Doing sales reveals all of your flaws

Learnings from a year of doing founder-led sales

There’s an oft-repeated truism that starting a company reveals all of your flaws. To that, I’d add that doing sales also reveals all of your flaws. Arguably, it’s an even better way to examine your own psychology since the feedback loop in sales is faster. When you’re demoing multiple companies in a week and juggling a bunch of deals, there are lots of opportunities to learn. Here are some of the ways that doing sales helped highlight potential areas for growth for me.

At the start of my sales journey, I had a laissez-faire approach towards prospective customers. The idea of convincing and leading someone to buy was uncomfortable to me. I think this stemmed from some amount of pride I had in being someone who conducted themselves in a direct rather than a “political” way. When people talked around my questions, my initial instinct was to be suspicious — the fact that you’re giving a long answer to a “simple” question means that you might have something to hide. So when prospects asked me questions, I answered them very plainly too. “Does Sensible do XYZ?” “No, it doesn’t.”

Pretty quickly I realized this approach didn’t serve my goals. The surface reason is clear — when you’re trying to show your product in the best light possible, it can be helpful to de-emphasize missing functionality and play up your strengths. But going down another layer, to-the-point answers can be counterproductive to the mutual goal that you and your prospective customer have: uncovering what problems they care about solving, what they value in a solution, and what it’d take for the organization to adopt it. It reminds me of what I’ve seen good teachers do. When a student asks a question, the teacher answers the initial question but also addresses the gap in understanding that’s implied by the question too.

As a salesperson, the information you’re trying to convey isn’t a feature checklist (they can just read your website for that), but rather your product philosophy, the why behind your differentiation, and what future you’re ushering in. And lo and behold, that can take some time to explain. The same applies when you’re giving a coworker constructive criticism or explaining a company pivot. Being “direct” can often be a convenient excuse for not putting in the effort to be empathetic to how your communication style might affect others (something I’ve definitely been guilty of).

At the beginning of Sensible’s existence, we knew that we needed to work on our security posture. We hadn’t started working on SOC II, hadn’t done penetration testing, and didn’t have a business continuity plan in the case of [insert natural disaster here]. (Any potential customers who are reading this now, we’ve since addressed all this 😊).

I found myself in a pattern of magical thinking where I was convinced that if I didn’t bring up security during a demo, it would never come up and everything would be okay. This was ridiculous and on some level, I knew I was being ridiculous. If a potential customer cared about security, it was inevitable that they or their security team would ask about it. And when it did, it becomes the kind of thing that can kill a deal right at the end when you think it’s locked in. I was being driven by my tendency to avoid conflict and desire to avoid (short-term) pain. But in actuality, the sting of losing a deal you’ve put a bunch of effort and time into is WAY WORSE than disqualifying a prospect earlier. Of course, the seller/buyer relationship is just one relationship where you need to proactively address conflict. It’s something that I’m trying to be more cognizant of in my other work relationships as well.

Working on Sensible over the last year has been an experience rich in learnings. It can feel uncomfortable and embarrassing to face your own unproductive thought/behavior patterns, so I’ve been reframing these learnings as an opportunity to not only improve as a salesperson and founder but also become a better friend and partner. Part of what drew me to start a company is the personal growth that comes from doing hard things, so I’m looking forward to more time spent outside my comfort zone in 2022.

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