How to Pick the Right Number of IT Cloud Team Members

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Coming up with a healthy, balanced ratio of the number of team members to number of clients is still a relatively subjective exercise. Not quite scientific yet. There are rules of thumb out there to start with, but it ultimately comes down to your requirements and the size of your B2B clients and B2C customer base. Also, the amount of request for new features or bug fixes spawns customer telemetry data that will factor into the ratio.

The following provides a rule of thumb starting point for your fine tuning needs based on personal observation in a consulting professional capacity over many years:

·         Solution Architects: 1 for every set of 4 or 5 typical quarterly release projects or B2C clients

·         Database Team: 1 to 5

·         Networking Team: 1 to 5

·         OS Sys Admin Team: 1 to 7

·         Monitoring Team: 1 to 3

·         Security: 1 to 5

·         R&D: 1 to 10

Continuously capturing and tracking team role and skill inventory will help in determining these ratios, calibrating them over time.

Example Cloud Team Structure: Monitoring and Alerting

How many cloud monitoring team members do you need to support B2B corporate clients?

The number of cloud monitoring team members required to support B2B corporate clients can vary widely depending on the size and complexity of the clients, the scope of the services being offered, and the level of support required by the clients. However, some factors that can help determine the appropriate staffing levels for a cloud monitoring team might include:

1.       Number and size of clients: The more clients you have and the larger their businesses are, the more team members you will likely need to support them effectively.

2.       Service scope: The more services you offer and the more complex they are, the more team members you may need to monitor and maintain them.

3.       Client service level agreements (SLAs): If your clients have SLAs that require a high level of service availability and response times, you may need more team members to meet these requirements.

4.       Automated vs. manual monitoring: The more automated your monitoring is, the fewer team members you may need to support your clients.

With these factors in mind, a typical cloud monitoring team for a B2B corporate client might include anywhere from 5 to 15 team members, depending on the size and complexity of the clients being served. This team might include roles such as:

1.       Cloud monitoring manager or team lead

2.       Cloud monitoring engineers or technicians

3.       Customer support specialists

4.       Product Managers/Owners, Project managers or coordinators

Hope this helps give your sprint planning a starting point. Determining the optimal staffing levels for a cloud monitoring team relies on various factors that are unique to your organization and clients. I recommend you thoroughly evaluate your clients’ needs, including number of users and groups, and the level of assistance necessary to guarantee that you have the right staffing levels to deliver dependable and excellent services.

Industrial Era Leadership Styles Don’t Work in the Digital Era

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Recall the bygone era of robber baron executives who drove the Industrial Revolution. If you’re not coughing from the endless plumbs of smoke from the chimneys of gloom that harmed many lungs, you might recall that the leaders of those 19th century corporations drove insane revenue goals at all costs. With some regulations and shifts in economic mindsets, things have improved, though the DNA of those industrial leadership styles still exist.

And then came the digital revolution.

The adoption of digital technologies and processes in manually intensive businesses has been ongoing for a while, and the COVID-19 pandemic expedited this movement as more employees had to work remotely. To enhance customer service and overall experience, businesses have been redesigning their processes using agile methods. Additionally, IT departments have been utilizing continuous Agile DevSecOps pipelines to provide cloud solutions. However, despite all of these efforts, one crucial aspect that needs to be addressed is the transformation of management practices.

Transforming management is the final frontier in achieving complete digital transformation. Although some organizations have realized this, many still have not, despite over two decades of agile thinking evolution. Failure to modernize management practices can lead to outdated practices and threaten digital transformation efforts. It’s like taking two steps forward and then taking three steps back if modernization of management practices is not adopted.

What Went Wrong with the Industrial Era Leadership Style?

The Industrial Era leadership styles were developed during a time when organizations were structured differently, and the work being done was largely manual and repetitive. The focus was on efficiency, productivity, and achieving economies of scale. The typical leadership style during this era was command and control, where managers were expected to be authoritarian and make decisions for their subordinates.

However, in the digital era, the nature of work has changed significantly. The rise of technology and automation has meant that much of the manual labor has been replaced by machines, and employees are increasingly required to think critically, collaborate, and innovate. As a result, traditional Industrial Era leadership styles don’t work in the digital era for several reasons:

  • Flexibility
  • Empowerment
  • Collaboration
  • Innovation
  • Emotional Intelligence

Flexibility

Digital era businesses need to be flexible and adaptable to rapidly changing market conditions. Leaders need to be able to pivot quickly and adjust strategies as needed. This requires a leadership style that is open to experimentation and willing to take risks.

Empowerment

The digital era workforce expects to be empowered and given the autonomy to make decisions. Leaders need to create an environment where employees feel empowered to take risks, make mistakes, and learn from them.

Collaboration

Digital era work often requires collaboration across teams and departments. Leaders need to be able to facilitate this collaboration by creating an environment that encourages communication and teamwork.

Innovation

In the digital era, innovation is key to staying competitive. Leaders need to foster a culture of innovation by encouraging experimentation and rewarding creativity.

Emotional Intelligence (aka “Technical Empathy”)

In the digital era, leaders need to have strong emotional intelligence to effectively manage and motivate a diverse workforce. This means being empathetic, listening to feedback, and understanding the needs and motivations of their employees. In agile practices, specifically regarding sprints, the retrospective at the end of the sprint is one of the best way to help hands on investors, executives and upper management be more empathetic with sprint team workers. I am planning an entire article on the importance of technical empathy in the chain of trust from investors, to executives, all the way down to sprint team members, and vice versa.

