Jan. 15, 2026

Navigating the 'AI Between Times': Why Systems Thinking is Your Sales Superpower

Navigating the 'AI Between Times': Why Systems Thinking is Your Sales Superpower

Welcome back to the blog, where we dive deeper into the fascinating topics we explore on the podcast. In our latest episode, number 68, titled From Practice to Performance; Preparing Sales Teams for an AI World, we had an insightful conversation with AI strategist and workforce transformation expert, Ben Tasker. Ben painted a vivid picture of the current technological landscape, and it got me thinking about how we, as sales professionals and organizations, can not only survive but thrive amidst this rapid evolution. This blog post is an expansion on those ideas, focusing on a crucial concept Ben highlighted: the 'AI Between Times' and why embracing a systems thinking approach is no longer optional, but a fundamental superpower for sales success.

Understanding the 'AI Between Times'

Ben introduced the concept of the 'AI Between Times,' and it resonated deeply with me. It’s this period of intense, accelerated change where new AI capabilities are emerging at a breakneck pace. We're not quite in a world where AI is seamlessly integrated into every facet of our professional lives, but we're also far beyond the point where AI was a niche curiosity. We are, in essence, in a transition, a chrysalis phase for AI adoption. This isn't a slow, evolutionary shift; it's a revolution happening in real-time. Think about it: just a few years ago, generative AI for content creation was nascent. Now, it's a tool many of us use daily. Predictive analytics in sales, once the domain of highly specialized data scientists, is becoming more accessible. This rapid acceleration creates a unique environment, one that's brimming with opportunity but also fraught with uncertainty.

This 'AI Between Times' is characterized by several key features. Firstly, there's an overwhelming amount of information and new tools constantly emerging. It's like standing in front of a firehose of innovation. Secondly, there's a palpable sense of "keeping up." Companies are scrambling to understand what AI can do for them, and individuals are trying to figure out how to leverage these new technologies without falling behind. Thirdly, and perhaps most importantly for our discussion, there's a high degree of experimentation. Organizations are trying different AI solutions, often without a clear long-term strategy. This experimentation, while necessary, inevitably leads to missteps.

Why Mistakes are Inevitable in This Transitional Phase

Given the rapid pace of innovation and the experimental nature of adoption, it's crucial to acknowledge that mistakes are not just possible; they are virtually guaranteed during this 'AI Between Times.' This isn't a sign of failure, but rather an inherent part of navigating uncharted territory. When you're building a new capability, especially one as transformative as AI, you're bound to encounter unforeseen challenges. These can manifest in various ways:

  • Technical Glitches and Misconfigurations: Early adopters might implement AI tools incorrectly, leading to inaccurate results or system malfunctions.
  • Misalignment with Business Goals: An AI solution might be technically sound but fail to address a genuine business need or, worse, create new problems.
  • Data Quality Issues: AI models are only as good as the data they're trained on. Inadequate or biased data can lead to flawed AI outputs and decisions.
  • User Adoption Challenges: Even the best AI tools will fail if sales teams don't understand how to use them effectively or if they don't see the value.
  • Ethical and Bias Concerns: Without careful consideration, AI systems can perpetuate or even amplify existing biases, leading to unfair outcomes.
  • Over-reliance and Loss of Critical Thinking: A mistaken belief that AI can do no wrong can lead to a decline in essential human critical thinking skills.

The key is not to avoid mistakes altogether – that's an unrealistic expectation in a period of such profound change. Instead, the focus must be on how we learn from these mistakes, adapt, and build more robust and resilient systems. This is precisely where systems thinking comes into play, transforming these inevitable stumbles into valuable learning opportunities.

Introducing Systems Thinking: Your Sales Superpower

So, what exactly is systems thinking? At its core, systems thinking is a way of understanding how seemingly independent parts of a whole interact and influence each other. Instead of looking at problems in isolation, systems thinking encourages us to see the bigger picture, the interconnectedness of elements within a complex system. For sales organizations, this means moving beyond viewing AI as just another tool to be implemented. It requires understanding how AI interacts with your existing sales processes, your people, your data, and your overall business strategy.

Think of your sales organization as a complex ecosystem. You have your sales reps, sales managers, marketing teams, customer success, product development, and of course, the crucial element of customer interaction. Each of these components is interconnected. Introducing AI into this ecosystem isn't a simple plug-and-play operation. It has ripple effects. For example, implementing an AI-powered lead scoring system doesn't just change how leads are assigned; it can impact marketing's lead generation strategies, sales reps' prioritization, and even the types of conversations sales managers have with their teams. Systems thinking helps you anticipate these ripples, understand the potential consequences, and design interventions that are holistic and sustainable.

