When sales teams underperform, leaders often scramble for quick fixes. While immediate action is critical, sustainable success requires a strategic approach that addresses both short-term needs and long-term growth. Like building a house, turning around a sales team means starting with a strong foundation, followed by structured improvements and ongoing maintenance. Here’s how to create a winning sales team in three phases: short term (30–60 days), medium term (60–120 days), and long term (120–365 days).
Short Term: Quick Wins (30 – 60 Days)
In the short term, your priority as a sales leader is to first stabilize the team by finding the levers to quickly improve win rates, and then taking a step back to more thoroughly assess the team and situation at hand. These immediate actions will help you generate momentum and clarify the path forward.
1. Focus on Improving Win Rates
The fastest way to boost revenue is by winning the deals already in your pipeline. Start by doing a detailed deal review for every opportunity. Are the deals qualified? Are the right stakeholders engaged? Is there a clear timeline or compelling event driving urgency? Use a deal management framework such as MEDDICC, BANT, or our proprietary method, PROTECT, to prioritize opportunities with the highest likelihood of closing.
PROTECT is a deal management method that looks at the core building blocks of all deals and assesses the strength of your deal and where there might be gaps you need to close.
By zeroing in on winnable deals and providing targeted support to your reps—such as improving proposals or engaging senior leaders in critical negotiations—you, as the sales leader, can create immediate revenue impact. One of the best ways to do this is to set up a few-hour pipeline review call, discuss each deal and each area, and formulate actions based on the gaps you see. These pipeline review calls will also help you inform future actions and training.
2. Assess Your Team
Even the best strategies will fail if you don’t have the right people in the right roles to execute them. Use a sales competency-based assessment, such as the Sales DNA Assessment, to evaluate your team. Identify individual rep gaps in key areas such as their will to sell, internal beliefs around selling, and tactical sales skills like their ability to hunt, consultatively sell, build value, and close. This step isn’t just about identifying weaknesses; it’s about understanding whether you have the right talent to execute your strategy successfully.
If you find significant skill gaps or poor alignment between roles and competencies, recognize this is a long-term issue. Without addressing it, you’ll face repeated underperformance down the line. Reach out to our team to learn more about how we can help you overcome gaps in training and structural alignment.
Medium Term: Building for Sustainability (60–120 Days)
Once the immediate issues are identified and addressed, it’s time to focus on building a sustainable foundation. The medium-term priority involves aligning talent, processes, and development to ensure consistent performance over time.
1. Top-Grade Your Talent
If your competency-based assessment revealed that some team members are not a fit for their roles—or the organization—you must act decisively. “Top-grading” means replacing underperformers with high-potential or experienced hires who align with your strategy and culture. While these changes can be difficult, they’re necessary to create a high-performing team. In our experience working with over 300 clients, we’ve found that you can turn a “C” player into a “B” player and a “B” player into an “A” player, but you rarely take someone from from “C” to “A”. If you have a majority of “C” players in seat, it’s often better to invest in hiring “B” players or greater rather than over-index on training. At The Sales Collective, we have developed a systematic approach to hiring top sales reps with a 92% accuracy rate. Learn more about our full-service sales recruiting partnership to see if it may be of interest.
2. Build the Right Training and Onboarding Processes
For even the most qualified new hires to succeed, you need precise and repeatable processes to ramp them up. Create a structured onboarding program that includes product knowledge, sales methodology, and role-specific skills. Consider implementing a buddy system or mentorship program to accelerate learning.
Start by listing out the actions that should be taken during each step and stage of the sales process followed by defining what “good” looks like at each of those stages. For example, common deliverables would include a list of the discovery questions to ask in every first meeting, the framework for a discovery call, the common problems your business solves, the company’s unique differentiators, and even a first meeting deck template that will be used to help drive urgency in the sales cycle. Every resource should be properly documented including the talk tracks for a demo, common objections and how to handle them, and strategies to gain buyer alignment at target accounts. The idea is, if it is a required action or best practice, then it is well documented and categorized so people know when and how to do the things.
