In the world of sales, the competitive landscape has never been more cutthroat and as such, continuous training and development is no longer a luxury, but an absolute necessity. The traditional method of training up front during onboarding and then praying for divine intervention doesn’t fly in today’s world where product features change monthly, competitive landscapes spin on a dime and buyer behavior morphs and shifts. Contemporary sales organizations have realized the most effective AEs are lifelong learners that are constantly honing their craft, adjusting to new processes, and getting out ahead of market shifts, and so they invest in formalized and graduated development. Fast moving-selling environments require agility, and that agility exists only by constantly honing and updating skills and knowledge. The ones that get this fundamental are experiencing great leaps in attainment against quota, deal velocity and overall revenue performance. By digging into best formats for training, this examination shows how top performing sales organizations continue to support and improve AE excellence at every stage of the sales career.
Why AE Training Must Be Ongoing, Not One-and-Done
The Selling Profession is Changing In recent years, the business of sales has experienced a monumental shift, now more than ever continuous learning is not just a competitive advantage, but a necessity for sustained success. Market dynamics change at an unprecedented pace–new competitors appear in the blink of an eye, and product roadmaps update each quarter–and customers compare your offerings to other providers’ as well as to techs that are up-and-coming. Despite this, studies consistently find that salespeople forget about 87% of what they are trained on in 30 days, unless that knowledge is reinforced through practice and use. This is a number that would scare any sales leader that spends a great deal of money on first-time training but doesn’t have some sustaining reinforcement mechanism in place. Today’s complex world of B2B sales demands that AEs learn not only about the product and sales methodology, but also about industry trends, competitor intelligence, financial literacy, and advanced forms of communication through various channels and stakeholder types.
This challenge is compounded by the transition from transactional to consultative and value-based selling, which has created a greater need for AEs to grow in their business acumen and industry knowledge to stay credible with more savvy buyers. Buyers today tend to know more about your product than your latest AEs, and they expect sales people to bring insights well beyond basic feature demos. Ongoing training is key to enable AEs to play at the strategic level today’s buyers expect, becoming trusted advisors instead of glorified product pushers. The best sales organizations have moved beyond the old model of a big push up front, followed by clear and choppy waters; they’ve adopted a culture of continuous learning where skills development is ongoing all the way up to an AE’s plateau. The approach not only enhances performance of individuals, but results in a more robust and flexible sales organization that is unfazed by market times or competitive threats.
1:1 Coaching Sessions – Tailored & Tactical Development
One-on-one coaching sessions are the most impactful A/E individual training format available because it provides depth of personal attention and actionable feedback unavailable in group trainings. These sessions help managers go deep on each rep’s individual challenges, drivers, and development opportunities, so managers can tailor their improvement plans to unique skill gaps and behavior patterns. The best 1:1s are structured and focused, consisting of call review and analysis, role-based practice scenarios, goal setting and accountability check-in’s, deal and activity strategic planning, and skill-specific scenarios practice. The right cadence for these won’t be one-size-fits-all, though it generally works out to weekly for less experienced AEs, and every other week for reps with more experience–although of course you should customize to the actual AEs on your team, their quantified achievement to date, and the individualized level of development they each need. During these sessions, managers give reps feedback on their recorded calls so AEs can learn what the patterns in their communication, questioning, and closing styles might be that are working against them.
The most effective 1:1 coaching sessions leverage call scorecards to help evaluate key competencies: discovery quality, objection handling, next-step clarity, relationship building, etc. They provide objective discussion frameworks and enable both the manager and the AE to see how things have improved (or not) over time. This is where SMART goal setting is vital, to direct developmental focus to those actions which will deliver specific, measurable results and prevent a general sense of wanting to improve. Promoting rep self-reflection prior to and during these meetings makes a world of difference in how effective they can be, as when AEs arrive armed with their own insights and questions, they are much more engaged and have more “skin in the game” when it comes to developing their selves. The best coaching sessions feature forward-looking components including practice for scheduled sales conversations, strategic planning for strategic accounts, and skill practice for tough situations the AE anticipates in future. This interplay between debriefing and future preparation offers an holistic development experience with an impact on performance.
