Five strategies to delight stakeholders while managing multiple projects

Learn the best strategies to manage & delight stakeholders while managing multiple projects

About stakeholder management

Project managers who successfully manage stakeholders' expectations race past ahead of those who don't. If stakeholders are unhappy and refuse to accept your project, then it will be considered a failure irrespective of the work you have put in. In contrast, happy stakeholders provide prompt support and build the perception of progress. They ensure a smooth ride for a project manager throughout the project's life. But, stakeholder management is easier said than done. In fact, it is the most challenging job you have as a project manager, more so when you are managing multiple projects. Why? Two reasons:

  1. Stakeholders and their needs are usually not evident upfront. You need to put in the efforts to identify them.
  2. With multiple stakeholders per project, engaging them in ways they want is too tedious to rely on manual management.

From internal stakeholders like department heads to CXOs to the external stakeholders like clients, each stakeholder has different expectations and needs different engagement from a project manager. However, there is one thing that remains the same. Irrespective of the individual KPIs, each stakeholder - internal or external, expects it from the project manager. It holds within itself the key to smooth project progress, high team performance, and superior career growth for you as a project manager.

It is respectful engagement.

Stakeholders, every one of them, want to be consulted with, receive relevant updates on time, and feel in control of the project's progress. In action, this translates to finding time to meet and listen to them, incorporating their ideas into the project, regularly collating data to send them the status reports, and at the same time, respectfully putting forward your suggestions. But this is the easiest part of the problem. The critical part of the problem is that you never really know if all these efforts are actually helping you and your stakeholders communicate better. There are no verification checks in place and no way to track information flow. I'm not talking about things like email read receipts; I'm talking about communication at the level of really understanding each other's point of view. And if you are managing multiple projects, this can overwhelm you in no time.

"The single biggest problem in communication is the illusion that it has taken place" - George Bernard Shaw

Now, when you know that communication is critical for a project's success, do you have the stakeholder management plan, tactics, and tools to communicate with your stakeholders in ways that engage them?

This is an actionable post on effective stakeholder management to engage them. You will be able to build superior stakeholder relationships. Specifically, I will discuss the communication around the challenges of:

  • Resource allocation to deliver the scope
  • Upfront delivery estimates at the start of the project
  • Scope creep [1] throughout the life of the project
  • Updates on project progress
  • Shifting of milestones and commitments impacting external stakeholders

Today, I will discuss strategies that you can use right away to win over these challenges and delight your stakeholders while managing multiple projects.

Let's get started.


  1. Alchemy of stakeholder delight
  2. The design of a lean data machine
  3. Reporting mastery
  4. Secrets of conquering the unforeseen
  5. Daily rituals of a warrior
If you manage software projects and want a simple yet powerful way to plan and manage projects while keeping stakeholders delighted and per project ROI high, sign up for free to Ruffly

1. Alchemy of stakeholder delight

Alchemy of stakeholder delight is the strategy to transform your relationship with your stakeholders into a highly understanding and supporting one so that you can deliver successful projects with ease. With an aim to persuade stakeholders to see things the way you see and consult them when you face challenges in their knowledge area, the process of delighting stakeholders begins with stakeholder identification [2] followed by stakeholder analysis. The goals here are to understand stakeholder expectations and their motivational factors.

The next step is to win their trust. To make them believe that they can count on you and your ideas are worth listening to. The two-fold strategy to win their trust is bringing original ideas to the problems and keeping your promises. When they see your ideas working, they start seeing you as someone they can count on.

In time, you would want to reach a stage where you can influence them. This will help you get guidance and help from them and help you design a highly effective stakeholder management plan.

Finally, you will never be able to please all your stakeholders all the time. So with the help of your stakeholder analysis, prioritize and be strategic about whom you are going to let down at some point in time. Even if you let some stakeholders down, you can avoid the adverse effects if you communicate your limitations to them honestly and politely, well advanced in time.

2. The design of a lean data machine

Disconnected data sources have plagued the domains of software project planning and management. When data of each stage lives in its own software, you as a project manager are forced to manually collate it from different sources to make sense of it. But it's not just about the data collation and duplication; data in silos makes synchronized decision-making difficult throughout the life of a project. For example, when the presales data lives in a quoting tool and the resource planning data lives separately in a resourcing tool, you never know why the project was planned the way it was when you start working on it. In other words, disconnected data leads to disconnected decision-making.And then, there is the problem of the loss of the narrative.

