How to get over your fear of cold calling, and a big sales “first”

Is there anything worse than a lingering cold?

I mean, probably yes.

But when you’re going through it, it feels like hell and the thought of just getting better is like heaven on earth. Suffice to say my runny nose is still sticking around, but hopefully back to 100% asap.

That being said, I’ve gotten into a decent groove with cold calling over the last few months and wanted to quickly chat about it.

Because I feel like over the years it’s fallen to the wayside, as everybody looks to automate everything.

Cold email campaigns, cold LinkedIn outreach, cold Insta DM’ing.

And some of those are great, if done well. But from what I see in my inbox, and the amount of terrible, ice cold LinkedIn crap I get – most of it probably isn’t all that great. It also means even more opportunity for those of us who haven’t given up on cold calling.

Because while everyone else is worrying about perfecting their cold tech this and that, I’m just having honest conversations with people, on the phone.

Which is probably the best way to present your product/service, instead of being 1 in a million emails/LinkedIn messages/etc. That being said, it ain’t easy. There’s a reason so many people love the cold tech stuff – they can sit behind their comfy computers, and just press a few buttons.

Now don’t get me wrong – some of that stuff can work, and work well. But there’s a reason cold calling has, and probably still is, the most effective way to close new clients.

The trick is, mostly, getting over your fear of it.

Because unless you’ve done a lot of it before, or are extremely comfortable starting cold conversations with random people, it’s probably at least a little bit intimidating.

I know it was for me.

But one of the things I’ve learned, after probably hundreds of cold calls now, is that it’s like anything else – the more you do it, the better you get, the more confidence you get doing it, and it’s a virtuous cycle.

The hardest part is mostly in the setup:

  • have a defined target market
  • get a good list of these people ahead of time (with contact info)
  • have a script ready for how you’d like the convo to go and key messages to get across
  • know the key outcome you want to get from the call (demo booked? free trial? followup call?)

That’s half the battle.

And I talk more about it in the recent short snippet video I posted on Youtube Shorts/Tiktok. We basically take snippets from the Grind Mastermind Podcast, and repurpose them.

Bite sized knowledge, from yours truly. Check out the video on Shorts here, or Tiktok here.

Also had a cool “first” last week in my cold outreach adventure.

As most of you know, it’s been a big focus on sales and growth for the last month or so.

Cold calling, emailing, scheduling demos, trying to get new users, etc. And we actually had a pretty good month of April, so that’s exciting. I’m also continuously trying to learn and improve my sales game, because if I’m being honest, I’m not an A+ in sales.

I think I’m pretty good at sales – heck, I’ve been doing it on-and-off for the last 6 years for my law firm, then in tech for Visto. But I’d say I’m more of an operations guy than a sales guy.

Which made my sales “first” today even more exciting. So what was it?

Well, as you know we sell immigration software, and so the usual flow is cold outbound, then try to book a demo, then do a demo, then get them to sign up for our free trial.

Now what my sales advisor told me to aim for was to try and close a new user in as few steps as possible. So instead of cold calling and trying to book a demo – try to do the demo live, on the cold call, and avoid adding an extra step.

Makes sense logically right? If you can sign up a new user in 1 step instead of 2 or 3, that’s ideal. First because it’s faster, and second because there are fewer chances for the lead to fall off (back out, skip a call, etc.).

Today, I landed my first new user sign up on a cold call – all in one step – and it felt great.

I made the call, confirmed they were in our target market and that they were interested in our product, then asked if they had 10 minutes for a quick demo on the spot. They said yes!

So I quickly swapped us over to a video call, gave the demo and got them signed up for our trial. All within about 25 minutes from calling them that first time.

Now for some of you A+ salespeople out there, that might just be another day in the office. But for a guy who hasn’t done a ton of tech sales, it was a fun accomplishment to convert a brand new user right from a cold call.

Suffice to say, I’m just warming up over here… and if I can keep up this work, and continue improving as I go, I think we’re going to have a good few months at Visto. Hopefully you’re enjoying the journey too, and if there’s any part of that story/sequence/sales content that interests you, hit reply to let me know and I can go into more detail.

I’d also say I think I crossed the cold calling chasm.

And what I mean by that is, I’m starting to get comfortable doing it.

Like anything that’s sort of new or a little intimidating, it can take some time to get settled in before feeling confident in a certain task.

Selling, creating content, riding a bike, you name it.

After some more reps and advice, I’m starting to feel pretty confident with my cold callng game, which makes waking up and doing it everyday that much easier.

And I think it comes down to 2 things:

  • being well prepared
  • doing it a lot

Doing something a lot is pretty simple. The more you do it, the better and more confident you’ll get, especially if you’re being intentional with it and adjusting along the way.

Selling, creating content, riding a bike, etc.

But the other thing that’s helped me a lot for cold calling is being prepared. In this case, with a really good script.

As I’m making calls, I’m looking over on my second screen to my script that lists exactly what to say at the beginning, what to say depending on their response, how to close out the call, etc.

With a good script, I know exactly what to say about 85% of the time. And when that’s the case, it’s just a matter of going through the motions and hitting your numbers to get results.

And it’s probably the same with anything – selling, creating content, riding a bike, etc.

Have a good plan/guide in place and it will make doing those things much easier.

Maybe overly simplistic, but hey, usually the best business advice is…

Have a great day, make sure to sign up for my daily solopreneur tips here, and keep grinding.

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