The Onboarding/Enablement Gap

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One stumbling block in sales organization – and it affects startups to tech giants is a lack of cohesive onboarding and sales enablement. One of the triggers of the Great Resignation is in part due to the fact employees don’t feel empowered to do their jobs effectively. While pay and quotas are the number one driver in mass exodus – I’d argue the second top motivator for shifting a job is lake of enablement.

The definition of sales enablement: the activities, systems, processes and information that support and promote knowledge based sales interactions with clients and prospects. Enablement provides employees with the most effective tools and content to sell more effectively.

Harvard Business Review reported that in 2016 359 billion dollars was spend on training and enablement, but despite the investment the enablement failed. 70% of employees reported they didn’t have mastery of skill and only 12% who were surveyed applied what they learned to the job. HBR states that “not only is the majority of training ineffective, but the purpose, timing and content is flawed.”

With businesses investing so much in onboarding and enablement – why is it so ineffective? Where is the gap?

I think this is a loaded question and obviously depends on the organization, but several themes I’ve noticed from speaking with workers is:

  • Little investment – some businesses don’t want to spend money on training. It might be because they are genuinely trying to scrape by – learn by walking through fire approach; or perhaps they just don’t know how to get started so nothing gets done.
  • Strong investment but no purpose and follow-up. Companies can invest all the money in the world in training, enablement and other tools (software, systems…) but if they don’t have the organization structure to back it up then the training will fall short.
    • Ex: company buys the best onboarding software and loads it will lots of cool videos and tests. They instruct the new hire to go through the training videos. This is a good step, but without follow-up training it will fall flat. Repetition is key. Adults learn best by doing – and I’m not talking throw you in the fire with no gear- learning by doing with actionable steps. Live training paired with on demand. The ability to shadow and practice. There are all sorts of ways to engage your hires to learn – but just having them watch a video once and forget it is ineffective
    • They don’t use the technology they pay for or don’t training employees on how to use it
  • Irrelevant training: How many sales orgs roll out the latest new methodology but have no sense how it pairs with the product you sell and your industry. You end up spending hours learning a new system of sales that doesn’t apply or managers don’t plan to execute.
    • Following up with ‘Failure to put a sales methodology in place that is aligned with defined business goals.
  • They have a sales methodology in place, but don’t back it up with sales knowledge
    • As sales people it is important to learn about best industry sales practices – be it SPIN,MEDDICC, BANT…How to Prospect…we need to know it and can benefit from it. Good discovery and the ability to follow sales methodology is key! However, you will NEVER close sales consistently if you do not know your product and understand the product value. You will build good discovery – but won’t have the ammo to close down the sale.
    • So many companies hire tenured sales people, give them a book and say okay ‘sell’ – but companies need to provide their employees with ongoing product knowledge so they can truly maximize the selling potential. Otherwise clients and employees get frustrated and the company bottom line suffers.

I recommend this great article by the RAIN group.

I wanted to put these thoughts into writing because I am a problem solver and I want to go in and help organizations improve processes – this improves the bottom line, customer and employee retention.

Onboarding Tips:

I genuinely believe most onboarding and sales enablement teams are trying to provide the best training they can – but many have unrealistic demands on them and limited bandwidth. This is so frustrating for trainers who really want to provide the best employee experience so that drives sales in the greater organization.

One tip that consistently comes from conversations with sales people in the field is around several key points (a few mentioned above)

  • Failure to build knowledge of product and how to prospect specifically to that product
    • Fix: everyone learns differently, but engaging new hires and long term employees in the content is critical. Videos and self-paced learnings are helpful, but need to be paired with live interactions – one on one/small group sessions, shadowing, targeted trainings on pricing, prospecting and product knowledge
  • Too much content at one time – information overload when you first come into a company/new role is par for the course, but it is important to prioritize the training based on immediate needs and stagger it to ensure information is retained. Repetition is key here – so repeating content on key company product drivers for sales is okay. Information needs to be put into actionable steps so sales people listen to learn and learn to comprehend.

Employee Side:

Unfortunately many organizations don’t want to listen or do not have the bandwidth to accomplish their goals. In these situations employees have to find ‘water in the desert.’ When your sales enablement and onboarding is leaving you hanging – mindset becomes key.

It is okay to admit you are frustrated. Make a list of the issues with the current set-up. Don’t be afraid to offer feedback, but if it is falling on deaf ears – don’t let that prevent you from giving your all to the job.


  • Mindful that onboarding/training/enablement is difficult – give yourself permission to be frustrated but let it go. Ask yourself what can I do on my own to improve and learn. Think ‘If I were in charge of enablement – what would I want employees to learn. How would I teach it?’ Figure out resources where you can gather the information work to create your own training schedule.
  • Don’t be afraid to ask for help. Loop in seasoned employees to help you understand processes and learn what has made them successful. Also ask them what hurdles they have faced and how they overcame them at the company
  • Speak with current customers about how they use the product – they can be a huge source of information. (Be conversational and curious – they love to talk about the business and the product with you.)
  • Think about your why and tie that motivation back to your job. Be curious about your product and how you can help customers. When you have a why driving your focus to overcoming the challenges
  • Search for relevant webinars geared towards customers and marketing content – this is a good way to learn more about your product and customer base
  • Remember – you will eventually gain mastery at your job – even if you don’t have training and consistent enablement (seasoned employees) – it just is a bigger climb. The feelings of being lost in a storm without a compass will fade and you will end up crushing your goals with persistence and positive focus

What other tips do you recommend from the field?

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