Document the process

Sometimes, “building the plane while you fly it” is unavoidable. You just have to take off, move fast, and figure it out on the way.

But here’s the real question: Are you building the plane with duct tape or rivets?

Too often, “building the plane as we fly it” becomes an excuse to cut corners. “Just get it done. We’ll fix it later.” But later rarely comes and temporary becomes permanent. And you’re left flying a patched-together machine at 30,000 feet.

Yes, getting thrown in the deep end can be a great way to grow. But what if you used the chaos to take a beat and build something that lasts?

Even in the rush, you usually have a choice.

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.

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.

When’s the last time you sat down with a list of your direct reports and asked yourself what they need, what they’re struggling with, and what growth for them that week could look like?

Chances are, the answer is either never or it was a long time ago.

Weeks go by fast, I get it. But just as Cal Newport argues for regular, dedicated, focused, “deep work” time in his book Deep Work, you need that same sort of intentional management time focused on your team and their needs that week.

Something to try this week: Make a grid of your direct reports’ names and answer these questions for each of them:

1. What do they need this week? This isn’t about what tasks they need to do; it’s about what resources they need. It can mean taking something off their plate to focus on more important tasks, a day off due to approaching burnout, or simply recognizing a job well done. Figure that out, then get it for them.
2. What are they struggling with? This may be a more complicated question to answer, and you may get it wrong. Many employees don’t bring up challenges with their managers, so you’re often left guessing. But ask the question to yourself, then ask them in a check-in, “Hey, I get the sense/wonder if you’re struggling with X. Is that true?” It could open the door to a really important conversation.
3. How are they progressing in their role and career, and what challenge can I give them this week? This isn’t about their day-to-day tasks, but rather about them progressing as a person. It’s tempting to focus solely on immediate deliverables, but your people have aspirations and growth goals that deserve attention too.

That’s it: just three questions to ask about your team this week. Don’t wait until the performance review to have these conversations. As a manager, you have a duty to spend intentional management time thinking about them and their needs.

One of the most common issues I see in management, especially with early-career employees, is a struggle to stay organized and manage time well.

I have empathy for it because I was the same way. In college and my early career, I bounced between to-do apps, note-taking systems, project management tools, paper journals, and weekly planning templates. It wasn’t until my late 20s that I landed on a system that not only worked, but that I could actually stick to.

Personal systems take time to develop. And they should be deeply personal. You can’t just adopt someone else’s setup and expect it to work without modification. Everyone’s wired differently. What clicks for me might drive you crazy – and vice versa.

When we talk about personal systems, we often think of task lists and calendars. But it’s broader than that:

• Macro tracking for fitness or nutrition
• Personal reviews and reflections
• Goal tracking
• Morning routines or end-of-day resets

All of these systems help us stay on track, but ask anyone who uses one and they’ll tell you they are tough to master. Good systems take time to create and refine, and they should make your life easier, not harder. If you’re constantly fighting to maintain it, it’s the wrong one.

If you’re still figuring it out, be patient. Experiment, reflect, and adjust as needed. The goal isn’t to get it perfect; it’s to get something that helps you show up for yourself and others consistently.

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 😉