The 5, 3, 1 on June Wrap Ups & Business Planning
Five days to July. Three peppermint stick ice cream cones and one ocean swim into summer—and what’s on my mind isn’t just sunscreen and sand. It’s the rhythm of Mid-Year Business Rituals and the real impact they can have on how the year ends.
We’ve all been trapped in endless planning decks—and we’ve also seen what smart, focused planning can do. Now, with AI in the mix, we have a real shot at reclaiming time for what matters: clear decisions, aligned teams, and meaningful conversations.
For those in banking or business, it’s time to reflect on where to improve and how to move faster. For consultants and sellers, it’s a moment to connect with clients and understand when planning cycles hit—when vendors get pitched, budgets get locked, and projects kick off.
So here’s my 5, 3, 1 on mid-year rituals to help you finish strong—and maybe squeeze in a few more beach days while you’re at it.
1. Assess with Action-Oriented Honesty
Mid-year isn’t about laundry lists - it’s the half-time locker room moment to assess how to maintain or regain momentum.
What worked? What impact did it drive - revenue, savings, momentum?
What broke? Why didn’t it land?
Where did things stall - people, process, or priorities?
What needs to change *now*?
What missing or outdated infrastructure is impeding progress?
Don’t lather, rinse and repeat. There is merit in learning from the past and identifying what could help propel you into the future.
2. Align with Purpose
This is a leadership and team checkpoint to ensure you are all working together..
Are your teams clear on what’s working—and what’s not?
Are all internal stakeholders aligned with priorities and plans?
Have you clarified where you need RFPs, reached out to vendors to start scoping what is needed to approve budgets and kick off projects?
Is the C-suite aligned on direction and priorities?
Can your plan be digested quickly and acted on?
Leverage AI tools to clarify, communicate and save time from the power point rabbit hole. Keep the team focused on defining the actions needed to drive outcomes and execution. And have fun along the way, it builds deeper trust.
3. Ground Strategy in Math and Meaning
Don’t plan in abstract—plan with evidence: what did math show about the first half of the year’s performance? What needs to be revised? For the future plans, can you tie planning back to measurable assumptions?
Define five must-haves:
What’s required to keep the lights on
What needs fixing to improve daily execution
What infrastructure must scale
What bets do you want to make
What headlines do you want to tell next year
Let the data tell the story—and back the bets that move the needle.
4. Sequence, Scenarios, and the High Cost of Indecision
Embrace scenario planning to help settle on budget, implementation impacts and outcomes. Simple GANNT charts are an effective way to showcase necessary sequencing to make it easier to see when decisions need to be made—and what depends on what. This forces a 5 point clarity check:
What is the optimal blend of impactful and realistic of the scenarios?
Have you aligned and assessed where/why to leapfrog with AI or build off existing infrastructure
What does each step take to get going, to build, to launch and to maintain?
What is the impact to all teams, not just the one cooking up the proposed idea?
What RFPs must be initiated, vendors selected, contracts finalized, or capabilities built?
Every delayed or skipped step pushes outcomes further out—and indecision is often the most expensive delay of all.
5. Three Prime Opportunities
Now is the time to crack the code on smarter customer and employee insights and engagement. The technology exists—and when paired with your team’s institutional knowledge, it can power smarter segmentation and deeper relationship understanding. Are you equipped to uncover your clients' full suite of needs—across personal, family, and business relationships? Can you map the entire business entity network, including locations, auxiliary lines, and the people behind them? Can your sales team build faster, smarter briefing memos to better understand the needs of their prospects and clients? Have you included the investment needed to make this a reality?
Rethink Your Talent Strategy: With AI accelerating, seasoned leaders retiring at a faster pace, and uncertainty on the rise, how are you evolving your workforce? Gone are the days when steady, detail-oriented order takers could keep the ship afloat. Today’s differentiator is talent that’s curious, adaptable, and capable of critical thinking—people who know how to prompt, challenge, and partner with AI to drive smarter, faster outcomes. The secret weapon isn’t just the tech stack—it’s the talent behind it. What are you doing to ensure you have the right culture, talent, and skills for today’s world?
Three Trains Can Leave the Station at Once: a) Keep the Basics Going and Growing – What needs to stop, adjust, or continue to sustain core performance?
b) Build for Near-Term Impact – What investments or changes must be made now to improve outcomes over the next 12 months? c) Invest for future potential – What big ideas need to begin today, because every delay pushes impact out—and risks losing not just time, but competitive edge?
The Final Point
Mid-year isn’t just a milestone maker to hit the beach, justify ice cream cone, or fill out some mid year accomplishments report. It’s a chance to reconnect, reflect and recharge.
