I was hired at Drift to build the Customer Team just over a year ago. Recently, someone asked me what the most challenging and most rewarding parts of the first year have been. My answer:
“All of the boths.”
At Drift, you’ll hear us use “both” (quite affectionately) as the answer to “Should I … do/choose/prioritize/experiment… with this or that?”
The answer is, almost always, “Both.”
It’s confusing at first. To optimize for maximum effectiveness, must all answers lead you to one precise path?
Nope. It’s both paths.
The Benefits of “Both”
When the solution to a problem is always “one thing” above or instead of “the other thing,” you unintentionally limit your thinking.
In the world of “both” as the answer, you don’t prioritize one thing over the other (even when the “boths” are in complete contrast). Instead, you develop an ability to balance the dissonance between the boths.
Still don’t quite understand the power of both? Below are five, real-world “boths” I’ve gotten to know well over my first year at Drift.
1) Lean into past experience and erase your mind of past experience.
Prior to Drift, I was in Big 4 consulting, working on projects before, during, and after the economic collapse of 2008, and after that, was part of HubSpot from incubator to IPO and through global expansion. I saw a lot of stuff happen during those years that was good, bad and great. Perspective from past experience is essential. It helps you avoid mistakes (“been there, don’t do that”) and charge with confidence through challenges you’ve faced and conquered (“I lived this before, here’s what we need to do”).
This perspective can also be horrifically limiting if you aren’t careful.
Although there are likely similarities to whatever you were part of prior to a new gig, you have to constantly remind yourself that everything is different. For me, this meant remembering Drift was entering a stage of growth in an entirely new decade to what I’d done before. Things that didn’t work might, in fact, work this time around (so get over what you saw before, this is a whole new world), and strongly held beliefs about we could or should do, should always be questioned.
The ‘Both’ Learning: Allow past experience to inspire you, but not blind you.
2) Roll up your sleeves and get in the weeds, and stay out of the weeds.
I used to think there were two kinds of leaders. Ones who picked up shovels and got dirty with their team, and those who stayed clean and just held the flashlight.
I always prided myself as the ‘get dirty’ kind. Covered in dirt, I could tell you the stories about everything at the edge. I knew the issues, the problems, and I was in the middle of every single one of them.
This was a problem.
If your team is going to survive the natural chaos that is hypergrowth, you have to (with dirt on your face) find the path forward, and spend the time looking for it. Only digging or only searching is never good enough.
The ‘Both’ Learning: Get good at using two tools at once. Bring your shovel, and wear your flashlight.
3) Find experts you can learn from, and bring on people with zero experience.
Finding people who are better, smarter, and more experienced than you at the thing you are trying to do is essential for getting teams to the next level. There is no need to invent something new, because this person has the playbook. They are the oracle. They assess, and quickly jump in and make things happen. It’s magic. When you’re looking for this person, you’re often asking “Who would see this problem and know exactly what to do? Who has lived this before? Who has conquered it already, successfully?”
Knowing when to make this hire is key.
Knowing when not to make this hire is hard…
Because you’re often asking the same questions, but the opportunity for innovation outweighs the security of a repeated play. Instead of someone who brings preconceived notions around how the problem should be (and has always been) solved, you invest in 100% fresh perspective, from a different industry or background.
The ‘Both’ Learning: You need a healthy mix of tradition and innovation. Too much or too little of either equals danger.
4) Do things that don’t scale, and build an enduring company
At a start-up, “scale” is the 5 letter word people wince at. You cheer and high five “who cares if this thing we’re doing doesn’t scale!” Send personalized notes to everyone (we can do it now!), walk over and talk to people (while we’re still small!), send a custom video to everyone, (because, why not!?). This is powerful. It builds the foundation of company culture, and pushes everyone to gravitate toward “things that don’t scale”…
But then you slip, and some of those scrappy things that were in dire need of strategy (systems, process, operations) that you knew wouldn’t scale, suddenly don’t look “scrappy” and powerful at all.
They look sloppy.
They eat away at the incredible, fast-moving foundation you built, for fear of “red tape”. While being nimble, scrappy, and all things “anti-scale”, you lost sight of the enduring company that was at the finish line of what you and your team were working toward. The winner isn’t who gets there the scrappiest.
The ‘Both’ Learning: It’s not a marathon or a sprint. You’re in the start-up decathlon. You need speed, precision, and pace to win.
5) A final (and personal) one — Commit to your career, and commit to your family.
When I joined Drift last year, my youngest son had just turned 1, my oldest son had just turned 3. We were in the throes of weening, potty training, preschool, and sleeping through the night. When I mentioned making a jump to Drift, people laughed at me.
“You’re in the thick of it right now as a Mom, you can’t do that. You’re crazy”
“You have stability and flexibility where you are, why change that and start over?”
I took on the role and haven’t looked back. I’m part of a team that challenges, exhilarates, humbles, and excites me every single day.
I’m also part of a leadership team with 23 kids between us. Almost everyone on Drift’s Senior Leadership Team is a parent, many of us new parents who are also going through the “thick of it”. I’m part of a team that supports, helps, and understands what that means every day.
This last one has been the best both.