Most sales managers have experienced the discomfort of watching a promising deal begin to unravel. The opportunity looked solid on paper. The early conversations were positive. The proposal was delivered on time and tailored well. From a process standpoint, everything was progressing as expected — until it wasn't.
Suddenly, the client went quiet. Follow-up emails were met with vague responses. Meetings were postponed. Internal confidence began to waver, yet the CRM still reflected a healthy probability of success.
At this stage, a common managerial instinct is to revert to pipeline discipline. The manager leans into forecasting frameworks, double-checks that the next steps are clearly defined, and encourages the rep to maintain momentum. These actions are rational and well-intentioned. But the question remains — if the process is being followed, why does the deal feel stuck?
What if the issue is not in the process, but in the system that surrounds it?
What if the barrier is not a tactical oversight, but an unseen dynamic — something emotional, relational, or contextual that isn’t being tracked in the CRM or surfaced in the usual deal review conversation?
And what if, by only coaching the deal itself, managers are missing a critical opportunity to develop the one thing that actually drives progress in complex sales environments: the thinking capability of the rep?
Understanding the Limits of Traditional Sales Coaching
In many sales environments, coaching has become conflated with inspection. Managers believe they are coaching when they ask reps about the next step in the deal or when they offer suggestions to overcome objections. But these conversations are typically transactional. They focus on immediate actions, not the underlying mindset or contextual awareness of the rep.
While these tactical check-ins are sometimes necessary, they rarely enable personal development or deep insight. Over time, this form of "coaching" reinforces a dependency model, where reps learn to bring problems upward rather than develop the capacity to reflect, problem-solve, and grow independently.
This is especially problematic in complex sales, where deals are rarely lost due to a missed follow-up or a forgotten stakeholder. More often, they break down because of unacknowledged power dynamics, internal conflicts within the buyer’s organisation, or a lack of clarity around value perception. These are not surface-level issues, and they cannot be solved by better forecasting or tighter control. They require perspective — a shift in how the salesperson understands the system they are operating within.
Systemic coaching provides that perspective.
How Systemic Coaching Surfaces the Invisible
At the heart of systemic coaching is the belief that the answers to many performance challenges already reside within the individual — they just haven’t yet been surfaced or articulated. This is particularly true in high-stakes selling, where experienced reps carry a wealth of intuition, pattern recognition, and situational awareness that may not always be accessible through linear conversation.
Systemic methods — such as constellation mapping or visual coaching — are designed to tap into this implicit knowledge. By asking reps to map out the elements of a complex deal using objects or simple visuals, they are invited to externalise what they intuitively know but cannot yet verbalise:
- Who are the real influencers?
- Where is their energy currently focused?
- What aspects of the deal feel energising — and which feel uncertain?
- What, or who, might they be unconsciously avoiding?
These are not abstract questions. They speak directly to the dynamics that determine whether a deal moves forward or stalls. And they often reveal far more than a status report ever could.
Reflection as a Leadership Lever
While systemic coaching provides structure, it is reflection that drives transformation. Reflection is not a luxury in modern sales leadership — it is a performance lever. Without it, reps operate from habit and reaction. With it, they begin to question assumptions, spot patterns, and build the internal capacity to manage complexity more effectively.
Claudia Filsinger, who has coached sales professionals and leaders across industries for over 15 years, describes reflection as the “superpower” of a great coach. It is the quality that distinguishes a manager who simply manages tasks from one who develops talent.
The pace of sales encourages forward motion — closing business, progressing deals, hitting targets. But without time to pause and look at what is happening beneath the surface, reps repeat patterns that may no longer serve them. Systemic coaching reintroduces that reflective space. It helps reps learn from the moment, rather than just move through it.
The Shift from Coaching Deals to Coaching People
At Consalia, we often work with sales managers who have been promoted due to their success as individual contributors. They know how to win deals — and that success can lead them to adopt a problem-solving mindset in their coaching conversations.
This creates a common pitfall. Managers jump in with advice, offer solutions too early, or dominate the conversation with their own ideas. While well-meaning, this approach reduces the rep's opportunity to think independently and grow.
Coaching complex deals requires a mindset shift. Managers must begin to see their role not as fixers, but as facilitators of learning and perspective. They must learn to coach the person navigating the opportunity — not just the opportunity itself.
Systemic coaching supports this shift by equipping managers with the tools and frameworks to ask better questions, stay curious longer, and help reps see themselves — and the deal within its systemic dynamics — more clearly.
What This Means for Sales Organisations
Sales teams don’t just need better technology or more enablement content.
They need stronger coaching cultures.
When coaching becomes a consistent, integrated behaviour — not just a check-the-box activity — everything changes. Deals move faster. Forecasts become more accurate. Confidence increases. Teams learn how to unblock themselves.
But most importantly, coaching becomes a strategic lever for performance — not an afterthought.
Ask yourself:
- Are your managers defaulting to deal inspection over development?
- Do your reps walk away from one-to-ones with clearer thinking — or just more tasks?
- Is reflection a natural part of your sales cadence, or something that only happens after things go wrong?
These are the questions that matter when you are trying to build a performance culture that scales.
Where to Begin
If you're ready to coach for complexity — not just compliance — start by giving your managers tools to have better conversations.
We’ve created a practical resource designed to help managers coach the behaviours and mindsets that customers actually value.
Download "Mindsets for salespeople: coaching checklist"
Or
Download a Coaching for Sales Transformation brochure
Let’s explore how to embed systemic coaching into your leadership culture — and close the coaching gaps holding your team back.
Because when your managers coach the person, not just the pipeline, you don’t just close deals.
You build the kind of capability that closes the performance gap.
