The science of estimation is an art rooted in risk management

I frequently find people mixing up estimation techniques between plan-driven and change-driven approaches thinking they are all completely different. While there are small changes, the art of estimation is simply looking at the level of accuracy when estimated and the extent of confidence in the given estimate for working on it! From that angle, the approaches like the analogous estimation, parametric estimation, triangular estimation, the special PERT estimation, affinity estimation, relative sizing, and storypointing can all be categoized into top-down, budget, and bottom-up estimation. 

Top Down Estimation

• The top-down estimate is often based on gut feel. It draws on the experience of previous projects (hence analogous). It could be driven off of someone's expertise (expert judgment) or based on knowledge tracked in historical records (corporate knowledge base). It is frequently done at the early stages of a project (initiation) where minimal effort is required to get a feel for whether an initiative should be undertaken or not! As a result, the level of accuracy is very low (-25% to +75%). This is why this technique is called rough order of magnitude (ROM) or order of magnitude (OOM). 
• In adapative projects where features representing a collection of stories and tasks not yet broken down are estimated, these collection of work closer to each other (hence affinity) are estimated in abstaction units such as T-shirt or Coffee-cup sizes. Hence such estimates are called affinity estimates in the backlog!

Budget Estimation

• As the project continues with planning, we look at increasing our confidence in the estimate. So, we get down to decomposing the details, such as the parameters required to estimate or seek opinion from multiple experts to narrow our estimate. Since we apply the parameters (number of rooms to paint * amount of paint required * price per paint can; number of virtual machines on the cloud * number of active hours * price per hour), we call it parametric estimation. The details of the parameters applied vary based on the industry and the project. 
• When it comes to seeking expert's opinion, instead of seeking estimate from estimate alone, we seek 3-points (optimistic, most likely, and pessimistic) to get the average. This average applies the statistical principle of central tendency to even out the variations. The same logic applies with PERT (program evaluation review technique) where multiple points are observed where the princple of normalization (bell curve logic) can be expected. So, PERT becomes a special case of triangular estimate. 
• For adaptive projects, the parametric thoughts carry forward. So, a team looks at a feature in relation to another feature (either delivered or to be delivered). So, if the new feature is twice the size of another feature which is either of small T-shirt size or 3 points, then, the new feature is either medium size or 8 points. These estimates may apply at the release level backlog giving the definition of ready (DoR) following the DEEP (Detailed Appropriately, Estimable, Emergent, Prioritized) property.
• Naturally, there is more time required to identify the parameters, seek opinions from multiple people, and perform this estimation. As the level of acuracy increases between -10% to +25%, the duration taken to estimate also increases.

Bottom Up Estimation

• When the project continues in its later stages of planning, then, increased level of accuracy and confidence are required to allocate work to someone and spend the money. Consequently, teams engage in more granular breakdown of tasks (activities) or modules (function points) so that these activities can be estimated, dependencies understood, and lead/lag factored appropriately to compute the 'definitive' estimate.
• In the case of adaptive projects, here is where the features or user stories are further broken following the INVEST (independent, negotiable, valuable, estimable, small, testable) property so that they are good candidates for sprint/iteration planning. In the sprint planning, the team does the cumulative estimate applying the central tendency to arrive at the stroy point (hence story pointing). The planning poker player at this stage is to faciliate the team level estimate as the expectation at the scrum level is that anyone should be able to pick up any story (cross-functional, multidisciplinary, T-shaped skills based, self-managed team). As work is constantly refined through backlog refinement, release level planning, and iteration level planning, the agile teams gain significant efficiency in sprint planning as the time taken to do this estimation is spread over time. 

Figure: Estimation Illustration by Sriram Rajagopalan

As you can see, the entire art of estimation is a classic risk management exercise where not only the management stakeholders but also the delivery team converge on the constraints, assumptions, risks, and dependencies (that I call as the CARD of the business goals and objectives). No wonder project management is not only a science but an art!

Thoughts? What do you think? 

Navigating and leading team and stakeholder journeys

 Navigating Team and Stakeholder Journeys: A Dynamic Approach

Team development and stakeholder engagement both follow structured stages—Forming, Storming, Norming, Performing, and Adjourning for teams, and Unaware, Resistant, Neutral, Supporting, and Leading for stakeholders. While these stages appear linear in theory, real-world challenges can cause regression. Poor collaboration, change introduction, lack of risk awareness, shifting roles, or inconsistent practices can push teams and stakeholders backward, making proactive engagement essential for sustainable progress.

