Episode 28 — Direct and monitor IT strategic planning so alignment does not drift (Task 16)
In this episode, we’re going to make I T strategic planning feel like something leaders can actually direct and monitor, because beginners often picture planning as a document that gets written and then forgotten while the real work happens elsewhere. Strategic planning only creates value when it stays connected to day-to-day decisions, and that connection is fragile because enterprises face constant pressure, shifting requests, and urgent incidents that pull attention away from long-term direction. Governance of Enterprise IT (G E I T) treats planning as a living discipline, which means leaders do not just approve a plan once and hope it holds, but instead guide how the plan is executed and watch for early signs of drift. Drift is subtle because it can look like progress, with lots of activity and many projects moving, while alignment quietly breaks as priorities scatter and tradeoffs are made without re-centering on objectives. By the end, you should be able to explain what it means to direct planning, what it means to monitor it, and how those two actions keep technology direction on-mission over time.
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The first concept to lock in is that directing strategic planning is about shaping decisions before they happen, not criticizing outcomes after they have already gone wrong. Direction begins with clarity about enterprise objectives, because strategic planning is supposed to translate the enterprise’s direction into the capabilities and outcomes technology must support. When leaders direct planning well, they ensure that objectives are specific enough to guide tradeoffs, and they make sure constraints are acknowledged so the plan is realistic rather than aspirational. They also define what alignment means in practice, such as which outcomes will be prioritized and which risks cannot be silently accepted, so teams can make consistent choices without waiting for constant approval. Beginners sometimes assume leadership direction is a speech at the start of the year, but in governance, direction is a repeated act of setting boundaries and priorities whenever the plan is interpreted. Direction also includes deciding what will not be done, because a plan that says yes to everything is not a plan, it is a wish list. When direction is clear, planning becomes a tool for consistent choices instead of a document that gets ignored.
Monitoring is the second half of the equation, and it is what keeps direction from fading as the enterprise moves through real work and real pressure. Monitoring does not mean micromanaging delivery teams or constantly changing priorities; it means leaders maintain awareness of whether the portfolio of work is still aligned to objectives and whether the assumptions behind the plan still hold. In practical terms, monitoring asks whether the enterprise is still investing in the capabilities it said it needed, whether promised outcomes are becoming measurable results, and whether risks are staying within the enterprise’s chosen tolerance. Monitoring also involves looking for patterns that signal drift early, such as a rising number of exceptions, a growing backlog of unresolved high-risk issues, or repeated re-prioritization that makes teams chase moving targets. Beginners often think monitoring is a finance-only activity, but in governance it is a leadership responsibility because monitoring is how leadership ensures the plan remains the steering mechanism for decisions. Without monitoring, plans become ceremonial, and alignment breaks quietly until a crisis forces an expensive reset. Monitoring is the habit that keeps strategy connected to action.
To understand how alignment drifts, it helps to see drift as a predictable outcome of normal enterprise forces rather than as a failure of character. Drift happens when new requests arrive faster than priorities can be evaluated, so teams respond to urgency rather than to strategy. It happens when different departments push local needs that are legitimate but not coordinated, so the enterprise moves in multiple directions at once. Drift happens when incident response consumes leadership attention, so long-term planning discussions are postponed and short-term fixes become permanent. It also happens when success is measured by activity, like how many projects started, rather than by outcomes, like whether customer experience improved or operational cost declined. Beginners often imagine drift as someone ignoring strategy on purpose, but drift is more often a result of missing checkpoints where leaders re-validate priorities and decide what tradeoffs are acceptable. This is why governance emphasizes repeatable decision points and transparent criteria, because drift thrives in ambiguity and inconsistent decision-making. When you treat drift as an operational risk, you can design monitoring that detects it early instead of waiting for obvious failure.
Directing strategic planning in a governance sense also means establishing who has authority to interpret the plan and to make tradeoffs when constraints collide. Strategic plans often contain goals that can conflict in the real world, such as moving faster while increasing control rigor, or reducing cost while improving resilience. When the plan meets reality, someone must decide how the enterprise will balance these tensions, and that is a governance decision, not an operational detail. Clear authority prevents the common failure where teams negotiate tradeoffs informally, creating inconsistent outcomes and political friction. In a mature governance model, leadership defines which tradeoffs can be handled locally and which require escalation, so decision speed remains high without allowing high-impact choices to be made silently. Beginners sometimes assume tradeoffs are solved by consensus, but consensus can become slow and unpredictable unless governance defines who decides and what criteria apply. Direction therefore includes defining decision rights for planning adjustments, making sure the enterprise knows who can say yes, who can say no, and who must own the consequences. When authority is clear, alignment is easier to maintain because decisions follow the plan’s intent rather than personal influence.
