Every organization is on a journey when it comes to strategic planning maturity. Some companies have well-oiled processes aligning every project and budget dollar to their big-picture goals. Others operate more ad hoc, with strategy and execution often out of sync. Wherever your organization sits on this spectrum, the key is recognizing where you are and continuously improving. A maturity self-assessment can serve as a candid snapshot of your current state and a starting point for growth. Use it as a benchmark, revisit it periodically, and take intentional steps to strengthen alignment between your enterprise strategy and day-to-day execution. In doing so, you set the stage for better outcomes from higher revenue and cost savings to mitigated risks through more cohesive planning.

Why Assess Your Strategy & Planning Maturity?

Adapt to the future of work: Studies show an overwhelming majority of executives believe the future demands new ways of working. Assessing your maturity helps you determine if your current planning practices are keeping up or if they need an overhaul to thrive in a changing business landscape.
Uncover alignment gaps: A self-assessment shines a light on disconnects between strategy and execution. You can identify weak spots for instance, projects that aren’t tied to strategic objectives or goals that exist in isolation. Recognizing these gaps is the first step to closing them.
Ensure all facets support the strategy: Enterprise Strategy and Planning involves multiple facets. By evaluating each one, you ensure that every critical aspect of your business is synchronized and pulling in the same direction. This holistic check-up can reveal if any piece is out of tune.
Drive better outcomes: Strengthening your strategic planning maturity isn’t just for show it directly impacts results. When strategy, plans, and execution are well-aligned, organizations tend to see higher ROI on projects, avoid wasteful spending on non-priorities, and reduce risks due to surprises or miscommunication. In short, better alignment translates to tangible benefits like revenue growth, cost savings, and improved resiliency.
Establish a baseline for improvement: Going through a formal maturity assessment gives you a baseline score of how you’re doing today. You can use this as a benchmark to measure future progress. Periodically reassessing lets you visualize improvements over time and celebrate wins as your scores rise. It turns strategic planning into a continuous improvement process rather than a one-and-done exercise.

Understanding Enterprise Strategy and Planning (ESP)

Before diving into the assessment, it’s important to understand what Enterprise Strategy and Planning (ESP) encompasses. ESP is the practice of setting your organization’s strategy and then operationalizing it through coordinated planning, execution, and evaluation. In other words, it’s about taking lofty strategic goals and making sure they materialize through concrete projects and actions across the company. This end-to-end process can be viewed as a cycle you define a strategy, plan initiatives to achieve it, execute the work, and regularly evaluate progress and outcomes, adjusting as needed.

Crucially, truly effective ESP covers six interconnected facets of the business. These six facets ensure that every angle of strategy execution is accounted for:

Goals: The measurable outcomes and objectives you aim to achieve. This facet focuses on how well you define clear, strategic goals (for example, using frameworks like OKRs Objectives and Key Results) and cascade them through the organization. Your strategy should be fully reflected in your goals, and every significant goal should tie back to a strategic priority or focus area.
Funds: The budgets, investments, and financial resources that fuel your strategy. This facet examines whether your strategic priorities are properly funded and whether you’re allocating money to the right initiatives. It’s about confidence that every dollar in your budget is aligned with strategic objectives and that you can track spending in relation to strategy.
Work: The tasks, projects, and initiatives that carry out the strategy. This facet looks at execution what work is being done, and is it the right work? It means having visibility into project status and progress toward strategic goals. Every project or piece of work should ultimately contribute to a strategic focus area, and you should be able to spot what’s on track or at risk in delivering the strategy.
Systems: The supporting technologies and tools that enable your strategy. This includes the software, platforms, and infrastructure needed for execution. The Systems facet checks if your strategy is represented in your technology roadmap are you building or configuring systems that support your goals? It also asks if current and future systems are aligned with where the business is headed.
Talent: The people and skills required to implement the strategy. This facet is about your workforce and how well aligned your talent is with strategic priorities. It considers whether the right people are working on the most important projects. High maturity here means you can dynamically allocate talent to strategy, identify gaps, and adjust in real-time. Everyone’s work, in an ideal scenario, connects to a higher strategic objective, so all your talent is contributing meaningfully to the big picture.
Updates: The progress reports, status updates, and performance tracking that inform stakeholders about how the strategy is advancing. This facet looks at how you monitor and communicate progress. Are you getting accurate, credible updates that tell the story behind the numbers? Mature organizations go beyond simple red/yellow/green project statuses their update cadence provides insight into what those statuses mean for the overall strategy and prompts action when needed. Every update or metric tracked should relate back to strategic goals, providing a full view of progress across all other facets.

