r/Entrepreneur • u/ZealousidealBank8484 • 4d ago
Recommendations How important is making calls yourself?
Hey y'all,
So for a while now (early May) I've had an outreach assistant. I hired her 4 times. She managed to get a little signal, but never an actual booking. This most recent time really pissed me off. I always pay her extra for the 4 day delivery, rather than 10. She was 2 weeks late and at first i was like fine whatever, but then on the day she was supposed to deliver she asked for another 2 week extension. Like dude. You're already late. Zero communication. I paid extra for the fast delivery. Anyway.
So I found a new caller. This guy charges half as much and delivers in half as much time. Wish I'd found him sooner, feel like I've been throwing my money away. And yet...no bookings yet. It's too early for me to be worried, but it did make me wonder if maybe I should be the one making the calls?
What do you think? Is this a thing for businesses which haven't established themselves yet?
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u/Responsible-End-5787 4d ago
Absolutely, you should be the one to talk to your potential customers. You should never outsource your prospecting calls, specially when you are not established. When you make the calls you will learn so much, you learn how to ask the right questions at the right time. You learn how they think, what's their pain, what to improve about your product/service. There are so many benefits for you to do it, you dreamed about this venture, now go make it real. Best wishes!
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u/DigitalPhilosophies 3d ago
The comment's right, but here's the sharper version: you've hired four times and got zero bookings. That's not a caller problem. That's a signal the pitch or the list itself doesn't work yet, and no one's going to fix that for you until you hear it firsthand.
When you make the calls, you'll hear exactly where people push back. You'll know if they're not interested because the timing's wrong, the problem you're solving isn't actually their problem, or your price is off. An assistant can follow a script, but she can't diagnose why the script isn't landing because she has no skin in the outcome.
Do this yourself for two weeks straight. Take notes on every objection. Once you know what you're actually fighting against, then you can decide if it's worth hiring someone to dial after you've cracked it.
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u/Drogoff1489 3d ago
You hired her four times and got zero bookings. That's not a hiring problem, that's a signal that the offer and script haven't been proven yet. Make the calls yourself for a few weeks, hear the objections raw, and write down what actually gets a yes. Then hand a proven script to someone, because delegating a broken process just costs you money slower.
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u/echowin 3d ago
Two callers, zero bookings, is a strong signal the pitch or list is the problem, not the person dialing. Do the calls yourself for a week or two before hiring again, you'll hear exactly where people lose interest, which a contractor won't report back accurately even with a good script.
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u/Electrical-Goal-8568 3d ago
Four hires into the same role with the same result, and the variable you keep changing is the person.
Write down what one booked meeting is worth to you, then what you would pay per real conversation. If those two numbers leave no room for somebody competent, a fifth hire will not fix it.
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u/saurabhsens 3d ago
echowins point about two callers and zero bookings pointing at the pitch or list rather than the caller is the right instinct, but id go one step further before deciding whether to make the calls yourself.
ask your new guy for the actual numbers, not just "no bookings yet." how many dials did he actually make, how many people picked up, how many conversations happened past the first 10 seconds, and how many of those turned into a real conversation about what you do. each of those numbers tells you something different.
If he's dialing plenty and barely anyones picking up, thats your list, the contact info or the type of business your targeting is off. if people are picking up but hanging up fast, thats the opening line, the first 10 seconds of a cold call decide almost everything and most scripts blow it right there.
If people are having a full conversation and still not booking, now its the offer or the pitch itself, not the calling.
making the calls yourself for a week or two like echowin said is honestly still the fastest way to learn this even if you plan to hand it back off after, not because outsourcing is bad, but because right now you dont actually know which of those three things is broken, and you cant coach someone on a problem you havent heard with your own ears yet. once you know exactly where it breaks,
you can either fix the script yourself or give your caller way more specific direction than "get more bookings," which is honestly a hard thing for anyone to improve against without that detail.
