Strategy vs tactics

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.

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?

I was listening to an interview with Sam Altman, CEO of OpenAI, who recently said that in the age of AI, we’ll start valuing different types of people – not just those with the right answers, but those who know how to ask the right questions.

That’s always been true in leadership. The best operators, managers, and strategic thinkers don’t start with great strategic plans. They start by asking good, important questions.

What are we trying to solve here?
What would make this simpler, faster, more scalable, or more valuable?
What does success here look like?
If this fails, why will that have happened?

Like Altman, I am a techno-optimist. While the development side of AI is still very closed off and expensive, access to the fruits of that development – the knowledge – is super affordable and accessible.

The people who can ask the right questions – whether to their AI or to their teammates – are those who I believe will truly excel in the coming decades.

Bonus: Some good questions that managers should ask themselves every week.

Every organization lives with the risk of someone being “hit by a bus.”

What happens if your development director, programs manager, or events coordinator suddenly disappears? For most orgs, the answer is chaos.

That’s because critical processes live in someone’s head, not in a shared place. There isn’t a playbook, a checklist, or documentation in sight.

A lack of process documentation isn’t just a risk for the worst-case scenarios, but also for common ones: someone quits, goes on leave, or changes roles. In those moments, you can be stuck scrambling to piece together how things worked, falling behind for months.

People leaving the organization is inevitable. It’s sad when they’re someone who does so much, but it doesn’t have to be devastating if you document the process.

Some tips for process documentation:

• Start with the recurring tasks: Anything that happens monthly, quarterly, or annually – think reports, events, renewals, or donor touchpoints efforts – is worth documenting.
• Use a format that fits: Paragraphs of text about how something is done is rarely the best approach. Whether it’s a checklist, timeline, screen recording, flowchart, or simple bullets, make the format fit the process.
• Record the who, what, and when: Ownership and timelines around each step are just as important as the step itself. Who do you work with to do that thing? When does it happen? Capture those details.
• Perfection isn’t the goal: When you start documenting, don’t focus on making it perfect – it can be messy and a little incomplete. Get a draft, then refine it over time.
• Store it somewhere central: For most process-related info, my org uses Confluence as a “wiki,” but any platform works as long as everyone has access and knows where to find it.
• Update regularly: Processes change from time to time. Set a reminder to take a look at your process documentation and update them as needed.

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.

The great Stoic philosopher, Marcus Aurelius, said that. And I forget it all the time.

Like when my partner loads the dishwasher in a way that makes my eye twitch. After all, I’ve spent almost a decade figuring out the most optimized way to load the dishwasher, and they’re throwing dishes in there like it’s a trash bin.

This is how I’m wired – and I know it’s not always easy to be around. But I value order and systems. I like things done with care, done efficiently, and done right. And I hold myself to that standard.

A problem arises, though, when I hold others to this high standard. I expect people to think the same way, act the same way, and have the same general mindset. And, surprise, that leads to way more frustration than contentment.

When I get too rigid about how others should operate, I’ve noticed that resentment begins to creep in. I start to feel frustrated and silently hold people to expectations they never agreed to. I get annoyed when they don’t approach things the way I would.

That’s not leadership. That’s immaturity. And it’s something I wanted to share that I’m working on in case anyone else relates to this dynamic.

The Stoics got it right – focus only on what you can control – even if that’s easier said than done.