The “Something Different” Series

Occasionally, a book arrives that doesn’t just inform, it reframes the way you think about projects, people, and progress. Over the holiday break I read (yes, our blogs are written by a real human being), Daniel H. Pink’s, When: The Scientific Secrets of Perfect Timing. With this book in mind it occurred to us that our readers may appreciate some of the other things we discuss at STEP, beyond software, hence ‘The ‘Something Different’ Series.’

In this book Pink explores how timing is a science, not just intuition, and how beginnings, midpoints, and endings shape success. He shows that knowing when to act can be equally as important as knowing how to act. While When isn’t a tech book, its principles map beautifully to challenging software projects – legacy modernization projects, where timing and pacing make or break outcomes for IT leaders, executives and entire companies are particularly suitable to these principles.

Pink talks a lot about the ‘fresh start effect’ and how there are 86 days that are especially optimal for ‘change’ success. With most people on the ‘New Year New Me’ mindset in January let’s unpack how this timing theory applies to real technology projects and what Pink’s research says about doing it right in 2026.

The Power of a Well-Timed Start

Daniel highlights that starting a task intentionally — not randomly — can increase the likelihood of follow-through and success. Beginning at the start of a natural unit of time (e.g., beginning of a sprint or quarter or any of the other 86 options) aligns energy, focus, and collective momentum. He also highlights that there is a similar momentum near the end of a natural unit of time – the ‘fast finish effect’ (think last quarter of a 5- year strat plan, or final month of a quarter).

For modernization:

• Begin when stakeholders are aligned, not only in IT but also in finance and cross functional business units. Early alignment creates clarity and reduces scope drift. Think, beginning of the quarter, or fiscal or right after a strategy session.
• Choose your tempo wisely. Starting at the beginning of a planning cycle improves visibility and commitment. Short bursts of activity like bi-weekly sprints are excellent ways to enhance productivity and maintain momentum.

Research indicates that modernization projects lacking clear goals and timing often stall or fail because scope and objectives are not clearly defined early.

The Importance of Deadlines

Deadlines create outer forces that help internal motivation. Pink details the psychology behind task completion when a deadline is present vs. when it is not. People, as with projects, struggle to sustain momentum in the absence of a deadline.

In modernization:

• Define incremental milestones rather than one distant end date.
• Milestones help you adjust budget forecasts and identify risks early, before overrun costs balloon.
• Create a ‘call in the experts’ deadline that you apply to the project if/when you discover your team has exceeded their skillset or the project timeline is going to be blown.

Legacy modernization efforts often fall into the trap of treating modernization like a background chore. Analysts highlight that without phased goals, these projects can become ‘wandering,’ with budgets stretched and objectives unclear.

Midpoint Evaluation: Overcoming the Trough

Pink describes a U-shaped performance curve: peak → trough → rebound, and how the middle(or trough) often represents the ‘danger zone’ for productivity, health and ethics.

In practice, this means:

• Your project peak energy is early after kickoff – move critical or big changes to the front end of the project to ensure they take advantage of the early momentum.
• A midpoint lull typically appears when enthusiasm fades and reality (integration complexity, data migration, testing) sets in.
• Anticipate the trough and prepare for it, try not to schedule complicated or critical tasks in the middle of a project.

Effective teams plan for this.

At the modernization project’s midpoint:

• Review progress against original goals.
• Re-validate priorities with stakeholders.
• Adjust timelines and expectations based on new insights.
• Require a midpoint evaluation/update from your project managers.
• Call in the experts if the need presents itself.

Modernization thought leaders warn that skipping midpoint reviews can increase the risks of misaligned outcomes and costly rework.

People Matter: Aligning Schedules with Team Rhythms

Modernization isn’t just code, it’s people. Planning around team energy and conscientious cycles increases collaboration quality and output.

Thankfully, we still live in a time where teams are primarily comprised of human beings, and humans are all unique. Pink describes a person’s chronotype and how their type impacts productivity patterns. Whether a team member is a ‘lark,’ ‘owl,’ or a ‘third bird’ matters.

Some practical takeaways:

• Schedule design workshops when cross-functional teams are fresh (morning for many, although 21% are better late in the day).
• Reserve deep dives or integrations when quality engineering focus peaks.
• Use checkpoint meetings to intentionally re-synchronize team momentum.
• Creative brainstorming sessions are often best applied to the afternoon.

Ultimately, check in with your project team and ask the question, “Are you best in the morning (larks) or better burning the midnight oil (owls)?” The results may surprise you and could result in shifting the project schedule to better align with your teams’ rhythm.

Financial Benefits of Smart Modernization Timing & Outsourcing

There is no secret that Legacy Systems drain budgets, we’ve written about how/why many times.

Legacy Systems can have:

• High support and maintenance costs.

• Limited agility and integration capabilities.
• Increased security and compliance exposures.
• Increased risk: Older UI frameworks often rely on outdated libraries.

Research shows that incremental modernization reduces risk and spreads costs, improving financial predictability. Further, collaborating with experienced third-party vendors can help:

• Avoid costly trial-and-error learning curves
• Accelerate discovery and risk mitigation
• Bring in reusable frameworks and best practices

A theoretical review of outsourcing literature also notes that modern outsourcing is not just cost saving – it can drive strategic innovation and improved outcomes when tightly governed.

Risks of Getting Timing Wrong (and How to Prevent Them)

Delaying modernization can cost you:

• Opportunity: slower innovation = slower time-to-market.
• Increased maintenance overhead.
• Security and compliance gaps (and associated fines).

A systematic overview of software process improvement finds that schedule and cost are two of the most commonly measured project attributes. Failure to measure and manage them properly can hurt ROI in the long-term.

To mitigate risk:

• Plan incremental phases with defined goals
• Perform midpoint reviews and adjust scope early
• Outsource high-risk technical work to trusted partners
• Align business and technical stakeholders on value outcomes

Final Thoughts

Whether you’re leading a modernization effort or just beginning the planning of one, When reminds us that timing is strategic. Well-timed starts, smart deadlines, mid-project checkpoints, along with team alignment matter just as much as the technology choices.

In 2026, legacy modernization won’t be just about what you build, but when and how you integrate it into your business rhythm. If aligned correctly, this year could be the year that you halt technical debt growth and unleash the innovation energy IT teams crave.

If you’d like help turning your timing strategy into an actionable modernization roadmap, STEP Software is ready to partner with you. Reach out and let’s ensure your legacy transformation is well-timed and worth the investment.