How to Provide Strategic Advice

In my work advising consulting boards, I have watched multi-million pound strategies fail not because of poor execution, but because of a partner’s unshakeable confidence in a flawed opinion. We have institutionalised the habit of treating confidence as a proxy for competence. We train junior consultants to speak with authority on subjects they have only just encountered. While this "fake it until you make it" culture might survive a slide deck presentation, it creates a structural risk for boutique firms. When the cost of being wrong is high, overconfidence is a liability, not an asset. True expertise is not the ability to form an opinion; it is the discipline of knowing when your opinion is likely to be wrong. We often fall prey to the Dunning-Kruger effect, where a lack of domain knowledge leads us to overestimate our own cognitive ability. For a founder, this leads to strategic advice that erodes client trust. I have observed five specific markers that should cause you to doubt a professional opinion. When these are present, the risk of error increases significantly: • Conflict with empirical data: If the available facts do not support the conclusion, the statement is an artefact of bias rather than analysis. • Logical inconsistency: If the explanation for a strategy relies on circular reasoning or gaps in "if-then" logic, it will fail under the pressure of implementation. • Ideological bias: When a recommendation is driven by "how things should be" rather than how the market actually functions, the advice becomes dogma. • Expert consensus: If the settled community of domain experts disagrees with your stance, the burden of proof rests entirely on you. • Lack of domain depth: Generalist skills are valuable for process, but they are not a substitute for deep, functional expertise in complex technical environments. To avoid these traps, we must recognise what does not constitute a valid argument. Relying on your own limited experience (the anecdotal fallacy) is a common pitfall. Just because a strategy worked for one client in the past does not mean it is a universal law. Similarly, the "bandwagon fallacy", where your immediate network agrees with you, is often just a reflection of an echo chamber. Research into the Professional Service Firm (PSF) model suggests that high-performing firms succeed because they balance "expert power" with rigorous internal challenge. When firms lack a culture of intellectual humility, they become prone to "collective overconfidence." This is often the root cause of disastrous M&A decisions or failed market entries. Before you present your next insight to a client, ask yourself: is this based on a rigorous interrogation of the data, or is it simply a well-packaged opinion? The most valuable consultants are not those who have an answer for everything, but those who have the intellectual rigour to verify their claims against evidence.

🚨 Most people still treat AI like Google. They're missing how to use it like a proper strategic advisor. The model already knows how to think strategically. You just need to trigger that mode by pushing AI to evaluate options against rubrics and run a trade-off. Instead of "What should I do about X?" try these 10 ways to force better thinking: → "Generate multiple distinct options" Not variations. Fundamentally different approaches. Force 5-7 alternatives that can't coexist. If they're compatible, they're not distinct enough. → "Map consequences at 3, 6, and 12 months" For each option: What's the state of play at each milestone? Which outcomes are reversible? Where do we lock in? What compounding effects emerge? → "Score against explicit criteria" Rate each 1-10 on speed to impact, resource efficiency, risk level, reversibility, strategic alignment. Make the scoring transparent. Debate the weights. → "Define constraints, then challenge them" State timeline, budget, no-go zones. Then ask: "Which constraint hurts most? What happens if we relax it? Which one is actually moveable?" → "Make the decision and own the trade-offs" Pick one. Then: "What am I accepting? What am I sacrificing? What's the leading indicator this is working? What's my reversal trigger?" → "Red-team your own recommendation" "What assumptions could be wrong? If this fails in 6 months, what will the post-mortem say? What would a competitor do differently?" → "Evaluate through conflicting lenses" Analyse from 3-5 different perspectives: user experience, business model, technical feasibility, competitive response, market timing. Force conflict between them. → "Map second-order effects" "What happens after what happens? If we succeed at X, what new problems emerge? What does this enable? What doors close?" → "Stress-test against edge cases" "What if: timeline gets cut in half, budget drops 30%, our lead competitor copies us, the market moves against us, our key assumption proves wrong?" → "Find hidden dependencies" "What has to be true for each option to work? What's within our control? What's the critical path? Where's the single point of failure?" LLMs are trained on business cases, research papers, policy debates. They need structure to access that mode. Example prompt to build on.

