Operations innovation

Role Playing and Simulations for Growth

2 Minute Read

In many sales roles, the development of a sales “story” and the cadence of that story is practiced during role-playing sessions. One sales team member will play “the customer” and the other “the sales rep.” It’s a way to practice your pitch and handle objections in a safe space.


Think of role-playing as the ‘sandbox.’ If you deploy bad code in the sandbox…who cares. Delete is and start over. Same goes for role-playing. If the cadence is clunky or you don’t handle objections well? You get to start over and learn from it.

Yet very rarely do we use actual role playing in the technology stack. Rarely do we build simulations to practice new skills or procedures.


At Wholestack Solutions, we do both!


Role Playing


One of the reasons sales organizations use role playing is because it provides a safe environment to make mistakes. Nobody lokes to make mistakes, but they are a part of the learning process! Instead of making mistakes in front of valuable customers, sales organizations let their teams practice with each other. It also gives junior sales reps the opportunity to learn from more seasoned veterans.


Developing a story and cadence is important in sales. It’s not just about “the close” it’s about creating and cultivating relationships through problem discovery, information sharing and understanding the customer’s internal processes and landscape.


This same approach applies in technology delivery. Instead of swooping in and trying to over-power customers with technical-wizardry, Wholestack approaches service delivery much like a sales-discovery process. We seek to understand our customer’s problems, both technical and political while also gaining insights into the landscape that our customer operates in.


During our role-playing sessions, we partner junior operators with senior engineers and take them through various scenarios to help coach them to discover the root cause of the problem, while maintaining empathy and understanding. By helping our team see beyond the simple technical task at hand, we enhance our relationship with the customer and build trust with them that we’re acting in their best interest.




The stock market is scary for the “Average Joe.” Many companies offer “simulations” that offer fake money that is “invested” in the real stock market (a simulation using live data). This allows the Average Joe to learn how the market works, how to place trades all while keeping their real money safe.


We do the same with Wholestack Solutions’ internal team. Our senior engineers build multiple environments and run simulated events that our junior team then engages in. Most of the time, our operations team doesn’t know that these are simulated environments…so, they believe the stakes are high!

This gives us an enormous amount of data to see where our training is falling short, which of our operators excel in various areas and what tools and resources we need to invest in to offer our team the best opportunity to succeed.


Pairing role-playing with simulations allows us to not only accelerate on-boarding and training of new operators but to continually sharpen the skills of our entire team. It is also an incredible benefit that operators get by working with us…an opportunity to add skills to their resume on the employer’s dime!


There’s an old story between a CEO and CFO where the CFO says, “what happens if we spend all of this money to train our people and they leave?” The CEO thinks for a moment and says, “what if we don’t spend the money…and they stay?”


Role-playing and simulations are an expensive investment in our team, but a necessary one. Only by “drilling-for-skills” can we ensure our team is ready to meet the rapidly changing demands that our customers ask of us in order to help them maintain their competitive edge.

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