Monitoring alignment requires more than checking whether projects are on schedule, because a perfectly executed project can still be misaligned with enterprise objectives. Leaders need a way to assess whether the portfolio of work remains mapped to strategic outcomes and whether that mapping is still honest as conditions change. This means monitoring should include signals about strategic relevance, such as whether funded initiatives still support the enterprise’s top priorities, and whether new urgent work is displacing planned work without a deliberate decision. Monitoring should also include signals about dependency and coherence, because alignment can drift when projects proliferate that duplicate capabilities or create incompatible data and integration choices. Beginners often focus on project-level status, but governance monitoring focuses on the system-level picture: what is the enterprise building, what value is expected, and what risks are accumulating. A practical monitoring approach also checks whether foundational work, like resilience improvements and compliance readiness, is being consistently funded, because these are often deferred under pressure even though they protect strategic outcomes like trust and continuity. When leaders monitor alignment at this level, they can intervene early by adjusting priorities, reinforcing standards, or reallocating resources before drift becomes entrenched.
A key governance tool for directing planning is establishing a clear link between strategic objectives and investment decisions, because money and capacity allocation is where planning becomes real. A plan that is not reflected in funding choices is not directing behavior, it is narrating intentions. When leadership directs planning, it ensures that proposals are evaluated against the plan’s objectives, that business cases reflect strategic outcomes, and that investments that do not align are questioned rather than approved by default. This approach also includes ensuring that benefit realization expectations are defined at approval time, so leaders can later monitor whether the investment produced the outcomes it was funded to achieve. Beginners sometimes think this is about controlling teams, but it is about keeping enterprise resources focused, because resources are limited and misaligned spending creates both waste and risk. Direction also includes limiting the number of simultaneous initiatives to what the enterprise can execute responsibly, because overcommitting is a common cause of drift and failure. When the enterprise funds too much, teams cut corners, take unmanaged risk, and lose the ability to deliver promised value. Directing planning through investment discipline is how governance turns strategy into action.
To monitor planning effectively, leaders need a small set of indicators that describe whether the plan is being executed as intended, without drowning the enterprise in reporting that no one uses. A helpful concept here is Key Performance Indicator (K P I), which is a measure chosen specifically because leadership can review it regularly and use it to guide decisions. A governance-oriented K P I should do more than show activity; it should reveal whether alignment, value delivery, risk discipline, and coherence are improving or drifting. For example, leaders might monitor whether benefits are being realized after delivery, whether high-impact risk acceptances are documented and owned, and whether the portfolio remains mapped to strategic objectives. They might also monitor leading signals, such as rising exception volumes or increasing cycle time for key approvals, which can indicate governance processes are becoming bottlenecks and encouraging bypass behavior. Beginners often assume more metrics create better monitoring, but too many metrics create noise and allow people to hide important signals inside a flood of numbers. The goal is to choose indicators that reveal drift early and prompt corrective action, making monitoring a decision tool rather than a reporting ritual.
Operating rhythm is what makes directing and monitoring sustainable, because leaders cannot rely on occasional attention spikes to keep alignment intact. A strong rhythm includes predictable points where priorities are reviewed, portfolio composition is rechecked against objectives, and major deviations are either approved deliberately or corrected. Rhythm also includes checkpoints where risks and compliance obligations are reviewed, because drift often shows up as quiet risk accumulation and deferred control work. When rhythm is consistent, teams experience governance as stable and usable, because they know when decisions will be made and what evidence will be expected. Beginners sometimes think rhythm means more meetings, but rhythm is about consistent decision-making and oversight, not about filling calendars. A good rhythm creates a feedback loop, where performance and risk information flows into governance forums, decisions are made, and follow-through is tracked so decisions become outcomes. Without rhythm, leaders are forced into crisis-driven governance, and crisis-driven governance is where alignment breaks because urgency overwhelms strategy. Rhythm is how governance stays ahead of drift instead of chasing it.
A major part of preventing drift is managing the flow of new demand, because new requests are one of the most common ways a plan gets quietly reshaped. Enterprises constantly receive new ideas, new requirements, and new urgent needs, and if there is no disciplined intake and prioritization approach, the plan becomes a suggestion rather than a steering mechanism. Directing planning includes establishing how new demand is evaluated against objectives and constraints, and how tradeoffs are made when new work displaces planned work. Monitoring planning includes watching for a growing pattern of unplanned work consuming capacity, because that pattern signals that the plan may be unrealistic, the environment may have shifted, or governance may be allowing local urgency to override enterprise priorities. Beginners often assume the solution is to say no to new work, but the real governance solution is to create a consistent way to say yes responsibly, by rechecking alignment and making tradeoffs explicit. This protects the enterprise from quiet scope creep, where the portfolio expands until teams are overloaded and control discipline collapses. When demand is managed through governance, the plan stays on-mission because changes to the plan are deliberate, visible, and owned.
Another source of drift is unclear accountability for planning outcomes, because when no one owns the outcomes, everyone can claim alignment while nobody is responsible for results. Directing strategic planning includes assigning clear owners for strategic objectives and for the major capabilities that support them, so there is someone accountable for progress and someone empowered to escalate when progress stalls. Monitoring includes holding those owners to measurable outcomes, not in a punitive way, but in a stewardship way that keeps attention on results rather than activity. This accountability also prevents the common failure where I T teams are blamed for business outcomes that required business process change and adoption, because governance assigns benefit owners and clarifies shared responsibilities. Beginners sometimes interpret accountability as blame, but in governance accountability is how the enterprise makes responsibilities visible so decisions can lead to action. When owners exist, monitoring becomes meaningful because there is a clear question to ask and a clear person who must respond with evidence and plans. Without owners, monitoring becomes vague status reporting and does not prevent drift. Clear ownership turns monitoring into a control that keeps the plan alive.
