Roadmap to Success: Communicate Your Project to Anyone! | Naomi Freeman | Skillshare

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Roadmap to Success: Communicate Your Project to Anyone!

teacher avatar Naomi Freeman, Founder. Entrepreneur.

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Taught by industry leaders & working professionals
Topics include illustration, design, photography, and more

Watch this class and thousands more

Get unlimited access to every class
Taught by industry leaders & working professionals
Topics include illustration, design, photography, and more

Lessons in This Class

10 Lessons (31m)
    • 1. Introduction

    • 2. What is a Roadmap?

    • 3. Tools

    • 4. Getting Started

    • 5. Creating Swimlanes

    • 6. Creating Milestones

    • 7. Adding Tasks

    • 8. Tagging Risks

    • 9. Adding Status Trackers

    • 10. Wrapping Up

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About This Class

Do you want to better communicate your business idea with your teammates, employees, advisors, partners, and even investors?

A project roadmap is a great addition to your toolbelt! The project roadmap is a graphical, high level overview of your company/project/product’s deliverables presented on a timeline. This isn’t a detail heavy project plan - think of it more as a snapshot that can be easily shared with a variety of people.

Whether you’re an entrepreneur starting your own company, a chief technology officer tasked with figuring out what needs to be built when, or you just want to sharpen your project communication and management skills, this class is for you.

You’ll learn how to develop a compelling, usable project roadmap for your company, project, or future business.

As a class project, you’ll use my template to create a project roadmap that gets employees, contractors, mentors and curious investors understanding your product, project or company like never before.

Through this video series we’ll work together to create an easy-to-understand product roadmap that includes:

  • project goals and objectives
  • a timeline
  • important milestones and deliverables
  • possible risks
  • dependencies (what work relies on other work getting done first)

No prior experience required!

Meet Your Teacher

Teacher Profile Image

Naomi Freeman

Founder. Entrepreneur.



I am Naomi, a founder and entrepreneur, living in the far corner of the world, in the mountains in Norway. I am an adventurer, lover of all things glitter, initiator, and a super book nerd. My full-time job is as an idea broker - I help people make their ideas become super real and super awesome.

I've been nominated as one of the Women of Influence for the RBC Canadian Women Entrepreneur Awards, and had an extraordinary opportunity as 1 of only 8 founders worldwide to attend the exclusive WSLab accelerator program in Silicon Valley, where I got all kinds of ship-shaping advice on everything from being a founder to how to figure out what an artificial intelligence's personality feels like.

I've worked in big tech and small non-profits. I love to create and ho... See full profile