Examples of some of the shortcomings of industrial era “robber baron” leadership styles

Industrial era “robber baron” leadership styles were characterized by a focus on maximizing profits at any cost, often at the expense of workers, consumers, and the environment. Some of the shortcomings of these leadership styles include, but not limited to:

Exploitation of WorkersRobber baron leaders often paid workers very low wages, subjected them to dangerous working conditions, and denied them basic benefits like sick leave and health insurance
Monopolistic PracticesRobber baron leaders used their wealth and power to buy out competitors, creating monopolies that stifled competition and innovation. This led to higher prices for consumers and limited choices in the marketplace
Environmental DamageRobber baron leaders often showed little regard for the environment, engaging in practices that caused significant damage to natural resources and ecosystems
CorruptionRobber baron leaders often used their wealth and power to influence government policies and regulations in their favor, engaging in corrupt practices that favored their own interests over the public good
Lack of AccountabilityRobber baron leaders were often able to operate with little oversight or accountability, as they wielded significant power and influence over government officials, regulatory agencies, and the media

Personifications of industrial era robber baron leaders include Andrew Carnegie, John D. Rockefeller, and J.P. Morgan. Their leadership styles were characterized by a focus on maximizing profits and accumulating wealth, often at the expense of worker safety, consumers, and even the environment. While these leaders were successful in their time, their legacy has been tarnished by the negative impact they had on society and the economy. Though many of these bad CEO shenanigans have been checked by regulation, it is undeniable that many organizations profess to do the right thing by their employees and consumers, but in practice, do the opposite. I won’t name specific companies, but you can Google recent lawsuits regarding employee wage theft, cancer causing products, etc.

How Different is Today’s Industrial Era Leadership Mindset Compared to Robber Barons?

While there may be some similarities between today’s hands-on investors and C-level executives and the industrial era “robber baron” leaders and investors, it’s important to recognize that there are also notable differences in leadership styles and business practices.

Similarities

One similarity is a focus on maximizing profits and achieving rapid growth, often at the expense of other stakeholders such as workers and the environment. Some investors and executives may prioritize short-term gains over long-term sustainability, which can lead to unethical or unsustainable practices.

Another similarity is a willingness to take risks and pursue aggressive business strategies. On the one hand, this can lead to disruption and innovation in the marketplace. But on the other hand, it can also create significant social and environmental challenges. In the 19th century, it was not uncommon for workers to work up to 18 hours a day, no breaks, 6 days a week, for under $2 a day. Even in those days, that was still not enough to take care of a family.

Differences

Thankfully, there are also several key differences between today’s hands-on investors and C-level executives and the industrial era “robber barons.” For example:

Without regulatory oversight, social responsibility, and stakeholder engagement, it’s likely that some of today’s hands-on investors and C-level executives would have leadership styles similar to their counterparts in the industrial “robber baron” era. In the absence of these constraints, there would be few incentives for these leaders to prioritize the interests of workers, consumers, and the environment over their own financial gain.

Without regulatory oversight, some investors and executives would be free to engage in monopolistic practices, engage in corrupt activities, and exploit workers to maximize profits. Without social responsibility, there would be little incentive to consider the long-term impacts of their business decisions on the environment and society. Without stakeholder engagement, investors and executives would be less likely to consider the interests of workers, customers, and the broader community. All of these can in effect increase the risk of failures in digital transformation as knowledge workers would be less motivated to innovate and more incentivized to hide or even “quiet quit.”

However, keep in mind that regulatory oversight, social responsibility, and stakeholder engagement are not the only factors that influence leadership styles. There are many other factors that can shape the way leaders execute the corporate vision, including their personal values, organizational culture, and the broader social and economic context. Therefore, while these factors can help to prevent some of the worst excesses of unregulated capitalism, they are not a guarantee of ethical and responsible leadership.

Conclusion

To succeed in the digital era, leadership styles need to evolve beyond those of the Industrial Era. Flexibility, empowerment, collaboration, innovation, and emotional intelligence are crucial for effectively managing a rapidly changing workforce and staying competitive in the global marketplace. While there may be some similarities between today’s hands-on investors and C-level executives and the industrial-era “robber barons,” modern leaders must take into account the regulatory oversight, social responsibility, and stakeholder engagement required in today’s business landscape. Leaders must recognize the challenges of the past and work towards creating a sustainable and responsible business model for the future. Exhibiting “technical empathy” via retrospectives and analyzing product and sprint backlogs can help leaders transition from the industrial era mindset to the digital era.

Introduction to Optimizing Cloud Team Structures for Continuous Product Improvement

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Since 2020, many organizations launched digital transformation initiatives to automate their processes and adopt or migrate their technology operations to the cloud. Surveys by large analytics organizations such as McKinsey and Gartner have suggested that most have failed for a variety of reasons.

It is difficult to provide a precise number of failed initiatives as there are no publicly available statistics on the number of digital transformations that have fallen short in corporations since 2020. However, it is generally accepted that the success rate of digital transformation initiatives is not particularly high, with various surveys and reports suggesting failure rates ranging from 60% to 84%.

There are several reasons why digital transformation initiatives can fail, including a lack of clear executive strategy and leadership, inadequate investment in technology and talent (including cloud team structures and staffing mix), resistance to change from employees and customers, and a failure to align digital transformation efforts with business goals and complex customer needs.

It is worth noting that the COVID-19 pandemic has both accelerated the need for digital transformation in many organizations and created new challenges for digital transformation initiatives. Many organizations have had to adapt quickly to new ways of working and engaging with customers, which has put additional pressure on digital transformation initiatives. This has led to an underestimating of complexity of cloud team structures which are needed for a continuous product improvement process that leads to high Quality of Service (QoS) for customers.

In any case, it is clear that digital transformation is a complex and challenging process that requires careful planning, execution, and ongoing adaptation to changing circumstances. While some digital transformation initiatives may fail, it is important for organizations to learn from these experiences and continue to pursue digital transformation in order to remain competitive in today’s fast-paced, digital-first business environment.

The implication is that optimizing the structure and staffing of an IT cloud team can be a challenging, often complex process. There are a few key considerations that executive leadership and upper management can take into account to make the most of their staffing resources:

· Define clear cloud teams, roles and responsibilities

· Determine the necessary skill sets

· Consider the size and complexity of the cloud environment

· Balance in-house and outsourced resources

· Foster a culture of continuous learning, research and development

Define clear cloud teams, roles and responsibilities

The establishment of precise roles and responsibilities within a cloud team is an integral component of accomplishing organizational objectives. This facilitates the comprehension of individual responsibilities, enabling team members to better grasp the impact of their contributions towards the overarching organizational vision. In other words, they see the direct value of their sprint team contributions to solving customer problems. This methodology also serves to remove redundancies and channel the team’s efforts towards areas of high importance. Further, it is imperative to ensure sufficient staffing levels in each role to guarantee optimal customer service delivery.