3. Address Key Development Areas
Your initial team assessment and ongoing observations will highlight specific skills or behaviors that need improvement. Focus on these areas by implementing targeted training programs. For example, if you uncover that your team struggles with prospecting, provide hands-on workshops or coaching sessions. If discovery is a weakness, introduce role-playing scenarios to build confidence. Do not do broad stroke training. Focus on the root cause analysis and align training to the specific problems you have surfaced.
To emphasize the importance of tailored training after a root cause analysis, let’s say you’ve identified the need to “improve win rates.” But do you know exactly why you aren’t closing deals at the rate you projected? It could be that your price is above market, or perhaps you aren’t communicating your company’s differentiators, or maybe your sales reps aren’t building the value narrative, getting to the decision-makers, and building the business cases. It could be that your team isn’t going deep enough on the discovery call.
Winning deals requires doing lots of things right, so do you really know the reason you are losing more than expected? If you don’t, you can’t solve the problem. This is the type of analysis you need to do to figure out how to really move the needle over the next 2 to 6 months.
4. Implement Deal Reviews
Just as we discussed as an action to take in the short term, implementing deal reviews is equally critical for medium-term success. But the difference here is that you want to prioritize having your team equipped to do these reviews themselves. Setting this precedent creates the behiavor change needed for your reps to spot their own gaps in deals and, along with your support, take the proper actions to steer deals back on course.
For reps to truly improve their abilities, they need to be able to complete their own deal risk analysis independently. But you can’t expect independence without the proper guidance – your reps first need a pre-defined process to follow and then the supplement training to execute. By having your reps own this process themselves, they will start to proactively identify their own gaps in deal execution and use the deal management practices you outlined to close those gaps autonomously.
Long Term: Building a High-Performance Culture (120–365 Days)
In the long term, the focus shifts from fixing problems to fostering continuous growth and adaptability. A true turnaround is only sustainable when the team operates as a well-oiled machine driven by a culture of learning and excellence.
1. Foster a Coaching Culture
The most successful sales teams don’t rely on one-off training events; they embrace a culture of continuous improvement. Invest in creating a culture that fosters coaching where managers regularly engage with reps to review performance, provide feedback, and set development goals. Use tools like our Sales DNA Competency Training Guide, call recordings, and deal reviews to inform your individual development plans and provide actionable direction for your team. Great coaching isn’t about micromanagement—it’s about empowering reps to reach their potential.
2. Commit to Ongoing Skill Development
Sales skills evolve with the market, so your team must stay ahead of the curve. Create opportunities for reps to refine their skills through workshops, certifications, or peer-led training sessions. Encourage knowledge sharing within the team by recognizing and rewarding top performers who mentor others. Ongoing development ensures your team remains competitive and adaptable.
3. Align Strategy with Long-Term Goals
By the end of the first year, your sales strategy should align seamlessly with your team’s structure, skills, and processes. Regularly review your go-to-market strategy to ensure it reflects changing market conditions and customer needs. A strong alignment between strategy and execution will set the stage for sustained success.
4. Measure and Optimize
Finally, use data to drive continuous improvement. Track key metrics such as win rates, deal velocity, and rep productivity to identify what’s working and what’s not. Use these insights to refine your processes and training programs. Remember: the goal is not to just hit your revenue targets but to create a system that consistently and reliably delivers results.
Conclusion
Turning around an underperforming sales team is a challenging but rewarding journey. By focusing on short-term wins, building a sustainable foundation in the medium term, and fostering a high-performance culture over the long term, you can transform your team into a revenue-generating powerhouse.
Remember, success doesn’t happen overnight. It requires a blend of decisive action, strategic planning, and relentless commitment to improvement. Start today, and by this time next year, your team will be firing on all cylinders—ready to tackle any challenge and seize every opportunity.
About The Sales Collective
The Sales Collective is a sales transformation company that helps B2B companies grow revenue through our custom solutions that address the full scope of go-to-market challenges. Our services include hiring, assessing, onboarding, process development, training for sellers and leaders, coaching, technology implementation, and more. To learn more reach out to our team here!
