Sales Coaching

Coaching is not just a skill. It is a commercial discipline.

And it should be a cultural norm across any serious sales organisation. The numbers are not ambiguous. Different studies and providers land in slightly different places, but the pattern is consistent:

• When sales coaching is formal, structured and part of a wider enablement approach, organisations see roughly a 30 percent uplift in win rates and high double-digit improvements in quota attainment compared to those without it.

• Analyses summarised by multiple ‘sales researchers’ indicate that teams with structured coaching programmes achieve around a 28 percent higher win rate than those without, and that coaching can drive an 88 percent productivity improvement when added to training, versus roughly 20 to 25 percent from training alone.

At the same time:

• Multiple reviews of CSO Insights data suggest that around 73 percent of sales managers spend less than 5 percent of their time coaching, despite its impact on performance.

• A separate time study at LinkedIn found that only 10 percent of manager time in their global sales organisation was spent on coaching, which ultimately led them to mandate that sales managers allocate 50 percent of their time to coaching and learning.

So, we have a situation that most CROs and leaders will recognise.

Coaching works - but coaching is not happening at the level required.

Coaching is the highest leverage activity a sales manager can perform. The challenge is not awareness. It is consistency. AI tools are improving visibility of behaviour and giving us richer data on calls and meetings, but they do not replace human coaching or leadership. You cannot outsource the development of judgement, confidence and capability to a platform.

The modern revenue context: complexity, pressure and capability gaps

We have all seen the data and insights. Buyers are more informed. Most will have formed a view of potential solutions long before they speak to a seller. Decision cycles have become more layered, with formal and informal stakeholders, risk committees, procurement scrutiny and an internal politics component that is rarely visible externally.

In that environment, three things are true:

• Tools matter, but the tools alone do not win deals

• Process matters, but process without judgement is just process

• Product matters, but parity is common and differentiation through features is hard to sustain.

What consistently differentiates the winning teams is capability - how well people think, qualify, run meetings, manage stakeholders, translate needs into value and navigate the internal and external politics around a decision.

Front Line Sales Managers sit exactly at that capability junction. They translate strategy into day-to-day expectations. They shape habits, reinforce standards and influence how the organisation shows up in front of customers. The quality of their coaching and leadership will ultimately show up in win rates, cycle times, forecast accuracy and team stability.

Research on coaching and enablement supports this view. CSO Insights’ work on dynamic coaching and sales enablement has shown that organisations with mature, formal approaches to coaching and enablement deliver materially higher win rates and quota attainment than those with ad hoc or informal approaches.

On the people side, Gallup’s long running engagement studies show that highly engaged teams - which are usually the ones receiving regular meaningful conversations and development - achieve around 18 percent higher sales productivity, 10 percent higher customer loyalty and 23 percent higher profitability than low engagement teams.

Capability compounds over time. Coaching is one of the main ways it compounds.

What coaching really is

Coaching is one of the most overused and least defined words in sales. Many things get labelled as coaching that are not:

• Running through the forecast.

• Moving opportunities from one stage to another in the CRM.

• Asking for “a quick update” on a deal.

• Telling a seller what to do next.

• Going through a slide deck and tightening the story.

Those activities may be necessary, but they are not coaching.

Coaching is the structured development of a seller’s thinking, behaviours and commercial judgement, with the explicit goal of improving future performance. Getting teams to think, take ownership and act, differently and better.

In other words, coaching is about how someone approaches their work, not just what they are working on today.

Good coaching:

• Builds autonomy rather than dependence on the manager.

• Increases clarity on how to execute the role.

• Strengthens the underlying skills and mental models that drive performance.

This distinction is important. A manager who only gives advice is effectively lending their judgement to the rep for that single situation. A manager who coaches is building their teams’ judgement for the next ten situations.

Teach a man to fish…

The coaching gap: why it still is not happening

Given the impact, it is reasonable to ask why coaching is still such a weak spot in many organisations. In practice, there are a few recurring reasons.

Time pressure and operational load

Most managers do not arrive at work intending to avoid coaching. They are simply pulled into other demands. Internal meetings, reporting cycles, last minute pricing and commercial escalations, requests from above and sideways, hiring, onboarding and firefighting all absorb time and attention.

Coaching is rarely the loudest thing in the diary, so it slides first.