The monitoring team, for instance, can be staffed adequately to proactively identify and troubleshoot customer problems before the customer discovers them. In the case of large organizations, the establishment of a personnel-to-client, product, or project ratio is a judicious decision to ensure the effective allocation of resources. Aligning team member counts to project ratios helps to provide good coverage to the number of clients and customers your organization has. This is especially important for B2B client scenarios, where having one or two developers may not be enough for 20 large B2B clients, each with millions of users.

Determine the necessary skill sets

For any given cloud or digital transformation project, there are certain skills need that must align with user requirements with emphasis on scaling the number of skilled workers with the size of the customer (B2B) or customer base (B2C). It is essential to identify the highly specialized skill sets required to support cloud infrastructure, including proficiencies in:

· distinct cloud platforms (SaaS, PaaS, IaaS)

· programming languages, and

· security protocols

This strategy aids in directing recruitment and training endeavors and guarantees that the team possesses the appropriate blend of expertise.

Consider the size and complexity of the cloud environment

The magnitude and intricacy of the cloud environment can significantly affect the personnel requirements of the team. A diminutive and less intricate environment may demand a modest team, while a vast and multifaceted environment may necessitate multiple and more specialized teams.

Let’s unpack this a bit. Assume that a company is using a public cloud service provider (CSP) for their operations. They have established a dedicated cloud monitoring team to oversee and manage their cloud infrastructure. In this scenario, the size and complexity of the company’s cloud environment would be the primary determinants of the necessary staffing levels for the monitoring team. Some organizations ignore this critical factor to their detriment, which is often where cloud migrations and digital transformations fail.

For a smaller cloud environment with limited cloud resources and services, the monitoring team may comprise a few personnel with a general understanding of cloud infrastructure and basic monitoring tools. The small mom and pop IT shops won’t be dealing with several major B2B clients or millions of users in their customer base. On the other hand, a larger and more complex cloud environment, with multiple cloud services and resources, may require a more extensive monitoring team with highly specialized roles, such as cloud security specialists, network monitoring experts, cloud architecture professionals, and data analysts.

In this way, the staffing requirements of the cloud monitoring team would depend on the size and complexity of the cloud environment, and the necessary skill sets for the team members would be based on the specific cloud services and resources being utilized.

Balance in-house and outsourced resources

It is crucial to identify the most advantageous equilibrium between in-house/onshore and outsourced/offshore resources. This could involve utilizing third-party vendors for particular functions, such as cloud security, while maintaining essential development and maintenance tasks in-house. For instance, cloud monitoring and alerting might require 24/7 operation with coverage in various regional time zones, necessitating multiregional team coverage.

Determining the optimal balance between in-house/onshore and outsourced/offshore resources can have several cost advantages and disadvantages for an organization. One of the primary cost advantages of outsourcing is the potential for reduced labor costs. Outsourcing to offshore locations may allow companies to benefit from lower labor costs in countries with lower wage rates, thus reducing overall operational expenses. Additionally, outsourcing specific functions, such as cloud security or data entry, may be more cost-effective than hiring in-house staff with the same expertise.

On the other hand, outsourcing may have a few drawbacks. For instance, communication issues may arise due to language/cultural barriers or time zone differences, which may impact project timelines and increase costs. Time zone difference can be a big factor in managing quality of service (QoS) for customer service level agreements. Monitoring and alerting, for instance, can be rendered useless if a major B2B client in the Central Time zone has to wait for Level 1 or Level 2 support in an Asian time zone. There may also be additional costs associated with managing the outsourced team, such as oversight and coordination expenses. Additionally, outsourcing may reduce the level of control and oversight that an organization has over its operations and data, potentially leading to security risks.

Maintaining in-house staff can be advantageous in terms of control and flexibility. An in-house team is typically easier to manage and can respond more quickly to changing business needs. Additionally, it can be easier to ensure the quality of work when it is done in-house. However, in-house staffing may also be more expensive than outsourcing, as it requires investing in hiring, training, and retaining staff with specialized skills and knowledge.

Ultimately, the most cost-effective approach will depend on various factors, including the size and complexity of the organization’s operations, the expertise required for specific functions, and the cost of labor in different regions. Therefore, it is essential to carefully weigh the advantages and disadvantages of each approach and determine the most effective strategy for the organization.

Foster a culture of continuous learning, research and development

Cloud technology is constantly evolving, so it’s important for the team to stay up-to-date with the latest developments and trends. Management can foster a culture of continuous learning by providing access to training and development opportunities and encouraging team members to stay current with industry developments. Having an R&D team, in association with a corporate training team, can ensure that the organization is discovering new technologies that can improve team productivity. The training team can continuously plan and coordinate training for new technologies.

Conclusion

In conclusion, there are certain strategies management can plan and implement to optimize the structure and staffing of their IT cloud team, ensuring that it is well-positioned to support the organization’s strategic objectives. The process of digital transformation is a challenging and intricate journey that necessitates meticulous planning, implementation, and continuous adaptation to dynamic conditions.

While a number of organizations may experience setbacks during their digital transformation (DT) initiatives, it is crucial to derive lessons from these experiences and pursue DT to remain competitive in the rapidly evolving, digital first business world. Industrial era management strategies are obsolete. Optimizing the structure and staffing of an IT cloud team while transitioning from the industrial mindset can also be a complex process.

As such, there are key considerations that executive leadership and upper management can take into account to maximize their technical staffing resources. By adopting a strategic and comprehensive approach to staffing, organizations can leverage the benefits of cloud technologies and improve their business outcomes.

