Timestamps

1:16 How did you get the no. 1 bestseller and LinkedIn top voice?

04:20 The note Cian wrote for his son

6:58 Mistakes companies make when losing deals

10:56 The true cost of not having a win-loss analysis in organisations

12:30 Real-world example of the loss of morale

14:25 3 metrics we influence in a material way

16:02 Most used assessment criteria in win reviews

21:44 How to create a safe environment for people to analyse wins and losses

25:43 Why do you need a platform?

About Cian McLoughlin

Cian is the author of the Amazon #1 Bestseller, Rebirth of the Salesman, Cian is a regular sales and marketing commentator in the mainstream media and globally recognised keynote speaker. His blog was voted one of the Top 50 Sales Blogs in the world for the past 4 years and he was recently chosen as a LinkedIn Top Sales Voice.

Cian is the founder and CEO of two businesses, Trinity Perspectives and Trinity Digital, and guest lectures at Macquarie University in their business Incubator. Prior to founding Trinity, Cian had more than 15 years of B2B sales experience, including senior roles at companies like Cognos and SAP.

How to Win More Deals by Turning Losses into Lessons

Cian shares invaluable insights on overcoming challenges, collecting actionable feedback, and refining strategies for success. In this blog post, we will explore how consistent win-loss analysis, effective feedback mechanisms, and strategic adjustments can build a winning team and business.

Let's dive in.

1. Cian’s journey to Amazon Bestseller and LinkedIn Top Voice

Cian, a sales and channel professional, transitioned from a corporate world at SAP to starting as a strategic consultant 10 years ago. He chose a niche and a problem to solve, which was conducting win-loss reviews at the end of a sales cycle. He realised that while he was spending time and effort on these pursuits, he never truly understood what influenced the customer's decision.

After focusing on win-loss reviews, gained insight into what influences customers to make their buying decisions. He has helped countless companies listen to customers, implement actionable insights and create winning teams.

Switch actionable tips

1. Specialise and Solve a Specific Problem. Identify a specific area of expertise within your industry and focus on addressing a particular challenge faced by your target audience. For instance, if you’re selling CRM systems for small businesses, addressing an unsolvable pain point will set you apart and positions you as a go-to expert in that area.
2. Share Insights Authentically and Engage Your Audience. Create engaging content, such as informative blog posts, webinars, or social media updates, that offer valuable insights related to your niche. Engage with your audience by responding to comments, asking for feedback, and actively participating in discussions.
3. Leverage Multiple Platforms for Content Distribution. In addition to sharing content on your website or blog, consider sharing it on professional platforms like LinkedIn, where you can connect with a broader network of professionals interested in your niche.

2. Creating a culture of open communication

Cian discusses the importance of creating a safe environment for children to discuss awkward or uncomfortable topics. He shared a note he wrote for his 11-year-old son, which he believes has been a powerful tool in their household. The note allows his son to bring up any topic he wants to discuss with Cian, whether it's a small or big issue.

The note has been a source of comfort and understanding for his son, and Cian believes that others could benefit from this approach.

Switch actionable tips

1. Establish Open Communication Channels. In a professional context, ensure that your team members know they can approach you with any concerns or ideas, regardless of how sensitive they may be. Encourage regular check-ins and make it clear that their input is valued.
2. Implement a Clear and Welcoming Policy. Create a written policy or guideline that explicitly states that all team members are encouraged to share their thoughts, concerns, or feedback openly, and that they will be treated with respect and consideration.
3. Lead by Example. In a team meeting, share a personal story or experience that highlights the importance of open communication. This can inspire others to feel more comfortable sharing their own thoughts or concerns.

3. Set expectations with customers and create a system for collecting their feedback

Companies often make key mistakes when losing a deal, such as not setting expectations with customers, focusing solely on losses, and not having a clear structure for win-loss analysis. This can lead to a lack of learning and improvement.

Cian shared that one of the main challenges is that many businesses do not consistently conduct win-loss analyses. Instead, they may call a customer and ask them questions that don't align with their buying journey. This can lead to a lack of consistency and a lack of actionable feedback.

Another challenge is that companies often don't have a mechanism to collect feedback from customers. When companies start doing win-loss reviews, they may not be able to identify what needs to be fixed internally, leading to confusion and a focus on sales enablement, pricing, or competitive issues.

To overcome this, Cian suggests that companies should focus on identifying the problem, deciding whether to fix it and spreading the learning across the business. This approach helps to identify bottlenecks and weaknesses that need to be addressed, ultimately leading to better decision-making and improved performance.

Companies should focus on consistent win-loss analysis, setting expectations, and implementing a mechanism to collect and act on feedback from customers. By doing so, they can create a more effective and sustainable business strategy.

