Sales Playbook

All Qualification, Discovery, and Closing Questions

Every qualification, discovery, and closing question, organized.

#Qualification Questions

How much revenue are you at?
How many active customers are you serving right now?
Talk to me about how you price your solution.
What does your sales tech stack look like? (good proxy for sales sophistication, budget, marketing mix)

#Discovery Questions

The purpose of these questions is to expose the areas where the prospect is currently failing and identify the most painful elements of their current process.

Expose Weaknesses
Sell Dream
Decrease Risk
Close Off Alternatives

Level One Questions

What’s keeping you up at night on the lead gen side?
What’s the biggest constraint right now in growing revenue?
Where are you seeing the most and least return on marketing spend right now?

Channel choices

The prospect’s current marketing mix reveals a lot about how they find new customers. Your goal should be to draw attention to weaknesses of each channel.
1. Paid Media (PPC)
  1. Pain Points
    1. Expensive
    2. Easy to spend money with zero ROI
    3. Leads can be unqualified
    4. Blackbox = no visibility or learnings
    5. Can be too broad, not super targeted
    6. Requires specialized expertise / resource / employee
  2. Questions
    1. Why not scale through paid advertising like Google or Facebook/Meta?
    2. What’s your return like on Google Ads?
    3. How qualified are the leads you’re getting through PPC?
    4. How much do you just love being at the whim of Google and Facebook?
    5. How much do you feel in control of your results from PPC?
2. Search Engine Optimization (SEO)
  1. Pain Points
    1. Slow to build traction / can’t scale up quickly
    2. Difficult to attract the right qualified leads
    3. Keywords can be competitive in saturated niches
    4. Requires specialized expertise / resource / employee
  2. Questions
    1. Why not double down and scale through SEO?
    2. What’s the qualification rate on those leads?
    3. How much time do you spend on upkeep, link building, dealing with algorithm changes?
3. Referrals / Network
  1. Pain Points
    1. Not scalable
    2. Not predictable
  2. Questions
    1. How do you feel about the percentage of your new sales opportunities that come from referrals vs. something a little more predictable?
    2. How much of your founder / CEO / your network is there left to tap?
    3. Do you have any referral mechanisms in place and why wouldn’t you just scale through those?
4. Internal Sales Development Team
  
  This is discussed also in the Process section below:
  1. Pain Points
    1. Expensive to hire W2 SDRs ($70-$120k fully loaded)
    2. High turnover rate for SDR role
    3. Lots of overhead to hire, train, manage an in-house sales development team
    4. Requires an Annual Contract Value of $20-50k for the math to make sense
    5. Statistically most teams underperform
  2. Questions
    1. How much are you paying per fully-loaded SDR?
    2. Why not just hire more SDRs?
    3. How many of your SDRs are hitting quota?
    4. Are your AEs calendars full?
    5. How many calls is each SDR generating?
5. Conferences / Events
  1. Pain Points
    1. Expensive
    2. Complex logistics
    3. Unclear ROI
    4. Not scalable (too few)
    5. Not consistent (not evenly distributed in time)
  2. Questions
    1. How are you setting up appointments for your sales reps at the shows?
      1. Are they really just walking around without a plan hoping for the best?
      2. Are they really scrubbing those lists and sending those emails manually before the show? How much time does that take? How much selling time do you think they’re losing to do that kind of stuff?
    2. How much money are you spending on conferences / trade shows per quarter or per year?
      1. What if we could sidestep the whole $10-20k booth and just send your reps there with a hitlist of 20 appointments with qualified leads?
    3. What’s your ROI for conferences / trade shows as a channel?
Messaging
1. Pain Points
  1. No bandwidth to test new messaging
  2. No dedicated team to test new messaging
  3. Bad copywriting
  4. No personalization
2. Questions
  1. How much time do you spend writing messaging for new segments or personas or campaigns?
  2. Why haven’t you run personalized campaigns to every segment/persona to see what works?
  3. How personalized is your messaging?
  4. How many dynamic variables do you include in each email?
  5. What percentage of any given email is 100% unique to the individual prospect or company?
Process
1. Pain Points
  1. No dedicated prospecting team
  2. No dedicated list building / data enrichment function
  3. Not enough time for full cycle reps to do everything themselves
2. Questions
  1. How much time does your team spend prospecting
Technical Setup
1. People who do it themselves
  1. Pain Points
    1. Sending cold emails through the wrong email marketing tool like Hubspot, Mailchimp, etc.
    2. Sending from their primary domain
    3. Sending too much volume
    4. Not validating their emails
    5. Not setting up DKIM/SPF/DMARC correctly
  2. Questions
2. People who outsourced it to agencies / freelancers
  1. Pain Points
    1. Low deliverability
    2. Spammy
List Quality
1. Not validating their emails
2. Not using intelligent or trigger-based approaches to approximate buying intent and prospect pain
3. Not able to find enough addressable contacts
Knowledge