Role-Playing and Objection Simulations: Building Confidence Through Practice
By role playing and doing objection simulation exercises in these safe environments, AEs can simulate challenging scenarios and build muscle memory around hard conversations so that they are more confident in high stakes situations without doing it on real deals. These training modalities are particularly effective because they afford AEs the opportunity to practice different strategies, get real-time feedback, and refine their skills until they master them. The best role-play exercises are based on actual objections and deal scenarios being used on today’s pipeline, so that the practice is immediately actionable in the daily world of the AE. This authenticity moves sales training closer to “in the moment” learning and enables reps to know that what they learn is going to directly help them in customer conversations. Using different techniques, based on the focus of the training objective, these can include manager-led programs for skill development, peer-to-peer practice for interactive learning, or “hot seat” contests that bring friendly competition and energy to the training process.
Manager-led role play provides intensive coaching with specific feedback while the manager changes buyer personas to challenge the AEs skills in multiple environments. Collaborative role-playing in pairs or small groups allows one AE to observe and learn from the techniques or “moves” of another AE, and can also strengthen team dynamics. The “hot seat” approach allows for one AE to be handling objections while the others are present in an observer/facility role to offer advice and critique, providing a stimulating session for both the participants and audience. They’re even better when you roll out specific methodologies and frameworks the organization has in play so AEs know how to practice “the play” in a structured, repeatable manner. The secret to a successful role-play scenario is to make it difficult enough to push beyond the capabilities of the AE — but still realistic and relevant thought their territory/people. With consistent objection role playing, AEs will master fast thinking and composure in awkward moments in real, live, customer conversations.
Live Deal Reviews and Post-Mortems: Learning From Real-World Experiences
Live deal reviews and post-mortems turns every meaningful deal into a learning event for the entire sales team, fostering a culture where wins and losses are seen both as the team’s collective experience and as opportunities to develop as individual contributors. These meetings identify what went right, what could have been handled better, and why one approach was successful in a certain situation and failed in another. The best deal reviews include contributions from all the various functional groups including Sales Engineers, Customer Success reps, Marketers, and anyone else that touched or observed the sale cycle. This interdisciplinary approach presents AEs with a more holistic view of the deal dynamics and enables them to see how their actions affect other aspects of the customer experience. Instead, the objective is to foster a culture of feedback, in which honest scrutiny and constant improvement take precedence over shielding egos or dodging difficult exchanges.
Post-mortems should be organized and should cover the whole sales cycle from first contact to win/loss with critical decision points, inflection points, and what-could-have-been-done-differently points that might have resulted in a more favorable outcome. Such reviews are especially beneficial when they look not just at winning deals, but lost deals, as the learning one gets from each source is unique. Won deals can help pinpoint repeatable best practices and successful plays that should be overlaid on like opportunities; lost deals often expose the holes in process, positioning, or skill that can be remedied through specific training and coaching. Central to these sessions is the creation of an environment in which AEs are encouraged to share their unvarnished evaluations and to ask questions about other ways to approach the situation, without blaming others. This psychological safety fosters the kind of candid conversation that contributes to real learning and development, as opposed to defensive behavior that arrests growth.
Call Listening Clubs & Reverse Demos: Learning Experiences with Others
Call listening clubs lead to strong peer-to-peer learning, as teams come together to listen and discuss recorded sales calls, dissecting what works, discussing what didn’t, and brainstorming alternative methods that could work. These are most effective when they cover discrete parts of the sales conversation (e.g., discovery questioning, objection handling.A does anyone know how to avoid the cut off? only to be given the let’s do it answer. /closing) and not the whole call in one meeting. In terms of knowledge sharing, these are super useful: AEs get to hear a range of opinions, plus they can see what techniques/approaches other reviewers use, which may be entirely different from their own. Team members can share lessons learned, best practices, tactics that could have worked, and how they could use a similar approach in their territory or with their own customers.
Reverse demo sessions where AEs pitch to each other or to their manager create non-risky practice environments that encourage them to sharpen their pitch, product positioning and value proposition. These workouts are especially effective for perfecting new features and product strategy, testing out your messages and preparing for high-stakes pitches for beta candidates. The reverse demo format promotes instant feedback and iteration, enabling AEs to fine tune their approach before taking it to real customers. Topics of focus for such calls should be: structure and flow of the presentation, the quality and timing of discovery questions, the clarity and relevance of the value proposition, and recommendations for the next steps that progress the deal. The secret to effective call listening clubs and reverse demos is that you keep a positive learning environment, feedback is targeted and actionable and, most importantly, everyone is trying to help, rather than take swipes. The sessions work best when they’re held consistently and when taking part is considered an investment in professional development rather than an additional demand for already overloaded AEs.
