Evolving Your Strategic Planning

Dave Bour
11 min readJun 15, 2021
Photo by JESHOOTS.COM on Unsplash

Hello! I build IT teams and design IT Systems for startups and nonprofits. I consistently encounter the same problems, so I set out to create a series of guides to help others navigate the IT Ecosystem. You can learn more about my philosphies via my website dave-bour.com or via my weekly newsletter.

Why Incorporate Strategic Planning?

Regardless of scale, a well executed strategic plan can be beautiful. You may be assembling 10+ large scale IT initatives over the course of 2 years or deploying a massive single sign-on initiative within 3 months. When things come together and it “just works” or you’ve successfully anticipated a business need before anyone else, it feels good! Meanwhile, an individual will create massive value for an organization through seamless strategic deployments.

If you want to become valuable, learn how to strategize.

This isn’t just because it’s difficult — humans are notoriously bad at long term planning! So how do you go from fixing a printer to deploying a single sign-on intiative to building an IT ecosystem for a large organization?

Everyone’s career progression is going to look different and there is no right path. In IT, some choose to become technical experts within their domain (SMEs and ICs) by deeply evolving their technical skillset. These roles require technical strategic planning (for the SSO initiative above). In contrast to a manager or director who is concerned with the role technology is serving within the organization and how people interact with it, this role is primarily focused on the technology involved in the iniative.

Others may assume more responsibility throughout their career and develop complementary skills to become managers, directors, and VPs. Versatility and breadth is an important part of this journey, but it often begins with performing hands-on work. Over time, this will decrease as the manager hires others to perform the work.

It is worth noting that the transition into a managerial role necessitates new skill formation vs. skill evolution. The executive candidate must develop their soft skills, business acumen, and political alignment while the IC will become adept at deciphering the particulars of their desired technical domain.

After personally feeling my way through the dark on this journey, I wanted to share some concepts that have helped me.

Start From Your Personal Zero

Similar to different career paths, each organization has a different approach to technology. While I primarily work in NYC startups, your experience may be different. Start by answering some of the questions below.

  • What are the conditions for making good decisions at work?
  • Do we make better long term decisions from 10,000ft, ground level, or while alternating between the two throughout the day?
  • What characterizes a good long term decision from a bad one?
  • Am I developing breadth or depth in my role?
  • Can I find opportunities to learn new technology and take responsibility for it’s development?
  • What are the core requirements for technology at work and what are the nice to haves?

As we’ll learn, strategic thinking requires a broad understanding of how people interact with technology and how technical services influence other technical services. Corporate IT is an ecosystem and planning strategically will require an understanding of how the parts interact. It’s like putting a puzzle together — sure, you have all the pieces, but wouldn’t it be nice if they fit together nicely? Thinking in this way requires practice.

Recognize Your Tactical or Strategic Modes

Believe it or not, one of the first steps is understanding when a tactical or a strategic approach is necessary to solve a problem. If you wish to achieve positive outcomes, then blending the two together is inadvisable as strategic planning requires a degree of separation from the details.

You’re likely operating in a tactical capacity when performing actions to solve a problem. It is short term, specific work often characterized by:

  • being hands-on (replace the hard drive),
  • day to day tasks (create the accounts),
  • problem solving (the printer isn’t working).

Whereas operating from a strategic position involves charting the path of a company, product, or department. Strategy is always proactive and often categorized as big picture thinking and includes:

  • prioritizing projects (roadmapping)
  • planning and designing the work,
  • allocating resources for work.

Strategic plans are often informed by tactical experience. To plan strategically, it helps to understand the tactical lift associated with certain projects and work. It is through performing tactical work that you will develop an understanding of the associations and dependencies between business things (communications, technologies, goals and aims, priorities, costs, etc).

Strategic thinking is not always about long-term planning, it can be employed short-term, too, such as when a quarterback calls an audible or a SWAT team lands on site without much information ahead of time. In business, short term strategy can take the form of figuring how to resolve an outage, while long-term strategy is about developing a B2C component of the business within 5 years.

