For companies that set their technology strategy on an annual, calendar-based schedule, the waning days of January and February mark a transition from developing your strategy to its implementation. This can be an exciting time, but also one that can test our resilience and abilities as leaders. Initiatives that seemed like “no brainers” when shared with colleagues might suddenly meet significant resistance from unexpected parts of the organization, just as seemingly-simple initiatives can bump against unforeseen challenges when it comes time to implement.
A well-crafted strategy is essential to the success of a tech organization, but it’s of little value without effective implementation. Just as a high-resolution map and the latest GPS technology are considerable assets in navigation, they’re of little use if you don’t know how to use the data they provide or how to travel over the right path to reach your destination.
As you begin executing your tech agenda, consider these tools to help turn your strategy into reality.
Identify Milestones and Measurements
Tech is generally a discipline that prides itself on having a firm grasp of data gathering and gleaning insights from data. Despite that, we sometimes fail to use the myriad data available to track the progress of our overall strategic agenda effectively. This isn’t typically due to a lack of tools or known data but a failure to set success criteria and define the milestones to achieve those criteria.
Ideally, this exercise should be completed as you develop your year’s strategic agenda. For example, a popular CIO publication provides a list of 8 Top Priorities for CIOs in 2023, with “building resiliency” at the top of the chart. This is a laudable goal, but how do you know that your tech organization is more resilient? What measures indicate your current level of resiliency, and what activities will you undertake to improve those measures? How will you know which measures are most effective?
Items like “building resiliency” are akin to vaguely-defined personal objectives like “improving fitness.” On their face, they’re laudable and appropriate goals, but they lack specifics on how you’ll measure progress and what activities you’ll undertake to achieve steady progress. Without thoughtful metrics and milestones, organizations with vague strategic goals will perform much like individuals who want to “improve their fitness”—perhaps making a few minor or dramatic changes for a short period, then returning to past behaviors.
Contrast that with an individual who translates the broad goal of “improving fitness” with a concrete measurement—their time to run a specific distance. They can quickly and repeatedly test their performance against that benchmark and create a plan with defined workouts to help them achieve that goal. If there’s a specific timeline in which they want to reach that goal, they can adjust their workouts or tweak the goal if progress comes faster or slower than expected.
A similar approach can be applied to an organizational goal like building resiliency. First, identify specific cases of how resiliency will manifest. This could be the time it takes to recover from a network outage, or a repeatable test, like a simulated hack or disaster recovery exercise. These activities serve as your measurements and gauge your progress as you implement your objectives.
You should also set periodic milestones, essentially progress checks, against your objectives. When you develop your strategy, set specific goals for each of these milestones rather than leaving them vague. Leaving some wiggle room can be tempting, but you’re ultimately doing yourself a disservice. By setting defined measurements and milestones as you develop your strategy, you’ll be able to assess how realistic your objectives are.
Should you find your team easily surpassing each milestone, perhaps your objectives were too conservative and should be adjusted. Conversely, suppose you’re missing early milestones by a wide margin. In that case, you may need to accelerate investment in that strategic objective or do some “strategy debugging” to understand why there’s a gap.
Set Appropriate Guardrails
Effective milestones and measurements should be paired with “guardrails” indicating acceptable results ranges. For example, if you’re measuring your team’s response time to a simulated outage and set a 24-hour goal, what does it mean if the team completes the objective in 6 hours? How about 36 hours? Upper and lower guardrails set the acceptable range for a particular measurement, and results outside that range should signal that further investigation is required.
Setting guardrails is often skipped, since it seems like an activity that will be self-evident during execution. However, when an outlier result occurs without appropriate pre-established guardrails, your team will be unsure whether that result should be concerning or within acceptable ranges.
Setting guardrails before beginning implementation in earnest also forces some critical strategic discussions. If you’re attempting to implement something new where your teams lack experience, broad guardrails may be appropriate, and you may even plan a measurement exercise that recalibrates future milestones. If you’re implementing a time-sensitive objective, you might require narrow guardrails that identify problems early.
Missing a milestone by 3% could be perfectly acceptable and laudable in one case or a danger sign requiring immediate attention in another case. Establishing guardrails in advance avoids debate during implementation and reduces the human urge to accept a result as “good enough” and move on when it could be an early warning.
Tune your “Implementation Machine”
There are dozens of bromides about the importance of execution of strategy, and they’re essentially correct. The perfect strategy with well-designed measures and milestones, paired with perfectly calibrated guardrails, is useless without effective execution and implementation.
As such, it is critical to assess and “tune” your implementation capabilities early in the process of implementing your tech agenda. Just as a brand new athlete is unlikely to perform at an Olympic level with a few months of training, your tech organization cannot complete objectives significantly beyond its ability to implement.
Make an honest assessment of your current implementation capabilities as you set your strategy and begin to implement your tech agenda. Think of these capabilities as an “implementation machine,” which has a particular set of performance parameters today and the potential for upgrading various components to increase those capabilities.
If you find a gap between the objectives of your tech agenda, and your implementation ability to execute those objectives, you have two options. First, you can scale back your objective. This might include modifying the measurements, milestones, and guardrails, to abandoning or significantly modifying that element of your agenda. The second option is to increase the capabilities of your implementation machine. Are there strategic hires that could enhance the performance of your team? Can you use a partner organization to provide enhanced capabilities immediately? Is there an option to buy new technologies or tools that enhance your implementation machine?
