A Dinner Party as an Analogy for Discovery


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You’ve invited a large number of friends and colleagues over for a dinner party – how do you prepare? As you begin planning for your party, you realize that it’s a big job and you want to make sure the party is a success – so you engage a professional Party Planner.

The process the Party Planner follows and questions asked provide a surprisingly good example for doing discovery in a software sales process. Before reading on, think about the questions you would ask if you were the Party Planner – this is an excellent exercise in practicing discovery. And, by rewriting the questions, you can use this as a “starter” template for your own discovery conversations.

[Disclaimer: I am not a professional Party Planner and, accordingly, quite likely have missed some important questions and topics to explore. If you use these questions and your party is a disaster, I’m very sorry – and I’m glad I wasn’t invited…!]

Party Planning

Here are example questions your Party Planner would expect to ask of the you, the Host:

  • What is the objective for this dinner? Is it to simply have an enjoyable evening and/or are you looking to develop or extend relationships, for example?
  • Is it a specific celebration of some kind (birthday, anniversary, successful end-of-quarter)?
  • How should this event compare with events you have previously attended? 
  • Are you operating under a specific budget?
  • What level of formality/informality do you have in mind? Is this a casual gathering, business-casual, or formal dinner? 
  • Will there be a “theme” for the event?
  • Where should the dinner be held? Will it take place at your home or another facility?
  • Should it be catered or will you do all of the preparations – or perhaps a potluck is the plan?
  • Will the venue need to be prepared? If it takes place at your home, how much cleaning and clearing of the daily debris is needed?
  • Are you contemplating a picnic, with (compostable) tableware or a sit-down meal? Should you use your “daily” service or break out your “formal best”? Do you have enough?
  • Will you do the venue and food preparation and serving, or do you want to have a 3rd party team handle this?
  • How much time should be allocated for venue and food preparation?
  • Similarly, what about post-event cleanup? Do you need recycling, compost, and trash containers for the event?

Note that these questions represent exploring the overall objectives for the event as well as many of the expected problems and challenges. In Great Demo! methodology, these align with the Critical Business Issue (why is the Host having the dinner) and Problems/Reasons (what makes it hard to execute).

The next set of questions are about demographics:

  • When are your guests available? What date and time will work for everyone?
  • How many people will come? Will you have a specific count or will it be a range?
  • What are the ages of the folks who are expected to join the dinner?
  • Anybody with special needs?
  • What about children – are they invited?
  • If a sit-down dinner, do you want to have designated seating or let everyone sit as they choose?
  • Any strategic or tactical placements?
  • Should there be a head table or children’s table? (Or perhaps a table for people acting like children?)
  • 9How will people arrive and depart – is parking an issue?

What will you serve?

  • Are you following a theme that would dictate the cuisine?
  • Any food preferences or requirements to be aware of? Allergies, likes/dislikes? Vegetarians? Pescatarians? Keto? Flexitarian? Paleo? Kosher? Halal?
  • How much food to prepare? Are these folks with big appetites or are some working under specific intake constraints?
  • Are you thinking of many small plates, a buffet, or a more traditional serving sequence of appetizers, salad, soup, mains and sides, and dessert? (Note: This question would need to be reframed depending on location – the dishes and sequence will likely change. I can already hear folks saying, “What? No cheese plate? Scandalous!”)

And, of course, what will people want to drink?

  • Alcohol? Beer, wine, cider? Mixed drinks? Open bar?
  • Non-alcoholic offerings – soft drinks, water (still or sparking), juice?
  • Do you plan to provide anything special or unique?
  • Are you contemplating pairings? Before, during, or after dinner?
  • Coffee, tea, or other caffeinated or non-caffeinated beverages?
  • What about mixers, ice, and applicable glassware or cups?
  • And what price-point do you have in mind for these?

Answers to these two segments represent the Specific Capabilities the Host desires – the deliverables.

What about activities and timeline?

  • Will there be an agenda to follow? Any time-sensitive items?
  • How long will the event run?
  • Any speeches, announcements or similar to incorporate?
  • Ice breakers? (E.g., “Tell us one thing about yourself that no-one else knows…”)
  • Games or contests?
  • Background music? Live or recorded?
  • Any other supplies to consider – decorations, candles, flowers?
  • Will gifts be involved – from the guests or for the guests? Should they be opened at the event?
  • Any weather-related considerations to plan for?
  • How should the party end – all at once or can the guests “trickle out”?
  • Will anybody need lodging?

Note that some of these questions explore timelines and implementation. This part of the discussion begins to establish a Transition Vision (of how the event will take place).