These six facets are deeply interconnected. Think of them as pieces of a puzzle: if one piece is missing or misaligned, the picture isn’t complete. For example, you might have well-defined goals and plenty of budget, but if your talent allocation is off say, your best people are tied up in low-priority work the strategy can still fail. Or you might track lots of project updates, but if those updates aren’t linked to specific goals or don’t prompt decision-making, they add little value. A truly mature enterprise planning approach means Goals, Funds, Work, Systems, Talent, and Updates all work in concert, each supporting and reinforcing the other. With that understanding, you can better evaluate how your organization stacks up in each area.

How to Self-Assess Your Maturity

Now that we’ve defined the scope, let’s outline a straightforward way to self-assess your Enterprise Strategy and Planning maturity. The goal is to produce both a detailed look at each facet and an overall maturity score. Here’s a simple three-step process to follow:

Answer a set of guiding questions for each facet: For every one of the six facets (Goals, Funds, Work, Systems, Talent, Updates), reflect on a few key questions that probe how well your organization is performing in that area. Coming up, we’ll highlight three important questions per facet. Be honest and objective in evaluating your practices this works best if you’re candid about where things stand. If possible, gather input from a few stakeholders or team members for a well-rounded view.
Score each facet and calculate the facet average: As you consider the questions for a facet, assign a numerical score to your performance on each question. You can use a scale of 0 to 100, where 0 means “not at all/no capability” and 100 means “excellent/fully optimized”. Don’t worry about extreme precision a rough estimate based on evidence and instinct is fine. Once you have scores for the questions in one facet, average them. This average is your facet score. For instance, if you rated your organization 60, 70, and 50 on the three questions for the Goals facet, the Goals facet score would be the average of those. This gives you a quantitative indicator per facet.
Calculate your overall ESP maturity score: After scoring all six facets, take the average of all the facet scores. This overall average is your Enterprise Strategy & Planning maturity score. It provides a high-level number that encapsulates how aligned and mature your strategic planning process is across the board. For example, if your facet scores were spread around, say, the 50s or 60s, your overall might be similar indicating moderate maturity. If you scored high in most areas, your overall will reflect that strength. Conversely, if several facets are lagging, the overall score will highlight the need for improvement. Keep in mind that this overall score is a snapshot, not a verdict it’s there to help you track improvement over time. The real value lies in the insights per facet and the actions you take as a result.

With the methodology in hand, let’s walk through each facet of ESP and consider the guiding questions. Remember, the purpose is not to obtain a “good” score for its own sake, but to highlight areas where you can strengthen the connection between strategy and execution.

Illustration of two people discussing finances in front of a credit card and performance gauge.

Goals: Setting Clear Objectives

When evaluating the Goals facet, you’re essentially asking how well your organization sets and aligns its objectives. This is the foundation of strategy execution without clear goals, even the best teams can drift off-course. Consider the following when self-assessing Goals:

Clarity and strategic alignment of goals: Are your organization’s high-level objectives clearly defined, measurable, and aligned with your overall strategy? For example, if you use Objectives and Key Results (OKRs), do those OKRs accurately reflect what your strategy is aiming to achieve? A mature practice means every strategic goal is specific and paired with success metrics, and together your collection of goals fully represents your strategy. If some major strategic aims aren’t captured in your goals, or if some goals seem tangential to the strategy, that’s a sign of misalignment.
Cascade and contribution: Do goals cascade effectively through the organization, and does each team or department understand how their goals contribute to broader strategic priorities? In a mature setup, top-level strategic priorities break down into departmental and team goals in a coherent way. Ask yourself what percentage of all the goals across the company eventually link up to a chief strategic priority or “focus area.” Ideally, every significant goal should ladder up to at least one strategic focus area. If you find pockets of goals that don’t connect to any higher strategy, those might be low-value or misdirected efforts.
Integration with other facets: Are your goals connected in a meaningful way to the other facets namely funds, work, talent, systems, and updates? In practice, this means for each major goal, you know what projects will drive it, who is responsible, how it’s being funded, which systems or technology are involved, and how you’ll track progress. A high maturity organization creates this web of relationships so that a goal isn’t just an abstract statement; it’s linked to budgets, people, and plans. If you can’t map your goals to those other elements, the goal-setting process may be happening in a silo, reducing its impact.