Digital Agile Strategies: When the Sales, Product and Sprint Teams Work in Tandem

The way a company makes money is by selling products and services to the public. Without sales, no revenue comes in. Revenue, and especially profits, are the lifeblood of an organization. Cut that off, and the company dies. Therefore, the sales staff must constantly sell, sell, sell at all costs to keep the company alive. It’s really that cut and dry.

Or is it?

Side note: This article also appears on Medium.com

True, the sales team is like the priesthood of capitalism that keeps the company’s future alive by sacrificing itself regularly. They should be applauded for this effort. But there is a limit on how much capacity the product team has to support a highly aggressive sales team. If you’ve been in technology long enough, even beyond IT, you know the delicate balancing act between aggressive sales on one hand, vs aggressive timelines to push out quality products based on features in the product backlog and tasks in the sprint backlog.

Product teams are caught in the pinch between the successful sales team, and the quality driven sprint team. If the sales team is too aggressive, product quality may suffer. If, on the other hand, sprint teams are behind schedule, the product team risks losing a sale that cuts the sales team commissions. Both of these scenarios can result in reputational damage as potential customers can get frustrated, terminate any sales agreements, and buy from a competitor.

Balancing the motives and goals of the sales, product and sprint teams is never an easy exercise as business forces can change dynamics rapidly. However, despite the temptation to revert back to ego driven knee jerk reactions to business events, it is crucial for

  1. The sales team to be in alignment with the agile product team to ensure that the product quality meets customer expectations
  2. The product team to be in alignment with the agile sprint team for the same reason

Aligning Sales and Product Teams

The following graphic highlights some strategies the sales and product teams can implement to ensure that product quality meets customer expectations:

Collaborate on product requirements

Working closely together at the sales and product team level improves the chances that customer requirements are well understood and documented. The sales team can provide valuable insights into the customers’ pain points, preferences, and expectations, which in turn can be used to prioritize quarterly product features and enhancements.

Attend sprint demos

The sales team should attend sprint demos to witness firsthand the progress made by the product team. They can also provide real-world feedback on how well the product is aligning with customer needs. This will allow the sales team to have some visibility into the product development process, as well as help identify any gaps or areas that need improvement.

Provide customer feedback

The sales team should be the primary source of customer feedback and possibly user story input for the product team. They should provide surveys or plain text feedback on customer satisfaction, feature requests (hopefully in the form of user stories), and pain points to help the product team adjust priorities and make product improvements.

Attend retrospectives

Some product teams may hesitate to invite the sales team to retrospectives, but there is some value at times in doing so. The sales team, once it understands the nature and importance of this exercise, should attend retrospectives to provide feedback on the product development process and collaborate with the product team to identify areas for improvement. This will help the product team to continuously improve the quality of the product and ensure it meets customer expectations.

Develop a shared understanding of quality

The sales team and product team should develop a common understanding of what constitutes high-quality products. This shared understanding should include customer expectations, usability, and performance metrics, among others.

In summary, by collaborating on product requirements, attending sprint demos and retrospectives, providing customer feedback, and developing a shared understanding of quality, the sales team can align with the agile product team to ensure that product quality meets customer expectations.

Aligning Product and Sprint Teams

Continuing, the chain of collaboration between the sales and product teams extend to the collaboration between the product and sprint teams. To maintain product quality, the product team must be in alignment with the agile sprint team continuously. A few ways the product team can align with the agile sprint team to achieve continuity include:

Collaborate on sprint goals

The product team should work closely with the sprint team to define sprint goals that are aligned with the product roadmap and customer needs. By setting clear goals, both teams can ensure that the work being done during the sprint is focused and contributes to maintaining product quality.

Define acceptance criteria

The product team should define acceptance criteria for each user story or feature being developed during the sprint. The acceptance criteria should outline the conditions that must be met before a user story or feature is considered complete and of acceptable quality. This ensures that everyone on the sprint team understands what is required to deliver a quality product.

Conduct high level code reviews

The product team should participate in code reviews, with the guidance of the solution architect assigned to the product backlog or at least the most senior technical leader of the sprint team. This approach is a best practice, helping to make sure the code being developed during the sprint meets the product team’s quality standards. This can include reviewing code for readability, maintainability, and adherence to coding standards.

Provide effective feedback and business guidance

The product team should provide feedback and guidance to the sprint team throughout the sprint. This can include reviewing and providing feedback on user stories, features, and design decisions, as well as providing guidance on how to address any quality issues that arise during development.

Collaborate in sprint reviews and retrospectives

The product team should participate in sprint reviews and retrospectives to provide feedback on the quality of the product and the development process. This will help identify areas for improvement and enable the team to continuously improve the quality of the product.

By collaborating on sprint goals, defining acceptance criteria, conducting code reviews, providing feedback and guidance, and participating in sprint reviews and retrospectives, the product team can align with the agile sprint team to maintain product quality. As a result, the emphasis on optimal quality will ensure that the product meets customer needs and expectations while adhering to high quality standards.

How agile sprint planning and sprint retrospectives can improve crucial conversations

Agile sprint planning and sprint retrospectives can improve crucial conversations between C-level executives, product managers, and sprint teams in several ways:

  1. Encourages collaboration
  2. Creates transparency
  3. Facilitates alignment
  4. Encourages continuous improvement

Collaboration

Agile sprint planning and sprint retrospectives are collaborative processes that involve input from all stakeholders, including C-level executives, product managers, and sprint teams. This might be surprising for some agile practitioners, but sprint planning and retrospectives are actually important business process in the digital era. In working together, they can gain a deeper understanding of each other’s perspectives, identify potential roadblocks, and find solutions to address them.

Transparency

Agile sprint planning and sprint retrospectives together promote transparency by providing regular updates on the progress of the project. Providing continuous updates can help C-level executives and product managers gain insight into the sprint development process, and identify areas where they can provide support or resources. The basis for C-level support of the team is what can be the basis of what’s called “technical empathy.”

Alignment

Agile sprint planning and sprint retrospectives help align the goals and priorities of all stakeholders involved in the project. By having a shared understanding of the project’s objectives and progress, C-level executives, product managers, and sprint teams can work together more effectively towards a common goal.