Additionally, these topics represent more about the overall plan and environment concerns. In discovery for a software sale, these are similar to questions about the prospect’s current or desired software infrastructure, integrations, and organization culture.

Finally, a good Party Planner would also ask:

  • How will you determine if the event has been a success?
  • Are there any specific measurements or feedback that you are looking for? (E.g., happy smiling faces during the dinner, heartfelt feedback on the food such as, “Wow, this is really good…!”, reciprocal invitations, positive comments, photos, or notes on social media, etc.)
  • If you did the whole job yourself, how much time would it take? How much time do expect to get back by using a Party Planner?
  • Similarly, since Party Planners are often able to purchase food and supplies at discounted rates – how much savings might you hope to enjoy as a result?

These questions explore desired Great Demo! Deltas (the value) and Value Realization Events.

Party Planning, Discovery, and Outcomes

You’d expect a good Party Planner to be prepared to ask these questions – and perhaps more. You’d want the Planner to gain a rich understanding of your goals and objectives, challenges and constraints, desires and anticipated outcomes. You’d expect the Planner to be thorough, leveraging the Planner’s deep experience in the process.

Your prospects expect the same level of discovery from you for their software buying processes.

Imagine what could happen in the Planner’s questions were insufficient – and some key items were missed or ignored. What bad things might happen?

Some small issues might include:

  • Too much food – or not enough (“I’m still hungry…”).
  • Guests arrive overdressed, underdressed, or similar (“Oh no, I thought this was a beach picnic…!”).
  • Folks who were supposed to bring gifts didn’t – or vice versa (“Sorry, I didn’t realize this was your birthday…!”).

Moderate issues:

  • People with violently different political agendas were seated together and argued loudly all evening (“You’re wrong and…!”).
  • Kids ran wild and broke things (“Oh no, that was a wedding present…!”).
  • Guests with specific food dislikes or diets were disappointed by the options (“I thought they knew I’m a strict vegetarian…!”).

Severe issues:

  • Guest is taken to the emergency room (“I’m violently allergic to shellfish…”).
  • Fire department is called (“Sorry, I didn’t realize that was a fake fireplace…”).
  • Police are called (“I guess we shouldn’t have sat those two together…”).

Clearly, the success of this evening relies of the Planner doing a complete job in the discovery process. How is this different from doing discovery for a software sale? It should be very similar!

A Dinner Party Situation Slide

Finally, for Great Demo! practitioners, note that the key information can be captured in a Great Demo! Situation Slide:

Job Title/Industry: Head of Household, Urban/Suburban Residence

Critical Business Issue: Successful dinner experience – extending network and friendships

Problems/Reasons: Unsure about too many factors – timing, length, formal/informal, guests, venue, amounts, tastes, diets, expectations, quality of experience, effort and cost; budget limited to $2000; worried that time will be a serious constraint; concerned about future relationships; can’t afford a negative experience

Specific Capabilities: Need to determine specific timing, level, dishes, quantities, likes/dislikes, diet preferences, allergies, guest expectations; need to manage the experience to the satisfaction of all parties; complete prep, execution and cleanup within timeline; would like guests to be “absolutely delighted”

Delta: Need to match previous experiences as a guest of others; need to secure reciprocal invitation; recover $100-250 of budget; complete prep, dinner and clean-up in 5 vs. 12 hours

Critical Date: Schedule the date before winter holidays consume available options (an easy Critical Date might be a birthday…!)

Value Realization Events: First expression of “Yum – this is really good!” by guest; happy social media posts by guests; receipt of reciprocal invitations

And a suitable Great Demo! Illustration for the Party Planner might be an example photo or two of a dinner, with delighted, toasting guests…

Situation Slides represent an example output of discovery, providing the sales team (your Party Planner, in this case) with an understanding of how to determine when sufficient information has been collected.

And if you do use these questions to plan your own dinner party, I hope you have a great time!

Copyright © 2021 The Second Derivative – All Rights Reserved.

For more demo tips, best practices, tools and techniques, explore our blog and articles on the Resources pages of our website at https://GreatDemo.com and join the Great Demo! LinkedIn Group to share your experiences and learn from others.

Republished with author's permission from original post.

Peter Cohan
Have you ever seen a bad software demonstration? Peter Cohan is the founder and principal of Great Demo!, focused on helping software organizations improve the success rates of their demos. He authored Great Demo! - how to prepare and deliver surprisingly compelling software demonstrations. Peter has experience as an individual contributor, manager and senior management in marketing, sales, and business development. He has also been, and continues to be, a customer.


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