Contracting Has Been Completely Transformed: What You Know Is Outdated

Michael Crosby, CEO of Leadership Connect, shares 10 key observations on how the federal contracting landscape is evolving.

This guide draws on more than 10 hours of in-depth interviews with senior procurement leaders spanning civilian, defense, and oversight agencies. Participants included contracting activity heads, chief information officers, IT directors, cybersecurity leads, and acquisition executives from organizations such as the Department of Defense, Air Force, the Department of Health and Human Services, the National Institutes of Health, and the Government Accountability Office. These discussions centered on how purchasing decisions are being made in today’s federal environment, the constraints influencing those decisions, and where contractors are gaining or losing ground.

Contracts with extended return on investment (ROI) are losing ground

“The philosophy of growing with the agency does not work today.”

• Multi-year modernization plans without near-term results are increasingly at odds with pressure to demonstrate progress quickly.
• ROI beyond 180 days is harder to justify internally, as the benchmark has shifted to 30-to-90 days.
• Agencies are sequencing differently: pilot first, measurable win second, scale third.
• Governance has been streamlined in some agencies, but certified project managers, funding clarity, and defined ownership are still required before enterprise rollout.

Transformation is not rejected. It is earned through early proof.

Software isn’t the first choice

“Start with the policy or process fix first.”

• Agencies are prioritizing needs before introducing new software.
• Policy or process fixes are considered before staffing or hardware.
• Software is viewed as a long-term commitment that adds integration complexity, sustainment cost, and oversight burden.
• Platform sprawl is increasingly seen as a long-term operational risk.

Innovation without rationalization is harder to justify.

Proof of concept is the entry point

“I expect vendors to embrace pilots free of charge if they want to win and win big.”

• Executive orders and leadership mandates are compressing early procurement timelines.
• Agencies are more open to pilots and prototypes as starting points.
• Pilots reduce risk, create internal champions, and support internal budget justification.
• Enterprise deployment still requires structure, funding clarity, and program management discipline.

Acceleration applies to validation, not abandonment of oversight.

Team tenure impacts performance

“It felt disjointed. We couldn’t see a vision.”

• High turnover and rotating sales representatives undermine confidence.
• Inconsistent messaging across sectors signals organizational instability.
• Stable account coverage and a consistent narrative are seen as indicators of operational maturity.

Consistency builds trust. Fragmentation erodes it.

Access to politicals is a hack (most of the time)

“If you have never sold to our agency, and don’t know a political, maybe you should start somewhere else.”

• Political appointees often open doors, but do not replace operational buy-in.

• Bottom-up engagement with action offices and technical SMEs builds stronger traction.
• Alignment to policy matters, but ROI and integration clarity ultimately determine momentum.

Access opens doors. Execution keeps them open.

The ex-govvie paybook is outdated

“How we work today is totally different from nine, 12, or 18 months ago.”

• Organizational turnover has disrupted legacy networks.
• Processes have shifted significantly over the past year.
• Hiring former officials, especially from the past two administrations, does not substitute for understanding current architecture and acquisition pathways.

Relationships still matter, but they must be rebuilt within today’s constraints.

Policy signals now shape sales strategy

“Tie it to an EO. That makes it easier to sell in the building.”

• Executive orders are operational signals, not background context.
• Agencies expect vendors to understand whether they are lead on a directive.
• LinkedIn posts from agency leaders increasingly reveal priority areas.

Policy awareness is now part of competitive positioning.

Proof is required earlier

“Paper is not enough.”

• Written proposals increasingly look similar, particularly in an AI-assisted environment.
• Agencies are relying more on pilots, peer validation, and direct reference checks.
• Leaders described calling counterparts at other agencies to validate performance beyond the Contractor Performance Assessment Reporting System (CPARS).

Proof reduces perceived risk in a capacity-constrained system.

Capacity constraints are driving behavior

“There’s nobody to process the information we’re requesting.”

• Contracting officer retirements and Contracting Officer Representative (COR) shortages are limiting oversight bandwidth.
• Workforce reductions have delayed modernization initiatives.
• Agencies prefer expanding existing contracts over launching oversight-heavy new acquisitions.

Solutions that simplify lifecycle management have a structural advantage.

Trust must be built deliberately

“Don’t trust. Prove it.”

• Default posture, particularly in cyber and defense environments, is skepticism.
• Trust often requires multiple substantive engagements and subject matter expert validation.
• Reference checks are active and informal.
• Four to six live meetings are the norm.

Credibility is earned through demonstrated alignment and measurable proof under current constraints.

Federal contracting in 2026 is not defined by new rules, but by new pressures. Agencies are moving faster with less capacity, higher scrutiny, and lower tolerance for risk, which means contractors must lead with clarity, proof, and measurable value earlier than ever before. The fundamentals have not changed, but the order of operations has. Vendors who recognize that shift and adjust how they position, sequence, and demonstrate impact will separate themselves quickly in a compressed, capacity-constrained environment.

Michael Crosby is the CEO of Leadership Connect. He has led several tech turnarounds in the public sector, financial services, and legal services, with the largest exit exceeding $100 million. He has helped transform Leadership Connect from a CIA take-private to one of the fastest-growing tech companies in D.C. focused on contracting and policy intelligence. He began his career in the U.S. as a product manager for AT&T’s web services business and then founded the hedge fund team at Thomson Reuters.

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