Be strict with yourself and tolerant of others

Today’s post is simple – please help the victims and communities affected by the devastating flooding in Texas over the Fourth of July weekend. As of this post, the death toll is now over 80 people, and 10 young campers remain missing.

You can donate here.

Every dollar helps.

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.

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 remember in college when I was a state officer for DECA. We had to generate a fifth-of-the-month report (FOMR) for our coach outlining the projects, wins, and challenges we worked through that month.

I hated them.

Then I got into the professional world and had to do more reports – some internal, some client-facing.

I still hated them.

I get it – writing a report is a big lift. Whether it’s weekly, monthly, or quarterly, they not only can take a lot of time to complete but there is always the fear of leaving something out or getting called out for something you include.

Despite their reputation, I am a big believer in weekly reports. They can be a powerful thing if done well. But most of the time they’re not. They become a formality or a Friday afternoon chore. A waste of time. The problem? No one ever explains why they’re important, or what a good one looks like. They should be seen as an opportunity to tell the story of the week.

Here’s how I approach weekly reports as a manager:

• They’re not a task list. They should tell the story of the week: progress, wins, challenges, and lessons learned. If it was a great week, the report should clearly communicate why. If it was a bad week… same thing.
• Provide a guide: If you want to avoid reports being phoned in, set clear expectations for what reports should communicate. I literally created a “good report / bad report” side-by-side comparison for my team when I noticed a pattern of unhelpful reports, and it worked.
• Good reports create better one-on-ones. The weekly report should be your pre-read for check-ins. That way, they can focus on coaching, providing context, working through challenges, and professional development – not just a project status that can be communicated another way.

When done correctly, weekly reports help leaders stay connected to what’s really happening on the team and help employees feel seen, supported, and celebrated.

Oh, by the way, managers: make sure you actually read them 😉

Neither is your organization. I know that’s really hard to hear or accept.

You’re not so unique that the basics of leadership, systems, and clarity don’t apply to you.

You’re not so unique that you just happen to attract bad hires. Maybe you have weak management.

You’re not so unique that setting clear goals, building a healthy culture, and creating clarity somehow aren’t “your thing.”

Saying you’re unique is convenient. It’s a way to avoid change, sidestep responsibility, and ignore the hard truths every other leader eventually has to face.

The good news is, you’re not alone. But you’re not exempt either.

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.