My Big Sister Advice for Young Professionals.
I’m the eldest of three daughters and I adhere to the archetype: responsible, rule following, tidy, and ambitious.
A natural leader born out of the burden of necessity: you must go first at everything—and the inherent responsibility to relay the learnings: here’s what’s coming, kiddo. A real trailblazer.
Other eldest siblings will understand me when I say: when you travel that terrain, you grow an air of confidence: I know best, that’s saddled by a desperation to save the heartache: listen to me.
I once said to my sisters in total sincerity, “Stick with me…and you’ll be alright.” But with it, I’d thrown a wink and a handgun gesture with the tilt of my head and a horsebit click out the corner of my mouth. Naturally, they crumbled into hysterics mocking me for my arrogance wrapped in nerd.
I replied unfazed, “And when have I steered you wrong?”
Since I’ve always been a few paces ahead—or 11 years in the case of the youngest—I’ve had the benefit of experience to be able to coach them through some of the nuanced ways of the working world, ultimately giving them a leg up here and there.
Like helping one of my sisters leverage an email from a former happy client to clinch a job offer at a new firm before she’d even interviewed for it.
Or helping my other sister leverage multiple offers to up her starting salary by 10% and add a bridge toll reimbursement to make up the difference (she wanted 15%); it was her first job out of college.
But how do you know how to do that stuff?
It’s really only learned through experience. It’s a way of being in the world, an awareness of how to see and connect and create opportunities.
And it’s not what school prepares you for. You want to have a thriving, successful career?
This is my Big Sis advice for you:
What you’ve learned in school is not what you will need to excel at work. School is structured and predictable: semesters and syllabuses, homework and tests. You are told step, by step, what to do, and if you follow those steps, you can be reasonably, reliably, “successful.”
Remarkably, it requires very little creativity or thinking for yourself. Do what you’re told. Follow the Rules. Get your A. In other words, there’s a playbook.
At first, your job will mirror this with “Onboarding Checklists” and monthly 30 minute “Mentor” calls or “Onboarding Buddies.” But those will be of little help to you in the long run because they’re largely unrelated to your actual every day job. And sooner than later, that checklist is going to run out and what you’ll be left with is the unstructured and unpredictable task of trying to swim towards goals in an ever-changing sea: wind, waves, and swells.
So then what?
I was good at following playbooks, obnoxious really: in my seat when the bell rang, class president, straight-A student.
And so I was alarmed at how unprepared I was for my first job in sales. I tanked. I trembled when I dialed the phone and I secretly hoped no one would answer when I did. I sucked. And I cried. (A lot.)
What I had learned in school was how to play a game by following a playbook, by knowing and responding to rules. And I tried to do the same in sales, I tried to follow the formula: make 100 calls a day, book 4 meetings a day, run 10 new demo’s a week, and on and on. But it wasn’t adding up to “success.”
It’s like baking: you can follow a recipe to a T—measuring and temperature and timing—and it can still come out wrong.
So what gives?
You have to move beyond the technical playbook and into the realm of intuition and insight and creative response: you have to get a feel for things. To know when to float with the tide or swim sideways out of a riptide.
The best way to do that? Apprentice yourself.
What you need to grow and become confident and successful is apprenticeship. You must make a commitment to apprentice yourself to your craft.
I will never forget closing my first sales deal. Because I didn’t close it, Dino Delic did. I owned the lead and by some miracle booked a first call with the prospect, but from there on out, it was Dino at the helm.
In those days we came to the office every day and had desks with M5 phones that you could listen in on any call happening, in the office, at any time. I would listen to Dino run the discovery, the demo, the negotiation. Everything sounded so silky smooth and effortless—and not just because of his Australian accent (though I don’t think it hurt). He knew exactly how to lead the prospect, anticipate objections, and remain in creative response to whatever came next: no playbook necessary.
I will also never forget, years later, closing one of my most important deals of the year: it was make or break for my number. But I didn’t close that one either, Laura Agarwal did. I sat with her in the office until nearly 11pm on the last day of the month as she called the man in procurement for the eighth time… “you know why we’re calling…” she said. You could hear the slight humor in her intonation—and not a trace of irritation by the man on the receiving end. How she could deliver such measured persistence while disarming—no, winning over—the person on the other line in what anyone else would consider… harassment? It was both fearless and brilliant.
Both of these experiences left me with the same impression: ”Wow, I want to be able to do that.”
They also taught me that I would never learn what I needed to learn by reading books or sitting in “enablement sessions” or using “sales playbooks.”
The type of skills development that I needed was what Life Coach and Lion Tracker, Boyd Varty, describes as: “a kind of transmission born of physical proximity; the teaching is not spoken but absorbed.”
And it’s what you need too.
Find someone to apprentice yourself to. Someone that you can saddle up to and absorb everything they do. Pay attention. Watch. Listen. Imitate.
Because the skills you need to hone aren’t transferable in verbal language: you have to see it—and experience it—to get a feel for it, like riding a bike, or skiing, or surfing.
For me it was hearing not just what they said to prospects and customers, but how they said it. The tone, the speed, the pauses. There was a playfulness and a creativity that I could watch unfold; responding to social cues and knowing when to push the boundaries—and, how far. There’s no playbook for that.
I would go on to close many deals of my own, and even a few I’m proud of.
But what I care most about now is giving back those opportunities for true apprenticeship: the kind of knowledge that can only be absorbed through witness and experience.
When I’ve worked with SDRs and DGRs, I try to give them total visibility. To every call, email, and problem solving, strategy session. (It’s a simple bcc, folks.) And I think they’re grateful for it.
You don’t need to find the top boss, just someone a step in front of you that you can watch—really watch—and try to imitate; a big sis, if you will.