Continuous Improvement

Agile sprint planning and sprint retrospectives provide opportunities for continuous improvement. During the sprint retrospective, the sprint team reflects on what worked well, followed by what didn’t. The team then identifies areas for improvement. This crucial feedback can help C-level executives and product managers understand the team’s needs, as well as identify ways to support the team in achieving their goals.

Conclusion

The product team finds themselves caught between the competing interests of the successful sales team and the quality-driven sprint team. If the sales team is too aggressive, it could lead to a decrease in product quality. Conversely, if the sprint teams fall behind schedule, the product team risks losing a sale, which in turn could reduce the commissions of the sales team. In both scenarios, the company’s reputation may suffer as frustrated customers could terminate sales agreements and turn to competitors.

Maintaining a balance between the objectives and goals of the sales, product, and sprint teams can be a challenging task as market forces can change rapidly. Despite the temptation to react impulsively to business events, it is crucial for:

  1. The sales team to work in concert with the agile product team to ensure that the product quality meets customer expectations
  2. The product team to collaborate with the agile sprint team to achieve the same goal.

Generally speaking, both agile sprint planning and sprint retrospectives create a collaborative and transparent environment that fosters (1) open communication and (2) continuous improvement. Avoiding breaks in collaboration keeps the sprint team alert and ready to respond to business events. By encouraging crucial conversations between C-level executives, product managers, and sprint teams, an organization can help ensure that each member of each team is working towards the same goals and priorities, which is not exactly an easy proposition in an ever changing digital world. At the end of the day, the project is has to be successful in meeting customer needs and business objectives for the given product.

How Executives Can Improve Their Leadership via Agile Portfolio Management

Note: This article also appears on Medium and LinkedIn

The agile revolution in IT, and beyond, has been transforming organizations of all sizes since 2001, when the Agile Manifesto first got unleashed on the public. Even before then, I was actively involved in the Rational Unified Process community where some of the minds behind the manifesto were also active. Back then (circa late 1990s), IT was going through the distributed client-server revolution as IT started to move beyond mainframes (which are still active in older organizations, mind you). Executives and upper management in those days demanded lots of technical documentation that would usually not be useful to the technical SMEs, but sat as trophies in the offices of corporate leaders.

But agile thinking came along to shatter the notion of “too much documentation.” Not that it was not important, but that teams should only produce just enough to satisfy leaders while being practical enough for sprint teams to find useful. In my opinion, this silent disconnect between the technical sprint teams and leadership was, and is, a symptom of a deeper rift in organizational transformation strategies vs tactics. Cloud computing, especially after the pandemic years of 2020-2022 with an accelerated digital transformation push, exposed even deeper rifts, resulting in most digital transformation initiatives failing. I’m relying on reports by McKinsey and Gartner on the stats for such failures.

This divergence between self-organizing sprint teams and executive leadership got me to thinking of my own observation as a consultant and executive level cloud solution architect over the years. I have seen companies that adopted and pivoted their strategies around agile management thrive very well, while others that resisted it or did not fully embrace it struggled. How can we turn this around for the latter? I my experience, enabling self-organizing teams and getting better acquainted with product and sprint backlogs should be one of the top work items for executives and even hands on investors who sometimes distrust their board’s pick of said executives.

Recently, I decided to do a little AI prompt engineering with ChatGPT to have a “discussion” on how large hands on investors, executives and upper management of larger corporations miss out on the hidden added value of agile management principles. I’ll simplify my AI prompts so that they seem more like casual questions rather than geek speak.

Me: How can c-level executives and hands on investors improve their leadership approach using reports and metrics from Agile portfolio management

C-level executives and investors can improve their leadership using reports and metrics from Agile portfolio management by gaining visibility into how the organization’s portfolio is performing and using that information to make data-driven decisions.

Here are some ways that reports and metrics from Agile portfolio management can help C-level executives and investors improve their leadership:

  1. Strategic alignment: Agile portfolio management provides a framework for aligning the portfolio with the organization’s strategic objectives. Reports and metrics can help C-level executives and investors understand how the portfolio is contributing to those objectives, and identify areas where adjustments may be needed.
  2. Resource optimization: Agile portfolio management can help optimize the use of resources across the organization. Reports and metrics can provide insights into resource utilization and identify areas where resources may be underutilized or overutilized.
  3. Risk management: Agile portfolio management can help manage risk by providing visibility into potential risks across the portfolio. Reports and metrics can help identify areas of the portfolio that may be at risk, and help the organization take proactive measures to mitigate those risks.
  4. Performance measurement: Agile portfolio management provides a framework for measuring the performance of the portfolio. Reports and metrics can help C-level executives and investors understand how the portfolio is performing against key performance indicators, and identify areas for improvement.
  5. Transparency: Agile portfolio management provides transparency into the organization’s portfolio and how it is being managed. Reports and metrics can help C-level executives and investors understand how the portfolio is being managed, and provide insights into the decision-making process.

By using reports and metrics from Agile portfolio management, C-level executives and investors can gain a deeper understanding of the organization’s portfolio and make data-driven decisions to improve its performance. This can help the organization achieve its strategic objectives, optimize its resources, manage risk, measure performance, and increase transparency.

Cloud computing devices

Me: How does agile portfolio management align with product management?

Agile portfolio management and product management are closely related and have many overlapping elements. Both focus on delivering value to customers by developing and managing a portfolio of products or initiatives. However, there are some key differences in the focus and scope of each discipline.

Agile portfolio management focuses on managing a portfolio of initiatives or products across an organization, with the goal of maximizing value delivery and achieving strategic objectives. It involves managing resources, prioritizing initiatives, and measuring performance to ensure that the portfolio is delivering the desired outcomes.

Product management, on the other hand, focuses on developing and managing individual products or services within the portfolio. It involves understanding customer needs, defining product requirements, and overseeing the development and launch of the product.

