Get to the point

Over the last few months, we’ve implemented something new across our leadership team: an organizational scorecard. It’s a simple idea, but it’s already changing how we operate.

Each week, our department VPs and I review and update a simple matrix of the organization’s most important metrics – the drivers that tell us whether we’re on track or not. We look at things like membership growth, events, fundraising, employee happiness, and a few other criteria. Nothing too complicated. Just a single, living scorecard that we update every week and apply an “on track” or “off track” label.

The purpose of a scorecard isn’t to add more reporting. It’s to keep the most vital indicators front and center. When you track these weekly, you can effectively predict the future. You start to see problems before they happen.

Every organization lives with the risk of someone being “hit by a bus.”

What happens if your development director, programs manager, or events coordinator suddenly disappears? For most orgs, the answer is chaos.

That’s because critical processes live in someone’s head, not in a shared place. There isn’t a playbook, a checklist, or documentation in sight.

A lack of process documentation isn’t just a risk for the worst-case scenarios, but also for common ones: someone quits, goes on leave, or changes roles. In those moments, you can be stuck scrambling to piece together how things worked, falling behind for months.

People leaving the organization is inevitable. It’s sad when they’re someone who does so much, but it doesn’t have to be devastating if you document the process.

Some tips for process documentation:

• Start with the recurring tasks: Anything that happens monthly, quarterly, or annually – think reports, events, renewals, or donor touchpoints efforts – is worth documenting.
• Use a format that fits: Paragraphs of text about how something is done is rarely the best approach. Whether it’s a checklist, timeline, screen recording, flowchart, or simple bullets, make the format fit the process.
• Record the who, what, and when: Ownership and timelines around each step are just as important as the step itself. Who do you work with to do that thing? When does it happen? Capture those details.
• Perfection isn’t the goal: When you start documenting, don’t focus on making it perfect – it can be messy and a little incomplete. Get a draft, then refine it over time.
• Store it somewhere central: For most process-related info, my org uses Confluence as a “wiki,” but any platform works as long as everyone has access and knows where to find it.
• Update regularly: Processes change from time to time. Set a reminder to take a look at your process documentation and update them as needed.

I was listening to an interview with Sam Altman, CEO of OpenAI, who recently said that in the age of AI, we’ll start valuing different types of people – not just those with the right answers, but those who know how to ask the right questions.

That’s always been true in leadership. The best operators, managers, and strategic thinkers don’t start with great strategic plans. They start by asking good, important questions.

What are we trying to solve here?
What would make this simpler, faster, more scalable, or more valuable?
What does success here look like?
If this fails, why will that have happened?

Like Altman, I am a techno-optimist. While the development side of AI is still very closed off and expensive, access to the fruits of that development – the knowledge – is super affordable and accessible.

The people who can ask the right questions – whether to their AI or to their teammates – are those who I believe will truly excel in the coming decades.

Bonus: Some good questions that managers should ask themselves every week.

That $5 donor can become one of your biggest donors.

That new follower can become your future business partner.

The shy intern may run the organization one day.

I’ve been amazed in my career at what the small moments can turn into with some cultivation and patience.

I’ve sometimes seen a desire to throw $100,000 in salary and benefits at a “bandwidth problem” when it’s really just a prioritization problem.

Sometimes, hiring is absolutely the right decision. But sometimes, the better solution isn’t hiring, it’s doing fewer things better.

Before you hire, ask these questions:

• Are we trying to do too much? The instinct to say yes to everything creates artificial capacity problems. What if the issue isn’t a lack of people, but a lack of focus?
• Can we cut or pause lower-priority projects? Every initiative competes for attention. Which ones could you shelve without meaningfully impacting your core objectives?
• Are we clear on what actually created results? If you can’t identify your highest-impact activities, adding more people just increases the confusion.
• Could we streamline operations or automate some work first? Process improvements and automation often free up more bandwidth than a new hire, without the ongoing cost.

Hiring should be a strategic growth move, not a reflex to wrangle chaos. Sometimes the real answer isn’t adding people, it’s tightening focus.

Greetings from day one of my week of PTO. Seemed like a fitting time to talk about one of my favorite benefits: unlimited time off.

A lot of people say unlimited PTO is a scam. And in many companies, it is. But that’s not a failure of the policy; it’s a failure of leadership.

I stand behind unlimited PTO 100%. We use it at my organization, and we make an effort to ensure it gets used. And that’s the key: leaders have to take responsibility for making it work.

You have to build a culture that respects time off. Make it clear people aren’t to be bothered when they’re out. Do a regular inventory of who hasn’t taken time and ask why. Then fix those barriers.

Most of the time, what stops someone from taking PTO isn’t laziness or neglect; it’s guilt. They don’t want to burden their team. Or maybe they’re in the middle of a big project. Or they treat PTO like a golf score, where the lower the number, the more impressive it looks.

Those are all management issues. If someone feels like they can’t step away, that’s often on leadership. Do you have a contingency plan so people can unplug? Are your timelines so inflexible that a few days off will derail everything? What message are you sending – directly or indirectly – about time off?

Your team is too valuable to screw up with a poorly executed unlimited PTO program. Build the systems to make it work.