LMS & Self-Paced Paths: Flexibile Development on Your Schedule
This virtual approach to learning allows AEs to train when it is convenient for them, enabling true lifelong learning by allowing real world salespeople time to success – Look for LMS and Asynchronous learning environments – Many will allow AE content to be loaded for training. The new age LMS systems have advance features to create personalized learning paths that are customized to individual skill gaps, experience-level, and role specific requirements. Such systems can provide specialized content that targets specific competencies (e.g., industry knowledge, product knowledge, sales skills, soft skills, etc.). The best asynchronous learning programs use microlearning formats, which dissect complicated topics into bite-sized, 5-10 minute modules that can be finished in the intervals between meetings or on commutes. This method acknowledges the true nature of AE schedules, but it continues to move learning forward in a steady, systematic fashion and not in fits and starts and oppressive masses.
Excellent LMS applications use interactive features like quizzes, assessments and scenario-based exercises to reinforcing learning and offering instantaneous feedback on understanding and skills. Gamification features such as the ability for coachees to gauge progress, earn badges, and compete for a digital trophy can boost engagement and inspire coachees to continuously engage. Complete learning is formally recognized and pathways toward skill advancement are clearly established through certification programs housed in the LMS. The threshold between maximum and minimum LMS effectiveness is the relevance of content entailed and its immediate applicability to the AE´s day-to-day weeds. The result is a learning platform that receives frequent content updates, incorporates user feedback, and tracks user performance to maintain relevance and quantifiable impact in improving AE performance. They should also consider how to optimize their courses for mobile so employees can learn during their commutes, while traveling or in other moments of downtime.
Emulating High Performers: Seeing and Being Coached
This mirrors-shadowing is likely seeing junior AEs learning through observation and mentorship. Both new hires, who can see successful sales techniques in action, and experienced AEs who want to learn new techniques or subskills, stand to gain a lot from these types of programs. Two of the most valuable ways to shadow are sitting with AEs during customer calls and listening to call recordings (this allows the AEs to share successful tactics in the moment and then to talk through the strategy and the thought process). This blend of observation and chat helps the apprentice close the gap between what works and why – allowing them to make best practice their own style in their own patch.
Guided shadowing programs should involve a briefing before observation, where the mentor explains why he/she is doing what he/she is doing and outlines his/her plan, active observation with note-taking and questions, and debrief afterwards, where he/she explains the logic behind specific moves. They might even be structured as formal AE mentorship pods that include several developing reps learning from one high performer peer learning and a mentor relationship. The best shadowing programs also have reverse opportunities, where the mentee displays his or her skills for the high performer and receives feedback. Such mutual sharing-operation provides a modulation for learning rather than being just the passive learning back propagation, and can also serve to give rises attachment to the emerging AE. Instituting guidelines and expectations for shadowing relationships is important, for example, identifying clear learning objectives, time commitments and evaluation criteria in order to provide participants value and reinforce the commitment.
External Workshops & Bootcamps: New Perspectives and Proven Structures
External training workshops and bootcamps provide fresh insight, established training techniques, and experienced guidance that can inject life into your internal training programs and introduce AEs to new processes and frameworks. When these type of programs are presented by established sales thought leaders, industry insiders, or training organizations that have pioneered new methodologies or techniques, they can be even more helpful. As an example, I am a big believer that major sales methodologies (like MEDDPICC, SPICED, NEAT etc.) are best taught via immersive external courses along with lots of practice. Out-of-house training also allows AEs to be around other peer professionals from other companies for networking, learning about best business practices and what’s new in the industry.
The best external training systems are those that offer intensive initial training with frequent follow-up and fast-path support. Companies should consider internal follow-up agendas that support AEs operationalizing what they learned into their territory and customer environments. This kind of internal reinforcement is vital because a lot of external training offers general frameworks that must be tailored to one’s specific industry, customer type or company positioning. When external training is best used is when it is intentionally chosen to fill proven skill deficits or identified developmental wants, as opposed to being chosen opportunistically because we can’t think of what to do in-hous or because “all the minds are in the room. Companies should also send more than one AE to the same external programs to help build internal cohorts who can encourage each other’s application and continued use of these new skills and methods. The return on investment for external training is maximized when it’s tied to complete development and not simply a stand-alone effort.