Strategic thinking is a mindset and a skill. Here are some tips I’ve used to develop it.

Create the Conditions for Successful Strategic Planning

From my observations, there are several conditions to employ for strategic planning. You have to intentionally make the space to plan.

Understand the role emotions play in your decision making processes.

Your attitude, personal impressions, and feelings will affect your strategic decisions. You may avoid working with certain departments with whom you’ve had difficulties in the past, or miss the mark on acheiving organizational goals when failing to understand how teams’ technical goals overlap.

Meditation and journaling are useful tools to reflect and unearth emotional obstacles.

Reduce interruptions.

Perhaps the most important, high level planning requires space to consider many variables and their complicated relationships. If you’ve ever heard that taking a walk is most condusive to problem solving, it can feel like coming out of a perception tunnel.

Blocking off time on your calendar and turning off notifications has been successful for me. Keeping the same time each week helps develop regularity.

Develop a high level understanding of the operating environment.

Analogous to understanding the rules of a board game before you play it, good strategic leadership requires a thorough understanding of the conditions and context of the playing field. This will have an added benefit of producing confidence in your solutions as you’ll be the authority on the topics.

Improve your political capital.

Even solid strategies fail without peer support or executive sponsorship. Identifying Stakeholders is one of the most important phases of planning a project for a reason. You simply cannot work in a silo while developing strategy.

Photo by Joshua Sukoff on Unsplash

For some, this will mean convincing your manager to support your plan. For others, it may require months of alignment between Directors, VPs, and other Executives.

Much like passing a bill in Congress, compromise and support is critical to the implementation of a successful strategy.

So let’s say you’ve blocked off time on your calendar and turned off notifications. You’ve spent the past few months understanding how the business operates and identified some pain points. You’ve developed positive relationships which provide feedback and contextual clues for organizational and departmental priorities and you’ve created space to reflect on your thoughts and emotions. It sounds like you’re ready to strategize!

Transitioning from Tactical to Strategic Thinking

To highlight the difficulty of this process, consider the difference between a commissioned and non-commissioned officer in the Army.

Out of all the military ranks, only the rank of Officer has two classifications — a non-commissioned officer (NCO) and and a commissioned officer (CO). The difference between them rests solely upon how the rank is acheived. An NCO generally enlists as a Private and works their way up to a Sergeant, then Staff Sergeant, and so forth. A CO enters the military with the rank of Officer by testing in through Offier Candidate School.

Why not test in at Staff Sergeant, Sergeant, or any of the lower ranks?

An NCO/CO relies on methodology, forethought, big-picture thinking, and other strategic traits to prioritize and resource missions, making them more of a strategic planner than a tactical worker.

It seems logical that strategic planning includes a practical understanding of the work required to execute the strategy and that a thorough understanding of this comes from having performed the work yourself. However, it seems to be the case that the two are separate and it’s more important to understand how to think strategically.

In other words, thinking strategically does not automatically come to those with the tactical background.

While the transition is difficult, I would argue that those who rise through the ranks have better chances of becoming great strategic planners. In the case of military rank, there is a bit of a disdain for those who test into the Officer rank. At a minimum, an NCO has the respect of those under her charge from the start.

In order to develop strategic skills, you’ll need to create space for yourself. It is all about creating time and space to think and plan. Here are some ways to do that.

(1) Create Operational Efficiencies

Many companies, especially startups, hire retroactively. When you join one, your days will be immediately filled with completing the backlog of tactical work. You won’t be able to see very far ahead because there are many high priority items that need to be resolved today.

As a result, you may have 0% of today to think about tomorrow and your week will look like this:

In this state, your goal is to work tactically while identifing immediate opportunities to create operational efficiencies across your workload.

Applying tactical methods to create efficiencies is creating opportunity for strategic thinking.

If you can create just enough room to spend 5% of your day planning for tomorrow, that 5% will compound. Within a week, you may have 8–10% of your day to plan for the future and then your week will begin to look like this.

A good place to find efficiency is through automating repeatable tasks, authoring a guide answering common questions, and creating processes.