1. Forming & Unaware: Laying the Foundation
Just like teams may be anxious unaware of what the initiatives are for in the forming stage, some stakeholders may be unaware of how these initiatives may impact them or what their role would be in them. Clear communication is crucial—leaders must articulate vision, objectives, and expectations early. For teams, setting norms and fostering psychological safety can ease transitions. For stakeholders, awareness campaigns, informative sessions, and targeted messaging help move them from unawareness to engagement. Essential documents here include business case, benefits management plan, and project charter.

2. Storming & Resistant: Managing Conflicts and Concerns
As teams enter the storming phase, conflicts emerge over roles, responsibilities, and approaches. Similarly, stakeholders may resist changes that disrupt their routines or priorities. Leaders must actively listen, mediate conflicts, and address concerns with transparency. Encouraging open dialogue, clarifying goals, and demonstrating quick wins can mitigate resistance and build trust. Essential documents include project charter, risk register, stakeholder register, stakeholder engagement plan, and team charter with a clear project vision/scope statement.

3. Norming & Neutral: Aligning and Strengthening Commitment
Once conflicts subside, teams begin norming, establishing efficient workflows and mutual respect. Stakeholders, too, may shift to a neutral stance, neither opposing nor actively supporting efforts. Reinforcing alignment through continuous feedback, recognition, and collaborative decision-making strengthens commitment. Encouraging stakeholder input in planning processes fosters a sense of ownership and investment in outcomes. An essential aspect here is the updates to all the management documents in the storming phase and primarily the team charter that the team creates themselves. 

4. Performing & Supporting: Driving Synergy and Value
High-performing teams operate with synergy, leveraging strengths for optimal results. Stakeholders at this stage move from passive acceptance to active support. Leaders should empower teams with autonomy, provide resources for innovation, and celebrate successes. For stakeholders, demonstrating tangible benefits, inviting deeper collaboration, and showcasing impact stories can strengthen their advocacy.

5. Adjourning & Leading: Sustaining Engagement Beyond Completion
Teams eventually adjourn as projects conclude or objectives shift. Engaged stakeholders, however, can continue leading initiatives forward. Capturing lessons learned, maintaining relationships, and transitioning responsibilities smoothly ensure sustained engagement. Recognizing contributions, fostering ongoing dialogues, and preparing for future collaborations reinforce long-term partnerships.

By understanding the dynamic nature of both team and stakeholder journeys, leaders can anticipate regressions and proactively address challenges. Intentional engagement strategies help navigate transitions, ensuring both teams and stakeholders remain aligned, resilient, and forward-moving in the face of change.

The 5 I’s of Stakeholder Engagement: Building Stronger Connections

I often say, "Tell me about the stakeholders identified and your engagement strategy for your project, I will tell you how successful your project will be!" My thoughts were modelled after the saying, "Tell me your friends and I will tell you who you are!" Since stakeholders are people that can positively or negatively influence or be impacted by the project's outcome, it is important to understand the insurmountable role of stakeholders in delivering the 5P's (project, process, product, program, and portfolio) of value delivery! 

Furthermore, since stakholders are not members that we can directly manage, we need to see how we can engage them effectively. This is crucial not only for the 5P's success but also for strategic growth of the organization and fostering strong partnerships for verticial and horizontal growth. In this regard, I feel that there are five magic ingredients of stakeholder engagemen. These are interest, involvement, interdependencies, influence, and impact. These elements help leaders navigate complex relationships and align objectives facilitating execution as well as governance. Understanding these dimensions ensures that stakeholders remain engaged, informed, and motivated throughout the journey.

1. Interest (Care or Concern)
Stakeholders must have a clear interest in the project or initiative. Identifying what motivates them—be it financial returns, innovation, or social responsibility—helps shape engagement strategies. Here, I come up with both care and concern. Care gives a positive spin of stakeholders while concern may give the adverse considerations they may have. In both cases, if they are silent observers, creative ideas to problem solving and decision making are are left out. So, the extent of the involvement is the next thing to understand. 

2. Involvement
Once interest is established, involvement becomes key. Encouraging active participation through workshops, feedback loops, and collaborative decision-making strengthens their commitment and enhances project outcomes. While adaptive approaches talk about "buiness people and developers must engage on a daily basis" to emphasise their involvement, plan-driven approaches also promote similar thoughts of specific stage/phase gate reviews. In both these project delivery approaches, it is important to understand how much stakeholders are involved proactively! The sooner you understand this engagement, the earlier you address risks through preventive action. 

3. Interdependencies
Stakeholders do not exist in isolation. Business units have their own objectives as part of their goals to serve the organizational objectives. So, in all the elements of 5P's, the stakeholders interact with each other in various ways, impacting (which by the way is the fifth "I") project dynamics. Recognizing interdependencies allows for strategic alignment, reducing friction and maximizing collaboration. Preparing the people in advance of how our work impacts others builds the surround sound required for success.