AE-Driven Training Meetings: Peer Teaching and Sharing of Know-How
AE-led training allows the sales team’s collective intelligence to contribute to these learning projects, and help their peers to make lasting connections with new information and leadership from the presenting AEs. These types of sessions are most effective when they focus on sharing success stories, best practices and lessons learned around targeted deals or customer situations. The “How I Won This Deal” format gives the most successful AEs the opportunity to share how they thought about the deal, what they did to model it out, and how the made the decision, then you can use those models for your own deals. This type of “learn from your peers” training is often more applicable and achievable than one given by managers or external trainers as it is from someone that you work with who shares the same limitations of time and resources.
AEs’ own accountability and continual improvement is also enhanced, as presenting AEs have to critically reflect on their own practice in order to share it in a valuable manner. This creative preparation also has the function of enhancing the speaker’s self-awareness and ability at the same time. A different presenter is rotated each month to bring different approached and perspectives and allows a number of the team to develop as communicators and leaders. These types of sessions can touch a wide array of topics, from deal strategies to industry insights, to product positioning, to handling objections, even building relationships. The most successful AE-driven training programs set expectations for slide quality and content relevance, but continue to be a nurturing environment in which it is safe to share and learn. These sessions are most successful when they are incorporated into standard team meetings rather than seen as an extra hassle, and when management actively takes part and underscores the importance of learning from peers.
Tracking Training ROI and Measurement Using Technology
Today, sales organizations are demanding proof of return on their training investment.They need advanced tracking and measurement systems that can link training activities to behavior change and business results. The best ways to measure follow the whole measurement cycle from participating in training to changing behavior to improving performance by metrics such as faster closing rates, shorter sales cycles, and larger deals. Your CRM can be customized to include fields for tracking training completions, skill assessments, and personal development goals, in addition to the standard sales numbers. Call analytics tools such as Gong and Chorus can deliver metrics for communication improvement, as well as the best quality conversations and how those new techniques are being borne out.
Survey feedback and self-assessment can capture the qualitative enhancements in confidence, perceived skill and comfort of application that would not manifest in quantitative metrics instantaneously, but would lead to subsequent performance improvements. The secret to measuring if training is driving ROI is to form baseline metrics before training begins and then to measure both leading indicators (like higher quality discovery questions or more confidence handling objections) and lagging indicators (like greater attainment of quota and deal velocity). With advanced analytics we can determine which training type and topic is having the most impact for the different AE profiles and levels of experience. This approach driven by data is used to continuously optimize training programs and to focus investments in development in the activities and formats that provide the highest performance benefit. Organizations can also monitor engagement figures like the percentage of training courses completed, those participating on a voluntary basis, and the level of peer learning activity, to understand the programs best received by their salespeople.
Growing Quality Through Holistic Training Ecologies
The best sales organizations out there understand that there’s no one silver bullet for AE development—rather, they build complex, all-encompassing ecosystems, that combine a number of formats and approaches to speak to different learning styles, skill levels, and developmental needs. The wisdom we are sharing here is this: that continuous training must be systematic, multifaceted and have a clear business results focus, not considered as a “sometimes do” or “box ticking” exercise. Standout participants in AE development tend to integrate formal, individual coaching with peer interaction/hearings; blending formal training with immediate application; and leverage technology for content distribution and impact measurement. The best training programs adapt to the feedback they are given, to performance data, and changing business needs, instead of staying the same year after year.
The formats covered in this article give you a solid scaffolding for an elite-level AE development program, but how you mix and match and what you emphasize has to align with your specific company context, challenges, and goals. The first important step is to assess how you in fact train now and to find any shortcomings, inefficiencies and potential for improvement. Why not survey all your AE’s on learning preferences, development priorities and perceived skill gaps and make sure that your training investments line up with actual needs and not how you think they learn? Snippet: Lastly, keep in mind that the most impactful programs are the ones which create sustained change in behavior (not just a week-long transfer of knowledge – this means reinforcement, opportunities to apply learning on the job, and real connections between learning activities and career development). Begin with one or two formats that cater to the development areas you need to resolve most urgently, and then broaden your training ecosystem as you grow capability and prove results.