Work: Tracking Strategic Progress

The Work facet examines how you execute projects and initiatives and whether you have a line of sight into progress against the strategy. It’s one thing to set goals; it’s another to deliver on them through well-managed work on the ground. When reflecting on this facet, think about how you monitor and guide the collective effort of your teams:

In a mature organization, leaders and stakeholders maintain an accurate and actionable view of all work being done in the context of strategic objectives. This means you can answer questions like: How is our strategic plan advancing through ongoing projects? and Are we on track to hit our targets? You should be able to see the status of key initiatives at the right level of detail not so granular that you get lost in the weeds of daily tasks, but not so high-level that potential problems stay hidden until it’s too late. For instance, you likely want to know which major programs or projects are on schedule and which are falling behind or facing obstacles.

If your work tracking is highly mature, you will have a clear picture of strategic progress beyond just task completion. You might use dashboards or portfolio management tools that roll up individual project statuses into an overall view of each strategic theme or focus area. This allows you to spot hotspots that put delivery at risk. Perhaps one strategic program is lagging because of resource constraints or a dependency on another project a mature process will surface that issue through timely updates so you can intervene.

Moreover, consider what percentage of all the work being done across teams directly contributes to a strategic priority. If a large chunk of projects or tasks cannot be traced to at least one strategic goal, that’s a red flag. It could mean teams are spending effort on initiatives that aren’t truly moving the company forward in the intended direction. High maturity organizations ensure virtually all work is justified by and aligned with the strategy either directly or through a clear chain of alignment.

Finally, integration plays a role here as well: each project or piece of work should be connected to relevant goals , tied to the talent working on it, funded appropriately, and supported by the necessary systems. If you have an important project but haven’t allocated budget (Funds) or assigned the right people (Talent), or you’re not tracking it in your reporting, then the execution is not fully synced with the plan. In summary, Work maturity is about having both control and context you manage projects efficiently and always within the context of strategic objectives.

Illustration of two people organizing tasks on a digital Kanban board.

Talent: Aligning People with Priorities

Even the best plan will falter without the right people to execute it. The Talent facet evaluates how well your workforce is aligned to the strategy and whether you have the insights needed to deploy talent effectively. Ask yourself these questions as you assess the Talent facet:

Visibility into talent allocation: Can you easily see whether the right people are working on your most important strategic initiatives? High maturity means you have transparency into who is doing what and you’re confident critical projects are staffed with the appropriate expertise and leadership. For example, if a strategic priority is to develop a new product line, are your top product managers and engineers assigned to that effort? If key talent is spread thin or allocated to lower-value projects, strategy execution will suffer.
Data-driven people decisions: Do you receive useful insights about your workforce that inform strategic trade-offs and planning? This goes beyond simple headcount numbers. It means you can assess your talent pool by different dimensions such as skill sets, experience level, location, or department and determine if those align with your strategic needs. A mature organization might track capabilities and capacity in real-time: for instance, knowing you have 5 data scientists available when a new analytics initiative launches, or quickly identifying a gap in cybersecurity expertise when planning an IT strategy. If you can “zoom in” on how talent supports strategy, you’re likely at a higher maturity level. If these insights are missing, decisions about staffing strategic projects might be more guesswork than informed strategy.
Everyone connected to the strategy: Ultimately, what percentage of your people can draw a line from their day-to-day work to the company’s strategic objectives? In a mature scenario, virtually all employees from leadership down to individual contributors understand how their work contributes to a focus area or goal. This doesn’t mean every single person works on high-level strategic projects all the time, but there should be a clear linkage. For self-assessment, consider how many of your staff are mapped to strategic priorities. If large groups of employees cannot see how their work matters to strategy, you have an alignment problem. Additionally, check if the Talent facet links well with the other facets: for example, do you adjust budgets when you need to hire or train people to meet a strategic need? Do project updates include information on whether talent constraints are affecting progress? A highly mature organization ensures that people, projects, and strategy move together in lockstep.