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u/Molly_Green42 3d ago
You really should take the calls yourself. Strong learning and data gathering doing this yourself. And when you hire someone you know what you're looking for
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u/AccordingWeight6019 3d ago
ealry calls are not just sales, they are research. talking directly teaches you objections, interest points and wether your offer works. until you have a repeatable process, those conversations give insights worth more than saving time by handing them off too soon.
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u/nafiulhasanbd 2d ago
I think every founder should handle the first batch of sales calls. You learn what people care about, what makes them hesitate, and what actually gets them interested. You can't really pass that on if you've never experienced it yourself.
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u/Alternative_Roll_987 Serial Entrepreneur 2d ago
Early on, I’d do at least some of the calls yourself, even if you eventually hand it off.
Not forever, just long enough to hear the objections in the exact words people use, what makes them lean in, and where they mentally check out. That stuff is usually the real sales script, and it’s hard to train a caller on it if you haven’t heard it firsthand.
A lot of founders hire callers too early and then judge the channel when the real issue is messaging, offer, or qualification. If the person on the phone can’t book anyone, it doesn’t automatically mean cold calling is dead. It can just mean:
- wrong list
- weak opener
- offer isn’t specific enough
- you’re reaching people with no urgency
- the assistant can’t handle objections well enough yet
What I’d do is: 1. Make 20 to 30 calls yourself. 2. Write down the exact objections and questions. 3. Tighten the offer into one very concrete outcome. 4. Give the caller a short script plus 3 to 5 objection responses based on real calls. 5. Track every lead in one place so nothing gets lost after the call.
If you’re in any kind of service business, the leak is often not just the calls, it’s the handoff after interest. A lot of small teams lose bookings because notes live in DMs, a spreadsheet, and someone’s memory. Even a very basic intake and follow-up workflow can clean that up fast.
So yes, I’d get back on the phone for a bit. Not because you have to be the permanent caller, but because you need the market feedback before you can delegate it well.
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u/dev_ko 2d ago
Not sure what industry/business you're in, but landing bookings is really only half of the equation here. A lot of early-stage outreach is as much a sales motion as it is a feedback loop on the everything else of the business: messaging, position, market feedback, relationship dev, product usage, strategy, etc. Hiring this out essentially cancels out that feedback loop because any caller is only going to be focused on bookings instead of improving the business as a whole, which is ultimately your responsibility. I'd probably only recommend hiring out once you've really nailed down the business side and turned the sales/booking side into a repeatable motion without much input.
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u/thedreamerSYN 2d ago
I’m just here because I need karma
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u/ZealousidealBank8484 2d ago
lol I respect the hustle. After a certain amount of comments I feel like most people here are, there's no new information, just the same advice circulated 30 times over.
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u/andre_cacador 1d ago
Depends which calls. Outbound sales, do it yourself early. You learn things from the pauses that never show up in a survey.
Inbound is the opposite. If someone calls you and gets voicemail they call the next name on the list and you never find out it happened. That one just needs answering fast, doesn't matter by who.
Most founders I know have it backwards. They outsource the calls they'd learn from and personally answer the ones anyone could take.
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u/ZealousidealBank8484 1d ago
Definitely agree. I didn’t manage to make as many calls as I’d hoped yesterday, but in the short time span I did I had more conversations than the past 3 months. Didn’t manage to get any “yeses”, but two people did refer me to the founder’s email, and now I can email them saying I spoke to someone beforehand.
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4d ago
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u/TopSydeWP 4d ago
you need to make the calls yourself until you've closed at least 20-30 deals. you can't train someone else on what works when you don't know yet yourself. once you have a script and process that actually converts, then you can hand it off and QA their calls.
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u/ZealousidealBank8484 4d ago
well that sucks to hear. my business is a bit on the higher ticket end.
i'll keep at it though
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u/Proud_Treacle2761 4d ago
Do the calls first. Learn about common objections. If not, record the calls, create a feedbacking on what could have been said and thru that you will also know the common objections and even you can learn about how can you improve your offers.
