Life, Work & Wonder

Tag: sales

  • In A Way, It’s A Resilient Optimist That Excels in (True) Sales

    Today we’re working on what essentially is a Request For Purchase (RFP). Not technically an RFP, but what essentially adds up to an RFP: a potential home seller who we met with already, met with again, gave a listing presentation to, met with again, and now after she went radio silent for a few months sent a list of 10 questions that she wants answered by the three agents she’s considering.

    So much “hurry up and wait” with this person who doesn’t seem able to make up her mind on when she wants to sell, if she wants to sell, and who she wants to sell with. I keep asking myself, are we just wasting our time in meeting after meeting after meeting after meeting and with all these various requests for information for a person who seems reluctant to just make a decision?

    To be honest, I’ve gotten increasingly cynical over the years.

    I think back to a software opportunity I had back in 2003.

    A client was upgrading their hardware and so many of their software vendors were charging exorbitant rates so that the client could continue the same exact software (pre-SaaS days) but on different hardware. So suddenly software that cost my client $2 million to run per year was suddenly going to cost $12 million to run per year although they weren’t going to be actually doing anything differently with that software (same business cases, same number of users, etc. etc. etc.). Of course, the client was very frustrated.

    Of course, I detected a chance to help the client. But jas as importantly, I smelled blood. We could take advantage of our competitors charging so much and look into replacing them for less money.

    It’s hard to remember now, but the economy wasn’t awesome in 2003. Companies were still recovering from their exorbitant spending on Y2K and “e-business” from the 1990s, still recovering from the post 9/11 and post-Enron layoffs of 2001, and just weren’t investing a lot of money in new software. So we software sales reps had to seize any opportunity we could when we could if we wanted to make quota and (like me) pay for our kids’ private school tuitions. And so I sprang into action.

    For four months, I had sooooooooooo many meetings with this client. I overviewed the general idea (replacing the more expensive competitors’ software with our software). I did discovery meetings to find out how they were using their software, then internal meetings to find out if we could indeed replace some of our competitor’s software for cheaper, then showing the client how we would run the software cheaper and doing demos on that software, then meeting with all the various stakeholders at the client site who used the competitors’ software to show them how they would be able to use our software in the same way, and so on and so on. And, by the way, the client was a three hour flight away and this was before Zoom so this meant nearly every week I was flying for three hours each way to conduct all these meetings.

    At any single step of the way, the client could have said, “Screw it, I’m not going to upgrade all my hardware,” which would have meant he didn’t have to deal with the software upgrade fees. Or a stakeholder could have said, “We’re not replacing our software! We’ll just increase our budget to continue running the same software.” Or the software companies we were looking at replacing could have said, “We’ll waive the upgrade fees.” And any single one of these scenarios would have killed my opportunity and erased all my hard work.

    But I continued on. Every week for four months I hopped on a plane, left my beloved kids and home (and car) for a few days, and tried to make magic happen because I believed that I could make this happen and that I would get a nice commission check at the end while saving my client a lot of money.

    Finally, at 6pm on Friday August 29th 2003 (I’ll remember the date for the rest of my life), after a hectic week where we were trying to get this signed before month end so my bosses could meet their monthly numbers and we could keep the higher-than-normal-but-expiring-at-the-end-of-the-month discounts that my desperate bosses had approved, the client signed. I’d done it!! That three hour flight home late Friday night? Some of the best three hours of my life. I sat there in silence, nursing a celebratory vodka soda, reveling in the joy and relief that it was over, grateful that my hard work was going to save my client money and fill my family’s coffers and also give my family a free trip to Hawaii for making quota. The deal was signed. The client was going to benefit, and my company was going to benefit and my family was going to benefit.

