Typical Questions Being Asked in Today’s SMEs by Investors, Boards, C-Suite Leaders and Stakeholders ?
Most SMEs don’t fail because they lack ideas. They struggle because leadership teams can’t answer (or evidence) the same repeat questions:
Where are we going?
How do we make money and protect cash?
What risks could hurt us?
Can we execute change?
In 2026, those questions increasingly include AI, governance, cybersecurity, talent and sustainability. This page groups the most common investor-board-c-suite questions into a practical checklist you can use for planning, board packs and transformation roadmaps.
The Top 10 Searches across ChatGpt, Grok, Genini and Perplexity by SME Leaders, Investors and Directors
What executives ask vs what “good” looks like ?
Theme: Strategy & direction
Typical question: “What’s the plan for the next 12–24 months?”
What good looks like: Clear choices, priorities, and measurable outcomes
Common pitfall: Activity lists instead of decisionsTheme: Cash & resilience
Typical question: “What happens if revenue drops 15%?”
What good looks like: Scenario triggers + actions + owners
Common pitfall: Forecasts with no operational leversTheme: AI & digital
Typical question: “Where will AI pay off in 90 days?”
What good looks like: 1–2 workflows redesigned end-to-end
Common pitfall: Tool pilots without adoptionTheme: Risk, governance & compliance
Typical question: “What’s our biggest operational or regulatory risk?”
What good looks like: Known risks, controls, evidence, accountability
Common pitfall: Policies that aren’t usedTheme: Talent & operating model
Typical question: “Do we have the right people for the plan?”
What good looks like: Role clarity + skills plan + decision rights
Common pitfall: Training without behaviour changeTheme: Sustainability & stakeholders
Typical question: “What do we measure and why?”
What good looks like: Material metrics + clean data + accountability
Common pitfall: Reporting standards
“Boards and investors don’t expect perfection. They expect clarity: what you’re changing, who owns it and how you’ll measure progress.”
Are you asking questions likes these ?
The Top 10 Searches across ChatGpt, Grok, Genini and Perplexity in 2025 by SME Leaders, Investors and Directors
Strategy & Business Model
Typical questions
What is our strategy for the next 12–24 months, and why will it win?
What are we choosing not to do?
Where are our biggest growth opportunities and threats?
What market or customer shifts should we plan for?
What’s our competitive edge, and can we prove it?
Does our business model still work at today’s costs and customer expectations?
Florido Guidance: What good looks like
A small set of strategic choices (market/customer/product focus)
3–5 priorities with clear measures and owners
A view of “what changes our mind” (triggers)
Finance, Cash Flow & Scenario Planning
Typical questions
What’s our cash runway and the plan to extend it?
What happens to cash if sales fall 10–20% or costs rise?
What are our working-capital levers (receivables, payables, inventory)?
Where are margins expanding or shrinking, and why?
What pricing changes are possible without harming retention?
What are the top financial risks in the next 6–12 months?
Florido Guidance: What good looks like
3 scenarios (base/downside/upside) with trigger points
Weekly cash visibility and clear actions
A plan tied to operational levers, not hope
AI, Digital & Technology Enablement
Typical questions
What is our AI strategy, and what outcomes does it target?
Where should we start to show ROI in 90–180 days?
What workflows should we redesign first (sales, onboarding, support, and finance close)?
What data do we need to make AI useful and safe?
How do we scale AI beyond pilots into daily operations?
Where should we not use AI?
Florido Guidance: What good looks like
One or two workflows improved end-to-end
Clear KPIs (cycle time, error rate, conversion/retention, risk reduction)
Human validation rules for sensitive steps
Measurement, KPIs & Value Creation
Typical questions
How do we measure impact beyond “people are using it”?
What are the leading indicators that the plan is working?
How do we prove we’re reducing risk as well as saving cost?
What does success look like in 30 / 60 / 90 days?
Florido Guidance: What good looks like
A simple scorecard reviewed weekly for 8 weeks
Outcome metrics (time saved, errors reduced, cash improved, churn lowered)
Evidence of adoption in the workflow, not in a tool dashboard
Risk, Governance & Compliance
Typical questions
What are our top operational and regulatory risks?
How do we govern AI responsibly (privacy, bias, model risk, third parties)?
What’s our policy on AI use internally?
What controls exist, and can we evidence them?
Who owns risk, and how are decisions documented?
Florido Guidance: What good looks like
Risk register that links to controls and owners
Short, usable policies that reflect how work is done
Evidence trail (approvals, checks, incidents, remediation)
Cybersecurity, Fraud & Trust
Typical questions
What’s our biggest cyber/fraud risk right now?
How do we prevent AI-enabled phishing and deepfake fraud?
What controls protect payments and sensitive requests?
How are we training staff and testing readiness?
What happens in the first 24 hours if we’re breached?
Florido Guidance: What good looks like
Verification steps for payments and identity
Training plus simulated tests
Clear incident playbooks and escalation
Operating Model, Execution & Delivery
Typical questions
Why does execution feel slow or fragmented?
What are the bottlenecks that stop us delivering?
Are decision rights clear, or are we stuck in meetings?
What’s the operating model that supports the strategy?
How do we sequence initiatives without overwhelming teams?
Florido Guidance: What good looks like
Fewer handoffs, clearer ownership, redesigned workflows
A realistic portfolio (less work, better delivered)
Visible leadership commitment to removing blockers
Talent, Workforce & Leadership
Typical questions
Do we have the right roles and skills for the plan?
How will AI change job expectations and capacity?
What capability gaps exist in leadership and management?
What’s our upskilling plan that actually sticks?
How do we retain key people during change?
Florido Guidance: What good looks like
Role clarity tied to business outcomes
Role-based learning and weekly practice
Changes in behaviours, not just training completion
Transformation, Turnarounds & Change
Typical questions
What is transformation, and how does it differ from a turnaround?
Are we stabilising the business or redesigning it?
What must change to protect value in the next 6 months?
How do we prevent transformation from stalling?
Florido Guidance: clarity: transformation vs turnaround
Transformation is a deliberate, forward-looking change to how a business creates value (strategy, operating model, tech, people, decisions).
A turnaround is reactive and time-critical: stabilise cash flow, cut costs, restore viability.In simple terms
Turnarounds stop the bleeding
Transformations change how the business works, so the problem doesn’t return
Sustainability, ESG & Stakeholder Confidence
Typical questions
What sustainability metrics do we track, and why those?
How do we gather reliable data without heavy overhead?
What’s our plan to reduce footprint or improve transparency?
How do we avoid greenwashing risk?
How does AI and digital change affect our ESG commitments?
Florido Guidance: What good looks like
A small set of material metrics with clean data capture
Accountability and measurable action plans
Clear narrative aligned to operations, not just reporting
Popular Questions asked by SME’s in 2025 & 2026
“Transformation doesn’t fail because SMEs lack ambition. It fails because priorities aren’t translated into how work actually gets done. When that gap closes, progress accelerates.”
Want to answer these questions with confidence?
FAQ’s
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No. These come up for most SMEs once there’s external scrutiny, complexity, or change: lenders, investors, boards, major customers, regulators, or key hires.
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Typically: cash resilience, evidence of traction, concentration risk, how decisions get made and whether the operating model can scale without breaking.
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Use a one-page scorecard: strategy choices, cash scenarios, top risks and controls, delivery priorities, and clear owners. Then ensure your numbers and narrative align.
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Transformation is forward-looking redesign of how the business creates value. A turnaround is urgent stabilisation to restore viability. Many SMEs do the turnaround first, then transform.