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1. Introduction: Hi. My name's Naomi Freeman, and I'm a founder and entrepreneur. I know from my own experience it could be a long, difficult, lonely journey. You have a great idea. You've got the vision. You know what needs to be done and no one else could get on board. Why can't they get on board? Whether you're working on your own personal project, you found yourself a chief technology officer leading a team or your founders starting out and trying to launch a company. You have to find a way to communicate what's in your head. One of the things that I found is really helpful is to create a product roadmap. This is gonna be a high level visual overview of all of the things they're going on in your head that you can communicate other people quickly in one page. Gold of the road map is to convey strategic direction, and this is tied directly back to the company. Strategy. Roadmap has a few different goals. Vision and strategy. Provide a guiding document for executing the strategy, get internal stakeholders alignment, facilitate discussion of options and scenario planning and help communicate to external stakeholders. The great thing about product roadmap is that there are all different kinds. There's executive engineering sales. Each uses the same principles and concepts with slightly different focus and use. For executive, you're going to be securing buying for vision and looking at high level strategy, an engineering. It's probably gonna be more granular in scope and have shorter timelines. I've even seen the roadmap used for sales more of a focus on benefits, and all of the features are grouped into themes. On top of these internal maps, you can create an external mouth for customers and prospects. These should be very visual, attractive and easy to understand. And it's best not to include dates on these maps you never want to. Over commit externally in this course will work together to develop a product roadmap with timelines or extreme swim lanes, milestones, tasks and these tests will have status. Trackers will also take a quick look at risk tagging on your map. Practically speaking, it'll look a bit like this. You can learn more about product road maps by joining the roadmap class today. I really hope that you join me and I'm looking forward to seeing your roadmaps 2. What is a Roadmap?: welcome to making a road map to begin with. We're just going to get an idea of the project that will be working on together. We're going to look at the difference between product versus project Management Will define a road map, discover the three key pieces of your map that you'll be building through this course and take a quick look at the final project that will be building to begin with. Are we talking about product or project management? There are all kinds of skilled professionals in both project and product management, with contemporary philosophy and technology management product and project management manifestos. They're sometimes pretty close on. Sometimes they're very different, and people will be. People will be very upset if you get the mixed up, so be careful. Typically, a product manager prioritizes initiatives and make strategic decisions about what gets built. Project managers, on the other hand, often oversee the execution of plans that have already been developed and approved it out as if there's a divide between strategy and execution. Well, this may be helpful in very large organizations. I think the divide between strategy and execution is almost impossible when launching a startup and not very true. When you're developing things in more contemporary frameworks, we'll be dipping a bit into both Stewart strategy and execution with our road map. So just know this. We're building a road map and it's gonna be awesome. So what is a road map? It is a graphical high level overview of goals, milestones, work stream, swim lanes and risk. Typically, this is a tool taken from the product management side of things, but I've used the same tool to map the early stages of launching to start UPS created a resource mount for investors to understand, and I've also mapped key project and product journeys and milestones. Our road mouth will be abroad. Visual overview of the 1st 6 to 8 months of your product, project or company together work to map your goals and milestones into work stream swim lanes against a timeline. We'll also briefly discussed tagging risks in along your mouth paths. At first it seems like a lot of components for one page, and that's the beauty of the road map. We're going to capture a lot of information in tow. One meat visual living document you can share with your teammates staff and advisers. It's also easy to transform this document into the kind of one pager your investors want to see when looking at your company. The road map is going to be composed of a few different pieces, a timeline, some milestones and work streams. Swim leads. As I said before, we'll also be talking a little bit about risk tagging on your mouth. But we don't have to worry about that too much. Over the course of the next half hour, we're going to put each of these key map pieces together to get you a working road map that looks something like this. In the next video, we'll discuss the tools you can use for this project, so let's get started. 3. Tools: Now that we know what we're going to build, let's take a look at how we're going to build it. There are all kinds of tools to choose from when developing a road map. These are a few of the websites that I found can help you build a road map. We have Ah ha. Hello, Focus Road Monk. For something a little bit different, you could try casual PM. They think about it a little bit differently. All of these air great software tools and they all make your presentations prettier. One thing I will say is that learning a whole new piece of software can be a challenge in and of itself. And of course, all of these products will want to earn money from you. My personal experience is that you should wait to do the actual software online, and for now we should just focus on actually building the product roadmap. I would highly recommend that we begin with Excel. Trusty Old Excel will be fine for us to work in what we build out our projects. Alternatively, you can work with Google Sheets and it will be share a bowl. Plus it's completely free. You don't have to worry about downloading anything or subscriptions. Recently, I found it's a lot easier than using Excel. But if you're more comfortable using an application on your desk top, stick with Excel. For now, of course, feel free to play around with the online software in the last slide for demonstration purposes in the videos all be mostly broadly, illustrating the components you can add to your spreadsheet. And near the end, I'll be showing you what the spreadsheet looks like. We don't have our projects set up yet, and we'll do that in the next video. But for now, chat with us in the community tab. It's like a little discussion, and you can just say hi to