If movies are to be believed, people don’t actually need training in order to sell. They’re either born to sell or not. And if they aren’t, they can learn everything they need to know in under two minutes a la Leonardo DiCaprio teaching his stable of sleazy salesmen how to create urgency in “The Wolf of Wall Street.”
Such a casual approach to sales training would never fly in the tech industry as sales leaders take training way too seriously — and with good reason. Tech sales is highly competitive and there are often more software and services providers than there are problems to solve. Deals are won on the margins by teams that take the time to perfect their craft.
Sales training takes many forms, from informal meetings between reps and team leads to talk through day-to-day problems to quarterly reviews that focus on big-picture goals. In addition to helping teams close more deals, these trainings enable salespeople to strengthen their existing skill set and develop new skills, like leadership, that they may not use on a regular basis.
All that is to say: Sales training is incredibly important and valuable. Here’s how to do it effectively according to three local sales leaders.
How often do you hold training sessions with your sales team, and what do those training sessions entail?
Our enablement brand at Red Canary is: expected, repeatable and consistent. One of the most important ways we deliver on that promise is through our regular cadences with the team. We start at the macro level, with a yearly sales kick-off, quarterly planning reviews and monthly all-hands meetings covering different enablement, product and operational topics. With more micro-enablement opportunities, we’ll leverage some of our new tools to do weekly and then daily training sessions and provide both self-paced and live-learning opportunities.
The content varies depending on our current priorities, but we aim to include the voice of sales alongside whatever else we are communicating. If there is a new product feature or update, we invite the product manager to discuss it and then ask a member of the sales team to talk about how they pitch it in the field. Sometimes I’ll even jump in and play my favorite character, “skeptical sales rep,” in order to make sure some typical questions and concerns are addressed. We always ensure we are including the “why should I care” and “how do I use this with customers” element for the sales team for any training we roll out.
Sales enablement is always best received when it is delivered alongside actual sellers.”
What techniques or approaches have you found to be particularly effective when it comes to sales training, and why?
Reps like to learn from other successful reps, so we always try to incorporate the “voice of sales” in all of our learning. Reinforcement and confirmation of learning through activities is also a really effective tactic for sales training. Very few learners can sit in a presentation and absorb all the necessary information and apply the learning to their job. Including a follow-up activity, even if it’s simply a conversation with other reps, is essential to solidifying enablement.
We used a lot of breakout rooms in Zoom over the last year to talk through new messaging, products and competitors in small groups and deliver outcomes like brief recorded pitches, decision trees or even just feedback on what else sellers needed to feel confident with the material.
One other successful method is to have sellers create their own documentation, rather than present pre-built material to them, and then have them teach it to their peers. That process involves consistent reinforcement of learning and a takeaway reference document that they designed in their individual learning style.
How do you evaluate the effectiveness of your training sessions, and how do you use that information to fine-tune your approach to training over time?
Sales enablement effectiveness is measured pretty simply: Are our sellers getting better over time? Currently, we collaborate with a business analyst on our operations team to utilize the sales velocity score in evaluating our reps. While the sales velocity score is a great view into rep success, we are striving to craft a more holistic picture using pipeline data, historic win rates, certification scores, and more. In turn, we use this evaluation as a reflection on our training and enablement.
If scores are growing, then to what extent is our training contributing to that? If they aren’t growing, then we can do custom gap analysis, let our trainers and coaches diagnose any concerns or areas of growth, fine-tune our process and facilitate training to fill the gap. This process recently enabled us to identify an area where we were struggling with a particular segment of customer size. Once we diagnosed it, we brought the right group together to brainstorm solutions and then built a new playbook to change our approach.
How often do you hold training sessions with your sales team, and what do those training sessions entail?
We host several training sessions weekly. The first session is an SDR/AE/SE opportunity review where the team has a chance to discuss any lessons learned from the week’s lost or rejected opportunities. We drill into the “why” and fit for the business and try to catch any fast-forming trends we are seeing. The second is an open office hour on Fridays where anyone on the sales team can drop in with their day-to-day questions, no matter how big or small.
Lastly, we have a 15-minute stand-up at the end of each day where we review any top-of-mind items across all opportunities. This quick-fire meeting helps set the stage for the next day’s planning. But more importantly, it gives the team a chance to learn from all deals in play.
Give everyone on the team the opportunity and ownership to train others.”
What techniques or approaches have you found to be particularly effective when it comes to sales training, and why?
I am a firm believer that sales training is a process, not an event, and should continue well after a salesperson “goes live.” The key to real growth is to always keep training engaging and applicable. I find it highly impactful to give everyone on the team the opportunity and ownership to train others. The goal is to have higher retention of knowledge and help each member grow as a leader within the team. It doesn’t always have to be sales leaders throwing down lightning bolts of inspiration and knowledge. Team training can be collaborative, and growth is more fun and exciting when it happens as a team.
How do you evaluate the effectiveness of your training sessions, and how do you use that information to fine-tune your approach to training over time?
We have created a sales competency document by role co-authored by managers and reps. This allows the rep to rate themselves by how confident they are in the key competencies and core knowledge needed to be successful at selling Cin7. This process creates an environment of ongoing learning where not knowing something is OK. Reps feel empowered as they gain competency and evaluate their own progress.
For example, our platform is highly customizable and new reps have to retain in-depth product knowledge as well as knowledge of pitching, the demo structure, proposals, pricing, integrations, ideal customer fit and HR items. It’s a lot! Inevitably, every rep has a different experience with this information. This process has helped us target those information gaps and address them quickly.
How often do you hold training sessions with your sales team, and what do those training sessions entail?
With a team that is all remote and scattered throughout the country, and only a few “local” sales professionals, it’s hard to find the time and places to hold “face-to-face training.” We have found several productive approaches to team training, though. First, we use a portion of our weekly sales team call to talk about key learnings from the week. This could be an industry nugget we heard from a client, an internal process that was modified or simply feedback on a sales process we could all learn from.
We also hold monthly trainings with our product team where we spotlight one of our product capabilities so everyone is informed and trained on how to work with a client on that particular product or solution set. Finally, and newer to us after reopening the office this month, we are trying to gather the whole sales team for an in-person training at least every six to eight weeks. This might include bringing in an outside firm for sales skills or using internal teams to learn more about process and product information. We are hoping to keep this momentum going into 2022!
We hold monthly trainings with our product team where we spotlight one of our product capabilities.”
What techniques or approaches have you found to be particularly effective when it comes to sales training, and why?
A few ways to keep training alive include documenting or live video recording trainings to create reference points and job aids to refer back to. It’s hard to retain and remember every nuance, and keeping a library has been helpful for the team. Also, bringing practice to life with newly acquired sales skills is helpful. Taking threads of the learning and incorporating newly acquired skills into things such as a strategic account or deal-planning puts those skills into practice and keeps the momentum going.
How do you evaluate the effectiveness of your training sessions, and how do you use that information to fine-tune your approach to training over time?
I have found that effectiveness in training is reflected in your results. Having regular one-on-ones with staff is not just about pipeline. It is also about the sales professional’s personal goals and development. It’s been very important to create a more personal safe space where individuals feel they can ask for additional training if needed. Often, others feel the same way but are apprehensive to discuss these needs in a group setting. It has been a great way to get a pulse on what is needed and how we can improve training the next time around.
