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Here's how you can navigate expectations with your boss for enterprise software deliverables.

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Navigating expectations with your boss regarding enterprise software deliverables can be a daunting task. It's essential to understand that these expectations are not just about meeting deadlines but also about the quality and functionality of the software. When dealing with enterprise software, which is designed to meet the complex needs of large organizations, clear communication and a strategic approach are key. You must be well-versed in articulating your progress, managing timelines, and setting realistic goals. It's not just about coding and development; it's about ensuring that the software will serve its intended purpose effectively within the broader ecosystem of the organization's operations.

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1 Understand Needs

To begin with, you need to thoroughly understand what your boss expects from the enterprise software project. This involves comprehending the business objectives, the problems the software is intended to solve, and how its success will be measured. Engage in detailed discussions to clarify these points, and don't hesitate to ask questions. This foundational understanding will guide your work and help you prioritize features and tasks. Moreover, it will enable you to set clear milestones and manage expectations realistically, which is crucial for maintaining trust and credibility.

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Ronald B. Webb Jr.

Expert in Product Vision and Delivery for Enterprise Software Solutions
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Stakeholder alignment is critical to understanding business needs. 2 stakeholder groups that require attention are the project champion and what I call “unsung heroes”. Of course aligning with the project champion is key because this person ultimately will decide if the project is successful. “Unsung Heroes” on the other hand are SMEs who know the process or product intimately but may have little authority on the project. These stakeholders are important due to their deep knowledge and experience and ability to influence others. Not only can these persons help with identifying important details but they can also be advocates for adoption. For a successful project remember the Champion and try to identify the “Unsung Heroes”!

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2 Set Milestones

Once you have a grasp of the project's objectives, work with your boss to establish clear milestones. These are specific checkpoints that will help track progress and ensure that the project is moving in the right direction. Milestones should be achievable and measurable, allowing both you and your boss to see the tangible outcomes of your work. They also provide opportunities for feedback and adjustments, which are vital in the dynamic environment of enterprise software development where changes and pivots are common.

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3 Communicate Regularly

Effective communication is paramount when navigating expectations for enterprise software deliverables. Schedule regular meetings or progress reports to update your boss on where you are with the project. Use these opportunities to discuss any challenges or deviations from the plan, as well as potential solutions. Transparent communication builds trust and demonstrates that you are in control of the project. It also helps prevent any surprises that could derail the project or lead to a loss of confidence in your abilities.

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Ronald B. Webb Jr.

Expert in Product Vision and Delivery for Enterprise Software Solutions
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There three areas of communication I would recommend for consideration. 1. DON’T oversell progress or capabilities. One of the key outcomes of good communication is managed expectations. Don’t be tempted to think exaggerate or over-promise even when business partners get demanding or impatient. 2. DON’T delay bad news. Whether it’s a schedule delay or missed budget, the need doesn’t get better over time. Once the issue is understood and a resolution is identified, notify the stakeholders so decisions to adjust can be made as soon as possible. 3. DO provide thought leadership. Leverage your expertise and experience to suggest better approaches when possible. This behavior allows you to become a strategic partner.

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4 Manage Changes

In the world of enterprise software, change is inevitable. Whether it's shifting market demands, new technological advancements, or internal company changes, you must be prepared to adapt. When discussing changes with your boss, focus on how they impact the project's scope, timeline, and resources. Be proactive in proposing adjustments and demonstrate how you can manage these changes without compromising the project's objectives. This adaptability is crucial for delivering successful enterprise software.

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5 Demonstrate Value

Throughout the project, it's important to continually demonstrate the value of the enterprise software to your boss. This means not only talking about technical accomplishments but also how the software will improve business operations, increase efficiency, or contribute to revenue growth. Use concrete examples and relate them back to the initial goals and objectives discussed. By showing the direct benefits of your work, you can reinforce the importance of the project and your role in it.

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6 Seek Feedback

Lastly, actively seek feedback from your boss on the deliverables. This is a two-way street that allows for course corrections and ensures that the final product meets or exceeds expectations. Feedback sessions can also be a learning opportunity for you to understand your boss's perspective better and refine your approach to future projects. Remember, constructive feedback is not criticism; it's an essential part of professional growth and project success.

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7 Here’s what else to consider

This is a space to share examples, stories, or insights that don’t fit into any of the previous sections. What else would you like to add?

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Ronald B. Webb Jr.

Expert in Product Vision and Delivery for Enterprise Software Solutions
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In my experience, a boss is looking for employees to have some sense of autonomy and ownership. One of the best approaches to demonstrate this is being a creative problem-solver. Every manager or leader needs to know about issues, but they are also looking to you to provide possible solutions. Be a project leader by not only being keenly aware of roadblocks or impediments, but also be the one who generates or gathers possible solutions that will keep your project moving forward. State the problem and then describe two or three possible solutions with the rationale for which solution you prefer. This will improve your effectiveness and transform how you are perceived by your leaders and your peers.

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Dr. Rafiu Aderemi Mustapha, DM, PMP

Head of Software Engineering Group | Talent Builder | Technologist | Result Driven | Strategist
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Be transparent about potential roadblocks and dependencies that may impact your delivery cadence. Discuss your proposed mitigation plans and seek for help early.

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Here's how you can navigate expectations with your boss for enterprise software deliverables.

1

2

3

4

5

6

7

1 Understand Needs

2 Set Milestones

3 Communicate Regularly

4 Manage Changes

5 Demonstrate Value

6 Seek Feedback

7 Here’s what else to consider

Enterprise Software

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Here's how you can navigate expectations with your boss for enterprise software deliverables.

1

2

3

4

5

6

7

1 Understand Needs

2 Set Milestones

3 Communicate Regularly

4 Manage Changes

5 Demonstrate Value

6 Seek Feedback

7 Here’s what else to consider

Enterprise Software

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