everyone. I'd encourage you to share the tools that you've been trying out and let us know if you find any cool new tools online or wherever you find them. Honestly, the most frustrating part might be trying to get your head in your hands around the software and the tools, so help each other out, tell us what's going on and show us where you're doing the work 4. Getting Started: Now that you've chosen the tool that you're going to work with, we can begin building our project in this video. We're going to work together on creating a timeline. We're going to define what a timeline is. Decide how to choose your timeline and define it, and we'll be starting your Project Road map project on skill share. So what is a timeline? It is, quite literally, a line on which you could mark the beginning and the end of a period of time. Yes, it's really that simple. We'll be using the timeline as our basic building block for our Project Road map. So it's really important that we all make sure we do this first step. How will we decide how long your timeline will be set for? I would recommend we keep it just to six months to begin with. You can start your timeline today, or you can start your timeline from an important month when your first key higher will come on, or the month immediately before that, when a boot camp starts when you know you will receive your first money. As we work through the road, MMA, we're going to be thinking about key dates, key deadlines and external dates and deliveries. Almost anything that is happening in your project or company could be slotted into these three categories, and we'll talk more about these when we define our milestone. For now, keeping your timeline short keeps it accurate. Focused on relevant in my own work, I found that beyond six months you really start to fill in a lot of guesswork. So far, what we have created together is a timeline. Every journey begins with a few small steps. Right now, it's most important that we get our Skill share class project set up so that we can share a work along the way. We'll use this first work that you've created your timeline to create your class project. What I have here is visual representation of what your timeline could look like. You should have your timeline created in Excel, Google spreadsheets or the online software that you've chosen to create this project with. So now we're going to create your class project on skill share. If you'll see in the tabs below the video, you can click on your project and then you're going to create a project using this blue button, you'll come to a blank page. It looks something like this, and we can work together to put in all of the parts that you'll need to upload your project and share it with us. I've put in a title Naomi's Project, Road Mouth and a description. I'm working on a new startup and mapping out all of our first tasks. Here's what my project looks like so far from there You can upload a photo, and I'll just be uploading a screen cap of what my spreadsheet looks like. And once you have that photo in there, you can actually create a ling and then linked to your project. If you want to link to your project, you'll have to upload it in Google sheets or dropbox. Whatever file that you're working on, you can create an online link to it, and then when you click on the image, you'll be able to link straight to your whole project. Of course, right now your project is going to just look like the timeline photo. But as we move along, your project will have more things in it, and you'll be able to create a link right from your image toe all of the work that you've done that once I've done that, I'm just going to write a little note below that. If you click the image, it will link you to my Excel spreadsheet template. Just gonna click the blue create button right at the bottom there. And that's gonna create your project so we can all see it on skill share. So what we've done in this video is created our road map by creating a timeline, and we've created our project on skill share. So be sure to upload your project title A couple of words about your project. You can add a cover image as well as the photo and a link along the way you're going toe update this very same skill share project page with all of your progress and updates in the course. So it's really important that you take the time now put that together, and it will make it so much easier to share your work as we move on 5. Creating Swimlanes: In the previous video, we created the foundation of your roadmap, Your timelines. Everything will be measured against the timelines in this video. We're going to create your work swim lanes. This will be where your work is plotted along. It will be plotted against the timelines and along the swim lanes. In this video, we're going to be working together on defining what a swim lane is. Drafting your swim lanes, adding the swim lanes to your road MMA and sharing your progress with your skill share class. So what is a swim lean? We can think of swim lanes as areas of work. Each swim lane is going to be a group of related skills and resources in a company. You might think of this as a department, your finance department. Each of these would have their own swim lane. So why don't we just call our swim lanes departments? Because I really want you to think about the different kinds of work that are going on to begin with. We're going to try and draft some areas of work so we can think about things that need to be done like your website. It's selling things. What about the other things that go on in the office. These aren't really departments. If you check in the project area, you'll see that there's a template where you can either use the pdf to write on the computer. Or you can print out the blank pages and brainstorm some of the areas of work that you have . Once you thought about some of the areas that are involved in your work, you can further break them down. A website, for example, could be broken down into different kinds of tasks front end programming and back him Programming. Selling things is obviously marketing and other stuff that happens in the office is business of men. When you start to think in Brainstorm, you'll realize that what happens inside one department might actually be broken down into a few different skill sets and areas of work. So instead of using, departments were going to use swim lanes and really define the types of tasks and the types of work that need to be done in their own areas. Once you've created your swim, Layton's, we're going to bring it together with your timeline so we'll have your timeline and then underneath we're going to have all of your different swim lanes. I've color coded them so that you can see the different types of work on our spreadsheet. We're going to represent the swim lanes as rose. Each area of work or swim lane will get its own rope again. Now that you've saved that part of your project, be short. Upload your progress into your skill share project. This time, you can share your draft work area sheets, and you can share your update a roadmap that has your swim lanes added below your timeline . Sharing all these draft ideas will help everyone with things to think about for their own swim lanes. Your draft work might not have made it through to your final swim lanes, but someone else might get some great ideas on what kinds of work areas they actually have in their project or company. 