Despite these differences, agile portfolio management and product management are closely aligned and can work together to achieve common goals. Agile portfolio management provides a framework for managing the overall portfolio, while product management provides a framework for developing and managing individual products within the portfolio.

For example, agile portfolio management can help product managers prioritize their product roadmap by identifying the initiatives or products that will deliver the greatest value to the organization. At the same time, product management can provide feedback to the portfolio management team on the success of individual products and initiatives, which can inform future portfolio management decisions.

Overall, agile portfolio management and product management are complementary disciplines that work together to deliver value to customers and achieve strategic objectives. By aligning these two disciplines, organizations can ensure that they are delivering the right products and initiatives to meet the needs of their customers and stakeholders.

Me: For those corporate leaders who may still be adopting agile principles, explain agile portfolio management?

Agile portfolio management is an approach to managing an organization’s portfolio of projects and programs in an agile manner. It involves applying agile principles and practices to the management of the portfolio to improve the organization’s ability to deliver value to its customers and stakeholders.

In traditional portfolio management, projects are selected based on a thorough analysis of their potential returns, risks, and costs. The portfolio is managed through a series of gates, with projects advancing to the next gate only if they meet certain criteria. However, this approach can be slow and inflexible, and may not adapt well to changing business needs.

Agile portfolio management, on the other hand, focuses on creating a flexible and adaptive portfolio that can respond quickly to changes in the business environment. It involves continuous evaluation and prioritization of projects based on their potential value, alignment with the organization’s goals, and ability to deliver results quickly.

The following are some key principles of agile portfolio management:

  1. Prioritization based on value: Projects are prioritized based on their potential value to the organization, with a focus on delivering value quickly and iteratively.
  2. Continuous planning and evaluation: The portfolio is regularly reviewed and updated to ensure that it remains aligned with the organization’s goals and can respond quickly to changing business needs.
  3. Flexible funding and resource allocation: Funding and resources are allocated based on the current priorities and needs of the portfolio, with the ability to adjust as needed.
  4. Collaboration and transparency: Stakeholders are involved in the portfolio management process and are provided with regular updates on progress and results.
  5. Continuous improvement: The portfolio management process is continually evaluated and improved based on feedback and results.

Overall, agile portfolio management enables organizations to manage their portfolio of projects and programs in a more flexible, adaptive, and value-driven manner. It allows them to respond quickly to changes in the business environment and deliver value to their customers and stakeholders more efficiently.

Me: You said a mouthful there lol. What steps are needed to setup agile portfolio management for organizations that have little or no experience?

Setting up an agile portfolio management process can be a complex task, but the following steps can provide a general framework to guide the process:

  1. Define the portfolio vision and goals: The first step is to clearly define the portfolio vision and goals. This involves understanding the organization’s mission, strategic objectives, and business goals, and identifying the portfolio’s role in achieving them.
  2. Establish governance and decision-making processes: Agile portfolio management requires a different governance structure and decision-making process than traditional portfolio management. The governance structure should include roles and responsibilities, decision-making processes, and guidelines for prioritizing and selecting projects.
  3. Define the portfolio backlog: The portfolio backlog is a prioritized list of all the projects and initiatives in the portfolio. It should be based on the organization’s strategic goals and objectives, and should be regularly reviewed and updated based on changes in the business environment.
  4. Identify the agile portfolio management team: The agile portfolio management team is responsible for overseeing the portfolio and ensuring that it is aligned with the organization’s strategic goals. The team should include representatives from different areas of the organization, including business, IT, and finance.
  5. Establish metrics and KPIs: Metrics and KPIs are essential for measuring the success of the portfolio and identifying areas for improvement. The metrics should be aligned with the organization’s strategic goals and should be regularly reviewed and updated.
  6. Implement agile portfolio management tools: Agile portfolio management tools can help automate and streamline the portfolio management process. These tools can include agile project management software, portfolio management dashboards, and collaboration tools.
  7. Conduct regular portfolio reviews: Regular portfolio reviews are essential for ensuring that the portfolio remains aligned with the organization’s strategic goals and is delivering value to its customers and stakeholders. The reviews should be conducted on a regular basis, and should include feedback from stakeholders and updates to the portfolio backlog.

By following these steps, organizations can establish an agile portfolio management process that is aligned with their strategic goals and enables them to respond quickly to changes in the business environment. It is important to note that the process should be continually evaluated and improved based on feedback and results.

Me: Great, thanks. Lets unpack metrics for a bit, what are the most common metrics and KPIs for agile portfolio management?

There are several metrics and key performance indicators (KPIs) that can be used to measure the success of an agile portfolio management process. The following are some of the most common metrics and KPIs used in agile portfolio management:

  1. Value delivered: This measures the value that the portfolio delivers to the organization and its stakeholders. This metric can be measured by looking at the return on investment (ROI) or other financial metrics.
  2. Time-to-market: This measures the time it takes to deliver a project or product to the market. This can be a critical metric in industries where speed-to-market is a key competitive advantage.
  3. Customer satisfaction: This measures how satisfied customers are with the products or services delivered by the portfolio. This can be measured through surveys, feedback forms, or other methods.
  4. Portfolio throughput: This measures the rate at which projects are completed and delivered by the portfolio. This metric can be used to identify bottlenecks and areas for improvement in the portfolio management process.
  5. Team productivity: This measures the productivity of the teams working on the projects in the portfolio. This can be measured by looking at metrics such as cycle time, velocity, and capacity utilization.
  6. Agile maturity: This measures the organization’s level of maturity in adopting agile practices and processes. This can be measured by conducting regular assessments or surveys.
  7. Portfolio predictability: This measures the portfolio’s ability to deliver projects on time and within budget. This can be measured by looking at metrics such as schedule variance and cost variance.

Overall, the metrics and KPIs used in agile portfolio management should be aligned with the organization’s strategic goals and should be regularly reviewed and updated based on feedback and results. It is important to focus on a few key metrics that provide meaningful insights into the portfolio’s performance, rather than trying to measure everything.

