How To Prioritize Projects: A Guide For Start-Up Founders

The secret to project prioritization lies in the methodology you use. Other smart people have gone before us and worked out the best way to meet objectives when embarking on the start-up journey. They’ve made mistakes, learned from them and come up with efficient ways to prioritize projects. The processes are scalable and repeatable, and that’s what leads to success. 

As a start-up founder (especially if you’ve done this more than once), you know that you can’t afford to make costly mistakes. Everything is limited. Your funds, your resources, your time, and even your patience (including the patience of the investors). This article is aimed at examining the project prioritization methods that have worked for others.

Curious?  Then, let’s learn from the best and get you on track to apply these project management techniques in your own business. By the way, included in this discussion are new and emerging AI project management tools that use the same methodologies as the foundation of their architecture. It’s fascinating stuff and geared to make the application of these processes so much easier in your business. 

Project methodologies to help start-up founders prioritize tasks

Choosing the right project methodology is the first step toward prioritizing projects. These methodologies provide a framework for decision-making and allow start-ups to stay flexible while still moving forward.

1. Agile Methodology

Agile is a project management approach that helps you prioritize tasks effectively. It is designed to create a flexible and adaptable approach to the project prioritization process. It originated in software development and has since been used by various industries due to its ability to respond quickly to changing circumstances—so familiar to start-up environments. 

Agile focuses on breaking down projects into small sub-projects. These projects are called sprints, and can last between 1-4 weeks. This allows you to break down multiple projects to their smallest components that get immediate attention. This is great for keeping limited resources focused on where they are most needed. The project tasks don’t go on for months and months, and project managers work in quick and focused bursts. 

Agile emphasizes constant communication and quick pivots. The most urgent tasks focus on strategic alignment and moving a project forward quickly and responsively. Team members are kept on the same page by keeping tight control over all the tasks and can easily pivot towards another sprint when needed. 

How Agile Helps Start-Ups

For start-ups, Agile allows for continuous iteration and feedback, helping teams avoid investing too much in features or products that might not resonate with the market. It’s ideal for environments where requirements are frequently changing and prioritization needs to be fluid.

Real life case study: Agile Methodology

To better understand what this project prioritization method looks like practically, let’s look at the real life case study of the development of communication app, Slack. The name “Slack” stands for Searchable Log of All Conversation and Knowledge.

Slack originated from a video game project called Glitch, developed by Tiny Speck, a company founded by Stewart Butterfield (co-founder of Flickr) in 2009. The game never took off, but during its development, the team created an internal communication tool called Slack. Given the iterative approach of Slack’s development, it’s highly likely that Agile methodologies were in place. How do we know this?

1. Slack was released in small increments and improved quickly based on user feedback = iterative development.
2. The communication was initially built for internal collaboration, encouraging constant feedback and quick pivots = collaboration.
3. Slack’s pivot from a failed game to a communication platform reflects Agile principles of responding to change rather than following a fixed plan = flexibility and adaptation.

The end result of using a project prioritization system like Agile was that Slack fully launched to the public in approximately 15 months from the initial concept. In 2014, this was a pretty significant achievement for Butterfield and his team. In 2020, Salesforce bought Slack Technologies for U.S. $27.7 billion. [1]

Project management software that supports Agile

Timewise Calendar

Timewise Calendar is highly useful for organizing focused work periods for sprint cycles. Timewise can automatically schedule time blocks to ensure your team has uninterrupted time for completing critical sprint tasks, balancing meetings with work time efficiently. Urgent and important tasks can be scheduled according to your project deadlines, and the more you ‘teach’ the program what you like, the more intuitive it becomes, suggesting schedule changes, and proactively avoiding task conflicts. 

The platform is highly adaptable, allowing you to prioritize meetings and tasks in one place. It also provides you with personal productivity insights, transforming the way you work each time you use it. 

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2. Lean Start-Up Methodology

The lean start-up methodology is built around the idea of finding out whether you should invest time, resources, and funds into future projects. To do this, Eric Reis, who developed the lean start-up methodology after spending six months working on software that no one wanted, suggests that you develop an MVP (or Minimum Viable Products). It’s a simplified version of what you’re trying to get to market and is built with the objective of testing whether consumers like and want the product. 