Several studies and time use analyses suggest that a large proportion of sales managers spend somewhere between 5 and 15 percent of their time in genuine coaching conversations, with CSO Insights related summaries putting roughly three quarters of managers below the 5 percent mark.

The LinkedIn example is instructive. Their own time study identified that only 10 percent of manager time in the global sales organisation was spent on coaching. Their response was not to send an email encouraging managers to “coach more”, but to reset expectations and design the system so that 50 percent of manager time was allocated to coaching and learning.

Make it a norm, make it cultural.

Lack of practical coaching training

Many front-line managers are promoted for being strong individual contributors. They have learnt how to sell, but not how to develop others. Surveys and practitioner articles consistently note that while managers are told to coach, relatively few receive structured development in coaching as a discipline.

The result is a lot of good intent with very mixed practice. Some managers avoid the more challenging conversations. Others default to advice and instruction. Very few are given a simple framework that separates coaching from inspection and that they can use with confidence.

Discomfort with developmental tension

Effective coaching is not always comfortable. It involves surfacing assumptions, pointing out gaps in thinking, asking the questions that were not asked in a meeting and unpacking decisions that were made on autopilot. That means spending time in a space where the rep may feel exposed or uncertain.

Without a clear approach and a level of coaching skill, many managers feel that it is easier to jump straight to the answer than to sit with that discomfort and help the rep work through it. It is faster in the moment, but slower for performance.

Confusing deal reviews with coaching

Finally, deal reviews often get rebadged as coaching. There can be some overlap, but they are not the same thing.

• A deal review is about the health of the opportunity and what is needed to progress it.

• A coaching conversation uses the opportunity as a vehicle to improve how the rep thinks and operates more broadly.

Both are necessary. Only one builds capability.

The commercial impact of effective coaching

When coaching is executed regularly and well, its impact shows up across three main areas.

Revenue outcomes

The most obvious impact is on core sales metrics. Structured coaching helps sellers prepare better for meetings, ask better questions, qualify more rigorously, position value more clearly and manage internal buying dynamics more thoughtfully. The compound effect is higher conversion rates, better deal quality and more reliable forecasts.

Studies that look at “dynamic” or “formal” coaching approaches show double digit improvements in win rates and meaningful gains in quota attainment compared with organisations that rely on informal or ad hoc coaching.

In practical terms, a 10 to 30 percent swing in win rate on the same pipeline volume is the difference between hitting the plan and missing it.

Engagement and retention

The second impact is on people. Coaching is one of the clearest signals a seller receives that their manager is invested in their development rather than only their number.

Gallup’s work on engagement is not sales specific, but it does show that teams in the top quartile of engagement - typically those with frequent, effective conversations about performance and development - achieve significantly better outcomes than those in the bottom quartile, including around 18 percent higher productivity in sales, 10 percent higher customer loyalty and 23 percent higher profitability.

Engaged sellers are more likely to stay, more likely to grow and more likely to put in discretionary effort. In a market where hiring and ramping experienced talent is expensive and time consuming, that matters.

Managerial efficiency

The third impact is on the manager’s own effectiveness. Managers who coach well tend to see fewer surprises in the pipeline. Risks surface earlier because the team is trained to think more critically about their deals. Escalations still happen, but they are less likely to be the result of poor qualification or basic execution misses that should have been caught earlier.

Over time, this reduces the amount of rework and crisis management that managers have to do, and frees up more of their time for strategic activities such as planning, cross functional collaboration and deeper coaching. The productivity figures quoted around coaching - the 88 percent improvement when added to training - are not magic. They are simply the compounding effect of better decisions being made, earlier in the cycle, by more people.

What good coaching looks like

Good coaching is not mysterious. It is usually quite straightforward, but it is deliberate.

While every organisation will have its own language, three elements show up consistently in effective coaching conversations.

Clarity of focus

Good coaching sessions are specific. They are anchored on a particular meeting, opportunity, skill or behaviour. For example, “how you prepared for this executive meeting”, “how you handled the pricing conversation” or “how you engaged the economic buyer”.

This level of focus makes it possible to explore what they will do, why they choose a particular path or approach and what alternatives are available. Vague sessions that try to cover “how things are going” tend to produce vague outcomes.

Constructive challenge

The second element is thoughtful challenge. The coach’s job is partly to help the rep see what they may have missed - assumptions they made, stakeholders they ignored, questions they did not ask, signals in the account they did not pick up.