6. Creating Milestones: now that we have defined our timelines and create it, swim lanes for work streams were going to be defining the key milestones and adding them to your project. Roma. Defining que milestones is the simplest adding markers for important dates on your timeline in each of your swim lengths. In this video, we will work together on defining what a milestone is. Learning the three key types of milestones. Defining your own project milestones and then adding these to your roadmap. Now that we have defined our timelines and create it swim lanes for work streams to get started, let's figure out what a milestone is. The first thing that comes to mind these days is a milestone is a significant notable achievement. You reach retirement age, you graduated. There's a feeling of milestones being huge in business. We tie them to a level of completion. The project was launched Well, some of these things are true about milestones. I'd also like to invite you to think a bit more about what a milestone really is when it comes to our projects. Recently, I've lived in Ireland and along the side of the road are these stones. I wasn't really sure what these stones were, but I looked into it, and it turns out that these stones are actually literal milestones. They mark the distance in miles to a particular place from that stone any place. So let's use this for a model for creating our own milestones in our project. Any place we need to mark the distance to from where we are now will create a milestone. Thes tiny markers along the way will best ensure we're on track. Think about the first people who laid a road. They had to lay straight road in the middle of nowhere on around earth. How did they accomplish it? Milestone markers on a smaller scale Think about when you have to cut a piece of paper straight that's a bit longer than a ruler. You can put three dots on the paper and be sure that when you're cutting your cutting straight, so long as you hit all of the markers along the way. So what kinds of milestones should be thinking about in our projects? So now that we're thinking about all of the little markers a long way, what should we be marking? There are three key areas we can look at key dates, key deadlines and external dates and deliveries. Thes might seem similar at first, but we're gonna look at how they're a little bit different and how we can put each of them into our project. Roma. Splitting these dates and milestones into different categories helps us think a little bit clearer about what needs to happen when key dates include launch parties, board meetings, product rollouts at any other key dates that mark significant pieces of your project. It can be helpful to include other one day events that are important for your team to keep in mind. They're not related specifically to building the project, but are important to keep track up. He deadlines are important to surface on large project plans, so your team can easily see what's coming up and planning quarterly. For example, the date that website development is completed or when customer conference registrations need to be returned to qualify for early bird pricing. Key deadlines are related directly to your project. Just keep in mind that they're not project tasks in and of themselves. We can use a key deadline as a milestone to reflect when a section of tasks or key task is completed. The third area we want to think about is external dates and deliveries. For example, a due date for a deliverable you're expecting from an agency or a date when you need to send out a piece of paper for your hiring manager for an offer letter, you could also think about things that need to be physically delivered to you, whether that's pipes or computers or anything else. Now that we have an idea of what milestones you should be tracking, let's get your milestones drafted. Everything that's in your agenda, all the events your teams would like to schedule times when you should receive completed work from agencies. You can just start sketching all of these into the template. Pause the video now and take some time to draft out a few ideas for your milestones. When is the pitch deck do? When's the follow up meeting for the logo draft set up for When do you need a computer delivered for a new higher to begin, and this should be before the new hire. Actually, drivers arrives, of course. Think about some project deadlines, but if you don't have them. Yet drafting in these other milestones will help you see what's already going on. So far, in this course, we've created a timeline and swim lanes for your areas of work. No, we're going to add the milestones for our purposes. Here. We're going to create small gray diamonds. For now, let's just at five milestones on the timeline from the draft work you just did on the template. Instead of writing the miles flown out in full, let's just put the number that corresponds to the number on your worksheet. Drop the milestone into the work stream it belongs to. If you have something like a team off site that belongs to all teams, you can drop it in everyone's late. It's really important to do this so that you can visually begin to get a sense of where the workload is. This could be important when you are asking for more money from investors to say the marketing team has 17 milestones coming up and we only have one person on the team. We need to add more resources there. It can also get you thinking if you can't expand your resources, can you change your timelines Or can you move some work from one work stream to another? For example, concealment in business of men pick up some user research interviews or someone in marketing. Help with some design for the front end are in that you may have to move some timelines on projects to later. It's also important that there is some space between your milestones. Remember that your teams need time to execute the tasks that make everything up. We'll be looking at that in the next video. Now that you've created some milestones, be sure to add the progress to your class project. You can share your draft template milestones cheat. Or you can show us the milestones you added to your timeline and the swim lane work streams . Sharing the drops ideas will help everyone with things to think about for their own milestones. 