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Stepping (Gingerly) Into Sales: Tales from a Reluctant Salesperson

March 17th, 2010 by Lauren · 8 Comments

When my business partner Emira announced that she was expecting a baby, my delight at her good news was accompanied by a creeping feeling of dread about taking on some of her key responsibilities at work while she went on maternity leave. See, we’d always divided the workload between us so that while I handled all of our studio’s design work, she tackled all of the sales. And sales work has never been high on my list of favourite things.

We briefly considered hiring a salesperson to help out in her absence, but as a web development agency, our sales process is highly consultative and technical, and we knew that training someone to take over sales would be far more challenging than hiring help on the design side. So it made far more sense for me to set aside my designer’s hat and put on the sales mantle.

Although I knew it was the most logical solution, I wasn’t sure I was cut out for my new gig. While I love the client-facing side of my work, I’ve always cherished the odd workday when I can turn off the phone, ignore email, and just cozy up to my computer to design something new. I’ve always considered myself to be 50/50 introvert/extrovert… but sales felt like an extrovert’s game. Would my phone-free days be a thing of the past?

Well, as it turns out, they are. But I’ve learned a great deal about my business in my first six weeks as a salesperson. And I’ve picked up a few things about sales, too — though I definitely have lots to learn in that department.

It’s become much clearer to me that sales work — at least, the kind of sales we have to do — is not so much about pitching your services to people as it is about asking and answering questions. I know that’s what sales gurus have been saying since the dawn of time, but I’m late to the party and just figured it out. When someone comes to me asking about a new website (or social media strategy, or whatever), more often than not they have decided on a tool before they’ve decided what their goals are, and it’s critical for me to dig deeper to find out what’s behind their decision-making process.

So I ask a lot of questions – and not just “What’s your budget?” and “What’s your timeline?” (although those are both important). I ask them to tell me about their organization and their goals – to tell me what led up to them getting in touch with us. Their response typically conveys information about the size and structure of their organization, as well as their motivators.

It turns out listening, and asking good questions, is a huge part of what I now do for a living. And I’ve got a lot of experience doing that, because it’s also a big part of what I do as a designer and web strategist.

This probably all sounds pretty elementary, and I know it is — it’s just that as a sales newbie, I’m finding it a novel concept that I might already have many of the skills I need in order to do my new job well. I’ve realized that the biggest source of my fear of sales was a presumption that I would need a major personality transplant. I thought I’d need to become magically super-gregarious, able to spin a sales pitch like a spider spins a web, and spot a business opportunity at a hundred paces.

But I discovered that you can be half-introverted and do sales work, so long as you have two key qualities:

  1. You take an interest in people, and
  2. You enjoy being helpful.

I’d love to hear from other reluctant salespeople – what surprised you about sales work? And what lessons have you learned about selling? Share them in the comments.

Tags: HR for the Self-Employed · Our Story · Thoughts

8 responses so far ↓

  • 1 krista - urbanite jewelry // Mar 17, 2010 at 6:55 am

    I think you make some great points, Lauren, and I think the two key qualities you point out at the bottom are spot-on.

    I have also been a reluctant sales person, but as the sole owner/designer/salesperson for my small creative company, I’ve found that I have to step into many roles–even some that may be a bit uncomfortable for me (I’d say I’m a 50/50 introvert/extrovert just like you).

    But as I’ve participated in public events and been able to connect with customers directly, I’ve discovered something important: our non-traditional, small creative businesses aren’t as hard to sell because we’re offering something personal and authentic. Because we offer products and services that people connect with/relate to/etc. and because we’re not huge, faceless companies, I think it puts people at ease and eager to work with us. I think that goes a long way in making sales much easier in a lot (but not all) instances! :)

    Just my two cents! :)

  • 2 Mahsa // Mar 17, 2010 at 12:58 pm

    Thanks for this article Lauren! I’m also a reluctant sales person and I definitely feel your pain. I’m about to ramp up my “selling” for my small PR/Communications company, and it helps to hear what other people go through when about to take on the scary world of sales!

    Best of luck!


  • 3 Melanie // Mar 17, 2010 at 1:00 pm

    I agree. I’m an extroverted business owner but I shy away from sales. Sales is such a hard thing for some people to grasp because in essence, you’re just trying to sell yourself. People buy ‘you’ and your knowledge in the long run and if they like you, they’ll want to work with you. Just having a helpful attitude and a lot of info to offer them is the best sales tactic.

    Good for you stepping out and making things happen! :)

  • 4 Mavis Dixon // Mar 17, 2010 at 1:12 pm

    Hi Lauren,

    I agree whole heartedly. I guess you could say I am a sales person, in that a fundraiser is engaging people in an exchange of funds. It’s not just the interest in people and the keenest to help, it’s also being a knowledgeable and responsive listening. In fact, I would say the third quality is the most important, and you certainly have that!

  • 5 Stv. // Mar 18, 2010 at 1:38 pm

    I do very little sales (and I’m definitely a very reluctant salesman), but I do a fair amount of “inside” sales, where I’m talking to existing clients about what else they might want/need. Being honest, I’m not convinced that either of your 2 major points apply to me – while I do enjoy helping people, my motivation is actually to solve interesting problems. However, I love listening to what people are thinking about, and applying my brain-power to their ideas, which is I suppose taking interest in them – at least their ideas/problems/what have you. It makes me genuinely happy if I can solve a problem for someone, whether it results billable work for me or not. Sometimes the best solution is actually to do nothing – and both trusting yourself, and having clients trust your advice on that is very useful.

    But I do find that regular, “no pressure” conversations with clients – checking in with them, is an excellent way to manage these. Again, not rocket science, but a 5-10 minute phone call once a month lets everyone know that you’re thinking about them and allows you to all more easily remain on the same page.

  • 6 Andrew // Mar 24, 2010 at 12:26 pm


    Great post. A lot of your experience resonated with me. I have found the best strategy for sales is delivering high-quality work. The majority of new work that I “sell” comes from existing clients asking me to help them out on other projects.

  • 7 Pammer // Mar 26, 2010 at 5:10 pm

    Absolutely. When you really break it down, sales is nothing more than consulting – listening to the client, asking the hard questions, understanding the focus, education and offering the appropriate solution. A good salesperson is all about the relationship. It’s a shame there are so many bad salespeople out there that give it a bad name.

    I’ve been in sales for close to 10 years now and am a raging introvert. The hardest part is picking up the phone. The easiest part is the discussion because I’m genuinely interested in the client.

    Also? * waves* Hi! Delurking. :)

  • 8 Felicia Lee // Mar 27, 2010 at 8:43 pm

    Hi Lauren

    I had long thought of sales as a dirty word, associating anything to do with sales with my experience of talking to a slimy used-car-salesman . Then I came across a Harvard Business Review article discussing the traits of top salespeople, and to my surprise, Empathy came out as the top trait. Your post really highlights this – by being sensitive to your customers’ needs and goals, you make a great salesperson. Maybe you’ll be keeping your Sales hat on even after Emira comes back? :)