The future belongs to those who ask the right questions

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.

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.

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.

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.

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.