    Looking back, it was such a long shot. I can’t believe it actually happened. I don’t know that I’d believe today like I did back then, that I would pursue it as doggedly today as I did back then, because the reality is I’ve seen too much since then. I saw the time that a rep was on the verge of winning the deal and — boom — the client was acquired and so the deal was called off. I saw the time when my peer did everything I did in 2003 and was about to ink a major deal with a 6-figure commission check except she was laid off before the deal was inked because the Suits In The Ivory Tower wanted to make their profit numbers so cut sales headcount. Not long after she was let go, the deAL was signed and our company got its money but another rep got the commission check for my peer’s amazing work. That’s the stuff that keeps me awake at night. That I hadn’t experienced or witnessed back in 2003 so believed anything and everything was truly possible with enough perseverance.

    Anyway, I’m realizing that to be a truly passionate sales person, a person has to be a resilient optimist to the extreme. To believe. To doggedly pursue. To doggedly jump over every single hurdle while continuing to believe that when all their hard work is over the contract will be signed and everyone wins. They have to be like Teddy Roosevelt Jr. on D-Day when everything seemed to be going awry and he said, “We’ll start the war from right here” then started doggedly moving forward in the face of (literal) death.

    Thinking on all this, I’m proud of myself. I’ve done it. I’ve done it more than once. I’ve done it as recently as the past few years, doggedly pursued the impossible and then come out ahead. And if I’m honest with myself I’ll do it again despite my reservations. In fact, we’re going to submit this pseudo-RFP and win the listing.

    And as much as anything, I believe this: a great sales person (not a lucky one, or a right-time-right-place one, but a great one, a truly great rainmaker, must be the resilient optimist to the extreme.

  • So Grateful That I (Literally) Fell Into Sales 25 Years Ago

    It has been nearly 25 years now, but I went into sales for the noble reason that my pregnant now-Ex Wife (”Ex-Wife”) fell down the stairs.

    Previously, I was a high school English teacher. For three years, I woke up every morning at 5am, made coffee, read the paper, got dressed (stylish slacks and a nice shirt), then zipped off to a large public high school where I spent my day trying to convince packs of 16 year olds that Shakespeare was still interesting and viable 500 years after his death. On evenings and weekends I coached debate, and during the summers I worked temp jobs as a receptionist, and all told I cleared less than 35K (in 1999) to support my young family of three.

    Then one evening in March I was playing with my son in the living room when I heard Ex-Wife scream followed by a thump-thump-thump-thump. What in the heck was that??? I jumped up and sprinted in the direction of the sound and found Ex-Wife sprawled at the bottom of the stairs in tears. “I fell down the stairs,” she exclaimed. Then added, “I think the baby is okay.”

    Oh my god!

    We rushed to the hospital and eventually talked to her OB, and we learned that the baby (thank godness!) was okay and although Ex-Wife was okay she needed to be on bedrest for the next few weeks to protect the pregnancy and baby.

    Oh my god!

    Ex-Wife was a self-employed part-time tailor. She never made much money, even before we had kids, but she made enough that with my salary we could (just) barely stay financially afloat. And her being on bed rest meant she wasn’t going to make any income which meant that we were no longer going to stay (just) barely afloat.

    Oh my god!

    I had to spring into action. My first thought was to take a night job to make up for the lost income, but that wasn’t practical because someone needed to keep an eye on our spirited toddler child and also look after now-bed-resting Ex-Wife. So I did something I truly truly (truly!) hated to do: I asked my parents for a loan, just to get us through the rest of the school year when I could look for a higher paying job.

    Then, when the school year ended a couple of months later, I updated my resume and hit the job market. At the time, tech was booming so I thought I’d be able to get into some entry level tech job. Turns out, I was wrong. Companies didn’t want to hire someone off the street with zero tech experience — they wanted to hire someone who knew something about tech. Who knew??? Hahaha. Anyway.

    Just before I was about to give up and ponder other options, one of the tech recruiters I talked to said, “You aren’t a match for our tech openings, but you seem like a natural salesperson. Have you considered looking into sales?”

    To make a long story short, I ended up in sales, partially because almost out of the gate I doubled my earnings going into sales.

    This was circa 2000. It was a different world for me then. Different from my previous world as a high school English teacher. And different from the current world of technology sales, although despite any claims otherwise the basic rules of sales haven’t changed: get someone to listen to me, listen to what they do, explain how we might be able to help, then try to align everything so that they make a win-win-win investment.

