Paying attention to your prospects doesn’t always work

March 6, 2013

Paying lots of attention to your prospects and clients can be a good thing, but it can also backfire. Mark, a designer, had it backfire so much he considered folding up shop.

Four months to go

By the time Mark booked a coaching session with me a couple of years ago, he was a few months into his solo venture, which he’d started after getting packaged out from his employer of eight years. He was giving himself four more months to make a go of his business before dusting off his resume.

Mark was struggling, not because he couldn’t find prospects, but because he had trouble closing them. After we talked in some depth, one of his behaviors struck me as the likely culprit. It was the kind of thing I’d seen with other freelancers while they’re starting out and trying to build a clientele.

The shoo-in

One recent big loss was a typical result of his mistake, so I’ll walk you through that. The prospect was the marketing head of a big resort up north. I’ll call her Asha. The resort’s property had recently gone through a massive expansion and they were redoing all their marketing collateral. Mark, who had lots of experience in the resort field, was referred to Asha by someone with a lot of influence, who let Mark know that so long as he impressed Asha, he was a shoo-in.

Oops, the shoo-out

Unfortunately, Mark did a few things during and after the meeting that made him a shoo-out.

The 5 mistakes

1. He went overtime. The meeting started at 11 and was booked for an hour. But as the end of the meeting neared, Mark, still deep in presenting his ideas, asked Asha if she had a bit more time. She said she did and so they went an extra half hour. Mark thought it was a good sign.

2. He offered to take her to lunch.  They hadn’t booked lunch, but Mark didn’t have any plans for the rest of the afternoon, so he thought it would be a swell idea to spend as much time with Asha as possible. She turned down the offer, saying she had to prepare for another meeting.

3. He told her he could devote the majority of his attention to her project, because he wasn’t that busy.

4. He threw himself into his proposal. He was so excited about the possibility of working with Asha that he worked all day and late into the night, sending off the proposal by email at 3 AM.

5. He made a follow-up call two days later.

The letdown

Asha didn’t return that call, or Mark’s call later in the week. Instead she emailed him two weeks later saying she’d decided to go with someone else. She thanked him for all his efforts, so it was a nice letdown, but it stung deeply.

The reek of desperation

While it’s sometimes hard to know exactly why you don’t earn the business, the five things Mark did can certainly swing the decision to a negative, even if you rock everything else. And here’s why. While each of the five acts might be completely acceptable in an established relationship, they carry the whiff of neediness when you do them with someone new. Also, while Mark might have gotten away with one or two, the combination of all five created a fairly powerful reek of desperation. And for a couple of probably obvious reasons, that’s a big turnoff for prospects.

The guy who can’t get past the first date

Firstly, it’s human nature to be repelled by neediness. We all know that guy who’s fantastic in so many ways, but just can’t get past a first date because he keeps the date going until she ends it, tries to secure a second date right away, and starts calling the next day. I know this all too well, because in high school—okay maybe even a little after that—I used to be that guy, until some kind female soul advised me to smarten up.

Oddly, I would eventually spend a few years in the dating industry, researching, writing and talking to tons of people about relationships and dating. I learned a whack from that period that helped me in my personal life, but also in business, because our instinct to be put off by neediness is perhaps surprisingly no different in business.

Signs of struggle

Secondly, in business needy behaviors are red flags. For example, while Mark thought his wide-open calendar would be a plus for his prospects, Asha probably saw it as a sign he was struggling, and perhaps wondered if his business would be around long enough to complete the project or offer ongoing service. It also indicated others were probably rejecting him, which she would have read as a negative endorsement.

My diagnosis rang true to Mark, but he still felt it was crucial to give his prospects the kind of attention some of his busier competitors might not be able to give.

Sure, I told him. His prospects want to know he’ll do a great job, but his professionalism would convey that.

The 3 tips for professionalism

I gave Mark the following guidelines on professionalism:

1. Stick to the meeting length. This will show your prospect that you’re a good time manager who will manage the project just as professionally as you’re managing the meeting. Just because Asha let Mark go overtime doesn’t mean it was a good move. We often let people do things that frustrate us because we’re polite and don’t want to be confrontational. I advised Mark to book appointments—haircuts, gym sessions, whatever—for right after his prospect meetings. Instead of being the hanging-around guy, he’ll be the man-in-demand, heading off to see others who want to work with him.

2. Send correspondence during reasonable hours. You might think you’re impressing your prospect by sending emails at 3:00 AM, but they’re more likely to see that as a little unhinged. Once you have a working relationship, you can do whatever feels right, but play it safe in the early stages.

3. Give your prospect time before following up. There are no magic numbers here, but unless your prospect has an emergency, give them a few days or couple weeks to evaluate your ideas or proposal. You want to convey that you’ve got other fish on the line and that their business isn’t going to make or break you.

Mark followed these guidelines for all his future appointments. At first he found it hard to act busy when he wasn’t, but he did start closing some deals, and eventually got genuinely busy.

The big takeaway: Focusing too much attention on your prospect can backfire because it can make you come across as needy. Lots of people trying to build a clientele make this mistake. If you think you might be losing business because of this, present yourself as a busy professional with a thriving business, even if it’s not true. It can be tricky, because when you’ve got all the time in the world, you might give off subtle hints of neediness that you aren’t aware of. To avoid that, make yourself busy by booking appointments, either personal ones or—perhaps better—set time for business-building activities like marketing, planning, research, skill development.

If you want to share your own story about how being too available hurt you or how presenting yourself as busier than you are won business, please let us know in the comments section below, or shoot me an email at donald (@) freshbooks (dot) com.

Author’s note: this post is based on a business owner I have coached. I’ve changed his name and some telling details.

about the author

Former Staff Contributor Donald Cowper is a best-selling author and head of content at .


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