Me: Along those lines, what are the best tools that measure metrics and KPIs for the agile portfolio management process?

There are many tools available that can help measure metrics and key performance indicators (KPIs) for the agile portfolio management process. The following are some of the most commonly used tools:

  1. Agile project management software: Agile project management software such as Jira, Trello, or Asana can help track progress, measure team productivity, and manage the portfolio backlog.
  2. Portfolio management dashboards: Dashboards such as Tableau, Power BI, or Klipfolio can provide real-time visualizations of portfolio performance metrics and KPIs.
  3. Collaboration tools: Collaboration tools such as Slack or Microsoft Teams can help facilitate communication and collaboration between portfolio team members.
  4. Business intelligence tools: Business intelligence tools such as SAP or Oracle can help collect and analyze data from multiple sources to provide insights into portfolio performance.
  5. Agile assessment tools: Agile assessment tools such as Agile Health Radars or Agile Maturity Assessments can help assess the organization’s level of agile maturity and identify areas for improvement.
  6. Customer feedback tools: Customer feedback tools such as SurveyMonkey or Qualtrics can help collect feedback from customers and stakeholders, which can be used to measure customer satisfaction.
  7. Financial management tools: Financial management tools such as QuickBooks or Xero can help track financial metrics such as return on investment (ROI) and cost variance.

It’s important to note that the choice of tools will depend on the organization’s specific needs, budget, and existing technology infrastructure. The most effective tools are those that can be integrated with each other to provide a comprehensive view of portfolio performance.

Me: A popular agile product management tool some executives and upper managers find useful is Aha! Can Aha! track metrics and KPIs for the agile portfolio management process?

Yes, Aha! is a product management and roadmapping tool that can be used to track metrics and key performance indicators (KPIs) for the agile portfolio management process. Aha! provides a variety of features that can help measure portfolio performance, including:

  1. Customizable dashboards: Aha! provides customizable dashboards that can be configured to display the most important metrics and KPIs for the portfolio. These dashboards can be shared with stakeholders to provide a real-time view of portfolio performance.
  2. Goal setting and tracking: Aha! allows users to set goals for the portfolio and track progress towards those goals. This can be a powerful tool for measuring the impact of the portfolio on the organization’s strategic objectives.
  3. Customizable reports: Aha! provides customizable reports that can be used to analyze portfolio performance and identify areas for improvement. These reports can be generated on a regular basis to provide a comprehensive view of portfolio performance.
  4. Integration with other tools: Aha! can be integrated with other tools such as Jira or Trello to provide a comprehensive view of portfolio performance.
  5. Customer feedback: Aha! provides tools for collecting and analyzing customer feedback, which can be used to measure customer satisfaction and identify areas for improvement.

Overall, Aha! is a powerful tool for tracking metrics and KPIs for the agile portfolio management process. Its customizable dashboards, goal setting and tracking features, and integration with other tools make it a popular choice among portfolio managers.

Me: Can aha! help with agile team capacity planning and utilization?

Yes, Aha! can help with agile team capacity planning and utilization. Aha! provides a variety of features that can help teams plan and manage their capacity, including:

  1. Resource allocation: Aha! allows teams to allocate resources to specific initiatives or projects, which can help ensure that resources are being used effectively and efficiently.
  2. Capacity planning: Aha! provides tools for capacity planning, which can help teams determine how much work they can take on based on their available resources and capacity.
  3. Team workload: Aha! allows teams to view their workload across all initiatives and projects, which can help them identify potential bottlenecks or areas where they may need additional support.
  4. Time tracking: Aha! provides tools for time tracking, which can help teams monitor how much time they are spending on specific tasks or projects. This can be useful for identifying areas where teams may be spending too much time, or where they may need additional training or support.
  5. Capacity reporting: Aha! provides customizable reports that can be used to analyze team capacity and utilization over time. These reports can be used to identify trends or areas for improvement, and can help teams make data-driven decisions about how to allocate their resources.

Overall, Aha! provides a comprehensive set of tools for agile team capacity planning and utilization, which can help teams work more efficiently and effectively. Its resource allocation, capacity planning, team workload, time tracking, and capacity reporting features make it a popular choice among agile teams.

Me: Good deal. How does Azure DevOps compare with Aha! and Confluence Jira?

Azure DevOps, Aha!, and Confluence Jira are all software development tools that offer different functionalities and serve different purposes in the software development lifecycle. Here are some key differences between these tools:

  1. Azure DevOps: Azure DevOps is a comprehensive software development platform that provides end-to-end functionality for planning, tracking, and deploying software products. It includes tools for agile project management, source code management, continuous integration and deployment, and testing. Azure DevOps is an all-in-one platform that provides a complete set of features and integrations, which makes it a popular choice for organizations that are looking for a single platform to manage their entire software development lifecycle.
  2. Aha!: Aha! is a product management tool that helps organizations plan and manage their product roadmap, features, and releases. It provides features for idea management, product strategy, and product analytics. Aha! is focused on helping product teams align their roadmap with their business goals and customer needs.
  3. Confluence Jira: Confluence Jira is a collaboration tool that allows teams to plan, track, and report on their work. It includes features for agile project management, issue tracking, and team collaboration. Confluence Jira is popular among agile teams as it provides features for creating and managing agile boards, sprints, and backlogs.

In summary, Azure DevOps is a comprehensive platform that provides end-to-end functionality for software development, while Aha! and Confluence Jira are more specialized tools that focus on product management and collaboration, respectively. Depending on the organization’s needs, each of these tools can be a good fit for different aspects of the software development process.

Me: How does agile portfolio management align with product management?

Agile portfolio management and product management are closely related and have many overlapping elements. Both focus on delivering value to customers by developing and managing a portfolio of products or initiatives. However, there are some key differences in the focus and scope of each discipline.

Agile portfolio management focuses on managing a portfolio of initiatives or products across an organization, with the goal of maximizing value delivery and achieving strategic objectives. It involves managing resources, prioritizing initiatives, and measuring performance to ensure that the portfolio is delivering the desired outcomes.

