The future belongs to those who ask the right questions

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.

One of the reasons I struggled in Spanish class was that I often confused the past tense with the imperfect tense. They looked similar, sounded similar, and both referred to the past… but they weren’t interchangeable.

Strategy and tactics are like that. Easy to confuse, but they play very different roles. It’s a common mistake, and I experience it often.

Think of strategy as the destination and tactics as the directions.

A good strategic goal should be simple and brief:

Increase brand saliency with Gen Z
Diversify donor base across three new geographic regions
Create a strong culture with above-average retention rates

The tactics are in the weeds: partner with Gen Z influencers, host fundraising events in X, Y, and Z cities, launch monthly employee surveys.

A quick gut check to help differentiate the two:

• If changing it would shift the overall goal, it’s the strategy
• If changing it would leave the goal intact but change how you get there, it’s a tactic

Strategy sets the direction, and tactics are the steps. If you and your team aren’t clear on the difference, you’ll end up debating details when you should be defining goals.

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.

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.

Imagine you’re in a race with competitors flanking you on both sides.

After the starting pistol goes off, there’s a strong temptation to keep an eye on them. You want to see how fast they’re going, whether they’re gaining ground on you. But the more you look, the more you lose your own rhythm and risk stumbling behind.

I’ve seen the same thing happen to organizations and individuals alike. They have competitors – or peers – that they can’t stop keeping an eye on. Maybe it’s FOMO, or just traditional fear, but with every bit of ground a competitor seems to gain, there’s a risk of losing focus on your own lane.

Competitors exist, of course. Awareness is smart, but constant reaction is not.

You need to know your space and who’s in it, but you also need to establish your lane and own it. Someone else’s path is not the path for you. Comparison often disguises itself as clarity, but it usually leads to distraction, loss of direction, and even resentment

Run your own race in your own lane.

If you dive into books or articles on building great organizations, you’ll find no shortage of frameworks, models, or operating systems. I’ve studied and used pieces of nearly all of them for about a decade now. But none quite fit the kind of organizations I’ve worked in: organizations created to solve big problems and create lasting impact.

After a decade of leading organizations, I’ve come to learn that every healthy and effective organization is built upon four foundations – Impact, Talent, Operations, and Ownership. And when these foundations are built well, they allow every corner of the organization to fire on all cylinders.