Sales training: A missed opportunity

The big Q1 kick-off is over: Now what?

Once a year your sales team will gather to chart out its focus areas, raise morale, ensure teams are clear on the strategy, and generally map out the year ahead. The timing and scale vary by company. At larger companies, for example, a destination off-site with marquee speakers may be involved, while at smaller ones, it’s a more low-key affair. Rapidly growing startups and scale-ups may not hold any kick-off at all, even though they may arguably need them the most (as often as every quarter). SaaS companies operating on a calendar fiscal year will usually hold their kickoffs in early Q1. And for media-driven businesses, many will convene in late Q4, ensuring the team is ready to hit the ground running in the new year. 

In each of these scenarios, there are a few common threads. This is typically a special, once-a-year opportunity to get all sellers and possibly client-facing teams in one space, which is why many companies incorporate some form of formal sales training into their kick-off activities. Everyone agrees that this sales training is a crucial investment, and the typical company spends thousands of dollars per employee to help them hone their skills. But across the board, regardless of industry, sales training often misses the mark. 

While it makes sense to use this one-time, centralized event to upskill sales teams, this strategy is rife with challenges: 

  • Retention: It doesn’t stick. Between 85% and 90% of sales training has no lasting impact after 120 days, according to ES Research, a digital marketing company. As a result, continuous training that reinforces learnings makes more sense. 

  • Focus and scope: You can only do so much in a day or two, so companies tend to focus the kick-off training on new business and hunter-type roles, while leaving out specific paths for other client-facing teams such as account management and client success. The one-size-fits-all strategy means the sales training won’t be relevant or useful for everyone. 

  • Timing: New year kick-offs often focus on introducing new products and training teams on the messaging and go-to-market (GTM) strategy. They typically can’t predict and therefore address potential problems and market pushbacks.

  • Intention: Kick-offs are meant to excite and energize teams, and they mostly focus on the positive aspects and highlight perceived strengths, without addressing challenges and weaknesses.

  • Team growth: Holding these kick-off and sales training events once per year means new members will miss out if they join the company later. Even if the event was recorded, new team members are still being onboarded with dated materials.  

Despite these challenges, everyone agrees that sales training is important and crucial to the success of any business. US companies spend around $15 billion each year training sales employees, averaging $2,236 per salesperson on annual training, according to the LinkedIn State of Sales report; the amount varies greatly by company size and industry, and we see anything from $500 to more than $5000 spent per employee on sales training. 

In spite of a relatively high level of investment, sales training has been remarkably resistant to change and adaptation. It overwhelmingly remains a one-off event at the start of every year with a curriculum that is predictably one-dimensional, without accounting for different modes (e.g., sales process or value selling), subject matter expertise (e.g., selling programmatic vs. to a specific vertical), or seniority levels (executive vs. management vs. individual contributor). It unfailingly takes a one-sided view, so if it centers on the GTM strategy, for example, an outside-in view will be missing. The broad-strokes approach can’t be customized to individual needs, so forget about feedback for trainees on how and where they can improve further.  

Why is sales training so ineffective? One reason may be that it often takes on a very compliance-first air, meant to be checked off of a professional development checklist. But since there often isn’t much new material presented, you won’t learn much by hearing the same material and frameworks over and over again. For example, if your previous company trained you on value selling, how much will you learn from another value-selling course taken during your current role? Most experienced sales people phone it in (and the employer wastes valuable training money on non-differentiated content). 


In sales training, most programs in market today address one of these three focus areas:

Sales techniques: This is the basic level, where the main goal is how to be a good seller. These programs usually cover sales techniques, process, methodology, tools used, etc. Many are presented as general guidelines, tools, and tips, and they are typically illustrated by a company-specific use case developed by the training company and sales leadership. They are usually evergreen across industries. 

Industry/vertical mechanics: This is the specialized level, where the main goal is how to be a subject matter expert. These programs typically do a deep dive of an industry-specific topic (i.e., how to think about programmatic advertising for media sellers) or a specific vertical (i.e., how to sell to the financial vertical). These are often geared toward individual teams and are designed to quickly get most people up to speed on specific topics. 