(2) Treading Water vs. Swimming to Shore

The goal of working in IT is to enable business processes. We research and learn new systems to develop versatility and implement solutions to problems. But repeatedly performing the same task cuts into available time (a resource), so we need to find a way to automate or streamline those tasks.

Repeatedly performing the same task is a lot like treading water, it exhausts your resources and doesn’t really get you anywhere.

For example, if you’re constantly fielding a request to map a shared drive on the local network, you can write a basic script that automates the task.

As you automate more tasks, you’ll eventually find yourself working on higher level problems, which is the fun part of IT!

(3) Create Policies & How-Tos

Over the course of a year, you may have 100 people ask you for a new computer. You may have to explain how to get a new computer and what options are available and so forth. If we take 100 cases times an average of 5 minutes per case, we can say that you’ll spend 500 minutes or roughly 8 hours, an entire work day, explaining how to get a new computer over and over again.

Alternatively, you can spend 2 hours writing a policy and link it each time you are asked or make it available in your company’s intranet or self-service knowledge base.

A policy has the added benefit of Looking Official. People will argue with you about why they should get a new laptop and why it shouldn’t be the standard computer, but generally, people don’t argue with documents. It looks silly.

Authoring how-to articles and videos also creates self-service opportunities for staff to reference existing materials for answers. People largely prefer to be self-sufficient, you need to create the space to enable this.

(4) Create Processes

Processes create order by structuring and defining how to accomplish work. A lack of processes is like paving a new highway and putting no lane markers down. There’s solid ground to operate a vehicle on, but congestion will result from the lack of clarity.

HR, IT, and Finance from an Engineer’s perspective

In IT, a process can define how to achieve a goal and is similar to an SOP and policy, but can be seen as an overarching function that encompasses the two. Functions like replacing a computer, how to sign up for a new service, how to deploy a firewall change — it is writing down how to achieve the high level objective.

However, it’s all for naught if you do not make the process known and available to all. Distribute it widely and reference it often!

Congratulations! You’ve recognized the differences between tactical work and strategic planning, created the space to think strategically, and developed the skills to succeed.

While you’ve come a long ways, you’ll want to be aware of the following pitfalls and avoid falling for them.

When tactical work is consistently reactive, it is an indicator of a lack of strategic planning.

While some days will be a barage of reactionary work, they should be the exception rather than the rule. If you find yourself constantly reacting to the environment, changes within it, or emergencies and problem — then either you need to start planning strategically or your company needs to hire a strategic planner.

Reactionary work does not produce long-term value.

Don’t get stuck in the details.

In the vein of military analogies, you never want to stop on the battlefield. Always keep moving, go! go! go! If you stop, you get stuck. At a startup, you must keep moving. New major initiatives should be constantly undertaken. Always be thinking a few steps ahead and start your next plan before the current one finishes.

Watch for shifts in the political tide.

Company politics rarely stagnate. New team members join and priorities shift. As a strategic planner, you need to be aware of these changes to align your long term plans with those of your teammates and the organization at large. When your plan is out of alignment, you’ll know — you’re going to spend an inordinate amount of time trying to justify it to others.

Good plans, that is to say, plans with alignment, sell themselves.

Be adaptive but not fluid.

Remember, IT is an ecosystem and ecosystems are under constant threat of change. Your house should sway but not topple. Plans can change, but radical change is indicative of inadequate foresight.

You should mostly build with wood — not stone, not clay.

Own your decisions!

Most importantly, the buck stops with you. As a strategic planner, you are a leader. Your vision is what will be sold, piecemeal, to the organization. Rest assured that if you’ve done the work, it will be great.

This is not to say do not fail, failure is part of the game. Own your failures, own your successes, and defend your strategy with confidence.

Thanks for sticking with me to the end! I hope this information is useful to you. No matter how hard we try, nobody gets it right 100% of the time. In my next article, I’ll share some of my experiences that help maximize the value of mistakes.



Dave Bour

Building IT infrastructure and teams where there was none before. Fitness, wellness, and adventure enthusiast. Engagements at theitplan.com