Avoiding Common Contracting Mistakes

Federal contracting rewards precision. Small and mid-sized contractors can do a lot of things right—identify a promising opportunity, assemble a capable team, even price competitively—yet still lose on details that could have been prevented with a more structured approach.

In a FAR/DFARS-driven environment, mistakes are rarely “small.” They can mean immediate disqualification, protest risk, cash flow issues, or a contracting officer deciding your team is simply too risky. The good news: most of these mistakes are predictable and fixable.

Below are some of the most common contracting mistakes we see, what they look like in practice, and how you can avoid them.

Weak Market Research and Targeting

What does this mean? A major setback could be that you're conducting the wrong research and targeting. Here are some things that look like: 

• Chasing every opportunity on SAM.gov without a clear agency focus.  
• Responding to bids where your past performance, NAICS codes, and core capabilities do not align with the requirement.
• Treating federal and SLED (state, local, education) opportunities the same, without understanding agency buying patterns, contract vehicles, or competition.

• Define a focused “sweet spot” by agency, NAICS/PSC codes, contract size, and scope.  
• Use opportunity and contract data to see who buys what you sell, how often, and through which vehicles.  
• Build a target agency list and prioritize opportunities that align with your differentiators and past performance.  
• Track expiring contracts and recompetes so you can shape opportunities early, not just react at RFP release.

Bidding Before You Are Operationally Ready

Bidding before you are operationally ready means pursuing opportunities while core systems, registrations, and internal controls are incomplete or outdated. Instead of a reliable delivery engine, you are relying on ad hoc processes, overextended staff, and optimistic assumptions about what can be fixed after award. This creates avoidable execution risk, undermines evaluator confidence, and can turn a “win” into a performance problem.

• Rushing into bids while SAM registration, small business certifications, or internal processes are incomplete or out of date.  
• Committing to performance timelines or staffing plans that your team cannot realistically support.  
• Treating capture, pricing, solutioning, and proposal development as last-minute tasks instead of integrated planning.

• Treat readiness as a gate: you only bid when key registrations, certifications, and internal controls are in place.  
• Use a repeatable checklist for bid/no-bid decisions that covers technical capability, capacity, teaming, and risk.  
• Assess resource requirements—including proposal development time—before you commit.  
• Align your pipeline with realistic delivery capabilities so winning does not create downstream performance risk.

Compliance Gaps and “Minor” RFP Deviations

Compliance gaps and “minor” RFP deviations occur when your proposal does not fully follow the solicitation’s instructions or requirements, even in small ways—such as missing certifications, ignoring specific formatting or submission rules, or only partially addressing evaluation factors. In federal competitions, these issues are almost never treated as minor; they can quickly lead to lost points, non-compliance findings, or outright disqualification.

• Skimming the RFP and missing small but critical instructions (font size, page limits, file naming, section order, submission portals).  
• Failing to fully address each factor and sub-factor in the evaluation criteria.  
• Overlooking mandatory certifications, representations, or security requirements until late in the process.

• Build a detailed compliance matrix that maps every RFP requirement to a section, page, or paragraph in your response.  
• Assign a compliance lead who is responsible for validating that instructions, forms, and certifications are correctly completed.  
• Use structured color reviews (e.g., RED and GOLD team) to validate compliance and responsiveness—not just writing quality.  
• Confirm cyber, facility, and personnel requirements early so you do not discover gaps at submission time.

Pricing That Does Not Match Your Story—or the Government’s Risk Profile

• Pricing that appears disconnected from the technical solution, level of effort, or staffing mix described in the narrative.
• Underbidding to “win” on price, creating execution risk and raising concerns about performance realism.  
• Overbidding because cost drivers, subcontractor rates, or indirects are not well understood or modeled.

How to avoid:

• Start pricing in parallel with solution design, not as an afterthought.  
• Tie every major cost element back to a clearly articulated requirement, task, or performance outcome.  
• Use a structured approach to rate build-up, burdening, and fee that can withstand cost realism and audit scrutiny.
• Validate your pricing against historical awards, incumbent patterns, and current market conditions.

Weak Proposal Structure and Evaluation Focus

• Proposals organized around your company structure instead of the RFP’s evaluation criteria.  
• Long, dense narrative that forces evaluators to “hunt” for required answers.  
• Generic boilerplate that does not clearly show how your approach reduces risk and creates value for that specific agency.

How to avoid:

• Mirror the RFP’s sections, factors, and sub-factors in your headings, tables, and proposal organization.  
• Use visual structure—clear headings, call-out boxes, and tables—to make it easy for evaluators to find proof points.
• Write to the evaluator’s scorecard: explicitly connect your approach to discriminators, strengths, and risk reductions.
• Replace generic claims with specific, measurable examples of how you have solved similar problems.

Underinvesting in Past Performance, Proof, and Relationships

• Treating past performance as a simple list of contracts instead of a strategic asset.  
• Limited or no proactive engagement with contracting officers or end users ahead of opportunities.  
• Capabilities statements, DSBS profiles, and digital presence that do not clearly communicate your value to government buyers.

How to avoid:

• Curate past performance examples that align with your target agencies, contract sizes, and technical domains.  
• Frame each reference in terms of outcomes: schedule, cost, quality, mission impact, and customer satisfaction.  
• Invest in clear, compliant capabilities narratives and profiles that make it easy to understand what you do best.  
• Build disciplined outreach and relationship plans so conversations with government and industry happen well before RFP release.

Treating Every Opportunity the Same

• Applying the same level of effort to a low-probability, low-value bid as to a strategic, high-value opportunity.  
• No standardized way to score opportunity complexity, fit, and internal readiness.  
• Burnout in your team from “chasing everything” without clear prioritization.

How to avoid:

• Implement a bid scoring framework that evaluates opportunity fit, complexity, and probability of win.  
• Calibrate your capture and proposal investment based on that score—more resources for high-priority, high-fit opportunities.  
• Use a structured gate process (e.g., pursue / don’t pursue, pre-RFP capture, draft RFP review, bid/no-bid) to manage the pipeline.  
• Regularly review outcomes and refine your criteria based on wins, losses, and debriefs.

How Structured Capture and FEDCON Tools Help You Avoid These Mistakes

Avoiding these mistakes is less about working harder and more about working within a disciplined system.

• Structured capture and Shipley-based proposal practices provide the framework to connect market research, solution design, pricing, and proposal development into one integrated process. This reduces rework, improves compliance, and ensures your narrative, pricing, and past performance all support a single win strategy.  
• VEX Marketing Program strengthens your visibility and credibility with federal buyers by aligning SAM/DSBS data, NAICS/PSC strategy, capabilities statements, and outreach. This supports better market positioning long before an RFP hits the street.  
• FEDCON All-Access Portal gives you structured access to federal and SLED opportunities, expiring and awarded contracts, and key contact profiles. This enables more targeted market research, smarter pipeline building, and earlier engagement with the right agencies and partners.