Your Midyear CEO Reset (In Under 10 Minutes): 5 Strategic Questions That Matter

June doesn’t need to shout. It’s already speaking volumes. We’re halfway through the year. And whether you’re celebrating record wins or quietly rethinking your Q1/Q2 optimism, one thing is clear: this is the moment to pause, audit, and adjust.

Not with performative journaling. Not with a motivational quote taped to your screen.

With real questions. Strategic ones. The kind that reveal what’s actually happening behind the scenes of your business - and what needs to change if you want to scale without spinning out. We did this exercise ourselves (over Zoom, naturally - side-eyes, spreadsheets, and the occasional snack break included).

Here’s what we asked, and what we recommend you walk through before setting a single Q3 goal.

1. What’s Actually Working and Why?

Start with evidence, not ego. What’s driving results - revenue, reach, retention - and what specifically is making that work?

• Is it a system you finally tightened up?

• A refined offer that’s meeting a specific need?

• A process that finally feels frictionless?

Too often, we acknowledge what’s working without fully understanding the mechanism behind it. Reverse-engineer your wins. That’s where repeatability (and scale) lives.

2. What’s Quietly Draining Your Business?

Not everything broken announces itself.

Some inefficiencies hide in plain sight:

• The offer you keep selling out of… but secretly resent delivering

• The team process that eats five hours to solve a two-hour problem

• The tool you’re paying for because it’s “industry standard,” not because it’s serving you

Energy leaks cost more than money. They cost clarity. Name them, then decide: keep, fix, delegate, or eliminate.

Pro Tip: Need structure? Use this format:

3. What Needs to Be Retired (With Zero Drama)?

Let go without guilt.

A service, a strategy, a habit, even a revenue stream - just because it worked before doesn’t mean it belongs in your next chapter.

This isn’t quitting. This is evolving. Smart founders move with data, direction, and discernment. That means cutting dead weight before it costs you your edge.

4. What Can Be Simplified, Systemized, or Delegated?

Simplicity isn’t a vibe. It’s a growth strategy. High-performing businesses aren’t more complicated - they’re more repeatable.

Ask yourself:

• What am I still manually doing that AI, automation, or an SOP could cover?

• What decisions am I making over and over again that should be standardized?

• Where could a template save me from re-creating the wheel every week?

Complexity is expensive. Discipline makes it scalable.

5. What Actually Deserves Your Focus for the Rest of the Year?

Your Q3/Q4 isn’t for trend-chasing. It’s for tightening.

You do not need five goals. You need one clear direction and the systems, people, and offers to support it.

Ask yourself:

• What initiative aligns most directly with my revenue or impact goals?

• What’s foundational now that will compound by year-end?

• What needs to get done - even if it’s uncomfortable - so that Q4 doesn’t become one long pivot?

No Overhaul Required, Just Intentional Adjustments

This isn’t about blowing up your business. It’s about zooming in on what matters.

A midyear reset, when done right, doesn’t require a dramatic reinvention. It requires leadership. Strategic leadership. The kind that steps back to see the full picture - then makes sharp, specific moves that shift everything forward.

At SKHB, we’re constantly recalibrating. This guide reflects the very process we walked through ourselves - and we’re turning it into a downloadable template that you’ll be able to use (and reuse) anytime you need to zoom out, reset, and refocus.

Want the full template?We’re putting the final polish on it now. Keep an eye on your inbox - it’s designed to help you think sharper, move smarter, and lead with clarity.