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Let’s begin with a seemingly basic question: Why spend time roadmapping when you have a long list of things to do?

From my point of view, the answer to that question is really embedded in the question itself. It’s precisely because you have such a long list of things to do that it’s really important to make the time to invest in roadmapping. Time is one of your most precious commodities, and there are opportunity costs to literally everything that you do. These costs are dangerous to ignore: if you’re at all like me, you have many more items on your to-do list than time available to accomplish those tasks, so choosing to work on one thing also is an implicit choice what not to work on.

When you’re faced with this situation, you have a few ways you could proceed.   Option one is to choose tasks randomly and not spend any time prioritizing or making deliberate choices about what you work on. Or you can go for coverage and try to do the best possible job on the most number of tasks. Again, no time wasted on planning.

Both of these approaches rely on the premise that everything on your list is valuable and important. That’s probably a valid premise, but it’s not likely that everything on your list is equally important. And that’s why it’s important to be strategic: if you can’t get to everything, you need to deliberately choose what you work on, when, and how much needs to get done before you move to the next thing.

I’d like to show you two ways that we often see this issue of “too many things on the to-do list and not enough time to get them done” play out as it relates to our customers.

Customer Use Cases

When we start working with a customer, one of the things we often ask if for them to identify their top organizational objectives. It’s not unusual for the answer to include 10, 12, or more different items. But 12 top priorities is kind of like having no priorities: when everything is special, nothing really is (words of wisdom, courtesy of Dash Incredible).

That said, I’m always excited to hear about 12 different items customers want to work on and improve, but at the end of the day, executing effectively on 12 top priorities simply isn’t, in most cases, realistic. As you are sorting through your top priorities, it is important to remember that your top priorities need to be practical and achievable, not only individually but also collectively.

The other way we see this issue show up is through the project boards that customers sometimes share with us. It’s not at all unusual for these boards to have 20 or sometimes even 30 different initiatives on them. In these cases, it’s likely that the customer is taking the second approach that we listed, where they are trying to get everything done but not completing any one task as well as they would have liked. Trying to do so many things at once typically fragments the team’s efforts and diminishes the overall impact on the business.

Both of these customer use cases demonstrate the importance of investing some of your precious time into strategic planning and roadmapping, as it is the most effective way we know of to maximize the impact of your efforts. But how do you set up this roadmap? What does it look like and what does it do? Let’s take a closer look.

Understanding Roadmaps and How They Relate to Your Priorities

A good roadmap accomplishes three things: it sets realistic priorities, it comprehensively acknowledges the issues facing your company or team, and it establishes an overall target or direction for your work. Effectively addressing all three of these areas is the key to developing an effective roadmap that won’t sit on the shelf, won’t get derailed, and will drive real action as well as align your technology with your business.

In order to do this, you and your team members will need to determine both what your top priorities are and what they are not. At the same time, you need to not ignore any of the things that are on your issues list, because that’s how problems fester. To some extent, these two goals are inherently in tension with each other, so let’s talk about how you can successfully balance both concerns.

The first step is to look at initiatives that might rank as top priorities, and I’d strongly encourage you to start by looking at things that are causing real pain: things that bleed money, cause a significant or undue operational burden, or hurt your customers or partners. You’ll likely be tempted to also consider growth-oriented initiatives, and while I whole-heartedly agree that growth is critically important, I think it’s really important to exercise some caution here.

One of the most common setbacks in strategic planning is that priorities get derailed during implementation. While that is sometimes a good thing – a sign of agility and innovation – it can also be a result of poor planning at the outset. Here’s why: Problems that are causing significant pain – wasting time or money or hurting your customers or partners – are candidates for becoming suddenly, unexpectedly critical as the pain level becomes untenable. So your team stops working on whatever it is you had previously set as a priority in order to go fight a fire. If you feel like you’re stuck in break-fix or your priority list has an escalating highest priority (“high” gives way to “urgent,” which gives way to “critical”), then your planning efforts likely aren’t adequately dealing with pain-causing issues..

This, however, is a common situation, and getting out of break-fix is often easier said than done. It’s also completely unrealistic to shelve growth-oriented initiatives to focus on fixing everything perfectly. Again, it’s a tricky balance to walk.

