The strategic habit your CEO wants you to build

You won’t impress your CEO with the nitty-gritty details of your plan. ‘Zoom out’ to tie your work to longer-term value creation.

👋 Hi, it’s Greg and Taylor. Welcome to our newsletter on how to make high-stakes professional and personal decisions in your 30s.

As CEO, details of your plan don’t interest me. 

I assume everyone on my leadership team has the details covered – if they didn’t, they wouldn’t be in their role. 

Instead, I’m constantly asking them to ‘zoom out.’ 

It’s great that lower pricing has driven sales this month – but what does that mean for ARR a year from now? Yes, our AI courses stand out now, but what will our catalog look like in 2025 when our competitors have caught up? 

Zooming out is what strategic operators do. And you need to build habits that force yourself to do it. 

It’s one reason I like board meetings. The meetings themselves are sometimes useful, sometimes not. But the prep is invaluable. Every quarter, it forces me, Taylor, and the rest of the management team to ask ourselves the same questions the board will ask: Not just “how did we do this month,” but “how are we building enterprise value for the next year?”

Here are 7 tricks that force you to ‘zoom out’ more on a daily basis. Choose the one(s) that will work best for you, and reply with your own.

– Greg 

7 ways to force yourself to ‘zoom out’

Here are our best tips to build a ‘zooming out’ habit. No one is doing all of these, all the time. But the best strategic operators choose 1-2 and build them as a muscle.

1. Create your own ‘board meeting prep.’ Like we said, we value board meeting prep because it forces us to ask big, long-term questions about the business. Obviously you can’t muscle your way into the board meeting if you’re not invited, so create your own forcing function. On our leadership team, we end the week with “3Ps” – progress, priorities, and problems. It’s an expectation that everyone fills it out by EOD Friday and we all read over the weekend. It’s not just a way to stay up to date – it also forces us to ask, “What did we do this week that ladders up to our overall company priorities?” 

2. Ask yourself, “What happens if this goes well?” I’m sure you ask yourself, “What happens if this doesn’t go well?”, aka the risks. What if no one uses this feature, what if your buyer loses their budget? But you should be asking, “What happens if this does go well?” just as often. 

When you ask, “What happens if this does go well?”, you’re asking, “If this initiative was wildly successful, would it”:

A) have a significant impact on our most important business metrics

B) make us want to scale it and invest in it (lots of initiatives are successful short-term but not scalable, or not good for the business/brand if scaled)

3. Sniff out bullshit metrics. It’s easy to fall in love with a bullshit metric – especially one you’re hitting consistently. For instance, we’ve set an internal goal to get 1,500 event sign-ups every month, based on projected conversion rates. But after 3 months of hitting this metric, is it driving conversions as we expected? We could hit the target every month and not convert a single subscriber. 

When you’re tracking ‘leading indicators,’ make sure you’re also tracking the thing they’re supposed to be indicating. 

4. Force yourself to do the math. It’s hard to zoom out if you never look at the numbers. Napkin math forces you to zoom out. When you have an idea, do some quick back-of-the-envelope calculations on its potential impact. We’re doing this all the time when evaluating distribution partners – a partner may sound great, but then we run the numbers, and their audience can’t drive more than $25K for us this year. Using napkin math to size an opportunity or problem inherently forces you to zoom out.

5. Think like you just got the job. New leaders often come into teams and say, “Why are we doing X, Y, and Z when it’s not having any impact?” It’s annoying to experience, but it’s extremely important to do. Twice a year, look at your “habitual initiatives” and ask, “What would I say or do if I were new to this team?” 

6. Ask: “What would the CEO say if they were here?” When you don’t have any executives in the room, it can be tempting to stay in the weeds of execution and focus on status items with your team. Instead, ask yourself: “What would [CEO’s name] say if they were in the room with us?” They’d probably question why you were prioritizing certain initiatives, why you were downplaying bad results, and what effect you were expecting 6-12 months from now. Ask the question out loud so that your team gets in the habit of thinking that way. 

7. Listen to the terms and phrases your boss uses (and look them up later if you don’t understand them). It’s your shortcut to understanding what matters to the CEO and the business. We’ve both been in meetings where a boss or CEO throws out terms we don’t understand. Taylor had to google “the rule of 40” while Greg was talking just the other day. Our best tip is to pay attention to this language and write it down.

Our advice

If you’re like most high performers, you are considered a high performer because you are a good operator. You sweat the details. You deliver the plan. 

But to be even more valuable – a strategic operator – you need to zoom out on a regular basis. Make sure your plan is connected to metrics the CEO / C-suite / board values, which probably translates to enterprise value creation somewhere down the line.

Don’t wait for your CEO to join a meeting and say, “Let’s zoom out for a second.” Do it yourself – become the leader who forces others to take a step back and consider medium- to long-term implications. Yes, you’ll impress people… but more importantly, you’ll feel more confident that the daily grind is adding up to something. 

To the next 10 years,

Greg & Taylor