Three Questions Every Leader Should Ask This Quarter
I recently arrived at our summer beach house in Maine.
One of the things I love about being here is that the ocean forces me to look farther ahead. You can't watch the water for long without noticing that conditions are always changing…tides, weather, wind, visibility.
It reminded me of a recent strategic planning session with two business partners last week.
As we mapped out their goals, team structure, responsibilities, and priorities for the rest of the year, a pattern emerged that I see often with leaders:
The biggest challenges in Q4 are rarely surprises.
They're usually visible months in advance.
A leadership gap that's growing.
A team member who is stretched too thin.
A communication issue that keeps resurfacing.
A process that's struggling to keep up with growth.
A founder who is spending too much time in the weeds.
The challenge isn't that leaders can't see these things.
The challenge is that we're often so busy solving today's problems that we postpone addressing tomorrow's.
Next week, I'll be speaking at the Millionaires Playbook Summit on decision-making and emotional intelligence. As I've been preparing for that conversation, I've been reflecting on a lesson I've learned through business successes, failures, and major transitions:
The strongest leaders don't simply react well. They anticipate well.
One exercise I encourage leaders to do at least once each quarter is to ask:
What is working that I need to protect?
What is creating friction that I need to address?
What opportunity is emerging that I haven't fully explored?
The answers often reveal where your attention should go next.
So this week, I have a question for you:
What challenge, opportunity, or decision can you already see on the horizon that deserves your attention today?
Sometimes the most valuable leadership work isn't solving the problem in front of you.
It's preparing for the one that's coming.
Wishing you a great week, as always I in your corner rooting for you!
Cheers,
Kasey
P.S. If you'd like the link to the Millionaires Playbook Summit, simply reply "Summit" and I'll send it over.
P.P.S. I have room for one additional Strategic Planning Session in June. If you're navigating growth, organizational changes, team structure, leadership transitions, or simply need time to think strategically about what's next, reply "Strategy" and let's start a conversation.