Funds: Funding the Strategy

A strategy without proper funding is just wishful thinking. The Funds facet centers on the financial side of strategy essentially, how well your budgeting and investment processes support your strategic goals. When assessing this facet, think about confidence and clarity in your financial alignment:

In a mature enterprise, there is a strong confidence that the strategy is fully funded and that resources are allocated to the right places. Start by asking: Do our investment decisions clearly reflect our strategic priorities? If your company has stated, say, that digital transformation is a top priority but only 5% of the budget is going into IT and automation initiatives, that’s a disconnect. A high maturity approach would involve regularly mapping out how each strategic focus area is financed and ensuring that the allocation makes sense relative to its importance. This might involve portfolio funding models or strategic budgeting exercises where leaders review spend vs. strategy side by side.

Another key question is whether each strategic priority is tied to an accurate account of funding. That means for every major goal or focus area, you can point to the dollars earmarked for achieving it. For example, if one of your strategic goals is expanding into a new market, you should know the total budget allocated to initiatives that support that expansion. If some strategic priorities have no clear budget associated, they risk remaining merely aspirational.

Also, consider the connectivity of Funds to other facets. Are your budget items and investments linked to goals, work, talent, systems, and updates in a meaningful way? In practice, this could mean you use financial tracking tools that tag expenditures to specific projects or goals, or that when project updates are given, they reference budget spent vs. budget allocated. If a project is going over budget, do you see how that affects the viability of the goal it supports? And are funding adjustments made when priorities shift? A mature organization will have financial governance that’s dynamic and integrated: money can be reallocated when strategy changes, and every major spend is justified by a strategic intent. On the other hand, if budgets are built historically without regard to current strategy, or if teams fight for funding in silos without a big-picture view, the Funds facet is likely underdeveloped. Aligning finances with strategy ensures that your brilliant plans have the fuel needed to run.

Systems: Enabling Strategy with Technology

Modern strategies often live or die by the tools and technology behind them. The Systems facet looks at whether your organization’s systems and IT roadmap are in sync with the strategic plan. In assessing Systems, examine both your current tech support and future plans:

Strategy representation in systems: How confident are you that your strategy is fully represented in your existing systems and upcoming technology roadmap? In other words, if the company’s strategy calls for certain capabilities, do you either already have the systems in place to support that or have concrete plans to implement them? A mature stance means there’s virtually no strategic initiative that lacks corresponding technology enablement. For instance, if one strategic priority is to improve customer experience, and that relies on a new CRM system or an AI support tool, those system projects should be identified and underway. If you find that strategic goals exist on paper but there’s no plan to update or acquire the systems needed to reach them, that’s a gap in alignment.
Mapping systems to strategic priorities: Take stock of each strategic focus area that requires tech work and ask if it’s clearly linked to specific systems. What percentage of your strategic priorities can you map to supporting technologies? Ideally, for any given priority, you could say “Here are the key systems or platforms that will help achieve this, and here’s our roadmap for them.” For example, a priority to enhance data-driven decision making might map to implementing a business intelligence platform by Q3. If you have priorities with fuzzy or non-existent links to systems, those could be vulnerable areas where execution might falter.
Integration with other facets: Systems should not exist in isolation they underpin almost every other facet. Check if your critical systems are connected to the other five facets in planning and tracking. For instance, when considering a new system facet, do you evaluate how it supports the strategic goals facet? Does its cost appear in budgets ? Do you plan training or hiring around Talent? And once implemented, are its impacts reflected in progress updates? In a high-maturity organization, technology planning is deeply woven into strategic planning, not just an IT department concern. If there’s misalignment say, IT is building something not on the strategic roadmap, or strategy teams set goals without consulting IT feasibility it indicates room to improve Systems maturity. By ensuring your tools and platforms are strategy-driven, you eliminate a major source of friction and unlock greater efficiency in execution.

