Product management – Cyber Security Leadership

Agile security. Part 2: User stories

In the previous blog, I wrote about how you as a security specialist can succeed in the world of agile development, where the requirements are less clear, environment more fluid and change is celebrated not resisted.

Adjusting your mindset and embracing the fact that there will be plenty of unknowns is the first step in adopting agile security practices. You can still influence the direction of the product development to make it more resilient, safe and secure by working with the Product Owner and contributing your requirements to the product backlog.

Simply put, product backlog is a list of desired functionality, bug fixes and other requirements needed to deliver a viable product. There are plethora of tools out there to help manage dependencies and prioritisation to make the product owner’s job easier. The image at the top of this post is an example of one of such tools and you can see some example requirements there.

As a security specialist, you can communicate your needs in a form of user stories or help contribute to existing ones, detailing security considerations. For example, ”Customer personal data should be stored securely” or “Secure communication channels should be used when transmitting sensitive information”. Below are a couple more examples from different categories.

When writing security user stories, you should try and elaborate as much as possible on the problem you are trying to solve, what value it will provide if solved and the acceptance criteria. Each story will then have points assigned which signifies how much effort a particular functionality will require. The process of arriving to the final number is quite democratic and usually involves playing planning (sometimes also called Scrum) poker in which every developer will estimate how long each story is going to take with some discussion and eventual consensus. You can do it with an app as on the image below, or the old school way with a deck of cards.

You don’t have to use the above number pattern, and opt-in instead for the Fibonacci sequence or T-shirt sizes.

It’s important that the security team is involved in sprint planning to contribute to the estimates and help the product owner with prioritisation. Other Scrum meetings, like backlog refinement and daily stand-ups are also worthwhile to attend to be able clarify your requirements (including value, risk, due dates and dependencies) and help remove security related impediments.

A culture of collaboration between teams is essential for the DevSecOps approach to be effective. Treating security as not something to workaround but as a value adding product feature is the mindset product and engineering teams should adopt. However, it’s up to security specialists to recognise the wider context in which they operate and accept the fact that security is just one of the requirements the team needs to consider. If the business can’t generate revenue because crucial features that customers demand are missing, it’s little consolation that security vulnerabilities have been addressed. After all, it’s great to have a secure product, but less so when nobody uses it.

Agile security. Part 1: Embedding security in your product

Outline security requirements at the beginning of the project, review the design to check if the requirements have been incorporated and perform security testing before go-live. If this sounds familiar, it should. Many companies manage their projects using the waterfall method, where predefined ‘gates’ have to be cleared before the initiative can move forward. The decision can be made at certain checkpoints to not proceed further, accepting the sunk costs if benefits now seem unlikely to be realised.

This approach works really well in structured environments with clear objectives and limited uncertainty and I saw great things being delivered using this method in my career. There are many positives from the security point of view too: the security team gets involved as they would normally have to provide their sign-off at certain stage gates, so it’s in the project manager’s interest to engage them early to avoid delays down the line. Additionally, the security team’s output and methodology are often well defined, so there are no surprises from both sides and it’s easier to scale.

If overall requirements are less clear, however, or you are constantly iterating to learn more about your stakeholder’s needs to progressively elaborate on the requirements, to validate and perhaps even pivot from the initial hypothesis, more agile project management methodologies are more suitable.

Embedding security in the agile development is less established and there is more than one way of doing it.

When discussing security in startups and other companies adopting agile approaches, I see a lot of focus on automating security tests and educating developers on secure software development. Although these initiatives have their merits, it’s not the whole story.

Security professionals need to have the bigger picture in mind and work with product teams to not only prevent vulnerabilities in code, but influence the overall product strategy, striving towards security and privacy by design.

Adding security features and reviewing and refining existing requirements to make the product more secure is a step in the right direction. To do this effectively, developing a relationship with the development and product teams is paramount. The product owner especially should be your best friend, as you often have to persuade them to include your security requirements and user stories in sprints. Remember, as a security specialist, you are only one of the stakeholders they have to manage and there might be a lot of competing requirements. Besides, there is a limited amount of functionality the development can deliver each sprint, so articulating the value and importance of your suggestions becomes an essential skill.

Few people notice security until it’s missing, then the only thing you can notice is the absence of it. We see this time and time again when organisations of various sizes are grappling with data breaches and security incidents. It’s your job to articulate the importance of prioritising security requirements early in the project to mitigate the potential rework and negative impact in the future.

One way of doing this is by refining existing user stories by adding security elements to them, creating dedicated security stories, or just adding security requirements to the product backlog. Although the specifics will depend on your organisation’s way of working, I will discuss some examples in my next blog.

Security product management

In one of my previous blogs I wrote about building a security startup. Here I would like to elaborate on the product management aspect of a venture.

There are many businesses springing up in the cybersecurity space at the moment. A lot of them are developed by great technologists yet still struggle. The market conditions might be right and the product itself can be secure but it often fails to get traction.

When I’m asked why this might be and what to do about it, my immediate response is to dive deeper and understand the product management function.

In truth, it’s not enough to have a technically flawless solution, it has to align with what your customers want. Moreover, the bar in new product adoption is high. As Nir Eyal famously pointed out in his book Hooked, “for new entrants to stand a chance, they can’t just be better, they must be nine times better … because old habits die hard and new products or services need to offer dramatic improvements to shake users out of old routines. Products that require a high degree of behaviour change are doomed to fail even if the benefits of using the new product are clear and substantial.”

Thankfully, it’s not all doom and gloom – there are things you can do to overcome this challenge.

Depending on the stage of your venture, the most important question to answer is: are people using your product? If not, get to the point where customers are using your product as fast as you can. Then talk to them and learn from them. Find out what problem they are trying to solve.

Provide that solution and measure what matters (revenue, returning usage, renewal rate) and build measurement targets and mechanisms into your specifications.

Disciplined product management is there to bridge the gap between business (sales and marketing) and technology teams. As a product manager, you should support these teams with market analysis, planning, prioritisation, design and measurement based on customer feedback.

Knowledge of the customer and their needs will help define your strategic position and overarching guiding principles to support decision-making in the company.

That strategy in turn should be supported by tactical steps to achieve the vision. We are now beginning to shape actual work deliverables and help the technology teams prioritise them in your development sprints.

Principles described here are applicable in any type of organisation, it doesn’t have to be security specific. The industry you are in matters less than the company culture.

People often focus on tools when talking about product management or adopting agile development. The reality is that it’s often about the culture of collaboration. Break the silos, make sure customer feedback is guiding the development and don’t lose sight of the strategy. Your customers will love it, I promise.