4. Influence
The combination of interest, involvement, and interdependcies are not adequate if one does not support the overarching objetctives by championing change. Influence therefore connects with the behavioral change people can exercise not only by hiearchical authority but also by expertise they bring to the team. Influence determines how much power stakeholders wield over decisions. Understanding their authority, expertise, and networks helps in prioritizing engagement efforts effectively.

5. Impact
At the heart of stakeholder engagement is impact—how actions and decisions affect both the project and the stakeholders themselves. Effective engagement strategies create value for all parties, fostering trust and long-term relationships. By aligning interests, managing influence, and leveraging interdependencies, leaders can drive meaningful change, ensuring projects achieve sustainable success.

So, operating between the two bookends (interest and impact) lies the involvement, interdependencies, and influence. While techniques such as the stakeholder register, stakeholder engaement assessment matrix, power-interest grid, salience model, and stakeholder map exist, the stakeholder engagement is more of an art than science! It comes only with practice!

Don't you think so? Thoughts?

Demonstration of Leadership in Instructional Design

I spoke in a conference focusing on the role of emerging faculty in leading learners in the AI driven world at Northeastern University College of Professional Studies Faculty Conference in Oct 2024. While there were a lot of concerns on the adoption of AI due to the plagiarism, the major concerns was towards the lack of critical thinking as people can always get the answers! The goal has become more on prompt engineering rather than critical thinking! 

While prompt engineering itself is not bad as it also makes one think of the Five Whys or Socratic thinking approaches, I found one example of a middle school learner asking why they should know about using calculators when they can ask Siri or Alexa! Perhaps I am outdate in my thoughts that I used the logarithmic book once upon a time. While scientific calculator was great, when it broke, I was not stuck! But, now, I see people not knowing how to read time on an analog clock or not knowing how to find time when their Alexa is out of commission! 

As I thought through ideas, I came up with a handout that trainers and teachers can use to augment critical thinking with specific methods and some tools. People felt and have since then mentioned that this was a very good resource and so I am sharing for my readers.

PROMOTE AI LITERACY AND CRITICAL THINKING 

Methods 

• Integrate AI into the curriculum, discussing its capabilities and limitations. 

• Teach students to use AI responsibly, i.e. fact-check and verify AI outputs 

• Encourage and invite students to critically evaluate AI-generated content 

• Assign projects that involve using and analyzing AI tools. 

Tools 

• AI ethics courses (e.g., MIT's "Ethics of AI" course materials). 

• Critical thinking frameworks (e.g., CRAAP test for evaluating sources). 

• AI-powered fact-checking tools (e.g., Factmata, Full Fact.) 

 

USE AI FOR PERSONALIZED LEARNING EXPERIENCES 

Methods 

• Use AI to ensure that lesson plans are current and relevant. 

• Use AI-powered tutoring systems for additional support. 

• Customize individual study plans based on AI analysis of student performance. 

• Employ AI to identify learning gaps and suggest targeted resources. 

Tools 

• Experiment with custom agents like Claude, OpenAI, Copilot, and Gemini. 

• Research AI thinking courses on MOOC and include as supporting content. 

• Evaluate dashboards of student learning outcomes weekly.  

 

LEVERAGE AI FOR AUTOMATED GRADING AND FEEDBACK 

Methods 

• Use AI to grade objective assessments and provide instant feedback. 

• Implement AI-powered writing evaluation tools for essays and reports. 

• Use AI to evaluate student work for plagiarism, ensure compliance with academic integrity standards. 

• Combine AI grading with human review for a balanced approach. 

Tools 

• Automated essay scoring systems (e.g., ETS e-rater). 

• Plagiarism detection software (e.g., Duplichecker, Turnitin, Copyleaks). 

• AI-powered feedback tools (e.g., Revision Assistant, WriteLab). 

 

INCORPORATE AI-ASSISTED CONTENT CREATION 

Methods 

• Use AI to generate diverse examples and practice problems. 

• Employ AI tools to create multimedia content for lessons. 

• Utilize AI for language translation to support multilingual classrooms. 

• Collaborate with AI to develop interactive simulations and scenarios. 

Tools 

• AI content generators (e.g., GPT-3 based tools can help with PPP structures.) 

• Text-to-speech and speech-to-text tools (e.g., Amazon Polly, Google Cloud Speech-to-Text.) 

• AI-powered design tools (e.g., Canva AI, Adobe Sensei); virtual reality platforms (eg. Labster, zSpace).