Strategic planning alignment is also threatened by fragmentation in technology and data choices, because a plan can drift even when objectives remain stable if the enterprise’s implementation choices become incoherent. Directing planning includes ensuring enterprise architecture and information architecture guardrails are applied so initiatives reinforce shared platforms and shared definitions rather than creating isolated solutions. Monitoring includes watching for duplication, unmanaged exceptions, and increasing complexity that slows future change, because those are signals that coherence is breaking. Beginners often think these are technical concerns, but they are governance concerns because fragmentation increases cost, increases risk, and makes future strategic moves harder. A plan might aim for faster delivery, but if the enterprise creates many incompatible systems, delivery slows over time because integration and support become heavy. A plan might aim for stronger trust, but if data handling is inconsistent, privacy and compliance risk grows. Governance directs and monitors these coherence factors because they determine whether the plan remains achievable. When coherence is maintained, the enterprise can execute strategy with less friction, and alignment stays strong because the system supports consistent decision-making.
Leadership must also monitor alignment through the lens of external change, because a plan that was aligned yesterday can become misaligned when laws change, market conditions shift, or the enterprise enters new regions or services. Directing planning includes defining how the enterprise will respond to external changes, such as how quickly policies and standards will be updated and how new compliance obligations will be integrated into decision criteria. Monitoring includes scanning for external changes that impose new constraints or create new risks, and then ensuring the plan is adjusted deliberately through governance rather than informally through scattered reactions. Beginners sometimes think planning failure means the plan was wrong, but often the plan was reasonable and the environment changed, and governance must adapt while preserving clarity. This is why planning and monitoring must be linked: monitoring detects when assumptions are no longer valid, and directing ensures the plan is updated in a controlled way. Without that link, the enterprise either clings to an outdated plan or abandons planning entirely, both of which lead to drift. Governance provides the disciplined path for adaptation, keeping alignment intact even as conditions change.
Another practical way governance prevents drift is by treating exceptions and escalations as signals about alignment health rather than as isolated administrative events. When teams frequently request exceptions to standards or to planning priorities, it can mean the plan is unrealistic, the shared services are insufficient, or the enterprise is facing constraints that were not accounted for. Directing planning includes defining how exceptions are evaluated and what authority is required, while monitoring includes tracking exception patterns to see where the plan is under strain. Escalations also provide valuable information, because they reveal where tradeoffs are hard and where decision rights may be unclear. Beginners often assume exceptions are simply bad behavior, but in governance, exceptions are information, and repeated exceptions often indicate a systemic misfit that must be addressed to prevent drift. Governance can respond by refining standards, improving shared services, adjusting priorities, or clarifying thresholds so decision-making remains workable. When leaders treat exceptions as learning signals, governance becomes more adaptive and alignment becomes more resilient. This approach also keeps governance from becoming punitive, which supports a culture where people raise risks early rather than hiding them.
To bring all of this together, think of directing and monitoring I T strategic planning as maintaining a stable steering mechanism while driving on a road that constantly changes. Directing is setting the steering angle and defining what lane the enterprise must stay in, using objectives, criteria, decision rights, and investment discipline to keep choices aligned. Monitoring is watching the road, the dashboard, and the vehicle’s behavior, using indicators, ownership accountability, and operating rhythm to detect drift early and correct it before it becomes a crash. This metaphor matters because it highlights the core governance idea that alignment is not a one-time achievement, it is a condition you continuously maintain. Beginners often expect alignment to be obvious, but alignment is often lost slowly through many small decisions made without re-centering on objectives. Governance prevents that by making re-centering routine, through regular portfolio reviews, consistent criteria, and clear escalation paths. When leaders do this well, the enterprise can move quickly without losing coherence, and can adapt without losing control. That is the practical value of directing and monitoring planning.
To close, directing and monitoring I T strategic planning so alignment does not drift means treating planning as a living governance discipline that shapes decisions before resources are committed and verifies alignment continuously as work progresses. Direction establishes clear objectives, decision rights, thresholds, and investment discipline so tradeoffs are made consistently and responsibly, while monitoring uses indicators, ownership accountability, and operating rhythm to detect weak signals and correct course early. This approach manages demand intake, prevents unplanned work from silently consuming capacity, and keeps architecture and information choices coherent so the enterprise remains able to change safely over time. It also integrates external change awareness, using governance to adapt plans deliberately rather than allowing scattered reactions to reshape direction informally. When exceptions and escalations are handled as controlled signals, governance learns and improves, making alignment more resilient under pressure. If you can explain planning as a steering system that is actively guided and continuously monitored, you are demonstrating a core G E I T capability: keeping enterprise technology direction on-mission even when the environment, the workload, and the urgency are constantly trying to pull it off course.