Contextual Coaching: The Sales Leadership Superpower

Contextual Coaching, The Sales Leadership Superpower Hiding in Plain Sight

I have spent most of my career watching good sales leaders beat themselves up for things that were never really their fault. They tell me they should coach more, coach better, coach earlier. They promise themselves they will carve out time next quarter, that they will set up a new framework, that they will finally get disciplined about one on ones. I used to nod along. I do not nod anymore.

Coaching is not broken because leaders are lazy or oblivious. Coaching is broken because we built it on a system that blinds the very people responsible for improving performance. I did not fully understand that until I started my own company and saw the pattern unfold across startups, public companies, and everything in between. Once you see the pattern, you cannot unsee it. Leaders are trying to coach without context. It is like being handed a wrench and told to fix an engine with the hood welded shut.

When I talk about contextual coaching, I am not pitching a buzzword. I am naming the single shift that separates the best performing teams from everyone else. It is the shift from content to context, from generic advice to precision guidance, from hopeful coaching to coaching rooted in truth.

The Lie We Tell Ourselves About Coaching

I used to believe I was a strong coach. Many leaders share that belief. I thought I could piece together what happened in a deal based on a rep’s summary, some stage updates, and whatever the dashboard decided to reveal. I was wrong. That belief is not arrogance, it is survival. When you lack visibility, you cling to whatever fragments you can find.

Reps do not remember everything that happened in a deal. They cannot. They are juggling dozens of conversations, priorities, and dependencies. Leaders, faced with partial information, fill in the gaps with intuition. Dashboards offer the illusion of certainty but operate on manually entered fields that capture a fraction of what actually matters.

Coaching becomes a kind of performance. Reps perform the story. Leaders perform the guidance. Both sides walk away with the uneasy sense that something is missing. Something always is.

I have had reps tell me they believed they were doing everything right until the quarter closed and the entire pipeline toppled like a house of cards. I have had leaders tell me they thought they were coaching effectively until they discovered gaps that had been hiding for weeks. These stories are not the exception. They are the norm.

The Gap Between Intent and Reality

I have never met a leader who did not want to coach. They simply cannot coach what they cannot see. Most coaching attempts are built on four shaky pillars that do not hold the weight we put on them.

Dashboards filled with lagging indicators
Rep summaries that flatten nuance
CRM fields that age like milk
Deal reviews that focus on stage progression instead of behavior patterns

Sales happens in conversations and inboxes, not in the CRM. Risk emerges between the meetings, not during them. Gaps grow in silence, not in the tidy summaries leaders hear during one on ones. When leaders tell me they feel like they are guessing, they are not wrong. They are trapped inside a system that rewards them for pretending the guess is analysis.

Content Driven Coaching, The Mirage That Looks Like Progress

Content coaching is the version of coaching most leaders default to. It feels natural. It feels structured. It feels like progress. It rarely is.

Content coaching sounds like this:

Try the framework.
Use the playbook.
Follow the script.

These are not bad ideas. They simply do not address what actually happened inside the deal. Content coaching assumes the leader knows what transpired. That assumption falls apart instantly once you examine real activity.

I have reviewed countless deals where the rep insisted they followed the playbook and the activity thread told a different story. Not because the rep lied. Because memory bends. Context disappears. Details evaporate. Leaders, as a result, coach ghosts.

The Power of Contextual Coaching

Contextual coaching grounds itself in what really happened rather than what might have happened. It operates in truth, not narrative. It examines signals rather than summaries. It exposes the story inside the conversation rather than the story told about the conversation.

Contextual coaching sounds like this:

This deal has not had stakeholder engagement for eight days, we need to fix that.
Your last follow up ignored the security concern the buyer raised, let us rewrite it.
Procurement surfaced two days earlier than expected, let us get ahead of the pattern.
Your competitor entered the thread yesterday, we should neutralize their position now.

These are not opinions. They are observations backed by real behavior inside the deal. Context does not care about optimism or excuses. Context does not get tired. Context does not forget. That is why contextual coaching creates precision and why precision creates performance.

Why Leaders Struggle With Context

The most painful part of leadership is wanting to do the right thing and lacking the conditions to do it. Leaders want to coach behavior, momentum, alignment, risk, intent. They want to focus on the signal, not the noise. They want to develop their people rather than police their pipeline. They simply lack the substrate that makes those things possible.

The traditional sales system rewards inspection rather than improvement. Leaders spend more time verifying pipeline than shaping performance. I remember sitting in meetings where the entire hour dissolved into stage updates while everyone pretended we were doing coaching. We were not. We were checking homework.

Leaders are not struggling because the job got harder. Leaders are struggling because the system failed to evolve with the job.

The Shift That Changed My Thinking

When I founded GTM Engine, I was not trying to create more dashboards. I had built enough dashboards in my life to know they do not change behavior. Dashboards tell you what is happening. Context tells you why it is happening and what needs to happen next.

The shift that changed my thinking was simple. I stopped asking how we could get better at reporting and started asking how we could get better at execution. Reporting is passive. Execution is active. Reporting shows outcomes. Execution shapes outcomes. Reporting gives you data. Execution gives you leverage.

A modern revenue system cannot rely on manual entry. It cannot rely on memory. It cannot rely on outdated fields that fail to capture the dynamic signals moving through every opportunity. To coach effectively, leaders need context to appear automatically, without rep effort, without interpretation, and without delay.

The Anatomy of a Contextual Coaching System

When leaders have a system that collects, processes, acts, and learns from real interactions, the entire coaching dynamic transforms.

A contextual system does a few things exceptionally well.

It collects every email, call, meeting, and message
It processes noise into signals that reveal risks and gaps
It acts through nudges, workflows, and recommendations that guide next steps
It learns from patterns in deals and behaviors over time

The goal is not to replace leaders. The goal is to augment them. The goal is to scale the best coaching behaviors across the entire team. The goal is to turn every rep into a high context rep and every leader into a high precision leader.

What Happens When Coaching Gains Context

Once context exists, coaching stops being a guessing game and becomes a performance lever.

Coaching becomes individualized

Generic advice gives way to targeted, rep specific guidance. Leaders coach patterns, not platitudes. Reps get feedback that maps directly to what is happening inside their deals.

Performance issues surface earlier

Risks do not hide until the end of the quarter. Misalignment does not linger. Deals that slow down send signals early. Leaders intervene when momentum shifts, not after.

Forecasting becomes credible

Forecasts stop relying on optimism or manual fields. Instead, they draw on buyer behavior, stakeholder engagement, sentiment shifts, and historical pattern matching. The forecast becomes a reflection of reality rather than a negotiation.

Reps reclaim time

When reps stop taking notes, updating fields, and reconstructing history, they are freed to sell. The immediate lift in productivity is impossible to ignore.

Leaders coach what actually matters

Leaders stop nagging about activity volume. They focus on stakeholder coverage, objection handling, qualification integrity, alignment, and momentum quality. Coaching shifts from performance theater to performance engineering.

The World Sales Operates In Now

Four years transformed sales more dramatically than the previous twenty. Buying committees are larger. Cycles are slower. Signal noise is higher. Reps rotate roles faster. CFO scrutiny is relentless. Pipeline quality swings wildly. Blind spots are unforgiving.

Intuition cannot keep up. Experience cannot keep up. Content coaching cannot keep up. The environment demands clarity, context, and precision. The teams that adapt will widen the gap. The teams that do not will burn out.