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The Outside Sales Coach

The power of the trusted outsider in high-value sales.


Ian H Smith

I would say that the most important thing about Sales Enablement is coaching. Let's take a look at why coaching matters in the high-value, high-touch sell, and in particular, why a trusted outsider can make a big difference to sales professionals.

Here are the five reasons I put forward for engaging an outsider in sales coaching:

  1. Atmosphere
  2. Motivation
  3. Performance
  4. Retention
  5. Knowledge

#1. Atmosphere

The atmosphere inside a sellside firm is the first thing a prospective buyer notices - forming an opinion based on how it feels inside the walls of the sellside firm's physical buildings or how sales professionals behave in online and face-to-face meetings.

In 'sensing' the atmosphere of the organisation, it is, to quote Colin Sworder in Developing Strategic Thought (1995), akin to asking 'can you hear the baby cry?' When the atmosphere in the firm is positive, everyone is 'tuned-in' to what is important - just like the mother, who hears the baby cry first - and above all other noise.

However, in the real world, sales professionals can find the pressure from management to deliver timely results an inhibitor to positive feelings, and unknowingly, may project their own fears onto a prospective buyer, when faced with a key moment in the buyer-seller conversation. This is where the friendly outsider, as trusted coach, can help the sales professional before they engage in a particular crucial stage of the buying and selling cycle.

As an outsider, it is easy to establish receptivity and rapport between coach and sales professional - in turn, leading to the trust that is crucial to both parties having those frank, yet unpressurised conversations that are crucial to effective coaching and learning. 

#2. Motivation

The late Sumantra Ghoshal talked about 'the pathologies of the inherited context': in plain English he went on to describe what this means in relation to what gets in the way of people's motivation to be genuinely innovative at work. This is the 4 C's: Compliance; Constraint: Contract; and, Control. What the outside coach in sales can do is overcome the worse interpretations of these four inevitable barriers, as challenges of everyday business life for the sales professional.

We must comply to the latest regulation, such as EU GDPR; we are constrained by the firm's budget; we sign an employment contract; and, say the buyside CIO controls the customer's IT systems. So, the 4C's are reality. But when the 4 C's are applied in an extreme way, it will have a corrosive effect on our motivation, as sales people seeking engagement with empowered buyers.

So, we need to counterbalance the 4 C's with 'the 4 E's': Empowerment; Empathy; Education; and, Earnings. And the last 'E' is not enough, if the other 'E's' are not apparent: money alone, is not a guarantee of employee motivation in the knowledge-intensive firm. Let's take a closer look at the '3 E's' that matter most to employee motivation:

Empowerment. If each sales person can be a sales coach too, then this is no longer about hierarchy, but capability. Everyone can learn, and everyone has something valuable to teach or share. If the outsider starts the sales coaching programme, it will inspire others on the inside to follow, across all roles, not just sales. It will give a true sense of empowerment to all employees. This means that the outsider embeds coaching as a way of life for everyone in the buyside firm - not simply the one-way conversation between coach and sales professional.

Empathy. Just as designers - or more broadly, Design Thinkers know, empathy is the key building block for building a foundation of trust between buyer and seller. It is the way people get to to talk and act truthfully. Empathy Mapping means seeing the other person's perspective - and in turn, this leads to creating buyer-seller receptivity, then rapport - and finally - and most crucially, trust. The sales coach can teach Design Thinking and Empathy Mapping as a powerful way to enable Mutual Value Discovery to counter the barriers of arm's length procurement mechanics in the high-value, high-touch sell.

Education. For many years, business schools have talked about creating a 'learning organisation' culture. This is based on the original thinking of Peter Senge at MIT Sloan School of Management. At the heart of this thinking is 'team learning': enabling knowledge and wisdom to flow across boundaries and with openness at its heart. As we enable boundaryless, open coaching in sales, it is appropriate here to mention the late Chris Argyris, Professor Emeritus at Harvard Business School, and his idea of moving from 'single-loop learning' to 'double-loop learning'. Double-loop learning is contrasted with single-loop learning: the repeated attempt at the same problem, with no variation of method and without ever questioning the goal.

#3. Performance

The truth about productivity in the knowledge-intensive firm is that we rarely think beyond the mechanics of financial measurables. Of course, the numbers and money matters, but so too, does the 'softer' things we can all do in business, This means things that have both a direct and indirect or positive impact on these tangible measures in the firm.

As Kim Scott argues in Radical Candor, before managers look at 'results' they need to, firstly, provide 'guidance', and then, secondly, enable 'team-building'. Clearly, coaching from an outsider can have a profound impact on these two steps in sales - leading to the measurable value outcomes. What Scott argues for is creating a culture of open communications; to 'get, give and encourage guidance'.

For guidance also read coaching - and in a non-hierarchical way - crossing boundaries and with an openness that supports the measurable value outcomes attributed to 'collective intelligence' supporting sales professionals. In knowledge-intensive firms, time is not something you can warehouse - it is an instantly perishable asset.

So, in a digital agency or management consulting firm, for example, when it comes to measuring billable hours against utilisation of people - it is clear that coaching beyond sales, and across organisational boundaries can greatly enhance the results here, where skills and knowledge become more transferable - hence, utilised more across ever-changing billable people hours environments. Hence the role of the outsider in sales coaching can go beyond the traditional boundaries of the sales organisation to many other areas of the organisation where people have key 'ProofPoints' or 'DecisionPoints' with buyers and influencers.

#4. Retention

The ability to retain great people obviously relates to the three points above: Atmosphere; Motivation; and Performance. The first three 'E's': Empowerment; Empathy; and, Education - are clearly related to employee loyalty and low churn rates. And whilst I have not made much about it in this post - the 'fourth E' - Earnings - is also another common sense factor in employee retention.

Coaching is a great way to underpin the 'sense of belonging' that features in all of these points about employee retention in sales. As we move away from the paternalistic incentives of final salary pensions, and as the notion of the long-serving 'organisation man' disappears, then employee retention is, of course, a relative measure today, compared to the distant past.

However, rapid churn is something that all managers in knowledge-intensive firms know comes at a very high-cost. So, by introducing the outside sales coach - starting as engagements in the field with sales professionals - employee loyalty will clearly go up.

#5. Knowledge

As discussed in the third 'E' - 'Education' - by introducing coaching in the knowledge-intensive firm, we move towards a 'learning company' culture, where 'double-loop learning' is contrasted with 'single-loop learning': the repeated attempt at the same problem, with no variation of method and without ever questioning the goal.

Once we introduce goals into learning, we make coaching in sales highly purposeful: it becomes a way to harness measurable 'collective intelligence'. In turn, this has a tangible impact on 'hard' business values - such as increasing people utilisation and therefore, maximising billable hours.

This means that the trusted outsider, as sales coach, must engage at crucial moments in the buying and selling cycle, ensuring that learning is accomplished in the context of real world scenarios and buyside decision-makers and influencers.  


Coaching is something that all senior executives can agree on: it is a good thing. But when considering the five compelling reasons for coaching, it will not happen unless the CEO and other senior executives empower the outsider, free from politics or the hierarchical 4Cs: Compliance; Constraint: Contract; and, Control.

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