Planning for Uncertainty: 7 Key Principles for Creating an Excellent Roadmap

Roadmaps are important. My summer plans often involve traveling with my f

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Roadmaps are important.

My summer plans often involve traveling with my family. If you’re like me, your summer travel plans have shifted from planes to local road trips. The global pandemic has changed our entire world and our summer travel plans found us considering more local destinations. We broke out roadmaps and looked for adventure driving distances from home. 

Having a clear plan and roadmap is important for a few reasons; budgeting, packing, alignment (convincing my kids), figuring out schedules. We also need to evaluate if it’s worth doing.  Driving to another town for adventure seems fun. Driving across the country, given the cost, time, and whining kids does not.

A lot of the same principles apply to your business (hopefully not the whining kids). Too often we find ourselves in the backseat on a journey we didn’t plan on. We’re not sure where we’re going, how long it will take us to get there, and if we brought along enough money for snacks. Even if we’re heading to a place we want to go, on a timeline that works for us, if we don’t have a clear sense of where we’re heading and when we won’t enjoy the trip.  And then you can expect a healthy dose of complaining from the back seat.

Change is the current trend.

The past couple of years in business have required some emergency trips.  We all had to get in and go along for our own good. 

Hopefully, we’re emerging into a moment where we have more time and focus to decide our direction. As we emerge into this moment it’s important to think about how we’re providing clear roadmaps to our organization. How are you building alignment, communicating budgets, and ensuring everyone in your organization knows how to play their part? Are you sure everyone in your company knows the destination and why you're going there?

How do you lead a group through change?

Every time you get a large group of people together in a room a natural diffusion happens.  A certain number of conversations start, people move around, and someone coughs. Someone else needs to go to the bathroom or grab a drink of water. To bring focus and quiet a small but familiar action needs to take place. A conductor taps a baton, the curtains open, the speaker clears their throat. In these moments change is expected, even anticipated. With the right cues in business, you can signal change and align your team and even get them excited about a new initiative. With the right plan and the right signals, you can successfully lead a group through change.

Roadmaps are important - but how do you craft one?

If you’re this far along I’ll assume you’re nodding along at the importance of roadmaps. However, maybe this is your first time creating one, or perhaps your experiences in the past were not successful. If you don’t have a clear roadmap for a current or upcoming project or change here are 7 key principles for creating an excellent roadmap.

1. Define your "Why?"

You might consider this your strategy or purpose, but identify why you're setting off in this direction of change. Ideally, you'd have a vision and goals you'd like to accomplish as part of the initiative or project. A really well-formed 'Why' statement should include your customers, what will be a priority for them and the business. You may also want to identify a plan to bring your vision to the market.

2. Define features and requirements.

Once you have your vision you need to add in the details of what factors will help you realize that vision for your organization. Two companies may have the exact same vision but have very different criteria to accomplish their vision. Amazon and a local startup may both have the vision to deliver the best experience for their customers at the lowest cost. But the details of what that means for each company may be very different. Take the time to identify what features and requirements will allow your organization to realize your vision. Start with sticky notes, arrange a group discussion and explore this with your company. 

3. Make sure your roadmap is visually clear and compelling

Road maps don't include everything. You don't have all the detail of what shrubs are beside the road or what potholes may be in your path. There's a trade-off map designers make so you can quickly scan information and understand whether to turn right or left. Include details that will help in decision making, and leave out any detail that will add noise and confusion.

4. Explain how each milestone on the roadmap aligns back to your vision/Why statement.

If a feature or requirement has made it through your filtering process and ended up on your roadmap it should be there for a very good reason. Ensure you take the time to identify what that reason is and describe it. As your journey unfolds you may need to make hard decisions about what you keep and what you leave behind. Make sure you know the value of each item on your roadmap so you can make the best decisions possible when you come to a fork in the road.

5. Update your roadmap frequently as you learn more from your team and leadership.

There are many great quotes about how plans change the moment you start on your journey. You have to expect that as much as you plan, listen to your team and consult leadership things will still change. Ensure as you're hearing important changes you reflect those in your roadmap and document what is different. If possible record the original state or keep versions and keep the latest version tidy and clean with the current direction and decisions. Sometimes knowing where you've come from can help you find your destination.

6. With enough explanation, you don't need to be there to explain it.

You're not always in the room when a roadmap is presented. Wherever you can add annotations, legends, notes, and details to ensure that your audience will understand the document even if you're not there to walk them through your masterpiece. You'll have to balance this with the point of ensuring your roadmap is visually clear and compelling. Some detail is useful and helpful, but too much detail becomes overwhelming. As you review your roadmap, if you're answering the same question multiple times, you may want to find a way to annotate the answer.

7. Identify levels of effort.

You may need to make tradeoff decisions on your journey.  If you have categories and levels of effort clearly identified on your roadmap, it's easier to make these decisions.  If one item is highly important to the success of the initiative, and low effort while another item is low importance and high effort - then it's an easy decision if you have to reduce scope or pivot.

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