This does not have to be harsh. In fact, the tone matters a great deal. But there needs to be enough stretch in the conversation for the rep to leave with a different understanding than they arrived with. If the conversation only confirms what they already believed, it is unlikely to drive change.

Practice and application

Finally, good coaching includes some form of rehearsal or application. That might be running through how to open the next meeting, practising a pricing conversation, role playing a difficult stakeholder interaction or mapping out the next set of questions.

Without this step, coaching risks becoming a reflective chat. Useful for awareness but not anchored enough in changed behaviour.

A simple test is to ask, at the end of a session: “What will you do differently as a result of this conversation?” and then to revisit that in the next one.

AI coaching: a powerful accelerator, not a substitute

AI based coaching tools are becoming more common. Conversation intelligence platforms, meeting summary tools and systems that score calls or emails against a set of criteria are now part of many sales stacks.

Used sensibly, they are helpful. They can:

• Analyse patterns across a large volume of calls that a human manager would never have time to review.

• Flag specific behaviours, such as talk time balance, question depth or pricing language.

• Reduce the time managers spend collecting information by providing clean summaries and key moments.

• Give sellers faster feedback on certain aspects of their performance.

In that sense, AI can make coaching more informed and more efficient. It can help managers arrive at a one to one with a clearer view of where to focus. It can also help create consistency across teams by applying the same set of criteria to conversations.

What AI cannot do is the human centred coaching itself (yet!).

It cannot understand the individual seller’s confidence level or motivation. It cannot sense when someone is stuck because of fear, rather than lack of technique. It cannot judge the internal politics of a particular account or the subtleties of a relationship that has built up over time. It cannot build trust.

It can say “in this call, you interrupted the customer five times”, but it cannot sit with the seller and help them explore why that happened and what they might do differently in a way that lands and sticks.

The most effective use of AI in this space is therefore as an input to human coaching, not a replacement for it. The machine does the heavy lifting on pattern recognition and data. The manager uses that data to have better conversations.

From a Leaders perspective, the key is to be very clear on this distinction.

AI can sharpen coaching. It does not absolve leaders of the responsibility to coach.

Leadership recommendations

CROs and senior commercial leaders are the only people who can turn coaching from an occasional activity into a genuine norm.

Individual managers can make progress, but the structural levers sit higher. Make it cultural and set the expectation (and build the capability muscle).

There are five practical moves that tend to make the biggest difference.

1. Treat coaching as an expected norm

If coaching is as powerful as the data suggests, then it needs to show up explicitly in how manager time is allocated. The LinkedIn example - moving from 10 percent of manager time to a 50 percent expectation for coaching and learning - is one way of signalling that.

Not every organisation will land on the same number but setting a clear expectation and then removing some of the noise that gets in the way is essential.

2. Provide a simple, shared coaching framework

Managers need a practical, repeatable approach to coaching that is distinct from pipeline management. It does not have to be complex. In many cases, a few core questions and a common structure for opportunity, skills and development coaching is enough.

GROW works well. It’s simple, effective and highly adaptive.

The important part is that it is shared, so the organisation can build a coaching culture with a common language rather than twelve different interpretations of what coaching means.

3. Invest in manager capability first

If front line managers have never been shown how to coach, it is unrealistic to expect them to be strong coaches. Given how much leverage sits in their role, structured development for managers is one of the highest return investments most revenue organisations can make.

This can be internal or external, but it should be practical, connected to the real sales environment and supported, not just a one-off workshop.

4. Use AI and tools to support, not replace, coaching

Where AI or conversation intelligence platforms are in place, position them clearly as support for managers and reps, not as “automated coaching”. The value is in faster insight and better focus, which in turn make the human conversations more effective.

5. Measure capability as well as outcomes

Finally, keep an eye not only on win rates, bookings and pipeline, but also on the indicators that show coaching is happening and working - frequency and quality of coaching conversations, behaviour change in key skills, engagement and retention of high performers.

What gets measured tends to get attention. If coaching is not visible in any metric, it will quietly lose out to whatever is. And ask your frontline teams if they are receiving coaching and being supported form a capability perspective.

Essentially, coaching is not a nice to have. It is a commercial discipline that sits at the heart of how revenue organisations build and sustain capability.

You need to make it a cultural norm!