When your developers use Jira, but you have to maintain an excel sheet or a Trello board for your stakeholders, everyone knows at what stage the project is, but no one knows how it has reached there. Even though projects are stories on how development has gone and why, when you use tools that are built to focus only on the current stage, you do not have easy access to the data in a usable form on what has already happened, what is going on, what is planned next and all the dynamic changes in between.

You know what I mean if you open your Trello board or excel dashboard and try to figure out what it looked like a week before. This loss of narrative limits your ability to maneuver and improvise in the face of setbacks. And then it limits your ability to apply learning from one project to the next one. As if it's not enough, run-of-the-mill project management tools have no idea what managing software projects mean. They neither understand the foundational concepts like scope vs efforts nor have features for resource and velocity planning to keep ROI in check.

Sadly, most project management software are nothing but fancy to-do lists. Excel sheets, Kanban-based Trello boards, and top-level Asana simplify the view of what's done, but they are not an effort vs velocity planner. Since each item in software development is dissimilar, and not all tasks are the same, your software must understand the concept of scope and effort for a task. It needs to provide ways to find how much effort a team can put in. A better approach to win over the challenges of disconnected data and the loss of the narrative is to use a lean data machine that deeply understands end-to-end planning and management of software projects.

This means one simple yet powerful software that can help you to:

  • plan a project during the pre-sales phase
  • plan resources to decide who is going to work on that project
  • manage the project while you are working on it,
  • engage with and update stakeholders in real-time, and
  • do it all for multiple projects all together in a synchronized manner.

...without data duplication and collation.

Finally, the design of this machine must empower you to easily use the change data and see what has been done, what is being done, why it was done, who has worked on it, and for how long. In essence, your machine must help you visualize a project as a continuous story.

Lean data machine

A very important part of software project planning that can make or break a project is resource planning. Right from the beginning, when you are planning and sizing a project for the first time, you need efficient ways to schedule resources — to be able to commit resources for the near future against the scope. And then, with every scope change, get to see the required changes in the resources in real-time. More so, in the case of agencies where you manage multiple projects at a time and per project ROI [3] is essential. Finally, you need to communicate resource planning against time and scope to your shareholders in ways they understand.

Ruffly is the future of project management. It uses data intelligence and heuristics of a good project manager to offer powerful features like effort vs velocity planner while being as simple as kanban boards at the same time. Ruffly helps in project planning and estimation, resource planning, day-to-day management of an ongoing project, and versatile reporting to stakeholders. In essence, Ruffly is the lean data machine for planning and managing software projects.

The fact that you can quickly bring in data to Ruffly from multiple tools — from quoting tool, time tracking tool, excel sheets, and your project management software to build an end-to-end view of your projects makes it super easy to get started with. And Ruffly's superpowers to relate scope with resources, show the impact of scope changes and new projects on resources, and use inputs like effort estimation and velocity planning of resources to build a powerful narrative for stakeholders make it truly native for software project planning and management. Knowledge comes from data. If you have been using wild guesses as surrogates for knowledge, it's time to level up.

3. Reporting mastery

Stakeholders depend on you for project updates. The better you report to them, the better they will understand the efforts you are putting in, the challenges you are facing, goals you are achieving, and the help you need. When your success depends on how well you report to your stakeholders, it becomes essential to master it. The foundation of reporting mastery is individual-specific communication i.e., communicate with relevant stakeholders in the way they want to be communicated. When some stakeholders need complete details of the projects, from top to the level of epics, while others want to manage high-level RAG, you need to create different reports in different formats to suit everyone's needs. But customized reporting is time-consuming, more so when you are managing multiple projects with each project having many stakeholders.

The trick is to balance between reporting and the time invested in it. You would want to provide all information different stakeholders need but without spending all your time on it. This way, you will have more time to manage the project. And the secret of striking this balance lies in the fact that stakeholders care about things they need to communicate to their stakeholders. They are trying to understand if the project is progressing in the right direction or do they need to intervene and re-calibrate it. And they want to understand it in real-time, well before it gets too late.

"How does a project get to be a year late? One day at a time" - Frederick Brooks

Thus, for delightful stakeholder engagement, you need to update stakeholders in real-time in various details and without a lot of manual work. Put another way: Your project management software must have a powerful feature to show project progress against the promise in real-time and accessible to all your stakeholders.

Ruffly, for instance, have roadmaps that visually showcase project progress and several other details for all stakeholders.

Another challenge around stakeholder engagement is ad hoc communication. When you are using emails, calls, Trello boards, excel sheets together, and bits and pieces of information are lying here and there. Such scattered information is not just a logistical nightmare; it also limits your stakeholders' ability to look deep into the projects. You need the continuity of the communication - one place for all your to and fro communication with stakeholders. And being able to do it without the duplication of the effort.

