Designing Inside Sales Training

Designing Inside sales training can be a complex, intricate topic.  For it to be beneficial, it must be designed in an effective and strategic way.  Within this overview, we will cover some of the key steps to designing successful training programs, specifically inside sales training.

With the rise in platforms such as Youtube, Linkedin, and various other aggregated training portals, one can find content on almost any topic. Despite this glut of information, companies invest millions of dollars into corporate and sales training annually.  Sales training alone is a $2.5 billion industry globally. So why do companies spend millions of dollars on training each year?  Training companies exist to make sense of all the various data available, and redesign it in a way that is most beneficial to a particular organization. Quality training has a way of adapting to different organizations without the need to fully customize the actual research and models.

Successful training design typically has three main components – pre-training, during training, and post-training.



Pre-training design and research is paramount to the success of an inside sales training program.  To design quality training, you need to understand the current state of an organization and compare it to the ideal future state.  There are many ways to learn about the current state of an insides sales organization; these include assessments, audits, and stakeholder interviews.

Pre-training is also a critical time for the inside sales team.  First off, communication is crucial.  There must be a detailed communication plan in place informing the participants about why the training is happening, what they can expect, and the positive impact it will have on the organization. Throwing your sales team into a half day training meeting or a quick webinar without any specific context isn’t going to be beneficial. The sales team needs to hear the importance of this training from senior leaders.

In addition to a detailed communication plan, it is very effective to assign some type of pre-training assignment or work.  These assignments can include readings or videos on discussion topics; for example, how to develop buyer personas or email marketing tactics.  In addition, it is highly recommended that the inside sales team arrive with a handful of target accounts in their assigned territory.  It is considerably more effective and beneficial if the inside sales team is working on actual target accounts as opposed to fake or hypothetical accounts.

Hand and notebook with charts and graphs.


Designing quality training starts with understanding the current state of the team and defining what type of behavioral changes you desire.  Once the behaviors are defined, a plan can be designed to ensure the participants learn the key components of the plan and retain the information learned.

One of the very first questions an organization needs to answer is what great performance looks like within your inside sales group.  Typically, there is a small subset of the group that is performing at a high level.  What are those individuals doing on a regular basis?  What types of skills or behaviors do they posses that make them great at their job?  It’s important that sales leadership can define exactly what they are looking for the training to accomplish.  For example, our team is at “x” and we want them all at “y” within a specific period.

One of the tools used to understand the current state of the salesforce is a skills and behavioral based 180-degree survey.  If you are not familiar with surveys, this is a survey where both the salesperson and the sales manager participate, rating the salesperson on specific skills and behaviors.  The results of this survey are then compiled, and the report provides good context for any gap that exists between the salesperson’s rating of themselves on specific skills and behaviors versus how their sales manager rates them.

Every organization is unique in what drives sales, so this assessment can also be used to understand exactly what skills and behaviors are contributing to these numbers.  These survey results can be compared to performance data, and call out specific skills and behaviors that high-performers have that mid or low performers do not.  This data can then be used to start building training that shrinks the gap of the mid to low performers on specific skills, and also helps high-performers double down on behaviors that are driving success.

With inside sales, it can be very tough to understand the current state of the group.  Most inside sales groups are constantly evolving.  New employees are coming onboard, people are getting promoted, turnover can be high, and due to the complex nature of the job people often get fired.  Previous inside sales people often provide the most beneficial data.

This is just one example of a sales assessment that can be used to design training.

In addition to assessments and surveys, stakeholder interviews are one of the best ways to truly understand what is happening within an inside sales group. When conducting stakeholder interviews we like to look at four distinct groups – the inside sales team, sales leadership, marketing leadership, and if possible customers.

We find that talking to the internal teams starts to paint a better picture of the true issues that need to be solved within the inside sales organization.  Each separate group usually calls out different priorities, or perceived needs for enhanced skills or behavior.

The customers don’t necessarily have to be from the specific company we are doing training for, they just need to be from the correct industry and a target buyer.  It’s crucial to understand the mindset, pain points, and day to day problems of your target buyer.  The inside sales team needs to understand the customer’s pain points to create messaging that truly differentiates them from their competition.  In addition, it’s great to get direct feedback from target buyers on the type of info they are looking for, and why they would take new meetings with vendors.  Gathering direct information from prospective buyers immediately gets the attention of the inside sales team during training sessions.

Graphs, charts, businesspeople and laptops.

Training Design

Once you have a good understanding of the current state of the inside sales team it’s time to start thinking about designing a program that will make an impact.  I say program because this should be a very specific plan over an extended period of time.  For inside sales teams, I like to think of training in 90-day intervals.  Given the turnover and career advancement that happens to people in inside sales, it can be tough to plan six and twelve-month training curriculums.

Every organization is a little different, but one of the most important things to consider when training is the different training modes that will be the most effective.  What this means is that there should be a mix of in-person, virtual, e-learning, skill boosters, and extensive 1:1 coaching and reinforcement.  The number one mistake we see in inside sales training is organizations holding one-off events where regardless of how good the event was, the skills are immediately lost because they are not reinforced after the event.

If there are essential skills that need to be learned by the team, there needs to be a conscious plan of how to reinforce the skills in an ongoing manner.  From our perspective, the most effective way to reinforce any skill is through quality 1:1 coaching.  Let’s say you’re working on building quality cold calling scripts.  You may have a 1-2 hour session on the script’s’ importance, how to build them, and what core communication should be included.  But after the session, who’s checking in with the team to ensure they are implementing what was learned?  Are there managers checking in with the team daily/weekly to talk through what is and isn’t working?  Are there any follow-up sessions that continue to enforce the right skills and behaviors that were addressed in the original training?  For the training to stick, it’s imperative that there is a sustainment plan built into the program design.

