Editor’s note: This is the second of a three-part series of articles intended to provide a view of the path to a brighter future for independent grocery as a whole and for independent grocers.
In the first part of this series, we discussed the future of our industry. Now, we dive into the tactical execution – what to do and when – starting on the first day of ownership and looking forward 30 years.
Whether you’re a founder building a store from scratch, a second-generation operator growing the legacy or somewhere in between, this guide outlines the milestones, mindset and mechanisms necessary to protect what you’ve built and ensure it survives – and thrives.
Day one/30-year plan: Build it right, build it to last
The moment you open – or take over an operation – you’re setting the tone for everything that follows. The best succession plans begin on day one, not year 29. Let’s break down five foundational moves:
Build the business to outlast you – Think infrastructure, culture, systems and people – not just margin, product mix or sales velocity. Are you investing in talent development? Are the processes documented? Can this store run without you? If not, start now.
Practice “what if” planning – What happens if you can’t work tomorrow? Succession starts with survivability. Have contingency plans in place for death, disability and divorce. Include key person insurance, emergency leadership protocols and operational documentation that keeps the store open regardless of who’s at the helm.
Create a “pitch book” – Document your value proposition, financials, store performance, vendor relationships and customer base. This is not just for lenders or potential buyers – it’s your business’s resume. Over time, it becomes the primary tool for financing, recruiting, measuring trajectory and, ultimately, transitioning. This is also the tool that in the event of a tragedy enables your family to maximize the value of what has been created.
Diversify financially – Too many grocers treat their business as their sole asset. Start building personal financial independence outside of it. Diversification enhances the negotiating position at exit and offers options if the industry takes an unexpected turn.
Keep your eyes open – Nothing stays the same. Markets shift. Family members change. Health and interests evolve. Build an operation that is flexible enough to pivot. Reassess the succession trajectory every five to seven years.
10-year plan: Position for legacy, freedom
It’s time to transition from survival mode to strategic positioning.
Grow for sustainability – At this stage, you’re not just growing to increase top-line revenue – it’s to create long-term viability. This means investing in automation, leadership training, possible vendor diversification and customer loyalty. Build a business that doesn’t rely on any one person, product or customer segment. 
Begin exit conversation internally – No, you’re not selling tomorrow. But plan for an intentional exit. And that requires clarity on three fronts:
- Financial reality: Can the business and your outside investments support a buyout structure that provides retirement-level liquidity?
- Emotional and physical readiness: Are you realistically prepared to leave the store, both in body and in identity?
- Operational succession: Is there a capable replacement – family or not?
Identify and begin mentoring talent – This is the decade where a successor should start showing themselves. Maybe it’s your daughter. Maybe it’s the store manager. Maybe it’s someone from outside the company. Whoever it is, this is the time to mentor, observe and assess.
And be practical: If someone is willing to wait until he or she is 60 years old, they’re not the right person to run a dynamic retail operation. Hunger and leadership go hand in hand. The right successor will expect a timeline. Respect that. Plan accordingly.
Retain the option to switch horses – Succession is not linear. If the successor falls short – on character, competence or commitment – there must be enough time and flexibility to pivot. Ten years allows for that. Waiting too long removes that option.
Let’s also be honest: It is early still and you may ultimately sell to an outsider – but you will have built a stronger, more valuable asset and a strong team at ground level.
Five-year plan: Operationalize the promise
Now the planning becomes real. Abstract ideas must be converted into contracts, timelines and measurable outcomes. There is a plan for an insider transfer or it is time to prepare the business for potential sale. Either way, it is time to “fish or cut bait.”
Make it official – This includes buy-sell agreements, employment contracts, financial commitments and key performance milestones. Stop talking in hypotheticals. Begin documenting real numbers and real dates.
Begin role changes – Begin a gradual transition of operational control. A successor must start making decisions, managing people and dealing with vendors and lenders. You, meanwhile, must begin to step back.
This is the phase where theory meets practice. It’s a test – not a simulation. And the successor’s performance should validate or challenge the plan.
Assess successor readiness – If financing is part of the deal, you have every right to test for full capability. Is the successor financially savvy? Can he or she handle crises and respect the culture? This is your legacy. Treat it with rigor.
Assess your own readiness – Are you emotionally prepared to let go? Can you walk away without micro-managing? Have you identified what comes next – personally and professionally?
If not, start now. Retirement is not a vacuum. Without something meaningful to transition to, you’ll struggle to transition from.
Watch the movie “The Godfather: Part I” – It’s not a joke. The film is a near-perfect case study in leadership transition. Vito Corleone prepares Michael over years. He watches closely, empowers slowly and never hands over the reins prematurely. It’s a masterclass in succession, minus the crime.
One-year plan/implementation
Lock it in, launch. You’re on the edge of execution. This is not the time for major changes. It is the time for final refinements and confidence checks.
Refine the business plan and pro forma – Ensure that the incoming owner has a three- to five-year financial roadmap that’s stress-tested, lender-approved and operationally grounded. This includes capital reserves, contingency plans, revenue and margin targets and debt service coverage ratios.
Legal and financial infrastructure – Bring in an attorney (to finalize sale documents, board structure, governance rights) accountant (to structure tax-efficient transfers) and banker (to align loan covenants and capital terms and potentially finance a significant part of the transaction).
If providing seller financing, this step is critical, though a few additional layers are required.
Seller financing protections – If financing any portion of the transition, do it while you’re physically and mentally capable of retaking control if needed. In addition, insist on life/disability insurance for the buyer, naming you as beneficiary. And secure a legal instrument – often a seller note with control provisions – granting rights that override standard lender protections.
That means: You can say “no” to raises, new debt or strategic pivots until you’re repaid; you’ll have a board seat; and you can inspect financials regularly.
Banks don’t understand grocery – you do. This isn’t about micromanaging; it’s about risk mitigation. You are offering an opportunity a bank is incapable of financing.
If the buyer doesn’t like the terms, fine. He or she can refinance and pay you off to remove the controls. Until then, stay in the loop.
Follow through
You’re not finished until the last dime is paid. Transition is not a date; it’s a process. Once the papers are signed, the monitoring begins.
Quarterly oversight at a minimum – Review P&Ls, balance sheets and operational KPIs. Not out of suspicion, but out of stewardship. Modern POS and back-office systems make real-time monitoring possible. Use the tools.
Stay engaged – Remain in an advisory role. Sit on the board. Attend quarterly strategy sessions. Be a resource, but not a crutch.
Know when to step back in. If the successor veers too far off-course – or if the business deteriorates – step back in until you are repaid in full; that’s one option. Have those contingency clauses ready.
Remember, the worst-case scenario isn’t that the successor fails. It’s that he or she fails and you have no way to recover the business or resell it. This isn’t about micromanagement. It’s about protecting equity and ensuring success. If the buyer disagrees with oversight, he or she is always welcome to refinance and release you early.
Also worth noting: some acquirers – like Harps, for example – are all-cash, community-oriented buyers with strong reputations and long-term commitments. When numbers align, these transactions can be excellent outcomes.
But more viable options are better than fewer. Sell to the right cash buyer and do so with confidence, knowing there are choices. The focus must remain on creating more viable buyers, not just relying on the few that exist.