I was recently tasked with identifying and purchasing a software solution to solve an internal documentation problem at Clearlink. We were sharing docs on Google Drive and struggling with creation silos. (More on that in another post.)

I did my due diligence in research, and finally made it to the stage of asking for demos and having conversations with individual product sales reps.

One sales person, though, repeatedly called when I sent an email. Literally:

10:02 am — Jess sends an email

10:04 am — Jess’s phone rings with a number she doesn’t know

And if I didn’t answer, there was a voicemail, a follow-up call, and finally, a follow-up email.

Old School Sales, Problem 1: Setting Expectations

One of the main reasons cold calling and pressure-based sales tactics don’t work well in a digital environment is they set the entire process off on the wrong foot.

We’re seeing younger project managers, specialists, and IT teams assuming responsibility for software purchases that will affect their entire companies. They are coming into the decision process well-informed, heavily researched, and looking for a tool that they can build a longterm relationship with — not something to test and drop if it doesn’t work.

Business employees at the younger end of the spectrum are not afraid of responsibility and not afraid of commitment. They want a tool (and team behind the tool) that they can cultivate trust with and build a relationship around. They want that justification that their money was well-spent. They’re careful and deliberate about which tools they choose to spend money on, and a lot of the decision-making is based on their intimate understanding of their company and co-workers. Which leads us to…

Old School Sales, Problem 2: Know Your Audience

As I went through my process to find and implement a solution to our document sharing situation, I noticed a few things that I believe are consistent across younger decision makers in business:

I am very well researched. Most of the sales people I ended up speaking with were surprised not only at my understanding of knowledge management as a business practice, but also of how thoroughly I had scoped and detailed the problem and our needs inside the company. They were impressed that I’d met with so many stakeholders, researched so many tools, and was already planning for change management before I knew what the change might entail.

I don’t care about cost. I do — there were budgetary requirements. But I knew that my first and primary goal was to find the correct solution, no matter the cost. Money is something that can be negotiated. Functionality, customer support, and adoptability are non-negotiable.

I wanted the right solution the right way. There were several tools that came in far under budget that could be customized or partially disabled to fit the requirements I outlined for our solution. But I wasn’t willing to pay for 25% use of a tool. That isn’t savvy — that’s settling. I wanted a tool that was designed to meet our particular set of needs, and I wasn’t going to quit until I got it. And I wasn’t going to take shortcuts.

I know who I’m buying for. I’ve worked at this company for four years. I’ve seen politics, I’ve seen tool adoption (or rejection in some cases), I’ve seen process shifts, and you best believe I have a clearer understanding of what will or won’t work for us than you (the sales person) do. Don’t take that as an insult — I’m your door to our company. I’m the representative. So if I tell you you’re barking up the wrong tree, pick a new tree or change your tune.

To succeed in sales with a target buyer like me, you’re going to have to work on building a relationship, clearly conveying the tone and response levels and feedback I can expect for my lifetime with the product, but also building trust by letting me be the expert. And respecting my boundaries, when I set them.

Old School Sales, Problem 3: Smartphones

I think, in all of this, the biggest problem was the disconnect between how a traditional sales rep uses a smartphone and how I use a smartphone.

For them, it’s an instantaneous way to get in touch — to answer questions immediately, to use emotion and a human voice to build momentum towards a sale.

For me, it’s a camera, a radio, Twitter, Uber, check deposits, text messaging, email, and maybe — if it’s a family emergency or I was expecting a call — a phone.

I do not answer calls from numbers not saved in my phone. I respond 10x more quickly to text messages or emails than phone calls or voicemails. I will spend time seeking out a live chat, scanning an FAQ, or hunting an email address than just calling the support phone number on a website.

But most sales approaches are still to either schedule a call (which feels ok), or call in reply to an email.

And even when I explicitly expressed my desire to communicate by email with them, several of the sales reps would still call as soon as I emailed, leave a voicemail, and if I didn’t call back in a few minutes, eventually respond to my email.

So How Do We Sell?

There are a few key things you can do that, tho they be but small, they be mighty:

Answer me in kind. If I call you, call me back. If I email, email back. If I text or send a carrier pigeon, respond in kind. Speak my language via the platform of my choice.

If I call you, call me back. If I email, email back. If I text or send a carrier pigeon, respond in kind. Speak my language via the platform of my choice. Cut the pressure. You need to realize I may not be the final signee on the contract. Or I may have a committee I’m beholden to, and I’m operating on their timeline. I generally don’t respond well to pressure, and I have a target deadline I’ve chosen, so I’m sticking to it. There’s not much you can say to change the forces that be on my end. So be a little flexible.

You need to realize I may not be the final signee on the contract. Or I may have a committee I’m beholden to, and I’m operating on their timeline. I generally don’t respond well to pressure, and I have a target deadline I’ve chosen, so I’m sticking to it. There’s not much you can say to change the forces that be on my end. So be a little flexible. Don’t ask about the competition. Maybe after I make a decision, we can talk about why I did or did not choose you. But instead of worrying about your competition, why don’t you make an effort to prove to me in the sales process why you’re the better choice? Send me articles that relate to topics we’ve discussed. Send me videos and insider tutorials and find a way to get me that free 10 day trial. (In PR, it’s the Give, Give, Get principle — give value several times without being asked, and you’ll get something valuable in return.)

I care more about finding the right tool and building a valuable relationship with the support team than I do about getting a bargain. And I know it’s a hard shift from cold calling, with kids these days and all their new-fangled technology, but consider this a warm lead. I promise it will work!

Kudos to Sarah O'Keefe for the snappy title. :)