How many more customers could you realistically handle over the next 3-6 months before something breaks?
What would it mean for your team if you were talking to 2x the number of good-fit customers?
How many qualified leads are you at right now per month, and how many would you like to be at?
What else is on your plate that you’re not doing right now because you’re focused on solving lead generation first?

Where are those leads coming from? Which channels are most fruitful?
What’s stopping you from scaling up on [Existing Channel}?
What’s driving your interest in outbound as a channel?
Why haven’t you tried outbound / cold email before?
Talk to me about other providers you’ve worked with. What went right/wrong, what would you have changed?
What was the pricing model for those other providers?
How satisfied were you with the results?

#Closing Questions

The closing process should be done on Call Two (or Call Three, if needed).

These questions should only be asked after sufficient qualification & discovery to make sure that the prospect is a good fit and we’ve illustrated and articulated their exact pain points.

The purpose of these questions is to trap the prospect into agreements that are difficult to unwind. These agreements force the prospect to acknowledge:

1) Their pain is strong and has measurable negative impact (magnitude)
2) Our solution can solve their pain (viable mechanism)
3) Our solution is the best possible method relative to alternatives (best mechanism)
4) They feel certain we can implement the solution successfully (trust)
5) The risk of trying it out is very low

It sounds like lead generation is the biggest constraint holding you back from doubling your business over the next 12 months. Is that right?
If you could get a predictable stream of high quality leads that closed without spending on ads or investing in W2 salaries, would that help you hit your revenue targets in a cost-effective way?
If we could deliver you leads that are the right title, right company, and that are ready to get on a call and learn more about your [Product Or Service], would you agree that would be the correct input for you to close new business?
Does the path that we laid out here, where we find lookalikes of your existing customers and send them examples of how you helped similar businesses seem like it might work to create sales opportunities?
If you got a preview of each lead’s job title, revenue, company website, and their exact response, would you feel good/confident/comfortable with the lead quality?
1. Alternatively, “more comfortable with the quality vs. a channel like Google or FB ads?”
Hypothetically, if we could deliver good-fit leads that you pre-approve on performance-basis, meaning if there’s no results, you don’t pay (or basically just pay life support on our server costs), would you feel comfortable testing this out?
If we totally solved lead generation for you, would that help you focus more on [Other Revenue Generating Activity]?
If we solved lead generation for your reps, would that help them focus more on closing deals?
Would your sales reps time be better spent on closing deals instead of prospecting?
Does the performance-based pricing component make sense here? Specifically the fact that in the unlikely case where there’ no results, you’re only on the hook for $500, and in situations where there’s a ton of results, yes the cost goes up, but you’ve pre-approved every lead beforehand?
Compared to alternatives you’re looking at across paid ads, SEO, hiring internally, doing it yourself, does this approach feel like the best option?
How soon would you want your first set of meeting-ready leads to hit {your inbox|your sales team’s inboxes}?