Why Most Field Sales Coaching Initiatives Fail

And what sales leaders can do about it!



Unpopular opinion: Most Sales VPs and CROs talk a good game when it comes to sales coaching, but few really commit to making it work, and even fewer actually succeed.


But when you get it right, the ongoing gains in productivity and performance can be enormous.


Here are the four main reasons we see coaching initiatives for B2B field sales teams fail, and some practical advice on making it work for your team.


1. Sales leadership based on pipeline alone

Most big problems in sales tend to start at the top.

The single biggest gap we see in sales leadership approaches is for VPs of Sales to manage by the numbers alone (quantity without quality).

If you’re running a large team, it’s obviously critical to be across your larger opportunities, pipeline, pipeline velocity, stalled deals and forecasts. After all, you’re ultimately there to deliver the revenue and margin.

But if that’s all you’re looking at, you’ve got two big problems:

  • You can see what and when, but not why? It’s difficult to diagnose problem areas if all you’re able to see is a low win rate or poor quota attainment.
  • You’re mostly looking in the rear-view mirror. Pipeline, after all, is really a snapshot of current status – in other words, what’s already happened. And the forecasts are only as good as your sales team’s ability to execute client meetings well and uncover the real position for their major opportunities – otherwise it’s garbage in, garbage out.

Unfortunately, Power BI won’t save you.


Pipeline data by itself will tell you that you have a problem, but it won’t tell you what the problem is.


If you can’t access data that helps you answer simple questions like “which of my front-line managers knows how to coach?”, and “what’s the quality of our client-facing engagements across the team”, your performance management will often fall back on whipping the team harder, demanding more activity, or a constant cycle of firing the underperformers and then re-hiring.

💡🌟 TIP 🌟💡

Invest in CRM tools that give you drill-down visibility to the quality of work on the front line – planning for major accounts, major meetings and major deals. This drives discipline and accountability, and lets you spot problem areas earlier than relying on pipeline (financial metrics) alone. Here’s one

VP of Sales - Hard turn to hit this quarter's numbers

2. Misunderstanding the role of a great front-line manager

This one is simple, but frequently overlooked.

Most VPs evaluate the effectiveness of their front-line managers overwhelmingly on one metric – do their teams hit their numbers? Again, this is critical, but leaves an important question out:

Can my managers increase the productivity of each member of their team over time?

The vast majority of untapped sales performance in complex sales comes from increasing the capabilities and skills of the “middle class” – the mid-performing sales reps who make up around 60-70% of most sales teams.

Great managers can identify specific capability gaps and coach these reps away. Poor managers never unlock this capability – they can coach deals, but not people, leading to both lower productivity, and higher churn.Your timeframe as a sales leader also matters. There’s always a trade-off between this quarter’s performance and that of the next few quarters – if you tell your front-line managers to drop everything at the end of each month to “go close”, they’ll do just that – go back to being a player vs a coach, at the expense of building capability.

Even your managers who know how to coach will be forced to switch back to co-selling – which might help save this quarter, but won’t help your next quarter, or the quarter after that.

💡🌟 TIP 🌟💡

Focus your Front-Line Manager KPIs not just on revenue, but on productivity growth (revenue growth per rep). Shift your focus as a sales leader beyond this quarter. Signal clearly the importance of this by allocating some, perhaps 15%, of the front-line manager commissions on driving productivity of their team, not just on total revenue.

3. Undervaluing client-facing execution

Distilled to its simplest, building an effective sales organization requires three main things:

  • Strategy – the big picture stuff – defining ideal customer profiles, pricing, customer segmentation and your go-to-market,
  • Planning – day to day management including opportunities, territories and forecasting,
  • Execution – the skills and capabilities of the team.

Many VPs over-invest in planning and underestimate the importance of sales execution skills. They assume that “my team knows how to sell”. If they hire salespeople with 5- or 10-years’ experience, they assume that some product training is all they will need to be effective.

This is often a dangerous assumption.


