Sales Performance Coaching

Best practices for building sustainable “sales muscle” in your field sales teams


The Sales Managers’ Dilemma

Most sales leaders recognize the importance of front-line manager coaching to sustainably increase sales rep productivity. The best front-line managers are good sales coaches first, delivering faster onboarding of new hires, higher quota attainment for the mid-performing salespeople, and higher retention / lower churn of their top performers.

With 6-10 direct reports and a typical AE quota in complex B2B sales of $1M-5M per sales rep, a great manager can build a high performance team quickly and add millions of dollars of incremental revenue compared with a mediocre one.

Yet most managers struggle to become great coaches and sales leaders. They are usually promoted because of their effectiveness as a salesperson, but remain “Super-Reps” – able to coach deals, but not people.

The most common reasons are:

  • Poor quality manager coaching programs and mentoring for newly promoted managers,
  • A lack of simple, CRM-integrated coaching tools to help establish and manage coaching cadences, and
  • A lack of genuine interest and focus by sales leadership (CROs and VP Sales) on coaching as a critical part of the sales manager role, forcing managers to drop everything to “push deals” across the line at the end of each month and quarter.

In this article, we’ll discuss sales performance coaching as a process, and provide advice on best practice methodologies and sales coaching techniques to accelerate team performance – all while hitting this quarter’s numbers.

Let’s dive in.

Understanding effective coaching as a process

Every sales organization has some form of sales cycle or process – the “funnel”, essential for managing pipeline, forecasting and performance management. Every high performance team can describe their sales cycle – its drilled into everyone’s brain through most sales training sessions and reinforced with the monthly opportunity forecasting cycle.

Every manager knows what their sales process, or funnel, looks like – but what about their coaching process? Ultimately it’s the skills of your front-line salespeople, driven by the coaching skills of their managers that drives (or limits) your pipeline velocity



But if you ask a group of sales managers to describe their sales performance coaching process, you will rarely get a good, consistent set of responses. Many managers, if they can answer at all, will describe “deal coaching”. You’ll often hear about weekly 1:1 in-person check-ins on open opportunities and advice on next steps in the sales strategy. For a “Super-rep” sales manager who was a great individual contributor but now finds themselves leading a team, this can become a “comfort zone” from which they never graduate.

But this deal coaching is often in the form of advice (“Here’s what you should do next”), which rarely builds effective sales “muscle” (know-how and confidence) in the sales reps. It’s like going to the gym and asking the instructor to lift weights for you.


Consciously or not, your best managers learn to coach people, not just deals.


Ultimately the skills of your reps sets the limit of your pipeline velocity. Consistent sales performance requires strong sales skills across your team, which requires skilled coaching from your front-line managers.

Successful sales teams implement a process for sales performance coaching, targeting each salesperson, not just their opportunities. Just like a good sales funnel, it doesn’t need to be complicated – it just needs to be embraced and followed. Here’s a simply framework for what we call “Closed Loop Coaching”.

  • Credibility First. Just like in selling, credibility and trust is a pre-requisite gaining the buy-in necessary for effective coaching. Managers should explain the purpose of their coaching approach to the team, the benefits, what metrics are important to sales leadership, and provide confidence that this won’t be a short-term initiative.
  • Observe and record competency gaps. Good leaders will devote time in the first couple of months to observation of each sales rep in action. Reviewing a rep’s account plans, pre-call plans and observing customer meetings on field travel provide the best, objective basis for competency assessment.
  • Segment the team (Tell, Coach, Motivate) Good leaders segment their team members by competency level, and adopt the right leadership style for each person as part of an individual coaching plan.




We like the simplicity of this segmentation:

  • Tell – A directive/teaching style suitable for onboarding, initial sales training and any reps being managed for underperformance.
  • Coach – A questioning style designed to elicit answers from the coachee themselves. This style will generate the biggest lift in rep performance, but is also the single biggest skills gap we see in new (and many experienced!) front-line managers.
  • Motivate – Suitable for top performers. Little coaching is needed; instead focus on setting optimistic goals, clearing internal obstacles, and encouraging “osmosis” to others on the team through joint sales calls and mentorship.
  • Day-to-Day – Coaching Deals. This is the regular weekly management process of updates, forecasting, strategizing on opportunities, joint calls and field travel. Most managers gravitate to only coaching deals, but the best ones use this process to make and record observations of any competency gaps of each team member that might be holding back performance of the individual.
  • Monthly/Quarterly – Coaching People. With competency and skills gaps identified, a slower cycle of semi-formal one-on-one coaching sessions can be scheduled to agree competency and revenue goals, and plans to achieve them.

The highlighted feedback path is the missing link in many sales organizations. By closing the loop to create a sales coaching process – with competency observations in real time, action plans to drive behavior change, and regular follow-up – you build an engine that can build sales muscle while the team works.

The GROW Framework for Effective Coaching Sessions

Inexperienced managers can find coaching conversations awkward and unproductive. We often see managers pivot almost immediately to a TELL (advisory) style with “What I would have done is…” or “I think you should…”, which for a reasonably competent rep becomes tiresome pretty quickly.

There are a number of good coaching models and methodologies that can help managers to structure these coaching sessions better, including OSKAR and WOOP, but we like the simplicity of the GROW model:

  • GOAL – Agree the goal including timeframe and measurable outcomes.
  • REALITY – Review current-state, and surface any gaps and hurdles to success.
  • OPTIONS – A conversation to explore different ways of achieving the goal.
  • WILL / WAY FORWARD Agree the plan including any resources and support needed and check-in intervals.

