8 signs you’ve mistimed a major IT initiative

Planning and launching a major IT initiative can be a CIO’s biggest challenge. Everything has to go right: the technology, the goals, the financial platform, and most important of all, the timing. Launch an initiative too soon and the technology may be premature and flawed. On the other hand, failing to start the project a timely manner could mean falling behind competitors, perhaps even fatally.

Knowing exactly when to launch a critical IT initiative requires deep enterprise, market, and technology expertise. Most CIOs already possess those attributes, yet it’s also important to know what not to do. That’s why it’s critical to avoid the following eight potentially fatal mistakes.

1. Defective leadership

Leadership is a key component in the successful timing of any major transformation project, ahead of strategy and technology, says Suneet Dua, chief revenue and growth officer for products and technology at business advisory firm PwC. Inadequate leadership and poor team engagement can lead to delays and time-wasting errors.

“Quickly identifying where mistakes were made and bringing your people along on the remediation journey, instead of keeping them in the dark, can be a powerful tool when doing damage control,” he notes.

Many IT timing mistakes boil down to a disconnect between IT and other enterprise departments. “To drive successful adoption of IT initiatives, IT leaders must operate outside the constraints of the IT department and bring every single C-suite leader along on their digital transformation journey,” Dua advises.

2. Poor planning

Defective planning often leads to poor timing, particularly when an initiative conflicts with established business operations. “Very often, IT teams don’t consider other, non-IT, activities that can affect their user base and their ability to collaborate,” says Seth Lively, US digital lead at IT consulting firm PA Consulting. Confusion results when the initiative inadvertently ruins departmental synchronization.

Lively believes that the best way to correctly time a major IT initiative is to create a transformation management office (TMO), or similar entity, that will coordinate activities and dependencies. “A TMO sets up the framework to track benefits for large transformation programs and provides a centralized team to connect parts of the business involved in the transformation,” he explains.

Mistimed initiatives ultimately result in poor adoption, Lively warns. “If dependencies and initiatives are properly planned, business stakeholders are engaged during the key parts of solution development.”

3. Overloaded schedules

IT leaders already have too much on their plates, observes Kevin Shuler, CEO of technology consulting firm Quandary Consulting Group. Therefore, most CIOs focus on business-critical operations, since maintaining existing enterprise systems is a top priority. “It’s about not drowning first, then using whatever additional time and resources IT has to meet other requirements,” he explains.

To create the time needed to nurture a potentially transformative initiative, Shuler advises CIOs to explore ways of augmenting their workforce without adding either extra cost or team members. He suggests using low-code platforms. “They can amplify the output of developers using prefabricated snippets of code,” Shuler says. “This drastically shortens development time, helping IT to catch up on tasks.”

Shuler adds that a citizen developer program can also free up extra time, although governance frameworks must be created to ensure that the program stays on track. “Still, delegating less-essential tasks to employees trained in low code can improve output without burning through IT resources,” he notes.

4. Weak commitment

Indecision and a poor risk appetite are two common reasons why CIOs frequently delay an important IT initiative. “Nimble, forward-looking leaders put execution speed at the center of performance discussions; indecisive IT leaders tend to rely on consensus decisions and endless risk evaluations,” says Colm Sparks-Austin, president and managing director of business advisory firm Capgemini Canada.

To correctly time a major IT initiative, the decision-maker should align the initiative with business goals. “If the business isn’t spearheading the initiative, or is not aware of it, it’s clear that something is wrong,” Sparks-Austin says.

CIOs should also ensure they’re analyzing all IT spend through a business goals lens, Sparks-Austin advises. This technique — combined with discrete measures of success matching business goals over a given time period — can repair the damage of a mistimed initiative, he notes.

5. Inadequate funding

Unrealistic funding almost always plays an important role in initiative timing, observes Ravi Malick, CIO at cloud-based content management, collaboration, and file-sharing tool provider Box. Overly optimistic funding is almost always a main part of the equation when an initiative fails, he notes. It’s always better to wait than to launch an underfunded initiative.

Underfunding doesn’t just appear out of thin air, Malick says. It occurs as a combination of things, such as hardware, software, and labor pricing. “Knowing where to focus your negotiation energy on getting the lowest price is key to staying within budget and making sure you don’t have to make trade-offs later, which will mistime the initiative.”

6. Trusting the status quo

Optimistic IT leaders expect that the business environment will remain generally the same, or perhaps even improve, during the initiative’s entire development and deployment process. This can be a dangerous assumption, however. “Macroeconomic events and internal profitability challenges have a dramatic effect on an organization’s willingness to continue investing in what are typically large, expensive, multi-year, and multi-provider initiatives,” says Eric Lefebvre, CTO of tax compliance software provider Sovos.

To avoid any unpleasant financial surprises, Lefebvre suggests breaking the initiative into manageable chunks that deliver incremental value throughout the project’s life. “For instance, instead of waiting three years for success, start with an initial six-month deliverable of some core minimum viable product [MVP] capability,” he recommends.

Quarterly capability increases, Lefebvre notes, will yield some level of benefit even while the full initiative may be months or years away from full deployment. CIOs should also plan with the expectation that funding could dry up after any given quarter’s results, he advises. “This [attitude] ensures the plan is defensible and can be easily paused until conditions are more conducive to investment.”

7. Poor business stakeholder coordination

IT initiatives frequently affect critical business processes, and not always in a positive way. Timing an initiative to ensure that impacted stakeholders can adapt to and adopt change with minimal risk is critical, says Ola Chowning, a partner with global technology research and advisory firm ISG.

“An example might be making changes to a financial reporting system during budget season, or prior to month-end or, even more impactfully, year-end-close,” she notes.

8. Distraction

IT leaders are responsible for an assortment of critical responsibilities that can result in time slipping away. Attending to a series of urgent daily tasks can result in mistimed initiatives.

While busy with other duties, a CIO can easily become reactive rather than proactive, says Jeremy Richard, head of IT and security for asset intelligence platform provider Armis. “In a constantly evolving technology world, IT leaders must be visionaries with strong planning skills, always keeping their eyes toward enterprise goals in order to ensure the proper timing and execution of major initiatives,” he explains.

Richard notes that the damage created by a mistimed initiative can be mitigated, and sometimes even repaired, with proper planning and open communication. “Teams should set clear, measurable goals and expectations to address the mishap, as well as plan for proper execution the next time around,” he says, adding that the IT leader should also analyze why the initiative was mistimed and what could be improved when deploying future initiatives.

The final countdown

There’s never a perfect time to launch a major IT initiative, particularly a project that has a wide cross-functional or entire enterprise impact. The best way to reduce disruption is with diligent planning, Box’s Malick says.

“Start by making people feel aligned and supported, then ensure governance is in place to help maintain focus, and defer projects that can be deprioritized,” he advises. “Finally, secure the necessary — not minimal — funding.”

Digital Transformation