Switch actionable tips

1. Identify and Address Internal Bottlenecks. Proactively identify and address any internal challenges or bottlenecks that may be hindering your ability to win deals. If there are slow response times or a lack of product knowledge among your team members, implement targeted training or process improvements to address these weaknesses.
2. Spread Learning Across the Business. After each review, hold a debriefing session with relevant departments like sales, marketing, and product development. Share key insights and discuss potential adjustments or improvements to strategies and processes.
3. Set Clear Expectations with Customers. Clearly communicate timelines, deliverables, and responsibilities during initial discussions with a potential customer. This ensures everyone is on the same page and reduces the likelihood of unmet expectations later in the process.

4. Losing deals affects team morale and staff retention

Cian emphasised how win-loss analyses can have significant impacts on team morale, retention of salespeople and leaders, and customer churn.

He also talked about the negative impact of a deal loss on the bottom line, as soft impacts ripple through the business, causing a loss of morale and exacerbating pressure to meet quotas.

Cian suggests that while the effects of a deal loss on the top-line perspective are evident, the bottom line is more complex. The ripple effect extends beyond the deal itself, affecting everyone involved and highlighting the need for change.

Switch actionable tips

1. Conduct Comprehensive Win-Loss Analyses. After each significant deal, conduct a structured review to understand the factors that influenced the outcome. For instance, consider what messaging resonated with the customer, how competitors were positioned, and if there were any specific pain points that played a crucial role.
2. Address Soft Impacts on Morale and Performance. If a team experiences a string of losses, consider organising a team-building activity or recognition event to boost morale. Similarly, after a significant win, celebrate the achievement and acknowledge the efforts of the team members involved to reinforce positive behaviours.
3. 3. Evaluate Bottom Line Implications of Wins and Losses. When assessing a recent high-value deal, consider how it not only impacted revenue but also influenced customer satisfaction, potential upsell opportunities, and the overall reputation of the company. This comprehensive view can guide future strategies and decision-making.

5. Customer feedback is the key to survival and success in a competitive market

Cian recounted his story about a vendor who had lost several deals over the past quarter and a half due to their lack of market shift. Despite their proactive and responsive sales team, they have effectively priced themselves out of the market.

The management team now recognises this is not an issue of sales execution but a complete shift in their pricing model.

As a result, the leadership team has decided to fix the value for money and pricing issue, and they have shifted their pricing in the last six weeks, starting to pick up deals worth 5-10 million.

This change in strategy has been considered fundamental, as changing the win ratio by 10 percentage points or higher can have a tidal effect downstream.

Switch actionable tips

1. Regularly Assess and Adapt Pricing Strategies. Conduct a thorough analysis of recent deal losses to identify any patterns related to pricing. If it becomes apparent that your current pricing model is deterring potential customers, consider making strategic adjustments to better meet market expectations.
2. Embrace Market Shifts and Adjustments. Recognise that in some cases, a change in pricing or value proposition may be necessary to stay competitive. For instance, if a vendor is consistently losing deals due to pricing, as in Cian's story, consider implementing a new pricing model that better reflects the value offered.
3. Monitor Win Ratios and Assess Impact. After implementing a revised pricing strategy, track the win ratio over a specific period. If there is a notable improvement, this demonstrates that the pricing adjustment had a positive impact on the company's ability to secure deals.

6. Take more time in discovery to get higher win rates

Three metrics that influence in a material way are win rate, deal velocity, and sales cycle closure. Cian shared that salespeople should identify invisible friction in the buying journey for customers and remove it to improve deal velocity, and win rate, and reduce the need to discount.

Poor discovery leads to poor sales execution, which in turn leads to the need for discounts. Improved discovery and responsiveness can lead to higher win rates and margins.

As the pipeline diminishes and sales cycles elongate, Cian suggests you should be doing more with less opportunity, focusing on the interconnected aspects of the buying journey.

Switch actionable tips

1. Prioritise Comprehensive Discovery. Instead of rushing through initial conversations, dedicate extra time to ask probing questions and actively listen to the customer's challenges. This deep level of understanding can lead to more tailored solutions and ultimately, higher win rates.
2. Swift Responsiveness and Proactivity. If a customer raises a question or expresses a concern, respond promptly with a solution-oriented approach. Anticipate any follow-up questions they might have and provide proactive information that demonstrates your commitment to their success.
3. Focus on Removing Invisible Friction. Conduct a thorough review of the typical customer journey, looking for any points where the process might become cumbersome or unclear. By proactively addressing these areas of friction, you can significantly enhance deal velocity and ultimately, sales cycle closure.

7. In reviewing your deal wins, measure your responsiveness, discovery, patience, cultural fit, and risk management

In win reviews, Cian shared that the key criteria to assess the situation include responsiveness, good discovery, patience, cultural fit, and risk management. 

Your question sets in win reviews should align perfectly with your customer’s buying journey. Ask customers about the catalyst for their purchase, the research conducted, and how well the vendor showed up in the early stages. Use quantitative scoring feedback alongside qualitative feedback.

