How Not to Sell

My company is thinking about purchasing a new payroll system. It’s a fairly hefty commitment, something on the order of $35,000 a year, with a huge amount of effort in both man-hours and stress during the “conversion” period. We did not have a nice experience the last time we did this, just before I arrived on the scene two years ago. So the owners have tasked me with heading up this little project.

We contacted three prominent payroll companies to come in, pitch us, and send in proposals. One company is a dinosaur too similar to the company that does our payroll now. It’s really a horse race between two newer, more technologically savvy companies. I could go with either one, so that means it will come down to numbers (if in fact we do decide to make the change).

One saleswoman from one company is so extremely and incredibly annoying that her presence alone almost negates their proposal. Not in an incompetant and possibly endearing way, but in a cold and calculating separate-you-from-your-money way. Based on my experiences with her, I’ve come up with a a primer on How Not to Sell, written not by a salesman but by a consumer.


(1) Stalk the target company’s key and not-so-key personnel.

Every three or four months we’ll all in the office get a barrage of phone calls from her. Over a week she’ll make a dozen or so calls. Woe to the person who answers one – she’s impossible to get off the phone short of hanging up on her once she gets her pitch a-rollin’. I’ve actually had to raise my voice over her (in those green days when I answered every call to my desk) and inform her I’d be hanging up.

(2) Make up cozy relationships with your client’s superiors.

She’d tell me how many “great” conversations she’s had with my boss, “sharing ideas and thoughts” on payroll. Yeah ... my boss can’t stand her and absolutely refuses to deal with her.

(3) Inform clients you’re too busy to attend their regularly-scheduled monthly vendor meetings.

Once a month we invite all potential vendors who want to do business with us to come in and pitch to the management and owners. She declined – “that doesn’t fit in with my schedule.” And then she wistfully tells me she regrets that it won’t be possible to speak with the owners of the company.

(4) Maintain an aura of over-aggression, talkiness, and fake cheerfulness.

Ugh. I don’t like dealing with women with more testosterone than me. And please, I’m a quiet guy, but please let me get the rare question in when I have one. It will be an important question.

(5) Get your personal facts wrong about the client.

Okay, nothing wrong with jotting down personal info about your client after the meeting, and refreshing it in your mind right before the next one. Makes for good chit-chat and establishes a personal connection with the potential customer. I get that. But get your facts straight. She knew exactly what I was doing the day before our last meeting (I told her as we were discussing our individual weekend plans during small talk) but she inquires about my “youngest son.” Er, don’t have one.

(6) Bring your twenty-something “manager” with you to the sales call and both of you display lots of cleavage.

Now, trust me, this really happened but it’s not as flagrant as you’re imagining. The result was that I was uncomfortable and the whole situation was weird and off-putting.

(7) Pout when your prospect doesn’t agree on the spot when he first sees your proposal.

This, too, really did happen. Though this time I was more amused by the reactions I was seeing.

(8) Don’t bring any hardcopies of the proposal with you when you go over it.

Dumb and unprofessional. No excuse for this. Had to be an ulterior motive for this.

(9) When you say you’ll email the proposal, don’t do it right then and there. Instead, email it twenty-four hours later after your prospect reaches out to you with an email, “Are you going to email the proposal to me or not?”

Again, this really happened. What’s her end game? Everything about her – even the pouting – seems cold and calculating to me. Is she “punishing” me for not instantly exclaiming, “Yes! I’ll take it! Where do I sign?”

(10) Micromanage your potential client’s next steps.

“So when do you think you’ll speak about our proposal with the owners?” “Maybe Monday.” “Okay, what time Monday should I call you?” “Uh, it’s not definite that I’ll be speaking with them Monday. I’m going to try.” “Okay, does a Monday afternoon call sound good for you?” “Listen, let’s not make this an hour-by-hour thing.” “Okay, how about a call Monday just to figure out what the next steps in the decision process will be.” “Argggggggggggggggggh!!!!”


There, salesmen and saleswomen of America, you have it. Ten concise steps on What Not to Do when trying to get The Sale. Straight from a customer looking to buy. Read these lines, memorize them, apply them, and – Happy Selling!