In the context of the 'AI Between Times,' systems thinking acts as your superpower for several reasons:

  • Proactive Problem Solving: By understanding the interconnectedness, you can anticipate potential issues before they arise, rather than just reacting to them.
  • Enhanced Adaptability: When mistakes inevitably occur, a systems thinking mindset allows you to see them not as isolated failures, but as feedback loops within the larger system, guiding necessary adjustments.
  • Holistic Implementation: It ensures that AI adoption is aligned with your overall business objectives, rather than being a siloed technology initiative.
  • Improved Collaboration: By understanding how different departments and functions are impacted by AI, you can foster better cross-functional collaboration and communication.
  • Sustainable Growth: Systems thinking focuses on long-term viability, helping you build AI processes that are not only effective today but also adaptable to future changes.

Systems Thinking in Action: Navigating AI Adoption

Applying systems thinking to AI adoption in sales is a journey, not a destination. It requires a fundamental shift in how we approach technological change. Here’s how it can manifest in practice:

The Interplay of AI and Existing Processes

When considering a new AI tool, don't just ask, "How will this tool improve lead qualification?" Instead, ask, "How will this AI-powered lead qualification tool interact with our current CRM system, our lead nurturing workflows, our sales collateral, and the daily routines of our sales development representatives?" A systems approach means mapping out the entire process, identifying potential bottlenecks, and ensuring that the AI integrates smoothly rather than disrupting the flow. For instance, an AI that generates personalized email drafts is only effective if sales reps have a clear process for reviewing, editing, and sending those emails, and if the CRM is updated accordingly.

Data as the Lifeblood of the System

Data quality is paramount. Systems thinking highlights that your AI system is only as robust as the data it consumes and generates. This means understanding your data sources, ensuring data integrity, and establishing clear data governance policies. If your AI is meant to predict customer churn, but your CRM data is incomplete or inconsistent, the AI will produce unreliable insights. A systems thinker would ask: "Where does our customer data come from? How is it entered and maintained? Who is responsible for data quality? How does the AI's output feed back into improving our data collection?" This feedback loop is crucial for continuous improvement.

People as Critical Components of the System

Perhaps the most overlooked element in AI adoption is the human factor. Systems thinking emphasizes that AI is meant to augment, not replace, human capabilities. This means understanding how AI will change the roles and responsibilities of your sales team. Will it free them up for more strategic selling? Will it require new skills? Are they equipped to handle the output of AI tools? This leads directly into the critical need for upskilling and reskilling.

The Role of Upskilling and Reskilling in an AI World

As highlighted in our podcast episode, upskilling and reskilling are not just buzzwords; they are essential components of a successful AI strategy within a systems thinking framework. When you understand AI as a part of a larger system, you recognize that the people within that system need to be equipped to interact with it effectively. Ben Tasker emphasizes that the goal isn't to make everyone an AI expert, but to empower them to leverage AI tools to amplify their existing abilities.

Upskilling involves enhancing the skills your team already possesses. For example, if your sales reps are excellent communicators but struggle with data analysis, upskilling might involve training them on how to interpret AI-generated insights and use them to inform their conversations. Reskilling, on the other hand, involves teaching entirely new skills. A sales role that previously focused heavily on manual data entry might need to be reskilled to manage AI-powered data analysis tools and focus on higher-value activities.

A systems thinking approach to upskilling and reskilling would involve:

  • Identifying skill gaps: Analyzing how AI adoption will impact different roles and identifying specific skills that will be required.
  • Developing targeted learning paths: Creating personalized training programs that address these identified gaps, rather than one-size-fits-all solutions.
  • Fostering a culture of continuous learning: Recognizing that the 'AI Between Times' is dynamic, and learning must be an ongoing process.
  • Integrating AI into learning: Using AI itself to personalize training, provide simulations, and offer on-demand support to sales reps as they learn new skills.

This ensures that your human capital remains a powerful asset, working in synergy with AI, rather than being a bottleneck.

Practical AI Applications for Sales Teams

The 'AI Between Times' is already offering a plethora of practical applications for sales teams. Embracing these, with a systems thinking lens, can lead to significant improvements in efficiency and effectiveness:

  • Enhanced Prospecting and Lead Qualification: AI can analyze vast datasets to identify high-potential leads, predict their likelihood to convert, and even suggest optimal outreach strategies. Systems thinking here means ensuring this AI integrates with your CRM and marketing automation platforms.
  • Personalized Content Generation: AI can assist in crafting personalized emails, proposals, and social media posts, tailoring messaging to individual prospect needs. This requires understanding how this content fits into your overall sales playbook and brand messaging.
  • Sales Forecasting Accuracy: By analyzing historical data and market trends, AI can provide more accurate sales forecasts, enabling better resource allocation and strategic planning. A systems approach ensures this forecast is communicated and acted upon across relevant departments.
  • Simulated Buyer Conversations: As Ben mentioned, AI can create simulated buyer conversations, allowing sales reps to practice their pitches, objection handling, and negotiation skills in a low-stakes environment. This practice needs to be integrated into the broader sales enablement program.
  • Automated Administrative Tasks: AI can automate time-consuming tasks like data entry, meeting scheduling, and report generation, freeing up sales reps to focus on building relationships and closing deals. The system needs to ensure these automations don't inadvertently remove valuable context or human touchpoints.
  • RFP Preparation Assistance: AI can quickly gather and summarize relevant information, significantly speeding up the process of responding to complex Requests for Proposals. The human oversight in ensuring accuracy and strategic alignment remains critical.

The key takeaway is that these applications are most powerful when viewed as parts of a larger sales engine, not as standalone tools.

Overcoming AI Adoption Hurdles: Processes, Data, and Alignment

Despite the promise, AI adoption is not without its challenges. Based on our discussion and common experiences, these hurdles often fall into three interconnected categories, all of which are magnified without a systems thinking approach:

  • Process Breakdowns: Implementing AI often requires re-engineering existing workflows. If processes aren't clearly defined and understood, AI integration can create more chaos than efficiency. For example, if an AI tool automatically updates customer records, but your sales reps don't have a process for verifying that information, you're setting yourself up for data integrity issues.
  • Data Deficiencies: As discussed, poor data quality is a perennial problem. In the AI era, it becomes an existential threat to your AI initiatives. Without clean, accurate, and relevant data, your AI will be built on a foundation of sand. This requires not just technical solutions but also organizational commitment to data governance and hygiene.
  • Lack of Organizational Alignment: AI initiatives often fail because different departments or stakeholders aren't on the same page. Marketing might implement an AI tool that generates leads, but if sales isn't aligned on how to follow up, or if leadership hasn't clearly communicated the strategic importance, the investment will be wasted. Systems thinking forces this alignment by requiring a holistic view of impact and buy-in.

Addressing these hurdles requires a deliberate, integrated approach. It’s not about finding a single solution, but about understanding how changes in one area (e.g., data quality) impact others (e.g., AI model performance and sales team efficiency).

Personal Branding and Visibility in the Age of AI

Beyond organizational adoption, the 'AI Between Times' also presents unique opportunities and challenges for individual sales professionals, particularly concerning personal branding and visibility. Ben touched upon this in our episode, and it's a critical aspect of staying relevant. Recommendation engines and AI-powered content discovery mean that how you present yourself online is more important than ever.

AI can be a powerful ally in building your personal brand. Tools can assist with:

  • Content Creation: Generating blog post ideas, drafting social media updates, and even helping to refine your writing style.
  • Audience Analysis: Understanding what content resonates with your target audience.
  • Optimizing Online Presence: Identifying keywords and strategies to increase your visibility on professional platforms.

However, the systems thinking approach here is vital. Your personal brand isn't just about the content you produce; it's about the entire ecosystem of your professional presence. This includes the consistency of your messaging, the authenticity of your voice, and how you engage with your network. AI can amplify your efforts, but it cannot replace the genuine human connection and strategic thinking that underpin a strong personal brand. It's about using AI to be more efficient and effective in building those relationships and demonstrating your expertise.

Conclusion: Embracing AI for Sales Success

We've journeyed through the exciting, and admittedly sometimes chaotic, landscape of the 'AI Between Times.' We've explored why this transitional phase makes mistakes an inevitability, but also why it presents an unparalleled opportunity for growth. The key takeaway from this blog post, and indeed from our compelling conversation in episode 68, is the transformative power of systems thinking. By viewing AI not as an isolated technology but as an integral part of your sales ecosystem – your processes, your data, your people – you can navigate this era with confidence.

Systems thinking empowers you to anticipate challenges, learn from missteps, and build sales organizations that are not only efficient and effective today but also resilient and adaptable for the future. It’s about fostering a culture of continuous learning, where upskilling and reskilling are embraced as core strategies. It's about understanding the interconnectedness of every element, ensuring that AI serves to amplify human potential, not diminish it.

As Ben Tasker eloquently put it, AI won’t replace us; those who embrace it will win over those who don’t. By adopting a systems thinking mindset, you can be among those winners, leveraging the 'AI Between Times' to transform your sales operations and secure your position at the forefront of innovation. Don't just adopt AI; integrate it thoughtfully, strategically, and holistically. The future of sales is being written now, and systems thinking is your pen.