If you’re targeting the right accounts, the speed of your pipeline is driven overwhelmingly by your team’s ability to execute their big client-facing meetings well. And this is where we often find massive gaps.


When we video-tape realistic meeting simulations as part of sales or negotiation training, we find significant gaps in even the most experienced salespeople, including:

  • A lack of intentionality – entering a meeting without a clear outcome (“Advance”) in mind,
  • Lack of confidence to set an optimistic agenda with the customer,
  • Subservience to the client vs engaging as a peer and equal,
  • Product-focus vs client pain-point focus,
  • Poor listening skills and the inability to pick up “tells”,
  • Failure to capture and monetize client value,
  • Unwillingness to make proposals early enough,
  • An inability to defend pricing, with unnecessary discounting the usual result, and
  • Hurried and ineffective meeting ends from a lack of time management in the meeting.

These gaps are eye-opening and sometimes even shocking to most Sales VPs. And in many cases, it’s also shocking to the front-line managers, who should be fully aware of the gaps from their field travel.

To quote Warren Buffet, “It’s only when the tide goes out that you can see who’s been swimming naked”.

💡🌟 TIP 🌟💡

Invest less in product training, and more in sales training that surfaces skills gaps (preferably with realistic video-taped simulations like this one). Don’t assume that 10 years of selling experience means your team knows how to sell.

4. Inadequate front-line manager coaching tools and training

The transition from an individual contributor to a front-line sales manager is one of the hardest ones in sales. Unlike, say, moving from mid-market to enterprise sales, or from a VP to an SVP, this transition is not incremental – it’s an almost completely new skillset.

Yet most VP Sales under-invest in their front-line managers. The initial promotion to a manager often comes with a day or two of training, often delivered by an internal learning and development team that hasn’t sold anything in years. There’s a lot of focus on pipeline and forecasting, but little effort invested to ensure they have the skills to build team capabilities.


Most new managers don’t even leave the training with even a basic understanding of the difference between feedback and coaching – and many never learn.


Great managers need more than this. At a minimum, effective manager training needs to include:

  • How to use call plans, account plans and field travel to identify problem areas early,
  • Advanced listening and observation skills (to diagnose gaps in their people),
  • Coaching people vs coaching deals (and the trade-offs involved),
  • How to segment their team (train vs coach vs motivate) and adapt leadership style accordingly,
  • How to set and maintain pre-rep coaching cadences (what we call “closed loop coaching”). 

And you need to give them the tools to manage coaching as a process, integrated with your CRM. Paper-based tools and email and excel files blow away with the breeze, and provide almost no accountability.

💡🌟 TIP 🌟💡

Deploy quality planning and coaching tools into your CRM like this to drive the right mindsets, cadences and behaviors from your front-line managers and their reps. Deploy a robust pre-call planning process for big meetings – it’s not only one of the best ways to lift productivity, but feeds an evidence-based competency assessment process for your managers so they (and you) can spot problems early.

Summary – Here are four ways to give yourself the best shot at driving sustainably higher performance from your team:

  • Don’t performance manage on pipeline alone – it’s a trailing indicator. Build or buy CRM tools like this one that give you visibility to the quality of work on the front line, so you can spot problem areas early and drive discipline and accountability on your front line.
  • As a sales leader, measure and track not just revenue, but productivity growth per rep. If your managers know you care about this, they’ll invest the time and effort to coach their people, not just the deals. Scalable growth comes from moving your reps beyond being “super-reps”.
  • Invest less time in product training, and more in selling skills and business acumen training. If possible, use highly realistic video-taped simulations to surface skills gaps you probably have but may not be aware of. Don’t assume that experience = sales capability.
  • Support your (new and experienced) managers with quality coaching training, and turn it into a workflow with effective CRM-integrated planning and coaching tools like this one.

If you need advice on any of this and would like a confidential consult, contact us.

Good selling!!!


Explore more insights:

Blog: Sales Coaching Software Evaluation Guide 

Blog: Sales Performance Coaching

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