The idea is that you then prioritize important tasks that allow you bring the product (or service) to market. Instead of relying on assumptions about what consumers want, lean focuses on testing these assumptions in the real world and then making quick changes to your product or service. 

How Lean Helps Start-Ups

By developing an MVP, founders don’t have to invest significant resources unless the project aligns with consumer needs. As a project management solution, it provides the guidelines for prioritizing all your projects while keeping a tight focus on validated information.

Real life case study: Lean Start-up Methodology

Dropbox began with Drew Houston’s frustration over forgetting his USB drive while studying at MIT in 2007. Houston envisioned a file storage solution that would allow people to easily sync and access their files from any device, anywhere. 

When Houston discovered Eric Reis’s Lean Startup Blog, the company used the method to iterate their product. They were able to prioritize projects based on what customers wanted, and in just 15 months they went from 100,000 registered users to 4,000,000!

Here’s how Dropbox used this project management tool to prioritize urgent and important tasks that would bring the product to market. 

1. Identify the core problem – Drew Houston was able to test his problem-solution fit by getting confirmation that people were keen to have a cloud-based storage platform. 
2. Develop an MVP – Initially resource allocation went into an explanation video that explained the concept of Dropbox, based on the feedback he then decided to allocate resources to its further development.
3. Feature validation – Houston kept getting feedback from customers and gave importance and urgency to features that received approval from customers. For example, one feature that gave Dropbox significant value was the ability to share folders. 

Project management software that supports Lean

Notion 

Notion is a flexible tool that allows Lean teams to organize ideas, document MVPs, and collaborate on projects. It can be used to track experiments, gather user feedback, and document key learnings.

Trello 

With Trello’s simplicity, teams can quickly build and track MVPs. Boards can represent different stages of development, with lists for feature ideas, in-progress tasks, and post-MVP learnings.

3. Critical Path Method (CRM)

CPM is a step-by-step project management technique that identifies the most crucial tasks (or critical paths) required to complete a project. It helps you visualize task dependencies and timelines, allowing you to prioritize complex tasks based on their impact on the project’s deadline.

CPM involves creating a flowchart that shows multiple tasks needed to complete a project, along with the time it takes to complete the highest priority tasks. The critical path is the longest sequence of tasks that must be completed to finish the project on time. Delays in any of these tasks will delay the entire project.

The remaining tasks that are not on the critical path can be delayed while resources are deployed to what matters. 

How Lean Helps Start-Ups

Start-ups with tight timelines and resource constraints can use CPM to focus on the most important projects that directly impact their goals. This avoids wasting time on less critical activities and ensures that efforts are concentrated on high-priority tasks.

Real life case study: Critical Path Methodology

Airbnb’s roots go back to 2007 when its co-founders, Brian Chesky and Joe Gebbia, struggled to afford rent in San Francisco. When a design conference came to town they decided to rent out air mattresses in their apartment to conference attendees and provide breakfast. The idea “Air Bed & Breakfast” (later shortened to Airbnb) led to the creation of a platform where people could rent out their personal spaces to travelers. 

Initially many challenges faced Airbnb and its success was not guaranteed, but then the platform seemed to take off, and what follows is an examination of the likely principles of the critical path method they used to figure out how to get Airbnb off the ground. 

1. Identification of several core projects – Four core projects emerged from mapping the critical path. Build a website, attract private home owners, create a seamless and secure payment gateway, and build trust and safety features to make people feel at ease in a stranger’s home. These tasks were interdependent and failure of one top priority task would mean business strategy failure. 
2. Map task dependencies – These are key project tasks that need to be completed before others. For example, the website had to be completed before homeowners could be approached, and a payment gateway integrated into it. 
3. Early launch for validation and to test project success – The launch at the 2008 DNC (Democratic National Convention) meant the strategic prioritization of the core project tasks. CPM would have helped them track progress and ensure that everything on the priority list got done. 
4. Iterative improvement and critical tasks – At the DNC the challenge of safety changed the priorities of the project as the team realized that safety features such as profiles, reviews, photos and emergency contacts would become critical tasks in the next step. 

Project management software that supports CPM

Timewise Calendar 

Although Timewise isn’t designed explicitly for CPM, it can help ensure that critical tasks receive the time and focus they require. By creating time blocks around key tasks in the critical path, you can ensure that these high-priority items get completed without interruptions.