GROW can be used in a quick, casual conversation, such as planning for an important sales call, or debriefing one afterwards. For example, after a difficult sales call:

  • “What was our GOAL going into this meeting?” —> ideally there was an agreed call plan.
  • “How did we actually go?” —> To objectively surface gaps between the GOAL and the REALITY. This forms the basis for a constructive coaching dialog to follow.
  • “Can you give me a few OPTIONS for next steps” —> This allows the rep (Coachee) to consider their own solutions, rather than the manager giving them.
  • “What WILL we/you do next?” —> agree the way forward.

The GROW framework can (and should) also be used in a more formal setting such as a quarterly coaching session to agree performance and capability development. It should still be conversational, but you should record the main points of the conversation for both parties to review and check in on progress later.

Optimizing the Coaching Process for Sales Managers


In-line Real-time Competency Observation

The best coaching is evidence-based and objective. Gaining buy-in of a coachee requires that they can understand the gap between current and desired performance. An inexperienced manager will often provide feedback based on “their gut” – the best leaders will be able to share specific examples.

Define a Simple Competency Framework

It helps to have all your managers aligned on “what good looks like”. Yet most enterprise sales teams lack a competency and skill set framework. Many have one, but it has been developed by HR rather than the sales enablement team and your sales leadership – these are often far too complex to be useful.


Don’t overthink it, and don’t allow the perfect to become the enemy of the good.


A good B2B salespeople (whether they are selling into small-medium businesses, mid-market or enterprise) will all exhibit the following:

  • They understand their policy constraints (regulatory, pricing, territory).
  • They understand not just product knowledge (yours and the competitors) but also the value propositions that different stakeholders care about.
  • They can manage their CRM effectively, including reasonably accurate forecasting.
  • They can manage their territory and the major accounts within it. (In simple terms, they are pointing at the right people in the right organizations, willing and able to chase the biggest prizes).
  • They have the sales skills they need to engage the right stakeholders effectively, from users to procurement to the C-Suite. Think of this as the ability to plan for, and execute, important sales meetings that ultimately move the needle on a complex sale.

Your managers’ competency observation process can then be directed at these “buckets” of competencies for consistency.

CRM Integration

We see far too many sales organizations use their CRM as their “system of record” for everything – except for coaching! It’s either done on paper, which blows away, or it’s redirected to a separate mobile phone app, which is disconnected from the rest of your sales force data.

The benefits of sales coaching functionality tightly integrated into your CRM are enormous:

  • Managers and reps can stay “in their workflow”, with records retained within the CRM, with sales coaching tips available in the moment.
  • The best coaching software incorporates account planning and pre-call planning as a “feed” into the competency assessment process and the coaching engine. For example, sales managers can review a pre-call plan from a sales professional, provide feedback to the rep, but also make competency observations to support coaching conversations later.
  • Competency observations can be tracked in software so that the managers don’t need to remember anecdotes when it comes time for a one-on-one coaching session.
  • The software can provide follow-ups and reminders through the CRM to help maintain coaching cadence and discipline.
  • Coaching records are retained, with sales leadership having drill-down visibility to the entire coaching process, driving accountability and discipline across even the largest sales teams.

Training Programs and Mentoring

We have strong views of sales training. (For example – https://swaggersales.com/why-most-sales-training-is-a-waste-of-money/)

The most effective sales training programs have the following characteristics:

  • Less focus on product, more on “big meeting” selling skills, expanded value propositions and on your customer’s businesses and problems.
  • A bias for investment purposes towards your front-line sales managers who ultimate drive the medium term productivity of their reps.
  • Make it a process, not just an event. New sales managers have to learn a very different set of skills to those of an individual contributor; typically we’d recommend monthly check-ins on to refresh training content and address any challenges, along with the allocation of a mentor who can provide discreet “just in time” advice.
  • Create a workflow so it becomes part of their DNA after the training. For coaching, the use of pre-call plans, account plans, negotiation plans to feed competency assessment is a game-changer (See above on the benefits of tight CRM integration).

Sales Leadership Messaging and KPIs


Supporting Coaching from the Top

The last issue is extremely common, and perhaps the most important.

Sales leaders clearly have a critical job to hit their numbers every year, every quarter and every month. But we often see a significant friction between this quarter’s numbers, and those of the next quarter, and the next, and the next…

Many sales managers’ “comfort zone” remains selling, not coaching. And if every month-end there is a decree from the CCO, CRO or SVP of Sales to “drop everything and close deals”, many of managers flip instantly back into salespeople because the short term win rate becomes more important than their team’s capabilities. They start pushing deals themselves. And this effort comes at the expense of observation and coaching – which will negatively affect next quarter’s numbers.

Here’s a scary thought. Most sales managers with 8 direct reports can invest only around 3% of their time into each rep (for field travel, reviewing plans and so on). So if the 3% of time together is spent with the manager leading the calls instead of observing, they cannot surface the competency gaps of the salesperson. And that gap is then applied to the other 97% of that rep’s time when the manager is not in the room.

Here’s another scary thought:


Many enterprise teams suffer from the 80:20 rule – 80% of revenue comes from the top 20%. That means that there is a 16x productivity gap between the top performers and the rest. Without good manager coaching skills, you’re unlikely to unlock that massive productivity potential that exists in your “mid-performers”.


Of course there will always be quarter-end pressure. Wall Street dictates it (and it’s getting worse each year). But sales leaders need to ensure that this cycle of urgency doesn’t come at the expense of coaching time for the team.

Optimizing Sales Manager Remuneration

The simplest way to do this is to align incentives. The best sales leaders clearly message the importance of coaching – not just verbally, but through the design of their front-line manager KPIs and incentives. These should track more than just revenue; some of the comp plan should be directed at the managers’ ability to credibly assess the strengths and weaknesses of each team member, and to coach the gaps. The best sales manager KPIs also reward not just total revenue, but productivity per rep. This rewards the managers who can fix the 80:20 rule above and bring the middle of the pack closer to the top performers.

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