5 Tips For Company Annual Roadmap Planning

The start of 2022 felt like the modern-day roaring twenties. Things were starting to open up from the pandemic, companies starting to promote going back into the office and a great resignation was happening. Every company seemed to be getting funded and growing at a rapid rate. Well now coming into the tail end of 2022, it's completely belly-flopped with budget cuts, layoffs, and talks of a cold recession coming at the start of 2023.

While roadmap planning may or may have not been a big priority for you before but this year we all have to think more tactfully. Every movement has to count and survival is the game every company is playing. Companies should be entering into the new year with a strong plan and ensure they have the right team in place to execute the plan. In this blog, we will discuss the 5 tips you need for company annual roadmap planning and how to set your business up for success. Whether you are a founder, executive assistant, or manager putting this together, these are the 5 tips to get you started.

Why You Should Do Company Annual Roadmap Planning

Let’s start with why it’s important to have an annual roadmap planning. As you get into 2023 planning, if you don’t have something outlined of where you want to be and what the main focuses are for the year, your team will continue to work on things that may not actually be important to the company. So it’s important to have a plan in place that everyone in the company is in agreement with and can rally around together. The best companies are mission-driven and what makes those companies mission-driven is having a clear path on what to work on together. This roadmap planning will help you get there. But keep in mind that a roadmap isn’t effective if people are not excited about working on these challenges together. Having a roadmap is only half the battle, ensuring you have the right people to push forward on that plan is key.

💡Protip: One way of getting companies excited about the road ahead is through swag. We suggest making a theme for the year's initiatives and making some swag for it!

Step 1: Start With The End Result

In startups and many businesses, it's very easy to get wrapped up in the day-to-day and forget about the long-term goals of a company. You can say we are so busy but in the end, if that busy doesn’t get you closer to where you wanted to be, are you actually busy working on the right things? This is why when planning your company roadmap it’s important to ask “What do we want to be?” Sounds like a very simple question but knowing what you want to be will make it easier to understand the steps needed to get there. For example, if you are planning to sell by the end of the year, your goal may be to have a lean team and get the company as profitable as possible to make it an attractive sell. Whereas if your goal is to work on more foundational work, you are going to have to have enough capital to keep the company running to fund that work. If you know the ending, you will know where to start.

So how to even being with knowing “What do we want to be?” It starts with the CEO or Founder. Where do they envision the company heading towards? It can be terms of 1 year or more long term like 3-5 years. If you are working alongside a CEO or Founder on this and they don’t seem to have a clear idea, put some ideas together to start the conversation. Set some time with them to determine what that goal should be. It may seem very obvious that a CEO or Founders should already know this but as mentioned before, it's very easy to get wrapped in day-to-day issues. Also, if you are working with a founder or are one, they may have not given themselves the mental space to really think about what they want both professionally and personally long term.

Step 2: Work Backwards

This may sound odd to think how am I going to work backward? Well if you know where you want to be after having step one completed, it's easier to know what it's going to take to get there. If you were an artist painting, they have a vision/ end goal in mind when they are painting what they want it to look like. An artist started with an outline and slowly begging to fill in the gaps section by section until the full picture is complete. Working backward works exactly like this.

At this stage, you will list all the steps that will be needed. It can be a mix of problems needed to be solved today, things that will be needed in the future, and maybe some silent killers where you know they are problematic but might know how bad it is since there's not much data to know. We suggest starting with listing it out. Within this list not only should you put what the problem is but maybe add the stakeholders and teams that it will impact. This will help you later on with knowing which stakeholders to invite.

Remember with roadmap planning in order for it to be effective you need to ensure everyone is on the same page and in agreement with the plan. Once you have this list put together you can meet with either your engineering team if this is tech-related or other major stakeholders to put how long each one of these items on the list will take to complete.

If available, place in there the cost and revenue for each task on the list. Why is this important to have? Well when meeting with all the stakeholders, it's important to weigh out how long and costly something will take. It also helps to know if you believe something is going to be impactful with revenue. This really helps with knowing the trade-offs and what you are willing to sacrifice long term and short-term. Again, everyone has to be in alignment with these trade-offs so having some metrics around some of these is helpful. If you are an early-stage company, you may not have all the metrics needed, you can always put estimates or calculate how long it takes to complete each project. For some projects, you may not be able to wait very long without the company losing revenue

⭐️ Did you know Amazon uses this method? At SwagUp we gift all new hires this book, Working Backwards: Insights, Stories, and Secrets from Inside Amazon.

Step 3: Establish Metrics

Similar to asking “What do you want to be?”, it's important to know “what numbers do we want to see?”. For some companies, their main driving metric is just one metric everyone in the company rallies around, while others have more than one. It’s important to narrow it down to no more than 3 metrics that can be used company-wide. It's also important to have a metric that everyone can help impact in some way. This helps companies be more mission-driven and also gives transparency to how the company is doing. If everyone knows what the number needs to be at to survive and be profitable there are no surprises when hard decisions are made. At SwagUp the metric we all look at as a company is the Number of Items Delivered. Every team within the company can drive this number up both from marketing/sales to operational roles. It's also a good indicator of clients being happy with their products since they are being used. Swag sitting in stock is not a good sign. Other companies like Southwest Airlines, use time in the sky as a metric everyone can work on together. You may have more than one metric in this, but keep it simple and make sure it's something you can actually measure.

Once you establish these goals, it's good to have scheduled reports to be shared throughout the company and even bulletins with the numbers for everyone to see. The more of a reminder you show with this metric the more people are motivated to work towards it. These metrics also hold everyone accountable for sticking to the roadmap and if it was successful planning.

Step 4: Connecting the Dots

Now by this point, you know where you want to be and all the things you need to get done. You can begin to connect the dots between where you want to be and the stages it will happen in. For example, you may have something on the list that you need to work on but you don’t have the team set up to run it just yet. So it may be something you do later on rather than today. In this stage, you start to prioritize the steps needed from today that will get you closer to that end goal and established metrics. You should be able to say by the end of the year 2023 we completed X and that got us closer to our end goal. Once you have each stage outlined, we suggest putting this into a Mirro board or Lucid chart since it will make it easier to share and view with other stakeholders. Also, these might change once you meet with other team members, so this will make it easier to make adjustments. You can put it into a gantt chart later on once the roadmap is agreed on with everyone. This part is just to get an idea going of what is needed and how you think the company should go about executing it. You will be using this as a guide to meet with other stakeholders to see if they are in agreement with this roadmap planning. We will warn you, it will change once you meet with other stakeholders or people within the company. It's a good sign if it does. Good discoveries should come from these meetings.

Step 5: Meet With Stakeholders

This is the fun part! You get to showcase to everyone the roadmap and let the healthy debates begin! We would suggest blocking off a few days to review these and in-person is best for these types of meetings. If you can’t get everyone together that is fine, but it is more effective when at least the main stakeholders and decision-makers are in the same room. We also suggest sending the material to everyone in advance so they can review it before the meeting. Have fun in this process and remember the roadmap you made is supposed to be a guide, not something set in stone. As long as everyone within the company is in agreement with the main priorities and roadmap to help move the company forward you will have a winning strategy!

The metrics established above will help guide the company to know if you are heading in the right direction. This is why metrics and data are important to define. If you realized you might be focusing on the wrong things, change them, but make sure you are following the steps to readjust any priorities.

By the end of your meeting with everyone, you should have walked out with a clear roadmap and plan ahead for the year!

🚀 Check out some behind scenes from our SwagUp Annual Summit Meeting!

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