Product management, on the other hand, focuses on developing and managing individual products or services within the portfolio. It involves understanding customer needs, defining product requirements, and overseeing the development and launch of the product.

Despite these differences, agile portfolio management and product management are closely aligned and can work together to achieve common goals. Agile portfolio management provides a framework for managing the overall portfolio, while product management provides a framework for developing and managing individual products within the portfolio.

For example, agile portfolio management can help product managers prioritize their product roadmap by identifying the initiatives or products that will deliver the greatest value to the organization. At the same time, product management can provide feedback to the portfolio management team on the success of individual products and initiatives, which can inform future portfolio management decisions.

Overall, agile portfolio management and product management are complementary disciplines that work together to deliver value to customers and achieve strategic objectives. By aligning these two disciplines, organizations can ensure that they are delivering the right products and initiatives to meet the needs of their customers and stakeholders.

Me: How can executives and hands on investors improve their leadership using reports and metrics from Agile portfolio management?

C-level executives and investors can improve their leadership using reports and metrics from Agile portfolio management by gaining visibility into how the organization’s portfolio is performing and using that information to make data-driven decisions.

Here are some ways that reports and metrics from Agile portfolio management can help C-level executives and investors improve their leadership:

  1. Strategic alignment: Agile portfolio management provides a framework for aligning the portfolio with the organization’s strategic objectives. Reports and metrics can help C-level executives and investors understand how the portfolio is contributing to those objectives, and identify areas where adjustments may be needed.
  2. Resource optimization: Agile portfolio management can help optimize the use of resources across the organization. Reports and metrics can provide insights into resource utilization and identify areas where resources may be underutilized or overutilized.
  3. Risk management: Agile portfolio management can help manage risk by providing visibility into potential risks across the portfolio. Reports and metrics can help identify areas of the portfolio that may be at risk, and help the organization take proactive measures to mitigate those risks.
  4. Performance measurement: Agile portfolio management provides a framework for measuring the performance of the portfolio. Reports and metrics can help C-level executives and investors understand how the portfolio is performing against key performance indicators, and identify areas for improvement.
  5. Transparency: Agile portfolio management provides transparency into the organization’s portfolio and how it is being managed. Reports and metrics can help C-level executives and investors understand how the portfolio is being managed, and provide insights into the decision-making process.

By using reports and metrics from Agile portfolio management, C-level executives and investors can gain a deeper understanding of the organization’s portfolio and make data-driven decisions to improve its performance. This can help the organization achieve its strategic objectives, optimize its resources, manage risk, measure performance, and increase transparency.

Me: Very informative. I knew there was a reason I like you. Can Azure Agile DevOps track metrics and KPIs for the agile portfolio management process?

Yes, Azure DevOps can track metrics and KPIs for the agile portfolio management process. Azure DevOps provides a range of tools and features that can help organizations manage their agile portfolio and measure its performance.

Here are some ways that Azure DevOps can help track metrics and KPIs for agile portfolio management:

  1. Backlogs: Azure DevOps provides tools for managing product backlogs, which can help organizations prioritize and track work across their portfolio. By tracking the status of backlog items, organizations can measure their progress and identify areas where improvements are needed.
  2. Dashboards: Azure DevOps provides customizable dashboards that can be used to track key metrics and KPIs for agile portfolio management. These dashboards can be configured to display information such as backlog status, sprint progress, and team capacity utilization.
  3. Reporting: Azure DevOps provides a range of built-in reports that can be used to measure the performance of the agile portfolio. These reports can be customized to display information such as velocity, burn-down charts, and team capacity.
  4. Integration: Azure DevOps integrates with a range of other tools and services, which can help organizations track metrics and KPIs across their entire software development lifecycle. For example, Azure DevOps can integrate with Power BI to provide more advanced reporting and analytics capabilities.
  5. Analytics: Azure DevOps also provides advanced analytics capabilities that can be used to measure and optimize the performance of the agile portfolio. These analytics tools can help organizations identify trends, uncover insights, and make data-driven decisions to improve their portfolio management processes.

Overall, Azure DevOps provides a range of tools and features that can help organizations track metrics and KPIs for agile portfolio management. By using these tools, organizations can gain insights into their portfolio performance, identify areas for improvement, and make data-driven decisions to optimize their portfolio management processes.

Me: Sweet. Finally, I know my sophisticated questions probably wore your AI brain out…Can Azure DevOps help with agile team capacity planning and utilization? Team capacity is one of the most powerful yet least used leadership tool that I think can help executives enable sprint and product teams to provide value and feel like their work makes a difference.

Yes, Azure DevOps can help with agile team capacity planning and utilization. Azure DevOps provides a range of features and tools that can help organizations plan and manage their team capacity in an agile environment.

Here are some ways that Azure DevOps can help with agile team capacity planning and utilization:

  1. Capacity Planning: Azure DevOps provides capacity planning tools that enable teams to estimate their available capacity for upcoming sprints. This helps teams plan their work more effectively and ensure that they are not overcommitting.
  2. Resource Allocation: Azure DevOps allows organizations to allocate resources to specific teams, projects, or initiatives. This helps organizations optimize their resource utilization and ensure that resources are being used effectively.
  3. Time Tracking: Azure DevOps provides time tracking capabilities that enable teams to track the time spent on specific tasks or user stories. This helps teams better understand how their time is being spent and identify areas where they can improve their productivity.
  4. Work Item Tracking: Azure DevOps provides work item tracking capabilities that allow teams to track the status of their work items and ensure that they are being completed on time. This helps teams identify potential bottlenecks and take corrective action to improve their efficiency.
  5. Reporting: Azure DevOps provides a range of reporting capabilities that allow teams to measure and analyze their capacity and utilization. This helps teams identify areas for improvement and make data-driven decisions to optimize their capacity planning and utilization processes.

Overall, Azure DevOps provides a range of tools and features that can help organizations with agile team capacity planning and utilization. By using these tools, organizations can plan their work more effectively, optimize their resource utilization, and improve their team’s productivity and efficiency.

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