    I’ll never forget my first week in training. The job seemed to good to be true. “Wait,” I said to my trainer. “I reach out to prospective clients, get them to listen to my story, get them to tell me their challenges, then align what we offer to their challenges?”

    “Well,” my trainer said, “It’s a little more complicated than that. But that’s the gist of it, yeah.”

    On top of that, I was making nearly twice my previously salary, got a commission every time someone signed something, plus I had an expense account and free coffee (we had to furnish our own coffee when I was a teacher). I honestly thought I’d died and gone to heaven.

    I can honestly say that nearly a quarter of a century later I’m just so grateful for that unexpected change in my life. Where I’d gone from working 50-70 hours per week for more 45 weeks per year for pennies on the dollar to working 40-50 hours per week 47 weeks of the year (including holidays and PTO) for dollars (multiple) on the dollar. Where I’d gone from barely affording my mortgage to actually having (a lot of) discretionary income and retirement savings. And I didn’t have to spend my youth studying computer science or engineering, or spending my free time studying computer science or going to graduate school. I just had to find out what a prospect’s problems were and try to align that to what I was offering. Which, honestly, was a HECK of a lot easier than teaching Shakespeare to packs of 30 16-year-olds.

    NOTE: None of this article was generated or edited using AI. It is 100% organically human written by me. 🙂

  • Going To Be A Career Day Speaker

    A week ago there was an email from my kids’ high school looking for adults willing to be a Career Day speaker wherein we prepare a 15 minute presentation about our career and then present it to the students during Career Day. I volunteered to talk about what it’s like being a Seattle Real Estate Agent. Today I learned I’ve been approved and will be presenting. I can’t tell you how excited I am!

    There’s that old joke that more people are afraid of public speaking than death, which means people would rather be the person in the casket than the person giving the eulogy. And time was that I thought I was a terrible speaker and hated giving speeches.

    But I’ve learned in recent years that I’m actually pretty decent at giving speeches when I like what I’m talking about. Following a prescriptive Corporate Powerpoint Presentation with all the typical “look how amazing we are” slides? I’m awful. Giving a QBR presentation? Very hit and miss depending on if I like the team and the presentation isn’t too formulaic.

    But give me a topic I want to talk about, give me some time to ponder how to go about presenting it, and give me an open format to work with, and often I’m decidedly okay giving a presentation and I actually like it and can be relatively funny.

    In late 2019 my moronic manager took my client presentation and tweaked it a short time before I was supposed to give the presentation in person while jet lagged. It didn’t go very well. Partially because he turned it into the same eye-rolling presentation a million other software companies deliver to the poor prospective clients, partially because the last second changes didn’t give me time to prepare the new presentation, partially because the changes ripped apart the flow I’d been rehearsing in my head for a few days before the speech, and partly because of the time I would have been physically (eating) and mentally (breathing) preparing for the speech I was trying to learn his last minute tweaks. When he tried to do the same thing two months later, I ignored his changes and did my original presentation that client presentation went much better (spoiler alert: we lost the first client opportunity and won the second).

    A few months later I gave a presentation to medical students about my experience with a rare lung disease. I had a few weeks to prepare, had an open format to work with, and was passionate about the topic. The result when I gave that speech? It went great! So great that even my ex-wife who was embarrassed by everything I did at the time and was in the audience as a medical student herself even seemed remotely impressed.

    I love real estate. I love being a real estate agent in Seattle. So I’m excited to talk about my career in a few weeks. And excited to talk about my career to a group of high school students who are trying to figure out this career thing. I’m grateful to be given the opportunity and am looking forward to preparing and then giving the presentation.

  • The Folly Of A To-Do List (AKA My Non-Existent To Do List)

    Something on your “to-do list” that never gets done.

    WHAT IS SOMETHING THAT NEVER GETS DONE ON MY TO DO LIST? Nothing. Because nothing is on my to-do list. Because the world doesn’t make time anymore for to-do lists. Explained…

    Years ago I carried around two notebooks everywhere I went.