7. Adding Tasks: Now that we have milestones, how are we going to get there? We're gonna do that by adding tasks to make up the milestones. In this video, we will work together on brainstorming tasks, creating your tasks, adding those tasks to our road mouth and sharing our progress. So now that we know the key milestones, let's pencil in a few of the key tasks that will get us to those milestones. Milestones can be made up of a variety of tasks from a variety of swim lanes, and it is important to understand that this chain of tasks often looks like a relay race, with developed work being passed from one swim lane onto the next. We want to stay high level here. Not very much detail is required again. You can download the template in pdf from the Projects area to brainstorm your tasks. Or you can just use your own piece of scrap paper. Adding your tasks to your timeline is gonna look something like this. We have each of our work stream swim lame with our milestones, and now the milestones are gonna have tasks leading up to them In the spreadsheet format. We can represent each task as its own rope. Some of my tasks are on the same line because the same staff would have to perform the task or the same number of stuff. So I might need to back and people to complete milestone six and nine and then I would need the other three back end people to finish the third milestone. Arranging the tasks like this helps us organize where our resources are and see if we need to add resources or move tasks toe other areas if possible. So now our project is looking more like this. So far, we have created a timeline Swim lanes for your areas of work milestones, and we've added tasks into our swim leads. Be sure to show us your progress. Add your progress to your class project. This time you're updating your roadmap toe. Have your swim lanes have tasks in them. 8. Tagging Risks: building on our tasks. Now we're going to take a look at where there are potential risks. In this video, we will work together on defining what risk is learning the three key types of wrists. Defining our roadmap wrists, adding risk tags to your road MMA and sharing our progress. So what is risk? It's an event or changing conditions that signals a need to reevaluate. M. Revisit the plan. Some risks are unforeseeable and unpredictable. Many risks arm affable, though you can predict, for example, that if your money doesn't come in, you'll have to change the plan. So if you know you could receive money in June, but it's predicated on an application being approved. You can mark June's income milestone as a risk area. Attacking potential risks in advance can help you plan other potential journeys through your mouth that work around the risk area, minimizing the potential costs of the risk. Don't get too caught up in risk management for this document. There are three key areas of risk in our roadmap that could be tacked scope, resource and scheduling. We can briefly take a look at what each of these kinds of risks could encompass sculpt is an easy one to think about. Risks here include scope, creep challenges, integrating different parts of the project and changes in dependencies in resources, especially in startups. We can think about the risks involved in outsourcing to another team to accomplish core tasks on boarding your own new staff or having them leave. Along with these, we can consider if the right skills are already on the team to make the project work or of your skills and your new work are concentrated in different areas. In startup life, a lack of funding is always a big potential risk. They're usually ways to plan for it. Better to plan, then pretend it's not a possibility. In terms of scheduling. We can think of all the cascading effects if external vendors don't make deadlines or equipment doesn't show up when it should. Another thing that falls under this area is natural disasters and political turmoil. It may seem a bit strange. Consider this with the other types of risks. But if you live in an area where there are frequently hurricanes in May, best to mark that potential risk planning for that includes considering scheduling but also making sure you buy insurance. I really don't want you to think too long and hard about risks. I'm sure there are 100 things already on your brains dressing you out about why your project or company can sail. We just need to grab a couple of these thoughts and mark them down on your roadmap. Take a few minutes, brainstorm the risks, and then we'll add them to your mouth. So let's bring it all together. So far, we have created a timeline. Swim lanes for your areas of work milestones, tasks. And now we've added a couple of risk tags to our road map to where you have risks tagged. Take a look and see if you can add resources to mitigate the wrists. Or can you ensure another task somewhere isn't dependent on the risky task. Of course, it's not always possible to work around the risks, but good planning and thinking can better prepare you. If something goes a little funny and trust me, it will go a little funny. Sometimes on your progress to your class project, you can share your brainstormed risks and your risk tags added to your road map. Sharing brainstorms will help everyone with things to think about for their own tagging 9. Adding Status Trackers: like the great thing about the project that we're developing is that we're going to ensure that it's a living document. What does it mean to have a living document? It means that we're not just gonna put this away once we've done it and say Great, we did a good job. No, we're going to make sure that other people could continue toe update the document to reflect where the project really iss A living document grows and evolves as the project grows. Involves we can ensure that our roadmap stays fresh by adding status trackers. So how do we had status trackers? We're just going to fill in the task trackers that we already have with different colors for our purposes. Here, we're going to represent task statuses as three different colored bars green for on track yellow for needs, help to progress read for critical needs to be addressed to make the milestone. Since this is a living document at any time, these colors can be easily updated by anyone when managing a project. If you notice the team member has updated something to yellow or red, it's probably best to do a check in. You need all team members to be ableto update the colors as they feel necessary so that you have a good sense of what's going on on the ground. Combined with your timeline, your project now looks something like this. We have the timeline, the swim lanes, milestones, tasks and the tasks have been colored to their appropriate status. Be sure to show us your progress. Add your progress to your class project. You should share that you have updated tasks with some stabs colors in them. 10. Wrapping Up: Congratulations. You made it. You have created a roadmap. Now you can communicate your timelines, your milestones and the work. Swim lanes toe Anyone who wants to see your project. Be sure the upload your final project into your project section here on skill share. And make sure the draft mark is on it. You never want to be sharing documents that don't say draft. For now, this is where a project is going to stay in future. I'm planning on running another class that lets you transform this document into a milestone document, particularly for your investors. It's been great to work with you and good luck.