How would you estimate the anticipated work for a new project without knowing its history?

Question

Anonymous · Accepted Answer

While knowing the history of a project is valuable, it’s not a prerequisite for
successful delivery. Estimating expected work involves understanding the
business problem, identifying key stakeholders, and analyzing the project's
current state. Here’s how I approach it:
 1. Understand the Business Need: Begin by meeting with stakeholders to grasp
    the business problem and expected outcomes. For example, in a past project,
    I was tasked with reviving a stalled initiative to deliver a risk management
    dashboard. Understanding the business impact helped prioritize what needed
    to be achieved.
 2. Assess Requirements: Determine if business and technical requirements are
    clearly defined and finalized. If not, facilitate workshops to fill the
    gaps. For instance, I once organized a session where we clarified ambiguous
    requirements, which reduced delays caused by misaligned expectations.
 3. Evaluate Tools and Processes: Identify the tools being used, such as Jira or
    Azure DevOps, and ensure they are being leveraged effectively. During a
    previous project, I streamlined workflows by introducing Jira dashboards
    that provided better visibility into progress and blockers.
 4. Analyze Team Composition and Responsibilities: Understand how many
    stakeholders are involved and their roles. I’ve worked on projects where
    siloed communication created bottlenecks, so I established cross-functional
    syncs to break down barriers.
 5. Identify Risks and Challenges: Track ongoing risks and unresolved issues.
    For example, in one project, I uncovered a major dependency on an external
    vendor that hadn’t been flagged. By escalating it early, we adjusted
    timelines and mitigated potential delays.
 6. Estimate Effort: Break the project into tasks, estimate timelines for each,
    and incorporate a risk buffer. This approach helped me on a project where
    tight deadlines were compounded by multiple unknowns. I created a detailed
    task matrix and used risk-adjusted timelines, ensuring realistic
    expectations.
 7. Plan for Blockers: Proactively address blockers by creating a risk table.
    For example, in a prior project, I anticipated delays due to limited testing
    resources, so I negotiated additional support early on, avoiding a crunch
    close to delivery.

When I was assigned to a project that had seen multiple unsuccessful delivery
attempts, I started by conducting a series of stakeholder interviews to clarify
the work required and uncover historical challenges. After understanding the
root causes of previous failures, I created a prioritized roadmap and secured
stakeholder buy-in. Through regular updates and a strong focus on execution, we
delivered the project on time, meeting business goals.
Handling Challenges: Unexpected challenges can always arise. For example, in
another project, a sudden scope change was introduced late in the cycle. By
maintaining open communication with stakeholders and reprioritizing tasks, I
ensured the team remained focused on high-impact items while minimizing
disruptions.
This approach balances structure with flexibility, allowing me to create a
realistic and comprehensive work estimate while adapting to dynamic project
needs.

Anonymous · Answer

Knowing the history of a project is good but not a requirement to successfully
deliver a project. The way to estimate the expected work, would be to understand
what is the business problem and then understand who are the various
stakeholders responsible for delivering the project. Here are a few bullet
points:
1) Having a clear understanding of the business need:
· I once organized a session where we clarified ambiguous requirements, which
reduced delays caused by misaligned expectations.
2) Are the business requirements completed?
· I’ve worked on projects where siloed communication created bottlenecks, so I
established cross-functional syncs to break down barriers and complete the
business requirements.
3) What tools are being used to track the project delivery? Jira, Azure DevOps
etc?
· I kept on-going discussions with the lead scrum master to identify what types
of meaningful dashboards would help us be transparent on the progress of the
project.
4) Are the technical requirements signed off on?
5) How many stakeholders are assigned to the project? Both on the business and
technical side?
6) Any on-going risks being tracked?
· There was a time when I flagged an issue with the data that would have become
a significant blocker later on, but identifying it early led to active
remediation steps.
7) When is the expected delivery?
8) List out all the tasks that are necessary to complete the project and
expected timelines for each task.
· This step helped me in a project where there were tight deadlines and the
project was complex with multiple unknowns. Having a tracker helped the team
stay on track.
9) incorporate any existing blockers into the timeline as a risk table to assess
how much work is required and when it is likely to be delivered.
I was once tasked with a project as a business analyst which had several
business analysts who had worked on the project in the past leading to
unsuccessful attempts in product delivery. When i was tasked to the project i
started by meeting with people and understanding what was required for the
project to complete. After a long series of meetings and understanding of what
work is entailed and getting all my questions answered by the stakeholders and
getting required sign off, I was able to ship the project.

