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Tech buying without regret
Too many technology decisions leave businesses tied to costly, underperforming tools. The solution requires CIOs to embed leadership throughout the buying journey and embrace lean and agile practices
Technology vendor spend is often the single largest line in an IT budget, yet CIOs rarely devote the same rigour, governance and leadership to the buying process itself. This imbalance carries a hidden cost, with recent Gartner research revealing 79% of technology purchases end in regret.
While it may seem straightforward to achieve business objectives through technology investments, the reality is more complex. CIOs must navigate stakeholder interests, technical constraints and commercial realities.
Regret typically emerges when expectations go unmet – when software underdelivers on promised outcomes, contracts lock teams into compromises, or buying committees lack clarity and cohesion. Instead of driving transformation, too many technology decisions leave CIOs tied to costly tools that fail to move the business forward.
To break this cycle, CIOs must rethink procurement as more than just a transactional process. Shifting from complex, risk-averse buying toward an agile business capability, empowers teams, sharpens evaluation criteria and fosters active collaboration with vendors. This enables CIOs to turn technology investments into measurable business outcomes.
Leadership matters
Achieving success in technology procurement requires more than setting objectives at the outset and hoping the process will deliver.
Too often, stakeholder engagement is limited to individuals focused on specific features or familiar vendors. This leads to a fragmented approach that overlooks commercial realities and broader business goals. Without continuous CIO and leadership involvement, buying teams can lose direction and critical decisions may be made in isolation. This undermines the very outcomes the investment was meant to achieve.
To address this, CIOs must embed business leadership throughout the buying journey and actively foster confidence in vendor engagement. This requires the business leader remaining involved at every stage of evaluation, negotiation and relationship management – not just during initial planning.
By investing in a deep understanding of vendor strategies and market dynamics, CIOs can also equip their teams with the negotiation leverage and market intelligence needed to engage vendors as equals.
The goal posts must be moved beyond the “done deal” to reflect that procurement extends throughout the life of the purchase and the vendor dependency it creates.
Ongoing leadership oversight and well-defined success metrics are essential to ensure vendor relationships continue to deliver on business objectives, from inception through renewal to solution retirement and replacement. This transforms technology buying from a transactional exercise into a strategic capability that delivers sustained value and minimises regret.
From rigid to agile
Traditional technology purchasing often relies on rigid processes that assume the buying team knows exactly what’s needed from the start and have perfect knowledge of the market. This limits learning and adaptation, making it harder to find solutions that truly fit evolving business needs.
Instead, CIOs should champion a learning and refining approach. Engage vendors iteratively to explore options, refine requirements and align technology investments with business outcomes.
To maximise success, buying teams must anchor decisions to business objectives rather than predefined solution categories. Rather than defaulting to familiar vendors or technologies, encourage open-minded exploration of the market, ensuring the chosen solution best supports strategic goals. This requires updating procurement policies to support agile, dynamic sourcing and investing in training.
In addition, contracts must be flexible enough to accommodate changing business needs and technology landscapes. CIOs should work with procurement leaders to future-proof agreements, outlining clear responsibilities and collaboration points for innovation, resilience and operational excellence.
By adopting lean and agile practices, technology buying can be transformed into a strategic capability that delivers lasting value.
Establish risk tolerances
No organisation’s activities exist without risk, especially when buying a technology that supports critical operations or interacts with sensitive data.
To make informed decisions, risk must be proactively evaluated, drawing on independent research, peer insights and expert consultation. This comprehensive approach enables buying teams to fully understand the risks involved and take steps to manage them effectively.
In some cases, stakeholders may aim to eliminate all risk or become overly focused on negotiation details, making compromise difficult. Instead, guide teams to evaluate risks against established tolerance levels and consider alternative mitigation strategies.
When consensus can’t be reached or risks exceed acceptable limits, decisions should be escalated to senior executives for informed judgement and resolution.
Beyond the contract
As digital transformation accelerates, technology procurement must evolve – and CIOs are the catalysts for change. By embracing agile and lean practices, updating policies and prioritising vendor relationships, organisations can avoid costly mistakes and achieve high-quality technology deals.
CIOs have an opportunity to extend their influence with their peers and replace regret to success by repositioning technology procurement into a strategic function.
Luke Ellery is vice-president analyst at Gartner
