When discussing retainers, you often want to assess the value being delivered by exploring things like the prospect's current expenses, the value of their time, and opportunity costs. But since these are financial topics, what if the person isn't comfortable sharing that information on a sales call and reacts defensively? How do you approach that?
There are cultural differences in how comfortable people are discussing their own finances on a call, but you can insulate against a lot of that defensiveness just by being socially aware. I'll never directly ask 'what are your current expenses' or 'what's the value of your time' — instead I'll ask things like 'how are you currently doing this?', 'what software are you using for that?', 'oh that's pretty expensive, are you on that plan?' — and by the end I've mentally added up their spend without ever asking directly. If my estimate is wrong, the client will correct me, so I still get the real number without them feeling interrogated — and every accurate estimate I make also demonstrates that I clearly know this space, which is itself a sales signal. Same approach for opportunity cost: instead of 'how much money have you made this month,' I'll ask 'how are sales going, mostly ads, inbound, or referrals?' and build up the picture indirectly from there.
My reply depends on the exact product I’m selling, but a reliable template is to give a broad price range that starts low and ends high, then explain that I need a bit more detail or scoping to give a precise number and invite them onto a call. At the same time I satisfy their surface‑level request for technical info with a high‑level overview—for example, I describe how I built an AI that autonomously scrapes job postings from LinkedIn, Indeed, and similar sites, then looks them up and creates a profile used to personalize the email, noting that this is the very system that got them to respond to my message. I like to show rather than just tell, and I often point out that being on the call already proves the system works in some fashion; I can frame it as queuing up opportunities and letting them take shots at the net, which makes the value easy to grasp.
I do this kind of thing in Maker School, where we run through what a sales call looks like, show how to do a high‑quality call, give bullet points, and talk about kickoff calls. I don’t gatekeep automation knowledge—I do the builds live. If you want sales help, check out Maker School. Briefly, here’s how I structure a call: first, I set expectations and frame the conversation (e.g., confirm we’re on the same page about time). I start by asking why you responded to my outreach, then a few more questions about your business, and finally I explain how I might solve your problem. I want you to walk away with something tangible, so I’ll prepare a free document, asset, or template to give you by the end of the call. After that, we follow the frame we set: I ask ‘why me?’ and ‘why now?’, then I run a customer audit—covering your acquisition, fulfillment, onboarding, client management, HR processes, etc. After you walk me through those, I discuss my solution and send a proposal with the scope. I prefer not to handle objections or do hard selling on the call; I’d rather let the value speak for itself, which comes from my background in heart‑based sales. That’s my approach.
To answer that question, I close deals primarily by not trying to close the deals. Prospects are extraordinarily attuned to sleazy salespeople; we're pretty sophisticated as a market. If someone pushes sales tactics, I think most qualified B2B leads—people who aren't broke, have money to spend, and have had some success—know the game. So I tend to close deals by being very straight-up with the person I'm talking to and treating it more as a consultation than a sale. I ask them questions about their business and see if I could be of value on the call by giving answers, not just when they pay me. I find that this congruence comes across better than lines like 'But wait, Pete, one last question.' or 'Jack, if I could make you this much.' That stuff is all nonsense nowadays. So I'd be a lot more congruent, not putting on a face. Simple things: don't negotiate against yourself; when you give the price, be quiet. Those little things aren't something you can't just read in a sales book by Chris Voss and then not get the 80/20. Hopefully I've answered why I don't live stream—I think it's restrictive in the schedule right now, I've tried it before, and I really need to stick to a weekly thing, which I don't want to do.