Operational excellence: This type of training – though rare – would be aimed at coaches or leaders, where the main goal is how to effectively work inside an organization. When we think of sales, companies tend to spend most of their time training the teams on outward-facing skills. A crucial set of skills to develop for any client-facing organization is really how to work effectively internally across teams. Since the internal team members don’t shift as often as client teams, these trainings typically involve internal cross-team assessment and communication styles. 

Instead of a one-off yearly event with a one-sided approach, companies should shift into a less tactical, more on-going approach akin to sports coaching. It can range from basic technique that would be needed to compete in a given sport to specialized training for a specific role or category, similar to training for  a basketball point guard or playing tennis on a clay court. A third level of training focuses on coaches so that they can successfully lead their teams, work effectively with others, and build cohesive staffs. 


A better way

Sales training can be so much more. It needs to be: 

  • Comprehensive: Ideally, sales training can combine what a team needs from foundational sales techniques, specific topical expertise such as challenger or value selling, and scenarios that arise in a company’s own day-to-day operations. It shouldn’t be duplicative, so companies should first ask sellers what types of coursework they have taken in earlier roles or independently. Training shouldn’t always solely focus on new business, and companies should consider whether it will be useful for account management and customer success teams. (If not, can relevant training be created?) While very important, most companies hand off their prized new logos to account teams that are not incentivized or armed with the right tools and approach to grow the account as aggressively as they were hunted. The hunter vs. farmer analogy comes in handy here: While most sales teams think of farmers as those who “tend to the land,” the key here is enabling teams to be proactive as opposed to reactive. If you’re planting a crop this year, what should you be thinking about next year? A different approach to training is required to shift from a reactive mode of waiting for client needs, to a more proactive approach of actively driving the account toward desired business outcomes. 

  • Ongoing: Instead of a flashy workshop once a year that is old news to many sales team members, teams need to be supported and learn and grow throughout the year with ample opportunity for course-correction. As 2020 showed us, the world can look quite different in a matter of months. Priorities change, challenges arise throughout the year, and you may end the year with an entirely different book of business. Continuous training can be crucial to company goals. Not everyone is meant to be a manager, so companies should take a continuous approach to building out a sustainable view of career pathing and how to grow and incentive their best individual contributors. 

  • Actionable: It’s critical to connect sales training and strategy to the day-to-day execution. Sales training could go so far as to provide analysis of prospect feedback or identify how to navigate and grow a seller’s influence map across a client’s organizational chart. These types of activities often fall under the purview of sales managers, who may easily miss wider trends or lack a critical in-market view. Coaches need coaches too. 

  • Multilevel, differentiated learning paths: From individual contributors to first-time managers and seasoned sales leaders, different levels in the sales organization have different needs. Managers, for example, may need to learn new skills and elevate to help their teams, while executives will likely need operational excellence support to improve their organizational structures, set-up, tools, quotas, and cross-team compatibility. Without good support for the manager and executive levels, no amount of stellar individual performers will be able to deliver on overall goals and ensure low churn. 

For companies, the biggest payoff from investing in effective sales training programs is low churn: Replacing sales people is, by definition, a costly affair. On average, you should account a quarter for ramp-up (possibly longer for complex sales or long sales cycles). This means you likely won't spot a poor performer until two or three quarters later by that time your sunk cost isn't just their base salary but the revenue they didn't generate. For smaller companies, with less than $10 million in revenue, a poor sales hire can quite literally put you out of business. It takes time to replace an underperforming hire, and time in sales-team parlance means revenue. 

When employees feel like they have partners that will help them succeed, they have fewer reasons to leave. Sales managers will also know faster if their teams are struggling with their quotas, and if they are, that will be easier to address. Critically, if a company’s client or  management team can shift from a reactive to a proactive approach, they will develop a deeper understanding of their customers’ needs, deliver better service, provide customer feedback to the company, and more aggressively pitch and acquire new business. That can only give companies a competitive edge and drive revenue growth and efficiency. 

Chances are that you are going to invest in a sales training program anyway. Can that five- to six-figure budget that is spent on kick-off training be better deployed throughout the whole year? We think so. 


One question

How do you measure the efficacy of various training efforts, especially if your kick-offs feature similar topics year after year?


Dig deeper


Thanks for reading,

Ana & Maja

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