Is Your Poor Prospecting Turning You Into a Sales Cliché? The 5 Cardinal Sins of Prospecting

Posted by Kristin Luck on 12/11/19 8:30 AM
Kristin Luck
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Is Your Poor Prospecting Turning You Into a Sales Cliché? The Five Cardinal Sins of Prospecting

I posted a similar missive last year around this time since it seems to be the season when sales folks switch into Q3/4 panic mode. Unfortunately, poor sales prospecting remains my top business pet peeve. Thus, this post bears repeating… and an update.

Make no mistake, prospecting is hard work so it’s no wonder that folks try to create as many hacks and shortcuts as they can to get to a target buyer. As a byproduct of being a researcher by trade, my prospecting techniques have always included a LOT of time researching the person I want to connect with before I ever ask for a meeting. And even more time researching the prospect and their category after the meeting is set.  

In many ways, I was fortunate to learn sales prospecting the hard way (with a much narrower array of data and information tools) - really doing the research to understand who my prospective client was and what might motivate them to buy.

That type of prospecting seems to be suffering a long slow demise. Barely a day goes by that I don’t receive some sort of email or LinkedIn message from a salesperson that clearly has no idea who I am or what my business is. Worse, the time and care they put into the outreach is so poor it’s borderline offensive. 

Here are 5 tips for getting prospecting right:

1. Prospect properly.

And by that I mean, do your background research. Don’t ask your prospective client to do it for you. As Eileen Campbell put it best during her tenure as CMO of IMAX, “emails asking me to do your sales prospecting are beyond the pale." One of my recent favorites,

“Hi Kristin, I’m looking for who handles the training content/courses for your company Decipher [note: my firm Decipher was acquired and I exited post-acquisition in 2014]. A kind reply and CC: with their names would be greatly appreciated.”

Strike 1, you haven’t bothered to learn anything about me or my company. Strike 2, you’re asking me to do your prospecting for you. Read on for Strike 3.

2. Respect your prospect’s time.

Aside from not asking your prospect to do your research for you, don’t assign them work. For instance,

“In the interest of your time [Note: this really means the salesperson’s time], I have attached a quick 2-minute video. Please watch this, it’s only 2-minutes, and let me know if we can schedule an additional 5-minutes that works for you.”

That’s Strike 3– now you’re asking me to pre-qualify myself to engage in a conversation with you that I’m not sure I want to have in the first place. Couching your sales and marketing content as “gifts” is no better. Some of my favorites include receiving a “gift” of a video library of 57 brand haikus from a brand strategy firm, and a “gift” of 15 sales videos from a sales consultant that connected with me on LinkedIn (how could he have guessed that I’ve been waiting my entire life for someone to send me over two hours of sales videos to watch?). To be clearyour sales and marketing content is not a gift.

3. Use technology wisely.

With the advent of AI and tools like or ZoomInfo, it’s easier than ever to automate the prospecting process. As Pierre LaManh (CEO of North America for Ipsos) recently posted on LinkedIn in response to an offer from Pittsburgh Technical College to “turn your associates degree into a Bachelor’s degree in 24 months,” “after decades of direct marketing, and DMPs, programmatic buying, machine learning algorithms etc..., personalized marketing still has a lot of room for improvement!” Don’t embarrass yourself or your firm by automating your outreach so much that it’s blatantly irrelevant to your prospect.

4. Always be helping.

The ABC’s of sales from the infamous sales movie, Glengarry Glen Ross, are “Always Be Closing.” I prefer Priscilla McKinney’s, CEO of Little Bird Marketing, take. She’s pivoted the ABC’s to ABH – "Always Be Helping." Assuming you’ve followed tips 1 and 2, you’ve done your research, and you’ve made the right connection, now it’s time to build a relationship. Maybe you’ve made your sales pitch and there’s not an immediate fit. What can you do to make sure you and your business remain top of mind?

Keep your prospective client engaged by showing you care about their business. Send them relevant articles, follow their company news and congratulate them on big wins, and offer to connect them to other firms or people you know that may have a positive impact on their business. Sales rule of thumb is that it generally takes 18 “no’s” to get a “yes”, so play the long game. And that takes us to tip #5.

5. Play the long game.

I can’t be the only one who has accepted a new connection request on LinkedIn only to receive, literally 30 seconds later, a poorly worded lengthy sales email that clearly was a copy and paste job. Good prospecting utilizes the same techniques you’d use when you’re trying to enter a personal relationship... don’t come in too hot and use the same bad line(s) on everyone you meet. You wouldn’t walk up to a total stranger on the street, grab them and whisper, “I love you” in their ear (at least I hope you wouldn’t). Sales is no different. Ease into it.

Tweet this! Good sales prospecting means doing your research, respecting your prospect's time, building meaningful relationships, and adopting a long game mindset.
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Too often salespeople are looking for the quick and easy win– anything that will boost their monthly or quarterly sales number and help them reach their goal. The issue with that strategy is that it doesn’t consider the lifetime value of a client. I’ve had deals that closed in two weeks and others that took two years. Doing the research, really learning your client’s business, and delivering a solution that compels them to work with you is a long game strategy and can have a significant positive impact on the lifetime value of the relationship.

There are no shortcuts– prospecting is work. Smart salespeople are availing themselves of technology solutions to help make the research and discovery process less arduous, but make no mistake, it’s still work. Do your research, respect your prospects time, use technology wisely, build meaningful relationships and adopt a long game mindset.

Topics: Lead Generation, Sales Strategy


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