Advice for technical sales staff, from a CTO/potential new client

James Wrubel


As a CTO I’ve sat through countless sales presentations so I apologize in advance for my gruff, jaded demeanor. I am actually interested in your product or you would definitely not be here in this conference room/virtual meeting getting your slide deck ready.

I’m also not as busy as my job title would imply. No matter how difficult it may have been to arrange this presentation, I’ve made time for this, and I’m here. So you don’t need to apologize for taking my time. But please don’t waste it.

I’m sure somewhere in a screen on your CRM my name and email are listed as part of a ‘qualified lead’. That’s okay; I may not be in a position to sign today or this quarter but if I’m attending this meeting, it’s probably because I’ve got something I’m trying to fix or build or change and I’ve made a determination that your product might help.

You might think your job in this presentation is to convince me of this. That’s a great goal, but let’s call that a stretch goal for now. Let’s start with this. Your job is to not do anything to change my mind. Statistically, most of you are not doing your job.

.I’m writing this article to talk about the ways (oh, so many ways) you are hurting yourself, and by extension hurting your quota. These are all pretty simple things to fix. Let’s begin.

Mute your phone. Don’t check it. Really it’s best to not even take it out of your pocket. If you have other members of your team with you, make sure theirs are muted too. Yes, I know, I should also do this and so should my team. If I do this, I’m sorry. I invoke client privilege here.

Corollary: If this is a virtual meeting, put yourself in Do Not Disturb mode. No email, Slack, text, not notification bubbles at all.

That whole mutual-introduction part of your agenda (you did send me an agenda, right?)? Let me go first. This might seem counterintuitive. After all we’re here to talk about your product (Wrong answer — we’re here to talk about my problem(s)). Let me rattle on (within reason) about this company, the empire I’ve built. I love to hear myself talk. But don’t let me stop without talking about my challenges. Specifically, the challenge that led me to take this meeting. Again I know this seems counterintuitive. You’ve probably been coached to keep control over the meeting and this seems like you’re immediately giving that away. You’re not. This is judo. Your goal is to use my forward momentum to steer me towards your product. Not to push what you have to sell on me.

Pay attention to my problems. Change your presentation on the fly so that you focus on them. Don’t walk through functionality that doesn’t help with the challenges I described. There will be time for that later and it’ll only distract the meeting. IT’S OKAY IF WE DON’T GO THROUGH THE DECK IN ORDER OR EVEN AT ALL. Sorry for shouting (not really sorry). I’ve sat through a bunch of presentations where everything is going well and the product is a great fit and the sales person decides to use the last 20 minutes to walk through the rest of their deck because they feel they need to. Kills the mood.

Test your AV before you come in. Be prepared for any of the following crazy scenarios:

  • My conference room projector bulb is terrible
  • I have no way to project audio, only video
  • There’s no public Internet access in the conference room
  • There’s public Internet but it goes through a very restrictive/slow firewall
  • I’m going to try and connect some remote participants

I (or someone from my team) will tell you about the meeting logistics if you ask ahead of time. So ask ahead of time. If we’re meeting online, don’t let me specify the platform. But be ready if I have trouble connecting to yours.

Bottom line here; if you sell a technology solution and you can’t get your AV working, I won’t say it’s over before it started but you’re going to have to nail the rest of the meeting.

Follow up. Don’t expect a certain outcome (like generating a quote) unless I told you to expect one. If you don’t have a specific next step, write me just to ask how it’s going with that problem you let me rattle on about. No need to put a hard sell in here; if you jog my memory about the problem I promise you my first thought will be “oh yeah, I need to fix that” and the fact that the reminder came from you will further associate your product as a way to fix it. Remember, this is judo. Keep me moving, but keep using your weight to steer me in the direction you want to go.

If you made it this far, thank you. I hope this was helpful. Understand that my goal here isn’t specifically to help you sell, it’s to make these meetings less painful for me. But if you at least follow the advice here it’s pretty likely we’re both going to get what we want out of this meeting.

James Wrubel

Written by

Dad, husband, proud @umich grad. Former CTO @thinkthrumath, now hacking on @_beergoggles and other things. I 🏊 🚴🏻 🏃🏼 in whatever time’s left.

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