Any meeting with a customer executive demands aligning with the executive’s business priorities, having meaningful ROI numbers at hand, and more. However, you also need to be able to nimbly navigate the twists and turns that can unexpectedly arise during your face-to-face conversation. To be ready for conversational pitfalls that take you off message, add role playing to your preparation.
If you’re not comfortable with role playing, get over it. It’s the best way to simulate the scenarios that can derail any well-rehearsed presentation and foresee how to effectively respond when the dialogue digresses.
Remember that this is the executive’s meeting, not yours. This person sets the agenda and can route the conversation in any direction.
For role playing, enlist a colleague or manager to play an executive and imitate that individual’s personality. Work your script against your co-worker’s portrayal of the hurried executive, or the skeptical executive, or the executive who recently had a poor experience with another sales professional.
By practicing your delivery in these less-than-ideal situations, you develop the ability to deviate from your plan yet still have a successful businessperson-to-businessperson dialogue.
If possible, have a third person observe the action. Ask your colleagues to rate you on how well you are able to cover the basics of any executive-level engagement. These include your ability to:
- Cite external factors to establish your credibility
- Link customer business initiatives to your proposed solution
- Demonstrate business impacts using meaningful metrics
- Articulate the business change you’re envisioning in parlance of the executive
- Engage the executive to validate opportunities
- Close the meeting with a call for executive sponsorship
More Meeting Tips
There are a few other key things you should keep in mind and have your role-playing cohorts watch for during these practice sessions as well:
- Get to the point. Don’t expect to have more than two minutes to engage the executive and deliver your value proposition. Make it succinct and understandable. You need to set both the scope and expectation right away.
- Listen more than talk. Once the stage is set, pay particular attention to who is doing most of the talking. After your value proposition is on the table, the ratio of dialogue should be 80 percent executive and 20 percent you. If this ratio gets reversed, it means you have not engaged the executive. Recheck your messaging and try again.
- Don’t run from tough questions. Be prepared for "show stopper" questions – questions you are not prepared for. Practice handling these, and clearly communicating that you will get back to the executive with answers. Ducking tough questions will reflect poorly on your trustworthiness and integrity.
- Focus on the pain point. Keep the discussion focused on the business problem the executive needs to solve, and resist the temptation to focus on your solution. Again, this meeting is about the executive and the executive’s issues, not about you and your quota. If your meeting is a success, you will gain sponsorship and your solution’s value can then be fully developed and quantified.
- Look for other sales opportunities. If an executive is not interested in your solution and insists on talking about other problems, don’t resist. Give up on your script and pay attention. This is a great time to practice your listening and questioning skills. The outcome may result in an even better sales opportunity than you expected.
Finally, pay attention to the overall tone and content of your message. This meeting should be all about the executive, not about you. A practice partner who is overly critical on this point will help you greatly.
Give a try and let us know the results!


{ 1 comment… read it below or add one }
This is great information. During my baby years of sales, my Sales Manager role-played with us for hours. We even had a meeting on Wednesday nights dedicated to role-playing. Five years later I still find myself role-playing (almost every aspect of my life)