Anonymous · Answer

Knowing the history of a project is good but not a requirement to successfully
deliver a project. The way to estimate the expected work, would be to understand
what is the business problem and then understand who are the various
stakeholders responsible for delivering the project. Here are a few bullet
points:
1) Having a clear understanding of the business need:
· I proactively organized sessions where we clarified ambiguous requirements
which helped increase transparency and ensured that the parties are on the same
page in terms of requirements and expectations.
2) Are the business requirements completed?
· I’ve worked on projects where siloed communication created bottlenecks, so I
established cross-functional syncs to break down barriers and complete the
business requirements.
3) What tools are being used to track the project delivery? Jira, Azure DevOps
etc?
· I kept on-going discussions with the lead scrum master to identify what types
of meaningful dashboards would help us be transparent on the progress of the
project.
4) Are the technical requirements signed off on?
5) How many stakeholders are assigned to the project? Both on the business and
technical side?
6) Any on-going risks being tracked?
· There was a time when I flagged an issue with the data that would have become
a significant blocker later on, but identifying it early led to active
remediation steps.
7) When is the expected delivery?
8) List out all the tasks that are necessary to complete the project and
expected timelines for each task.
· This step helped me in a project where there were tight deadlines and the
project was complex with multiple unknowns. Having a tracker helped the team
stay on track.
9) incorporate any existing blockers into the timeline as a risk table to assess
how much work is required and when it is likely to be delivered.
I was once tasked with a project as a business analyst which had several
business analysts who had worked on the project in the past leading to
unsuccessful attempts in product delivery. When i was tasked to the project i
started by meeting with people and understanding what was required for the
project to complete. After a long series of meetings and understanding of what
work is entailed and getting all my questions answered by the stakeholders and
getting required sign off, I was able to ship the project.
Handling Challenges: Unexpected challenges can always arise. For example, in
another project, a sudden scope change was introduced late in the cycle. By
maintaining open communication with stakeholders and reprioritizing tasks, I
ensured the team remained focused on high-impact items while minimizing
disruptions. This approach balances structure with flexibility, allowing me to
create a realistic and comprehensive work estimate while adapting to dynamic
project needs

Anonymous · Answer

Knowing the history of a project is good but not a requirement to make a project
successfully delivered.  The way to estimate the expected work, would be to
understand what is the business problem and then understand who are the various
stakeholders responsible for delivering the project.  Here are a few bullet
points:
1) Having a clear understanding of the business need
2) Are the business requirements completed?
3) What tools are being used to track the project delivery?  Jira, Azure DevOps
etc?
4) Are the technical requirements signed off on?
5) How many stakeholders are assigned to the project?  Both on the business and
technical side?
6) Any on-going risks being tracked?
7) When is the expected delivery?
8) List out all the tasks that are necessary to complete the project and
expected timelines for each task.
9) incorporate any existing blockers into the timeline as a risk table to assess
how much work is required and when it is likely to be delivered.
I was once tasked with a project which had several business analysts who had
worked on the project in the past leading to unsuccessful attempts in product
delivery.  When i was tasked to the project i started by meeting with people and
understanding what was required for the project to complete.  After a long
series of meetings and understanding of what work is entailed and getting all my
questions answered by the stakeholders and getting required sign off, I was able
to ship the project.