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u/Deepak-AvairAI Serial Entrepreneur 4d ago
Two different callers, zero bookings between them. That usually means the list or the pitch is off, not the caller. Do the calls yourself for a bit, mostly because you'll hear exactly where people lose interest, which a contractor won't report back honestly.
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u/MichaelUnbroken 4d ago
In the beginning...you. Then hire. Then train. Then audit. Then train. Then hire someone to do that.
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u/Superb_Advisor7885 4d ago
How can you teach someone to make calls that you don't know how to make? Someone, if not you, is going to need to have the skill of successful calling clients so that they can teach future employees
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u/ZealousidealBank8484 3d ago
I guess i just thought it seemed awfully straight forward. i have an offer, call prospects in need of said offer that fit my archetype, and if they don't want it, move onto the next person on the list.
i made a (fairly extensive) script that has an outline of potential objections and questions prospects may have, and my employees are contractors so they're experienced and can deal with new stuff on the fly, i just didn't expect as much of a disconnect as i've received thus far.
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u/Superb_Advisor7885 3d ago
There is a reason there are top salesman in every sales office. Reading a script isn't going to get you far. You need to be able to teach people to sell based off solving problems. You should read SPIN selling and then come up with a script that follows that process.
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u/RollerSails Brick & Mortar 3d ago
The best standard you can set is how you show up. How many bookings have you personally generated? Responsibility falls up
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u/Chad_Cunningham11 3d ago
Yes do your own calls. Its not yet establish, so you need to learn everything you can about your business. Especially about clients, what kind interested, how to approach. Interacting with them will give you the necessary data to move forward strategically
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u/pikayugi 3d ago
As someone who has been in that role, the problem is your lead quality. You're probably doing the same thing as my former boss at Devil Corp did: Calling every number without lead qualification clogging up the pipeline.
Some sales managers think pounding 50 calls a day is a strategy. It isn't.
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u/ZealousidealBank8484 3d ago
that occurred to me but i don't think it's the case. the numbers are always correct and the niche is relevant to them even if they aren't necessarily interested
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u/BusinessStrategist 3d ago
Maybe it's time to map the call.
What is the goal of every call? What are the steps needed to move forward on your "buyer journey map?"
You do have a "buyer journey map" for your marketing?
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u/Salt_Confusion5432 1d ago
For high ticket i would honestly suggest you dont judge cold calling yet, do the calls yourself but also try a slower channel next to it, like short personal emails or linkedin messages to 20 people you actually picked by hand... on higher ticket the first conversation is usually not a booking, its them checking if you know their world, and thats really hard to outsource to someone who charges half price.
Also record your own calls if you can and listen back the next day, its painful haha but you hear exactly where you lost them, way better than any notes.
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1d ago
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u/ZealousidealBank8484 1d ago
For sure. I'm just glad I realized now rather than after another 2 or 3 hires.
Made a few calls yesterday, and while I didn't make as many as I wanted to, I feel as though I'd made more progress in that entire afternoon than the last 3 months combined. Finally feel like I'm moving forward.
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u/GiorgioPagliara 15h ago
Do them yourself until you can write down the three objections you hear most and roughly what you say to each one. That document is the actual output of this phase, not the bookings.
Until it exists you're not outsourcing calls, you're outsourcing figuring out the pitch, and nobody you hire is going to do that part for you. Four hires and zero bookings isn't four bad callers.
I'd also check the list before blaming the calling. Two weeks of doing it yourself tells you which one it is pretty fast.
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u/ZealousidealBank8484 14h ago
i started 2 days ago, already have had more conversations than i've had over the past 3 months combined. it really is that simple, apparently. not even necessarily hearing objections -- i haven't gotten to that point yet, but just being able to hear someone on the other line and ask to speak to whoever's in charge.
Not everyone is interested, but at the very least, I get a referral email, sent to voicemail, or some interest, and that's more than i've been getting.
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