Add Timewise to your CRM toolkit

Microsoft Project

Microsoft Project is a go-to tool for CPM. It allows users to create detailed timelines, map task dependencies, and calculate the critical path automatically. It’s ideal for large, complex projects with multiple dependencies.

4. MoSCow Method

The MoSCoW Method is a prioritization technique that categorizes tasks or features into four categories: Must Have, Should Have, Could Have, and Won’t Have. 

Let’s take a look at the key principles more closely. 

Must Have	These are non-negotiable tasks or features that are critical to the project’s success.
Should Have	Important tasks that will add significant value but aren’t absolutely essential.
Could Have	Nice-to-have items that will add value but can be postponed or eliminated if time or resources are limited.
Won’t Have	Items that are out of scope for the current project but might be revisited in the future.

By sorting tasks into these four categories, MoSCoW empowers teams to prioritize effectively with a visual representation of the work that requires immediate attention. 

How Lean Helps Start-Ups

MoSCoW allows start-ups flexible decision-making capabilities, collaboration, focus on essential tasks, and risk mitigation by addressing ‘must-have’ tasks early on in project execution. This method is particularly useful when you’re on a tight deadline and need to focus on delivering a product quickly while ensuring core functionality.

Real life case study: MoSCoW Methodology

Spotify was founded in 2006 by Daniel Ek and Martin Lorentzon in Sweden. Spotify’s goal was to deliver fast, legal, and user-friendly music streaming with minimal buffering and high-quality sound. But this was a significant challenge.

To bring the product to market, they would have dealt with the following challenges:

• Secure licensing deals with major music labels.
• Develop a robust streaming platform that could handle large-scale user demand.
• Create a seamless user experience that would convince people to switch from piracy to a legal service.

Given the complexity of these challenges, Ek and Lorentzon had to prioritize these features carefully to meet its initial launch goals. This is where the MoSCoW method likely came into play.

Must Have Features	Music Licensing, Streaming Technology, Basic User Interface, Freemium model with ads
Should Have Features	Offline Mode, Enhanced Playlist Management, Mobile Apps
Could Have Features	Social Sharing, Personalized Recommendations, Lyric Integration
Won’t Have Features	Video Content, Third-party Integrations (these features were not part of the initial app, but later on Spotify added these features)

By categorizing priority tasks like this, Spotify would have been able to allocate time, money, and other resources to the key features that would bring the product to market. This method saved precious time, and Spotify was able to operate in both Europe and the U.S within 5 years (2006-2011). Now this might seem like a lifetime in the world of software development but bare in mind that music licensing is filled with legalities that other industries do not have. 

The MoSCoW method would have kept the team on track with continual focus on getting the ‘must-have’ features finalized, and as a result Spotify became the world’s most used music streaming platform. 

Project management software that supports MoSCoW

Clickup

ClickUp allows you to customize task categories and prioritize work using the MoSCoW method. It supports lists, boards, and Gantt charts for visualizing task dependencies and priorities.

Timewise Calendar 

By using Timewise Calendar, you can allocate focused time to “Must-Have” tasks and ensure that less critical “Could-Have” tasks don’t interrupt the flow of essential work. The AI technology will intuitively adapt to your preferences, scheduling ideal times for important tasks and putting the “Could-Have” tasks on the back burner. 

Test the MoSCoW process using Timewise Calendar

Project Success: Everyday, All-the-time

In this article, we’ve discussed project prioritization processes that have worked for some of the world’s best known companies. Through focused application of these processes, they’ve been able to turn their one (or two) man shows into global success stories.

It’s all about applying the correct process to the product, service, or idea that you want to launch and then latching on appropriate productivity software that will help you drive the processes. Choose software that is AI powered, and will help you to take all the mental energy out of task prioritization. This will allow you to spend that energy focused on solving high-level problems. 

The turnaround time for bringing a viable product or service to market is becoming shorter and shorter as competition increases, mainly due to the use of sophisticated AI technology. So don’t be left behind. Give your start-up the best chance of success by being smart about your processes and tech-savvy. Isn’t that what start-ups are about, after all? Taking big risks and getting big rewards if the risks pay off?

Your product could be the next Airbnb, Spotify, Slack, or Dropbox. We hope it will be.    

References:
1. Salesforce buys Slack Technologies