Take the time to understand your current capabilities; if they’re insufficient, consider adding some combination of improvements to your implementation machine to your agenda. Don’t forget to consider your strategy’s impact on your implementation machine from a portfolio perspective as well. You may have appropriate capabilities to implement each item on your tech agenda by itself. Still, when combined, your agenda as a whole may outstrip your implementation machine’s capability or capacity.
This exercise can also create a compelling proposition for hiring additional staff or using partner resources. Suppose you have a consensus on your tech agenda and can readily demonstrate where your implementation machine needs more horsepower. In that case, you may be able to shortcut cost and resource justification debates.
Start with Small Victories
With your tech agenda set, measures and milestones established, and your implementation machine in running order, the daunting task of execution begins. If your strategy is the least bit ambitious, it can feel overwhelming merely identifying where to start.
In many organizations, you might be tempted to embark on seemingly necessary groundwork activities, ranging from building consensus across various teams to designing the ideal operating model or waiting for supporting digital tools to be implemented. These activities can quickly turn into mini-projects that consume inordinate amounts of time while your strategy sits waiting in the wings and decidedly without forward progress.
While these groundwork activities might be important, make sure they play second fiddle to identifying and executing small victories. Small victories are any manifestation of your strategy that can be quickly achieved and shared with internal and outside teams and stakeholders.
Small victories accomplish two critical objectives. First, they create an initial momentum and bias towards action. Seemingly simple accomplishments can shift the momentum of your teams profoundly. Just as half the battle of getting to the gym or going for a run is lacing up your sneakers, so too can a seemingly minor accomplishment shift your organizational focus from planning to doing.
Secondly, small victories prove to your teams that they can be successful. Your tech agenda likely has several ambitious goals, potentially delving into areas where your teams lack experience or, in extreme cases, ask you to achieve something that’s never been done before. Focusing on these objectives in their entirety can lead to analysis paralysis, where it’s more comfortable analyzing and pontificating than going for fear of failing.
These small victories can also reduce skepticism among your stakeholders. There’s nothing like success to silence doubters, and if you can string together a series of small wins, you’ll find critics becoming neutral or even supporters of your strategy.
As a leader, try to identify small victories that are part of a larger, more challenging objective. Set your teams up for success when approaching these objectives, even going so far as to provide more resources or time than you think is required. Share these wins with the broader team and organization, and highlight the behaviors that created the success rather than the sheer brilliance of your strategy.
Small victories give your teams and your tech agenda a metaphorical tailwind that can propel them to more significant successes.
Don’t be Afraid to Tune (or Abandon) Elements of your Strategy
While failure is anathema to many leads, in the case of a strategic tech agenda, if all your items are easily completed as originally designed, you’re likely being too conservative. In the current economic climate, there’s legitimate concern around avoiding technology-driven boondoggles, whether in untried technologies or massive hiring sprees, but that doesn’t mean you shouldn’t have a few “stretch” objectives in your tech agenda.
Part of including these stretch objectives is understanding when they should be modified or abandoned altogether. This might occur for various reasons, ranging from goals that were simply too ambitious to changes in market conditions that force a significant adjustment to your tech agenda. In these cases, take the time to tune some element of your plan, or consider abandoning that effort and redirecting resources elsewhere.
The best indicator that it’s time to adjust an element of your tech agenda is having set appropriate measures and milestones early in the process of defining your strategy, ideally before implementation begins. If you’re well outside your guardrails when arriving at a milestone, attempting some debugging of the outlier result is essential. The outlier indicates that some element of implementation is dramatically different than what you assumed when designing your strategy.
Avoid the temptation to consider an outlier result “close enough.” It would be best if you had designed your measurements, milestones, and guardrails with the best information and understanding you had when you set your strategic priorities. If the actual results are outside those expectations, assess whether your expectations were flawed or if there’s an unforeseen challenge facing the execution teams.
A positive outlier might indicate that you significantly overestimated the difficulty of a particular initiative. In this case, you may want to tune that initiative by diverting resources elsewhere or making the scope of the initiative more ambitious.
A negative outlier could indicate that you inadequately estimated the effort required to deliver an element of your agenda or that there’s something incorrectly configured in your implementation machine. In either case, the outlier should serve as a warning sign that requires immediate attention, lest you allow an emerging problem to grow until it derails your initiative.
These tools should create a successful feedback loop that quickly alerts you to any parts of your tech agenda that are at risk. An analysis process that starts with checking and validating the assumptions you made when designing that initiative, alongside the performance of your implementation machine, should identify whether the problem lies in your strategy, your execution capabilities, or some external change that should trigger a reassessment of both.
There’s relatively little overhead to instituting these tools before diving headlong into executing your tech agenda. At the cost of a few days of discussions and defining clear measurements, milestones, and guardrails for each of your strategic initiatives, you’ll have a high-performing feedback loop that allows you to monitor the progress of your implementation machine. Seeding the effort with some small initial victories will keep the metaphorical machine firing on all cylinders and maximize the chances of successfully implementing even the most ambitious tech agenda.