Using Band-Aids to Drive Strategy

One thing that really helps is to understand what you’re really trying to address. For instance, are you trying to address an underlying issue or just slap on a fresh coat of paint?

Here at Mission, we are really big fans of root cause analysis and fixing root causes to solve underlying issues. But the reality is, you don’t always have time to do root cause analysis, and sometimes that fresh coat of paint is just the ticket. Sometimes, all you need to do is lessen the pain as a way of buying time so you can work on other things. Fixing the root cause is great, but there may be other things that are better uses of your time right now. So a great approach is combining a short-term Band-Aid fix with a longer-term root cause fix. This two-phased approach is the one we often take with customers who come to us worrying that they are wasting money on their technology infrastructure.

We’ll often begin by cleaning up spend. We’ll look for places where customers have overprovisioned some resources or have some old devices running unnecessarily and so on. That will lower their costs right now (lessening the pain), but it does very little or nothing to address the root cause of their inefficient spend or their sub-optimal return on spend. We’ll plan to address those more fundamental issues later in the plan, prioritized appropriately in comparison to the other things that we want to do for our customers. The key is to address that critical issue (in this case, wasting money) at the “good enough” level, so we can turn down the urgency, buy some time, and address the bigger issues strategically.

The Well-Architected Framework

Another effective way to approach setting priorities is to spend some time benchmarking your infrastructure and technology operations against best practices. Benchmarking is useful for two reasons: First, it will provide valuable insight from an outside perspective into how well-architected your environment is and help you determine the severity of any issues.

Second, it will help you decompose larger tasks into smaller ones, which is really helpful as you try to balance competing top priorities. When you decompose tasks effectively, you don’t have to try to choose between working on security over cost optimization or performance efficiency over reliability.  Instead, effective benchmarking can help you identify more specific tasks within each of these areas so you can prioritize them more strategically and with more granularity.

Fortunately, AWS provides a useful tool to help with benchmarking. The AWS Well-Architected Framework is organized around five pillars (operational excellence, security, reliability, performance efficiency, and cost optimization) with specific standards and best practices in each pillar. There’s a Well-Architected Tool that allows you to self-assess your environment and operations, or if you prefer, an AWS partner like Mission can conduct a Well-Architected Review for you.

Setting a Strategic Direction

It’s worth noting that most of what we’ve been talking about so far is fixing things that are broken or causing pain. That’s definitely an important starting point, but good strategic planning looks at that as only part of the equation; the upside is also critically important to building a vibrant technology environment that supports a growing business.

There are two parts to this: (1) what do you want to do and (2) how does that get done. As you think about that first question, don’t let the second question get in the way. It’s important to stay focused on setting a direction rather than detailing the specifics of the journey. You don’t have to know how to leverage containers or even what containers are to know that you want to be able to iterate on your application more rapidly and with less risk.

Which is not to suggest that the how is irrelevant. To the contrary, it’s really important, and just as smart decomposition is critical to balancing competing priorities for things that need to be fixed, so too for these upside initiatives. Particularly given the dizzying array of tools and services that are available on AWS, it’s easy to see how organizations fall behind, accumulate tech debt, or get stopped in their tracks.

That’s one of the things we at Mission can help with. It’s our job to stay on top of the rapid change in AWS, and we can help you identify the tools and technologies that you could help you achieve your strategic vision.

Of course, we can help with the other aspects of developing and implementing a strategic roadmap as well: the quick identification and application of Band-Aids, expert root cause analysis, smart decomposition of initiatives into tasks that are more easily balanced. To learn more about scheduling a free one-hour consultation with a Mission Solutions Architect, click here.

About the author:
author
Chandler Collison

Vice President, Sales



Chandler Collison is the Vice President, Sales at Mission. After nearly 15 years as a teacher, he made the leap to corporate America, where he has made a career driving strategy and innovation for companies in industries as diverse as audio technology, handcrafted fashion, insurance, and (of course) cloud computing. At Mission, he leads a team of really smart people committed to helping businesses and other organizations transform their technology infrastructure in the AWS public cloud. He’s a cum laude graduate of the University of Pennsylvania.


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