Table of Contents
Inspired by The Sandler Way Book.
1. Bonding & Rapport Questions #
- Purpose: Build trust, establish credibility, and set a conversational tone.
- “How did you get started in the vacation rental industry?”
- “What’s your favorite part of managing vacation rental properties?”
- “What inspired you to grow your business in this specific market?”
- “How do you currently market your properties to attract more direct bookings?”
- “What’s something unique about your vacation rentals that guests love?”
2. Pain Questions #
- Purpose: Identify specific challenges or frustrations the client is experiencing.
- “What’s been your biggest challenge in getting more direct bookings?”
- “How do you feel about your current reliance on OTAs (like Airbnb or Vrbo)?”
- “What’s happening now with your marketing that isn’t producing the results you’d like?”
- “How much time or effort are you currently spending on managing your digital marketing?”
- “What would happen if these issues continued for the next 12 months?”
- “How do these challenges affect your ability to grow your inventory or revenue?”
- “Are you seeing consistency in occupancy rates across peak and off-peak seasons?”
3. Budget Questions #
- Purpose: Understand the client’s willingness, ability, and constraints for investing in marketing, while uncovering their revenue model and fee structure.
General Budget Questions #
- “What kind of budget have you allocated for marketing efforts like paid search, social ads, or email campaigns?”
- “When it comes to marketing, how do you prioritize spend between OTA commissions and efforts to increase direct bookings?”
- “How do you determine whether your marketing budget is delivering a good ROI?”
- “What’s your strategy for balancing short-term bookings with long-term revenue growth?”
Probing into Fees and Revenue Breakdown #
- Fees:
- “What percentage of your bookings currently come from OTAs like Airbnb or Vrbo?”
- “What are your average OTA commission rates, and how much are they impacting your bottom line?”
- “Have you calculated how much you’re paying in fees to OTAs over a year?”
- “How would reducing OTA reliance affect your overall profitability?”
- Revenue Per Booking:
- “What’s your average revenue per booking, and how does that change between direct bookings and OTA bookings?”
- “Do you have a sense of how your revenue per booking compares to your competitors in the area?”
- “What percentage of your revenue is reinvested into growing direct bookings or improving guest experience?”
- “How does your cancellation policy affect revenue, and is that an area you’re trying to optimize?”
Investment Scenarios #
- “If you could redirect some of the money spent on OTA fees toward marketing that generates direct bookings, what would success look like for you?”
- “If we could show you a path to recover just 10% of your OTA fees through direct bookings, would that feel like a meaningful win?”
- “How comfortable are you investing in strategies that yield measurable, long-term results versus quick wins?”
- “What’s your current customer acquisition cost (CAC) for direct bookings, and are you happy with it?”
Follow-Up Financial Questions #
- “Have you compared the lifetime value of guests who book directly versus those from OTAs?”
- “How often do you calculate revenue per property, and does that affect how you allocate your marketing budget?”
- “Do you have any goals for increasing average booking value or length of stay, and how does marketing fit into that?”
4. Decision Questions #
- Purpose: Identify decision-makers, timelines, and their internal decision-making processes.
- “How do you typically evaluate and choose a new marketing partner or agency?”
- “Who else on your team is involved in making decisions about your marketing strategy?”
- “What does your decision-making process usually look like for a project like this?”
- “Are there any upcoming deadlines or business goals we should align with?”
- “What needs to happen internally to move forward with a solution like ours?”
- “If we both agree this makes sense, when would you like to start seeing results?”
5. Fulfillment Questions #
- Purpose: Validate that your solutions align with their needs and expectations.
- “What would success look like for you in six months if we worked together?”
- “How important is it for you to reduce your dependency on OTAs?”
- “If we could help you increase your direct bookings while saving time, how would that impact your business?”
- “What kind of guest or homeowner feedback would signal to you that your marketing is working well?”
- “Are there any specific marketing channels you’ve been hesitant to try but are curious about?”
- “Would consistent reporting on campaign performance help you feel confident in the investment?”
6. Post-Sell Questions #
- Purpose: Prevent buyer’s remorse and solidify the commitment.
- “What questions or concerns might come up from your team about moving forward?”
- “If we hit the milestones we’ve discussed, what’s your long-term vision for growing direct bookings?”
- “What challenges do you think might come up as we start implementing this?”
- “How would you feel about us periodically revisiting goals to make sure we’re still on track?”
- “Who do you think would benefit most from knowing about what we’re doing together—anyone you’d recommend I speak to?”
Additional Strategic Questions #
These help you differentiate BuildUp Bookings and encourage prospects to think critically about their needs:
- “What’s your strategy for growing your portfolio by attracting more homeowners?”
- “How much do you currently rely on repeat guests versus new bookings?”
- “What’s one thing you’ve always wanted to try in your marketing but haven’t had the bandwidth for?”
- “How would you like to see your business positioned in your market over the next three years?”
- “What kind of feedback are you hearing from guests about your booking process or website?”
Here are some questions that you may want to ask during a discover call with a vacation rental manager looking to improve their digital marketing efforts.
Questions To Consider #
- How long in business?
- Number of units managed? (sidebar: divide number to get a rough sense of growth rate. Example: 100 units in 4 years: 25 properties added per year on average).
- What is your annual gross booking revenue? (sidebar: you can also ask average daily rates X around 65% occupancy and then sum up all of those properties)
- What are your current efforts around digital marketing? DIY, a team member, an entire team, an agency, none of above?
- How many email marketing newsletters have you sent in the last 6 months?
- How would you grade your current SEO efforts and results? Why that grade?
- How would you grade your current PPC efforts and results? Why that grade?
- How would you grade your current organic social media efforts and results? Why that grade?
- How many new properties have you added in the last 6 months?
- How many have you lost/churned? Why have they churned?
- How many people are on your team? Full time vs contractor? (sidebar: do they run payroll)
- Do you have Google Analytics installed? Can we have access to it?
Research Items To Perform Ahead Of Time #
- Do they have their own website? What platform is it on?
- Do they have established brand standards? Logo/color/brand kit?
- Do they have Google Analytics installed on their website? If so, how many sessions in the last 30 days?
- Do they have a Google My Business listing verified?
- What PMS platform do they use?
- What is the TAM of their market?
- How restrictive/severe are the STR regulations? How much smaller is the TAM of legal properties?
Who is the largest PM in the market and how many units do they have? (sidebar: this is the “ceiling” perhaps in short-term in terms of company size. Markets like OBX may support 1,500+ unit managers, while smaller markets may only have a 100-200 unit manager).
Google Analytics Questions #
- Reports -> Monetization Overview – Last 12 months: the question – are they tracking Google Analytics ecommerce bookings and how many bookings are coming in / measured direct?
- Acquisition -> Traffic acquisition – Last 12 months: the question – where is traffic coming from and how is it converting into bookings?
- Engagement – > Events: the question – what events are firing in Google Analytics? Last 12 months.