Additionally, since consistent win rates can be attributed to high responsiveness throughout the sales cycle, you should also have patience in guiding the customer throughout their buying journey.

Customers see sales and pre-sales people as personifications of the brand they are buying from. To improve your win rates, make sure your team is knowledgeable about why they’re culturally fit with the customers’ businesses.

Meanwhile, risk management is a top decision-making criterion for customers, and vendors that mitigate and manage risks are more likely to win. So, be astute about risk conversations by factoring them into commercials.

Overall, to win more opportunities, vendors should focus on responsiveness, deepening risk management, and making themselves easier to buy from. This approach covers more ground than just consultativeness and helps to lift the bar on what sales teams often focus on.

Switch actionable tips

1. Enhance Responsiveness Across the Sales Cycle. Prioritise and maintain high levels of responsiveness throughout the entire sales cycle and customer buying journey. For instance, aim to respond to customer emails or calls within a set timeframe, demonstrating a high level of attentiveness and professionalism.
2. Strengthen Risk Management and Mitigation. Conduct thorough risk assessments for each deal, addressing potential concerns or challenges that may arise. This might involve creating contingency plans or offering solutions that minimise perceived risks for the customer.
3. Facilitate Ease of Doing Business. Provide clear information, transparent processes, and user-friendly interfaces to guide customers through the buying journey. Consider implementing tools or platforms that simplify transactions and interactions, ultimately making it easier for customers to engage with your offerings.

8. Build an environment where people can feel comfortable discussing success and failure

Cian discussed that while many businesses have negative feedback from customers, constructive feedback is usually more beneficial. This feedback can be influenced by the vendor's culture, as they may not want to point the finger at the source of the loss.

He also shared that most companies are open to listening and taking action, but the best ones close the loop with the customer and explain how they have addressed the issue. Cian also appreciated the value of detailed feedback, which is why organisations must treat it as a precious gift.

One good example of handling feedback is how a successful vendor traffic lights feedback in three colours, which represent negative, neutral, or good. He then puts work teams on to address the issues and close the loop with the customer. Next, they discuss what they have done based on the feedback, which ultimately leads to increased success and market share.

Cian also highlighted the untapped resource of feedback and goodwill from customers and prospects, which many businesses overlook due to a lack of understanding or lack of a mechanism to capture it. By being proactive in their thinking, businesses can extract valuable insights and improve their performance.

Switch actionable tips:

1. Encourage Constructive Feedback Culture. Promote an environment where team members and customers feel comfortable providing feedback about wins and losses. Emphasise the importance of constructive feedback in driving continuous improvement.
2. Close the Feedback Loop with Customers. After receiving feedback, ensure that your organisation takes action and communicates with the customer on how their concerns or suggestions have been addressed. The best companies, as highlighted by the speaker, close the loop with the customer, demonstrating their commitment to improvement.
3. Implement Feedback Traffic Lights and Action Teams. Categorise feedback into different levels, such as negative, neutral, or positive, and create dedicated teams to address the identified issues. The example of a vendor using traffic lights for feedback categorisation is a practical approach. By assigning teams to specific issues and following up with customers on the actions taken, businesses can enhance their success and market share.

9. Invest in a platform for reviewing your wins and losses

Cian discussed the importance of a platform for organisations to capture customer intelligence and achieve a competitive advantage, especially during times of fewer deals and extended timelines. They discuss a platform they developed for capturing customer intelligence and analysing deals, which was previously expensive and time-consuming.

He then shared their experience with a consulting service that was built into a clickable prototype. They tested the prototype and found that customers responded with detailed, honest feedback, which was a valid resource. They announced a partnership with Salesforce to integrate the platform into their CRM system, allowing customers to review and schedule deals without leaving Salesforce.

Cian emphasises the importance of value in sales, regardless of the size of the organisation. He believes that sales professionals should be learning from their mistakes and acting professionally. They are adding a step at the end of the sales cycle, which is a "win-loss review," capturing feedback, and getting value in return.

This approach aims to improve the sales process and make it more efficient for organisations to gather and analyse customer intelligence.

Switch actionable tips

1. Implement a Customer Intelligence Platform. Allocate resources to adopt a customer intelligence platform similar to what Cian discussed. This investment can lead to increased efficiency in gathering valuable customer insights, ultimately enhancing your sales process.
2. Leverage Clickable Prototypes for Customer Feedback. Create a clickable prototype for a new product or service and gather feedback from potential customers. The interactive nature of the prototype allows for a more engaging feedback process, which can lead to meaningful improvements.
3. Integrate Customer Intelligence into CRM Systems. Consider reaching out to CRM providers like Salesforce for potential integration opportunities. This can streamline the sales process and make it more convenient for both your team and customers.

Final thoughts

I learned so much from Cian. After our talk, I learned that win-loss reviews are not a static process but a dynamic force for evolution. So, let the reviews not be an end, but a beginning—a compass that continually steers your teams to victory.

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