    The first notebook were my notes. Every call, every meeting, every day, I jotted down the date and who I was talking to and then took detailed notes in real time, often writing in my notebook while keeping my eyes focused on the person in front of me (i.e. I was the master of the no-look note-taking 🙂 ).

    The second notebook was my to-do list. After every single meeting, I copied my to-do items into that list, then every single day I religiously reviewed that list to make sure I was addressing everything I needed (or promised) to take care of.

    Sometime in the early 2010s, I switched to Excel — I had a tab devoted to my to-do list, and then in 2015 I moved from Excel to One Note for keeping track of Asks. In fact, OneNote — and the tables feature in particular — was awesome!

    One of the things I’m most proud of was in 2019 when I had a critical opportunity I was working on. My larger team was struggling (way behind in its numbers) so needed the revenue from this major opportunity I was working on, and my client really needed our (or at least someone’s) SaaS solution to increase their online sales by 400%. Because it was important, the opportunity had a lot of people weighing in on it: my CEO, the client’s CEO, my client’s CFO, my client’s head of PMO, my client’s dozen mid-level people contributing to or influencing the buying process, and the Client Executive Sponsor who was funding the project, not to mention my internal sales engineers and stressed out sales manager who needed the deal to close to presumably keep his job.

    Every single day during the critical middle-few months of this opportunity several items were added to my to-do list for that opportunity, and each of them had multiple facets. In short, I had a to-do list that was scores of items long that contributed to whether or not I would win a $4.1M contract and help a client. If I’m honest, it was a daunting undertaking.

    But I’m happy to say I did it, and I did it successfully. I juggled all those items, completed them to satisfaction in that the client said my follow up is what won us the opportunity (vs the two other primary competitors), we signed the contract and basically I owe it all to my use of the tables feature in OneNote wherein one column was the to-do item, the next column was the requestor, and the third column were my running notes on where I was. First thing every single morning at 5:30am, while most of the world was still sleeping, I started running through that to-do list to make sure all my i’s were getting dotted and t’s were getting crossed and everything was moving forward schedule.

    But that was then.

    Now I don’t have a to do list.

    Why?

    Because life is too fast for a to do list.

    It’s fast and it’s too overwhelming.

    There are too many asks from too many sources and a modern-day expectation of instant turn-around times. (I remember a client asking for information in 1999 — I got it to her early the next morning and she said, “That was too fast! I thought it would take a week or so.” But in the 2020s I feel like everyone expects follow-up information not next week and not today but RIGHT FREAKIN’ NOW). So there is almost no point to a to-do list because by the time I jot the item down the requestor is already wanting it to be done.

    So, instead I take notes, bold the key items as I type them in case I need to reference them later, and then get it done as soon as I possibly can, which is usually right now. If something is worth doing, it’s generally worth doing now. And so now is generally when I try to do it. If it’s important enough, and it takes more than a few moments to complete, then I’ll remember to do it, and if it’s not important enough to do right now or to remember that I need to do it (sort of like I don’t need to put down on my to-do list to pay a bill — paying bills is important enough that I’ll remember it). then maybe it shouldn’t be on a to-do list anyway.

    It’s ironic that in an over-busy world a To-Do list has become almost outdated. Because if I take a few days to respond, then it’s probably too late, and if something has been promised and is important enough to promise, than I should do it now not tomorrow. So there just is no point to a to-do list.

    So, when I’m asked what never gets done on my to-do list, I say this: nothing. Because there is nothing on my to-do list. If I’m being honest, I wish that weren’t true — it was a friendlier and less stressful world 25 years ago, when I had a notebook filled with my to do items and a week was acceptable except in case of major fires. But it is what it is, and all I can do is adapt to what is.

    DISCLAIMER:

    • Every day wordpress issues a prompt and I’m finding myself enjoying answering that prompt. Today’s was: What is something on my to do list that never gets done.
    • No AI was used in the creation of this response. It is 100 percent organic which is why it isn’t all that great hahahah