An efficient way to win over ad hoc and scattered communication challenges is to use the power of commentary. It is the power to add comments to milestones on a project's roadmap. You can add comments for your stakeholders and tell them things like:

  • "These are the reasons we have made decision X"
  • "Keep in mind Y while looking at the project progress"
  • "This is why Z is delayed, and here is how we are course-correcting"

and so on. With commentary, you provide an enriched experience to your stakeholders, preemptively handle objections and save everyone's efforts. Another way Ruffly supercharges your stakeholder management is the ease with which you can look into the history of changes in it. In a few clicks, you can go back in time and look at the state of the project and compare it to now. The change history in usable form paints a complete picture of the project from the beginning to the present. It enables your stakeholders to get a full understanding of its progress. Reporting to stakeholders is a daunting but necessary task. However, the success of your stakeholder management strategy depends on how well you can implement it. When you have the right tools on your side, it can be fully automated.

4. Secrets of conquering the unforeseen

In the game of Tetris, you never know what the future blocks look like. When it comes to unforeseen events, software projects are much like the game of Tetris. Every new presales opportunity means a new shape that has to fit in.

Project management is like double-ended Tetris

But unlike Tetris, in software projects, even the blocks at the bottom change constantly. You have to be ready for scope and resource changes that can present themselves at any time. Scope and resource interdependencies are arguably the biggest unforeseen risks to a project's success. Since one change, if not managed, can potentially ripple up all other pieces of the project. To some extent, you can reduce the interdependencies risks at the planning stage by analyzing different scenarios. And then, prioritize the riskiest activities first. You can do this by allocating the resources to such tasks on priority.

However, the extent to which you can carry out a scenario planning depends on the tools you use. The usual practice of tracking interdependencies on a resource-by-resource basis or a requirement-by-requirement basis does not perform well in practice because they are very tedious. And dependency management is way too critical to be left to chances.

A more practical approach is to design a way to get the same level of signals from the project's overall progress without having to manage dependencies on an individual item basis. The thing about interdependencies is that you can't remove them. The best way to manage them is to discover risky signals well ahead of time so that you and your team have enough space for maneuvering.

Thus, the five strategies for conquering the unforeseen are:

  • Scenario planning
  • Prioritize the riskiest things first
  • Resource allocation as per the priorities of the tasks
  • Design a system to get aggregate signals instead of managing individual dependencies
  • Get those signals well ahead of time

With Ruffly, you can implement all these five strategies in no time. Scenario planning is very beneficial but is limited by the tools you use. To change a plan in an excel sheet is a pain where there are multiple dependencies because you have to make little adjustments at many places. And what happens when something is tedious to do? It's not done often.

With Ruffly, you can make one change and see how it ripples through everything in your project planning. Ruffly's planning feature ties the resources to the scope, which means for every scope change, you can see the change in resources needed in real-time. This is immensely beneficial when you manage multiple projects and want to know how a change in one project affects the resource allotment of other projects. Thus, you can easily prioritize tasks and allocate resources to them in Ruffly.

To provide aggregate signals instead of individual interdependencies, you can use phrases in Ruffly. With phases, you focus on a bundle of scope or bundle of resources instead of individual items. Thus, when a dependency is created between two phases, you can clearly identify what needs to be done at first. And then, you have the resources allocated to complete the first phase before moving to the second phase. As the project progresses, Ruffly reflects the true state of what's happening. You can use these signals to infer and keep the plan up to date.

5. Daily rituals of a warrior

Successfully delivering software projects needs everyday efforts. Small wins every day add up to your project being successful in the end. Thus each day, you must take actions that will lead to success. But in the world of project management, it's easy to get entangled in urgent tasks and lose sight of the important ones.

When it comes to stakeholder management, the most effective daily ritual is to allocate time to engage with them. When you have a dedicated time to think about and interact with important stakeholders, you will not compromise stakeholder engagement under the pressure of urgent tasks.

Another very important strategy is assessing and managing risks. As a project manager, you should spend less time on data collation and more time removing the barriers to progress for your project team.


A large part of the project success is decided by the stakeholders. Therefore it is essential for you to carry out stakeholder analysis and have a stakeholder management plan. The goal here is to engage with them and delight them. However without the right tools, you will not be able to manage the stakeholder engagement in spite of your best efforts. Ruffly is built for planning and managing software projects and gives you an end-to-end control over project progress.

If you manage software projects and want a simple yet powerful way to plan and manage projects while keeping stakeholders delighted and per project ROI high, sign up for free to Ruffly