Solving Projects with AI: Ex Standard & Poor's CTO Reveals Why Projects fail, How to Streamline you Project

Contents

• JOURNEY INTO LEADERSHIP

• AGILE VS WATERFALL

• C-SUITE LEADERSHIP LESSONS

• SOLVING INFORMATION AGGREGATION

• WHY MOST PROJECTS FAIL

Diverse Leadership Roles

Jora’s career progression demonstrates the value of diverse experiences:

• Started as a project manager for small teams, focusing on prioritisation

• Moved to larger project and program management roles.

• Became CTO at Standard & Poor's, combining technology, product, and business vision.

• Transitioned to different industries including media (The Economist)

• Currently serves on boards of major companies and as CEO of tech startup ConnectingYouNow.

Challenges in Project Information Management

As his teams grew larger and more distributed, Jora identified key issues:

• Project managers spent 75-90% of time just collating information.

• Dispersed teams across different locations led to multiple versions of project status.

• Decision-making was hindered by outdated information due to slow data collection.

These challenges led Jora to found ConnectingYouNow, aiming to:

• Reduce information collation time from days to seconds.

• Provide real-time project insights for faster decision-making.

• Integrate data from various tools like Slack, JIRA, and SharePoint.

Underrepresentation of Tech Leaders on Boards

Jora notes a significant gap in corporate governance:

• Only 10% of leaders on FTSE boards have a technology background.

• Boards typically comprise CEOs, CFOs, and marketing executives.

• There's a need for more tech expertise at the highest levels of corporate decision-making, which will add extra depth to delivering business strategy.

We explored the evolving landscape of project management methodologies and when each approach works best.

The Resurgence of Waterfall

While agile methodologies have dominated recent years, Jora notes a trend towards a hybrid approach:

• Large-scale projects, such as ERP implementations or cloud migrations, often require significant upfront planning.

• Financial departments and boards typically demand detailed cost estimates for major projects.

• Traditional documents like functional and technical specifications still play a crucial role in complex transformations.

When Agile Shines

Agile methods are particularly effective in certain scenarios:

• New product development where product-market fit is uncertain.

• Established businesses entering new markets or targeting new demographics.

• Projects requiring rapid prototyping and frequent user feedback.

The Hybrid Approach

Jora suggests a combined method for large-scale projects:

1. Use agile principles at the project's outset to identify potential issues.

2. Develop initial business cases using agile methods.

3. Transition to a more waterfall-like approach as the project scope becomes clearer.

Fishing boat vs. Rowing Boat

Jora offers a compelling analogy to illustrate the difference between agile and waterfall approaches:

• Waterfall is like a rowing boat: suitable when the destination is clear and the path is straightforward.

• Agile is like a fishing boat: ideal for navigating choppy waters and adapting to changing conditions.

Scaled Agile for Large Enterprises

For enterprises looking to increase agility:

• Frameworks like SAFe (Scaled Agile Framework) are gaining popularity.

• These approaches help large organisations transition from slow-paced change to more agile methods.

• Iterative funding releases tied to demonstrated value can drive more creative, startup-like thinking for larger enterprises.

Confidence is Key

1. Early in his career, Jora noticed a lack of confidence among technology leaders:

   • Technology departments were often seen as subservient to "the business".

   • Tech leaders hesitated to voice their opinions.

2. Jora emphasises the importance of confidence:

   • Not to be confused with arrogance.

   • Having the confidence to question yourself, your team, and your leadership.

   • Raising concerns when you have a gut feeling about potential issues.

Building High Performing Teams

• There's no one-size-fits-all approach to creating high-performing teams.

• An individual's performance can vary greatly depending on the company culture and work environment.

• Leaders must tailor their approach to building teams based on specific needs and contexts.

The Power of Reflection

The importance of taking time to reflect:

• Observing team dynamics and questioning current processes.

• Considering more efficient ways of working (e.g., automated testing, CI/CD).

