Mastering The Art Of The Playbook

Adam Lawrence is the former COO of Bolt, an online checkout platform startup that was one of Fortune's 2020 50 Best Small Workplaces, among other accolades. Prior to that, he started, built, and sold HR company, Liveli, and was the first hire at Addepar . Adam...

Mastering The Art Of The Playbook
Mastering The Art Of The Playbook

Adam Lawrence is the former COO of Bolt, an online checkout platform startup that was one of Fortune’s 2020 50 Best Small Workplaces, among other accolades. Prior to that, he started, built, and sold HR company, Liveli, and was the first hire at Addepar. Adam enjoys building companies from the ground up and is particularly passionate about recruiting the right people for those companies. Check out more of his thoughts on startup operations on his website.

You brand yourself as “a playbook guy” in your bio. How did that start?

Playbooks started as a crutch for me. I have a bad memory, so if I wanted to get the same outcome for processes, I needed to write them down. This quickly proved useful as we started to scale teams and hire people to do parts of what I owned.

Early on in my career, I read The Checklist Manifesto by Atul Gawande and was compelled by how smart professionals could improve their performance through lightweight processes. Air travel is an everyday example of this; we are safer in incredibly complex aircraft than in cars or other transit modalities because of the thorough checklists and processes in place.

Like airlines, if you want a consistent outcome in companies, build a checklist or playbook.

What’s a playbook that you’re really proud of?

I've helped a bunch of startups build and refine their early recruiting playbooks. The default recruiting failure modes are 1) to be super busy with activities or 2) only take who comes from inbound. Both are wrong: the first wastes time and the second limits your talent pool to those actively looking and already aware of your company.

At Bolt, I helped grow the team from 15 to 175 by defining the outcomes we wanted and working backwards to build talent playbooks to achieve those outcomes. Our hiring playbook went beyond just the hiring process and included a scorecard articulating not only what would make someone great for this role but also their initial expected outcomes. When applied well, that powered the search process and set the new employee up with clear goals for their first 6 months. Too often, hiring processes are a series of disparate steps that result in a mismatched employee journey, and we wanted more continuity.

Where do you get ideas for processes?

I’m not smarter than other people nor do I think my experience trumps that of other builders, but I am good at synthesizing complex problems and looking for shortcuts to solve them. Charlie Munger calls this “lattice work” — the idea is that you pick and choose the best of what others have created and apply that to your business. Innovation should be part of the product, not necessarily the business.

The first step towards building repeatability is to define and align on the expected outcomes. From there, work backwards to build a hypothesis of how you can get those outcomes. As you prove out that hypothesis, codify the process with playbooks. Lots of people start by building the playbook at the first step; instead, I think it’s absolutely key that you focus on the right outcomes. From there, it’s so much easier to articulate the steps.

For further reading, Ray Dalio, Charlie Munger, and Naval all have good principles about it.

What’s your process for setting up playbooks when you start at a new company?

First, I figure out what I need to do to provide value to our prospective customers. Once we start to see product market fit, I document what’s working well. There’s two reasons for this:

  1. It’s much easier to iterate and improve upon a written hypothesis.
  2. When you get to repeatability with that hypothesis, a written document (i.e. a playbook) will make it easier to share that knowledge with the next person.

In operations, we’re asked to be good at a lot. How do you deal with the parts you aren’t as strong at?

You have to know yourself. Self-awareness is key in most roles, but doubly so as a generalist. It’s easy to commit to projects that are outside of your circle of competence when you’re playing a catch-all. When I’m tempted to do that, I ask myself whether that’s the best use of my time and if the company is getting the most out of me in that situation. If not, I figure out a way to either delegate it or ignore it.

Delegation seems unnatural to many startup generalists, but hiring a bookkeeper or getting a contract reviewed by a lawyer will free you up to work on higher value tasks. Yes, you’re trading money for time, but you get time that can be better leveraged.

As Bolt scaled, I was asked to hire for and own entire departments that fell into this category. The key skill there is evaluating and managing talent. I needed to get great at recognizing greatness and then getting out of their way.

What’s your system for staying up-to-date on moving parts across the company, especially when scaling quickly?

I broadly look at information in two categories: bottoms up and top down.

Top down is easier; I construct scorecards. As things deviate on the scorecard, I dive in to understand the causes and if corrective action is needed. A good scorecard is outcome-orientated but also includes a handful of earlier indicators to help identify problems before they become critical. In practice, this might look like a weekly sync where you assign Red, Yellow, Green to each scorecard metric. When a metric is in yellow or red, you’d also review the cross-function actions that are either underway or planned to alleviate that risk.

Bottoms up is harder. I cannot be everywhere, so I need to develop a communication system for identifying and flagging issues. The best way I’ve done this is by creating a cultural norm of stopping the production line when there’s a defect and celebrating the identification and resolution of said defect. This can be difficult because it goes against human nature.

As an operator, it’s important to dive in cross-functionally to gather information and assess whether things are moving in the right direction. Well-structured reporting and metrics are great, but having a regular set of 1:1s with a diverse cross-section of team members is key as well. Meet with people who do the work and listen to their concerns — they’re the leading edge of success or failure.

What’s a process you’ve figured out the hard way?

Every single go-to-market process. Early customers are rarely representative of your later customer mix. It’s often a challenging iterative process to go from early adopters to the middle majority to the laggards, especially when the selling processes and the product need to evolve to do so.

It’s never a matter of changing just your sales process. Done well, you need to migrate the entirety of your go-to-market motion. It’s always hard, and there are no corners that you can cut. At Liveli, we ended up completely transforming our process multiple times. We went from self-signup (with a marketing-driven approach) to an inside sales SMB approach, then finally to a key accounts model in which we sold to large accounts and let everyone else self-serve.

What startup do you find most interesting at the moment?

I think Pipe is really interesting. They're unlocking SaaS revenues and giving people an alternative way to fund growth.

I'm also continually amazed and impressed by Stripe because their infrastructure is more expansive than what anybody else has thought of, maybe anywhere else on the internet. They will be the platform for platforms.

In your user guide, you mention that work notifications are limited or off entirely. How did that evolve over time?

I decided I didn’t want to be a slave to my phone. I had become conditioned to the “ding” of new email. Each one was urgent but few were important. I realized that I’d be happier if I carved out more time to do deep work without interruption. My time is precious, and I’m lucky that I get to choose what interrupts it.

What have you been reading lately?

I started listening to Obama’s latest book over Thanksgiving. It’s interesting to hear how he handled giant decisions as President. Other recent reads include:

  • Shackleton's Way — an interesting collection of leadership lessons from an expedition
  • Good Profit by Charles Koch — proof that I don’t have to agree with someone to appreciate how they grew their business
  • Boomtown by Sam Anderson — the story of Oklahoma City intertwined with the Oklahoma City Thunder (but fuck Clay Bennett for stealing the Sonics!)

What’s a great piece of advice you've received?

What matters is what the other person hears, not what you say.