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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.

There’s probably something big you’re avoiding right now.

I’ve been there too: Staying in a job I no longer liked because starting a new one felt like a pain in the ass. Keeping a toxic employee around because I didn’t want to have the awkward 20-minute conversation to let them go. Waiting until the last minute to start a big project because I didn’t know how to get started.

In Traction, Gino Wickman calls this the “36 hours of pain.” He tells the story of a manager who knew one of his longtime employees was no longer the right fit for the role as the company grew. The thought of letting them go was agonizing. But after the 36 hours leading up to the termination, once he finally did it, the work environment changed overnight. His team even thanked him for making the tough decision.

We trade long-term peace for short-term comfort all the time. Over time, these constant tradeoffs deteriorate our motivation, mental state, confidence, and even our physical health.

A tough moment today – a decision, a conversation, a confrontation with reality – can save you from months or years of frustration.

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.

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.

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.

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.

The world doesn’t need another podcast. But this post isn’t really about podcasts. It’s about the pressure to jump on what other organizations are doing – a newsletter, a blog, an influencer program, a local ambassador program, you name it.

These things could very well advance your organization. But “because everyone else is doing it” is not a strategy. And for us, these were intentional add-ons that pay returns.

Start with the problem you’re trying to solve or a specific audience you’re trying to reach. Then ask: Is this the best tool for that job?

Not everyone should be a manager. More people need to say that out loud.

We think moving up means moving into management. Organizational leaders assume the only way to promote someone is to give them people to manage. Early career professionals assume it is the only path to advancement and higher pay.

One of the worst, most draining mistakes you can make is stepping into management when you are meant to be a strong individual contributor.

Management means putting down your craft to lead people and develop the next generation. Being an individual contributor means building deep expertise. Both paths are valuable. Both are needed. You have to know which one fits you.

Management brings its own stress: hard decisions, hard conversations, and responsibilities you can’t just check off. But the reward of helping others grow is real.

Some people thrive as specialized individual contributors. They become highly valued and well paid, without managing a team.

Success comes in many forms. Pick the one that fits you.

They say clarity is kindness, and I tend to agree. The clearer we are about vision, expectations, roles, deadlines, deliverables, etc., the better our teams become.

I’ve learned that clarity doesn’t appear out of thin air. It’s an intentional commitment an organization makes to its people. And the way you create greater clarity, in my view, is through building better systems.

Consider a few common sources of stress in an organization:

• Unclear roles: When people don’t know what they own or what others own, you need a system that proactively defines roles and responsibilities.
• Projects are vague: The deliverables and deadlines are fuzzy, so you likely need a better project kickoff and management system.
• Poor communication: If key people aren’t “in the loop,” you might need an internal comms system that makes sure updates flow the right way at the right time.
• Decision-making bottlenecks: If people don’t know who can make what decisions, you may lack a system for defining authority and approvals.
• Mission drift and shiny objects: If your team struggles to stay aligned on long-term goals, or too many “exciting ideas” keep popping up, you need a system for setting plans and regularly reviewing goals.

Again and again, when an organization lacks clarity, it’s not just a communication issue, it’s a systems issue.

If you want to create greater clarity, try identifying the missing system.

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 😉