Building the plane while you fly it

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.

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.

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.

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 😉

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.