During Training

 We will spend less time talking about what exact content should be included in the actual training versus how we would recommend the training is structured.  The type of information covered in a training session is highly dependent on the results from the pre-training assessments and stakeholder interviews; however, there are some main components that we feel help make the actual training sessions successful.

To start the training, we always recommend an executive or manager from the organization kick the training off with some context on why exactly the organization is investing in training, relating it to key business issues or initiatives.  As discussed before, having buy-in from senior executives is essential, and it’s very important that the participants hear why the training is important from executives.  In addition to executives, it’s great to have direct managers act as co-facilitators in any type of purchased or third party training.  Having an inside sales manager there to provide additional context and reinforce the learning and how it relates to the organization is a crucial step.

After the initial overview by an executive, it’s great to start with some type of activity.  If you start with a bunch of slides and content you run the risk of losing the group immediately.  One of our favorite activities is breaking into small groups of 2-3 and working on building a compelling elevator pitch.  In less than 30 seconds describe what your organization does, how you differentiate, and what that means to the customer.  This is good training for cold calling, as many times the inside sales group will be asked for a brief overview of the organization’s capabilities.  Provide some type of compelling incentive, such as the winning group gets to have lunch with the CEO or an executive.

We find that these types of quick, small activities help get people engaged and learning information crucial for their role.  We recommend scheduling some kind of activity at least every hour within a training plan to break up some of the other skill building that is happening.  Outside of activities, we recommend lots and lots of practice.  Learn a skill for 10-15 minutes then break into smaller groups and practice the skill.  Practice on sample accounts that the inside sales team is targeting.  Work on building messaging and things that the team will actually be doing during after the training.  Push the small teams to interact and provide feedback on exactly what has worked in the past.  You want the training and skill building to be a challenge, make sure the team is really working hard on solving actual day to day problems they will face.

Another thing to consider during the training session is how many major topics will be covered in one session.  This can be highly dependent on the location of the inside sales team. For example, if the team sits in the same location, you don’t have to plan full day retreats where you are almost forced to fill the entire day.  When the team is in the same location it may be more effective to 1-2 hour training bursts where only a couple major topics are covered.  When you have longer training sessions, such as full days, there is a better chance of people becoming overwhelmed with all the content.  So, be thoughtful about how much time is actually spent in class.  There’s a well-known 80/20 rule in the learning world: only 20% of the actual learning should be happening in class, and the rest should be on the job.  Many times when training is designed there is too much of a focus on what’s happening in the session despite the fact that the real learning happens on the job.


I don’t want to beat this drum too hard, but I will say it again: sustainment of the learning after the training and on the job is absolutely vital.  If you can’t relate the training to the inside salesperson’s job, then the learning won’t stick.

a binder with a bar graph going upward.


The most significant drop off in learning is shortly after the training session, so it’s necessary to focus on how to sustain the learning.  When designing inside sales training it is essential to reinforce the training multiple times within a 30 day period.  For example, if you have a half day of training on email and cold call techniques, we would recommend you have 5-6 additional check-ins within the next 30 days.  Check-ins could mean a lot of different things, anywhere from a manager checking on the progress, to the inside sales team getting back together to discuss what has and hasn’t been working with the specific behaviors you are trying to enforce.

We find that many inside sales managers and training companies try to pack too much information into too short of a span of time.  If you are learning new concepts you need to ensure you have enough time blocked within the next 30-60-90 day window to reinforce what was actually learned.  For true behavior change to happen, there must be significant thought into designing a sustainment model.


We believe the best way to sustain learning is through coaching, so it’s vastly important managers and leaders are enforcing the behavior changes as well.  To use the example from above, let’s say your team went through cold calling and email effectiveness training.  If cold calling and email effectiveness are critical to their job (which it had better be), as the coach, I would dedicate time each week to cover those topics in my 1:1 coaching sessions.  I would have each member of my inside sales team bring recent campaigns they built and would sit down and talk about the effectiveness and variations that they could try.  If cold calling is important I would use a software tool like that records cold calls or initial meetings and go through calls with each team member, using actual calls as opportunities to reinforce the most appropriate behaviors.  Coaching is the best way to reinforce training and develop employees, period. There’s no debate!

We believe in coaching so strongly that I would recommend great coaching in lieu of any type of training program.  I don’t care how innovative the content is, if no one is reinforcing the concept on a regular basis, the chance of it sticking is very unlikely.

If you don’t have the time, or the resources to build a full training program, I would double down on coaching specifically (assuming you have the right manager in place).


So to recap, the biggest issues we see as it relates to sales training (whether inside sales or not) are centered around two areas.  The first is that there is no defined current versus future state, and organizations are just training for training’s sake without any kind of goal in mind. The second is that the training that they are doing is not being reinforced in a smart, productive manner.  There’s no coaching, there’s not plan after the session, and therefore what was learned just slowly (and sometimes quickly) goes away – ultimately resulting in a waste of your organization’s time and money.  If you want to design effective training, make sure you spend enough time pre and post training – the actual training session is only a piece of the puzzle.

At OutboundView we’ve trained hundreds of inside sales reps as a part of implementing outbound marketing programs.  If you are building and inside sales team and need assistance, don’t hesitate to reach out and schedule an intro call.