Updates: Monitoring and Adapting

The Updates facet is all about how you track progress and communicate it during the strategy’s lifecycle. Even a great plan with the right people, funding, and tools can go off-course if there isn’t proper visibility and feedback. When self-assessing this facet, think about the quality and utility of the updates you receive (and give):

At a high maturity level, your organization gets accurate, credible, and meaningful updates on all strategic initiatives. This isn’t about creating bureaucracy or endless status meetings it’s about having timely information that reflects reality and supports decision-making. Ask yourself: Do our progress updates tell the true story of what’s happening? For example, if a project is marked “on track” in a report, do you also know why it’s on track or the context? If something is “at risk,” do the updates explain the underlying issues and their implications for the broader strategy? Mature updates provide narrative and interpretation, not just traffic-light indicators. They give leaders insight into whether the strategy is working and where adjustments might be needed.

Consider what percentage of all your routine updates are explicitly linked to strategic priorities. In a strong alignment culture, progress reports are structured around strategic goals or themes. For instance, instead of a departmental report listing activities, you might see a strategic dashboard where each focus area has a status summary. This ensures that updates aren’t just noise but directly inform how the strategy is faring. If you find updates floating around that don’t ladder up to any strategic objective, or teams reporting metrics that aren’t tied to strategy, there’s likely a lack of focus. Every update should answer, “How does this impact our strategic direction?”

Integration is also key here: effective updates draw from all other facets. A project update might mention that a goal is X% achieved, Y amount of budget has been used, certain blockers require more people or skills, a system rollout is delayed, and what work tasks are completed or pending. When your update mechanisms tie all these threads together, you give a holistic view to stakeholders. This helps in making informed decisions perhaps reallocating funds, changing timelines, or shifting priorities on the fly. If your current status reports or strategy reviews don’t connect those dots, then important context can be lost. Improving the Updates facet might involve developing integrated dashboards or cross-functional review meetings where all aspects are discussed in concert.

Finally, the Updates facet feeds into continuous improvement. By monitoring progress and outcomes, you learn what’s working and what isn’t, allowing you to adapt your strategy or execution approach. An organization with mature update practices won’t be caught off guard by a failing project or a changing market condition the signals will surface through its reporting rhythms, prompting proactive tweaks to the plan. In that sense, good updates are the heartbeat of the strategy: they keep the organization informed and agile.

Illustration of a team analyzing charts and graphs on a large digital screen.

Wrapping Up

Self-assessing your Enterprise Strategy and Planning maturity means taking a hard but constructive look at how well your company links vision to action. By examining the six facets Goals, Work, Talent, Funds, Systems, and Updates you gain insight into specific strengths and weaknesses. Maybe you’ll find your goal-setting process is solid, but you lack the systems to support execution. Or perhaps day-to-day work is well managed, but not everyone understands the bigger strategy. Whatever the results, remember that a low score in some area isn’t a failure it’s an opportunity. The real power of this assessment is in guiding improvements. After scoring yourself, focus on the facets that scored the lowest or matter the most to your business outcomes, and create an action plan to elevate them.

Continuous improvement is the name of the game. Consider revisiting this assessment regularly to track how your facet scores evolve. Over time, you want to see those numbers rise and converge, indicating a more balanced and integrated strategy execution machine. Some organizations even visualize their maturity changes over time you might plot facet scores on a radar chart year over year to spot growth. This kind of tracking can be motivating and illuminating, showing the impact of the changes you implement.

Finally, as you work on strengthening your enterprise planning maturity, don’t hesitate to leverage outside help. Aligning strategy with execution across an entire enterprise is challenging, and it’s okay to seek guidance or tools that facilitate the process. Whether it’s adopting new work management software, training your leadership team on OKR best practices, or bringing in experts to help configure dashboards, support is available to accelerate your journey.

Interested in learning more? Contact Atlas Bench to book a complimentary consultation with our Certified Atlassian Experts.

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Atlas Bench is an Atlassian Platinum Solution Partner with deep Cloud Specialization, helping Data Center customers move beyond migration and fully transform on the Atlassian Cloud Platform. We deliver Atlassian’s System of Work end to end through four collections: Strategy, Teamwork, Service, and Software, connecting planning to execution, aligning teams around outcomes, modernizing service delivery, and accelerating software development.

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Self-Assessing Your Enterprise Strategy and Planning Maturity