Anonymous · Answer

Knowing the history of a project is good but not a requirement to successfully
deliver a project. The way to estimate the expected work, would be to understand
what is the business problem and then understand who are the various
stakeholders responsible for delivering the project. Here are a few bullet
points:
1) Having a clear understanding of the business need:
· I proactively organized sessions where we clarified ambiguous requirements
which helped increase transparency and ensured that the parties are on the same
page in terms of requirements and expectations.
2) Are the business requirements completed?
· I’ve worked on projects where siloed communication created bottlenecks, so I
established cross-functional syncs to break down barriers and complete the
business requirements.
3) What tools are being used to track the project delivery? Jira, Azure DevOps
etc?
· I kept on-going discussions with the lead scrum master to identify what types
of meaningful dashboards would help us be transparent on the progress of the
project.
4) Are the technical requirements signed off on?
5) How many stakeholders are assigned to the project? Both on the business and
technical side?
6) Any on-going risks being tracked?
· There was a time when I flagged an issue with the data that would have become
a significant blocker later on, but identifying it early led to active
remediation steps.
7) When is the expected delivery?
8) List out all the tasks that are necessary to complete the project and
expected timelines for each task.
· This step helped me in a project where there were tight deadlines and the
project was complex with multiple unknowns. Having a tracker helped the team
stay on track.
9) incorporate any existing blockers into the timeline as a risk table to assess
how much work is required and when it is likely to be delivered.
10) Handling Unexpected Scope Changes:  There are times when sudden scope
changes due to requirements unfolding can create an urgency situation and
increase timelines and scope.  In a project, there was a situation where a
technical requirement had additional dependencies which required cooperation
from other teams.  By identifying clear steps of what was required along with
making sure that the team stays on track with their existing priorities, a
smaller task force was created to resolve this scope change.   We were able to
allocate time and resources for the scope change by rigorous planning and
swapping out some lesser priority items with this item of higher importance.
There was a time when i was tasked to a project as a business analyst which had
several business analysts who had worked on the project in the past leading to
unsuccessful attempts in product delivery. When i was tasked to the project i
started by meeting with people and understanding what was required for the
project to complete. After a long series of meetings and understanding of what
work is entailed and getting all my questions answered by the stakeholders and
getting required sign off, I was able to ship the project.

Anonymous · Answer

Knowing the history of a project is good but not a requirement to successfully
deliver a project. The way to estimate the expected work, would be to understand
what is the business problem and then understand who are the various
stakeholders responsible for delivering the project. Here are a few bullet
points:
1) Having a clear understanding of the business need:
· I proactively organized sessions where we clarified ambiguous requirements
which helped increase transparency and ensured that the parties are on the same
page in terms of requirements and expectations.
2) Are the business requirements completed?
· I’ve worked on projects where siloed communication created bottlenecks, so I
established cross-functional syncs to break down barriers and complete the
business requirements.
3) What tools are being used to track the project delivery? Jira, Azure DevOps
etc?
· I kept on-going discussions with the lead scrum master to identify what types
of meaningful dashboards would help us be transparent on the progress of the
project.
4) Are the technical requirements signed off on?
5) How many stakeholders are assigned to the project? Both on the business and
technical side?
6) Any on-going risks being tracked?
· There was a time when I flagged an issue with the data that would have become
a significant blocker later on, but identifying it early led to active
remediation steps.
7) When is the expected delivery?
8) List out all the tasks that are necessary to complete the project and
expected timelines for each task.
· This step helped me in a project where there were tight deadlines and the
project was complex with multiple unknowns. Having a tracker helped the team
stay on track.
9) incorporate any existing blockers into the timeline as a risk table to assess
how much work is required and when it is likely to be delivered.
I was once tasked with a project as a business analyst which had several
business analysts who had worked on the project in the past leading to
unsuccessful attempts in product delivery. When i was tasked to the project i
started by meeting with people and understanding what was required for the
project to complete. After a long series of meetings and understanding of what
work is entailed and getting all my questions answered by the stakeholders and
getting required sign off, I was able to ship the project.
Handling Challenges: Unexpected challenges can always arise. For example, in
another project, a sudden scope change was introduced late in the cycle. By
maintaining open communication with stakeholders and reprioritizing tasks, I
ensured the team remained focused on high-impact items while minimizing
disruptions.

How would you estimate the anticipated work for a new project without knowing its history?

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