• Carving out time for reflection to become a better leader.

Strategic Thinking for Tech Leaders

Discussing the lack of technology leaders on corporate boards:

• Many tech leaders focus too much on technical details in board discussions.

• Successful tech leaders on boards start with strategic questions:

  • "What problem are you trying to solve?".

  • "How can technology play a part in that?".

• There's a need for technology leaders to develop and demonstrate strategic thinking skills.

Advice for Aspiring Leaders

1. Develop confidence in your expertise and opinions.

2. Focus on building teams that fit your specific organisational needs.

3. Make time for reflection and strategic thinking.

4. When presenting ideas, start with the business problem, not the technology solution.

5. Cultivate a broader understanding of business strategy beyond technical expertise.

Challenge 1: Centralising Disparate Data

• Project teams often use multiple tools like JIRA, QA systems, and messaging platforms.

• ConnectingYouNow aggregates all this information into a central AI repository that is searchable.

• This centralisation provides a single version of the truth, enabling more informed decision-making.

Challenge 2: Two-Way Conversational Engine

• The platform allows users to query risks and other project details.

• It can identify specific risks, such as a lack of UX resources, by analysing data from various sources.

• This helps teams pinpoint issues and adjust their strategies accordingly.

Challenge 3: Risk Mitigation Recommendations

• After identifying risks, the AI suggests mitigation strategies.

• These recommendations provide a starting point for team discussions and further analysis.

• The goal is to enable quicker course corrections and more proactive project management.

Reducing Time Spent on Reporting

• Traditional project management involves significant time spent collating and organising reports.

• ConnectingYouNow aims to provide real-time data, reducing the time required for report preparation.

• This allows teams to focus on productive work rather than administrative tasks.

Improving Decision-Making

• Real-time data enables timely and informed decisions.

• Teams can prioritise critical tasks and adjust their focus as needed.

• This proactive approach helps prevent projects from going off track.

Challenges with Traditional Steering Committees

• Often, steering committees are not effective due to delayed information sharing.

• By the time issues are raised, it may be too late for effective intervention.

Enhancing Steering Committees with AI

• Providing real-time data to steering committees can make them more effective.

• Senior leaders can make informed decisions earlier in the project lifecycle.

• This reduces the risk of projects reaching a point of no return where major adjustments are needed.

Jora cited the statistic that 66-70% of technology projects fail to deliver their intended value, and asked for my take on whether this is accurate based on my experience. Here are the key takeaways:

Firstly, I agreed this failure rate is likely accurate, possibly even higher! Reasons for this high failure rate are multifaceted.

Key Factors Contributing to Project Failures

1. Expectation Management

   • Initial baselines often set unrealistic expectations.

   • Desire to retain funding can lead to overly optimistic projections.

2. Lack of Cross-Team Collaboration

   • Teams often focus on their own budgets and goals.

   • Insufficient dependency management across delivery teams.

3. Fear of Transparency

   • Reluctance to report problems or setbacks.

   • Tendency to present overly positive updates until projects are critically behind.

4. Inadequate Work Breakdown

   • Not segmenting work into manageable iterations.

   • Attempting to build complex solutions in one go rather than incrementally learning, prioritising and continuing to build only what is needed.

Recommendations for Improvement

1. Embrace Agile Methodologies

   • Release functionality iteratively where possible.

   • Focus on go-to-market features first, then build upon them.

2. Manage Expectations Continuously

   • Redefine "failure" in the context of shorter-term, achievable goals.

   • Set expectations for quarterly or annual progress rather than long-term end states.

3. Encourage Transparency

   • Create an environment where teams feel safe reporting challenges.

   • Use status reports proactively to indicate potential issues before they become critical. It’s better to be pessimistic in reporting rather than too optimistic around the status.

4. Improve Cross-Team Collaboration

   • Take a portfolio view of projects and resources.

   • Encourage resource sharing and dependency management across teams.