Warning signs your outbound sales strategy is about to crash and burn before it even begins.

If you’re about to drop a lot of money on a new outbound strategy, let this be a cautionary tale of what to look out for, so you’re not digging yourself into a hole.

In 2022, I took a 50% ownership stake in a new company at an enterprise level cold calling center. I was so excited.

We were launching into a market that I already had a lot of experience with… real estate agents. I just knew our strategy was going to be a smash hit.?

I launched the ad strategy to book appointments on a rainy Monday morning.

The goal was to sell real estate agents more listings. I spent $6500 in two weeks. It may not seem like much money…?

But… I had moved my family to a totally different country (from Canada to Colombia) and this campaign was supposed to prove my ability to scale this company quickly.?

If I couldn’t do it, would I have moved my family in vain?

Two weeks later… zero sales.?

This failure taught me a very important lesson.?

I recognized that just because I knew the market, didn’t mean I could launch a cold campaign and get the attention I needed. We had just added to the noise.?

Over the next year, I would learn exactly the warning signs that I had missed, and now help my clients avoid them. So what are they?

1. If you’re getting less than 21% conversion with your already established connections on LinkedIn, that’s a sign that your messaging is off.
2. For every 100 connections, you should get 21 calls from one DM.
3. Anything less than a positive 1% reply from a cold email means the market is not resonating with your offer
4. You should have done at least 20 customer interviews to understand your customer’s problems and their desired outcome.
5. You’re completely obsessed with the features of your product vs focusing on what the market wanted in the first place.
6. If your prospects are showing up to their first sales call with you, not knowing who you are or how you help, you need to work more on your selling environment. Prospects must be warmed up before you meet with them for the first time.?
7. If you’re no show rate is anything higher than 75%, the offer you put out in front of them to get that appointment booked is probably one they’ve seen before. Remember, a good offer is: Product/Service + Relevance + Reason To Act Now + Transformation + Specificity = Offer

So, what’s the takeaway? It’s simple—just because you know the market doesn’t mean you’ll automatically stand out in it. As my experience showed, failing to watch for these warning signs can cost you big time, not just in money, but in credibility and momentum.

It’s critical to pause, take a deep breath, and ask yourself: is your message landing, are you obsessed with features instead of benefits, and have you truly nailed your offer? If you can spot these red flags early on, you’ll save yourself from the crash I experienced—and set your campaign up for the success you’re after.

Don’t wait until it’s too late. Test, tweak, and make sure you’re playing the long game.