilities, and livelihoods. The cultural debt actually does outweigh the benefits, and DevOps transformations need to focus on cultural issues first before attempting to implement the associated technologies. This is common sense that we learned from observing lean manufacturing transformations in the ’90s, which involved a similar change situation where technical practices became a function of culture.

Cultural debt, like technical debt, can be hard to detect. If your business does not have a strategy for paying off the debt, or at least one for paying down the interest, the result will be a heavy load of cultural issues weighing down decisions and processes.

Key Measures for Managing Cultural Debt

  • Understand your stakeholders. In an agile world, it is easy to overlook stakeholders. We can learn from the disciplines of business analysis and project management, though, where stakeholder analysis is a core competency and key practice in work management. It is not possible to do a thorough breakdown of stakeholders for every technical decision, but an actively maintained stakeholder matrix will increase your mindfulness and can be referred to for a free sanity check when needed.
  • Understand your culture. Your organization is filled with cultural artifacts — if you are not aware of them and taking the time to manage them, you will not be able to assess cultural impacts. These artifacts can include mission and value statements, organizational and tribal structures, meeting cadences and compositions, control systems, routines, rituals, symbols, and even legends. Think through your cultural artifacts and ensure that they match intention and are understood by leadership.
  • Obtain buy-in. Getting buy-in means giving people a stake in the game. Imposing technology decisions on people will not only result in a requirements mismatch, but it fosters discontent and mistrust. You can make a large down payment on your cultural debt by bringing affected parties into the decision-making processes early. This has been shown to be very effective in helping pass decisions even when they have negative consequences.
  • Embrace the “Three Ways.” We can borrow from the DevOps movement the Three Ways, which provide a solid foundation for undertaking any technical work: Systems thinking encourages considering how decisions impact the whole system, not just the local area; feedback loops allow continuous feedback and communication about impacts; and continual experimentation and learning ensures that the organization is adaptive and resilient. Leadership that embodies the Three Ways is issued debt on very good terms.

PPeter Drucker is quoted as saying that “Culture eats strategy for breakfast,” and the examples we’ve seen here highlight this. The best technology in the world cannot compensate for a broken culture, and a broken culture can be the result of a succession of ill-considered technology decisions.

Understanding cultural debt is a key differentiator in being able to leverage Conway’s Law rather than be trapped by it. A key aspect of managing technology going forward will, therefore, be to identify and control this cultural debt as it is being created, and ensure that the organization is able to function with full-capacity engagement.

Software Engineering Manager @ Cisco Cloud Security

Sign up for Buy/Sell/Hold

By Marker

A newsletter that's 100% business intelligence, and 0% investment advice. Take a look.

By signing up, you will create a Medium account if you don’t already have one. Review our Privacy Policy for more information about our privacy practices.

Check your inbox
Medium sent you an email at to complete your subscription.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store