I joined Meltwater's Table Stakes 2026 series this week. The theme: AI as accelerator. Not replacement. If you swipe through, you’ll see insights from Brian Keenan, Rose Jia, Jim Reynolds, and me. I want to dig deeper on my quote and offer practical advice. If you're being rushed, working on tight deadlines, have limited resources and high expectations...welcome to reality. AI makes it dangerously easy to move something from draft to deliverable without ever truly thinking. Something relatively "easy" ... Create a Standards Guide. Attach with prompts or add to memory and instructions. Strategic Communications AI Standards Paste This Into ChatGPT Before Generating Strategy You are assisting with executive-level strategic communications work. Generic outputs are unacceptable. Surface-level summaries are insufficient. All recommendations must meet the following standards. 1. Context First — Never Assume Before generating strategy, ask clarifying questions if any of the following are missing: Primary business objective (growth, funding, risk mitigation, positioning, etc.) Target audience Competitive landscape Risk factors or regulatory constraints Timeline Resource constraints Internal stakeholder dynamics If context is insufficient, request more information before proceeding. Do not produce a generic plan. 2. Question-Led Analysis Do not immediately generate a strategy. First, analyze using questions: What assumptions are embedded in this request? What blind spots may exist? Where could this strategy fail? What would a skeptical CFO or board member challenge? What second-order effects should be considered? What risks are being underestimated? Present this analysis before presenting recommendations. 3. Adversarial Review Layer After generating recommendations: Identify structural weaknesses. Provide counterarguments. Compare to likely competitor approaches. Identify scenarios where this becomes obsolete. Flag reputational or regulatory exposure. Assume the output will be scrutinized 4. Elevate to Business Impact Translate all tactical recommendations into executive implications. Every recommendation must state: What decision it influences What revenue it supports or protects What risk it mitigates What perception it shapes What happens if no action is taken If impact cannot be articulated, revise. 5. Differentiation Filter Before finalizing: Could this apply to any company in the industry? Does this sharpen unique positioning? Does it reinforce narrative architecture? If transferable to competitors, increase specificity and differentiation. 6. Cognitive Expansion Provide: Three alternative strategic paths (conservative, balanced, aggressive) Tradeoffs for each Risk tolerance required for each Do not default to a single answer. 7. Clarity Over Volume Use: Clear headings Decision framing Risk flags Executive-ready language Avoid filler, clichés, or marketing tone. Copy, paste, revise and enjoy.

As a VC, here is exactly what I emailed every portfolio CEO before we joined their board: “Most BOD meetings create a huge burden on the CEO and are unproductive. You don’t have to make pretty slides (unless you’re visually inclined). A written memo format works too. Just make sure to send out any BOD materials at least 3 days ahead. Assume everyone has read it in advance so you can focus on the big picture. Think of the BOD meeting as a chance to get free advice on 1-3 strategic topics where you think other BOD members can help you. Aim for less than 20% of the time to be focused on metrics and at least 80% on the strategic topics of your choice. It all starts with how you structure the agenda. Don’t give too much time to the financials & metrics (as long as you sent them out in advance). Here’s an example of a format that can work well: 5m: CEO update 5m: Financial update 5m: Metrics update 5m: Industry updates 20m: Strategic Topic 1 20m: Strategic Topic 2 20m: Strategic Topic 3 10m: CEO & BOD members only discussion An example of some strategic topics to discuss might include: - We have 9 months of cash left, how should we manage burn - Our customer base is too concentrated. Let's chat about diversification. - Privacy policy changes in the industry and our reaction? - Can we get input on next year's proposed annual plan? - Should I promote this internal candidate or go external? - Our team and I are feeling burned out, what are we doing wrong? - I want to pivot the business, let's walk through my plans. Feel free to bring in other executives or fractional leaders if it helps sets context but make sure there’s enough time for just you & the BOD (e.g. the executive session).” No one gave me any of this advice and just expected me to know what to do. I wasted so much time putting together slides and then felt obliged to explain every single metric. It was also so boring for everyone involved. When you focus on strategic topics, you can put your BOD members to work for you and help you think through things that are important to you. It took years and years of making these mistakes until I finally figured out how to use this time wisely… so I truly hope this helps other Founders.

Over the past 12 months, I’ve trained almost 100 accountants in business advisory. And I’ve seen the same patterns show up again and again, holding many firms back. Here I share 12 learnings firms must overcome to build a thriving advisory department. 1. Advisory is strategy, not reporting. Management reporting looks backward. Strategic advisory looks forward, helping clients make decisions for the future 2. Too many firms are stuck in compliance The cycle of deadlines and lodgements leaves no space for strategic work, so advisory never gets off the ground 3. Without structure, advisory feels instinctive and inconsistent. And that makes it impossible to scale beyond the partners 4. Advisory is undervalued. Too often it gets given away for free, rolled into compliance, or squeezed into “over lunch” chats 5. Advisors think they need the answers. In reality, clients already have them. The role is to ask better questions and guide clarity 6. The hardest part isn’t strategy - it’s starting the conversation. Many accountants know what to do, but lack the confidence to begin 7. Human skills unlock the real problem. Without rapport and trust, clients only share surface issues. With it, you uncover what really matters 8. Reactive is easy. Proactive is hard. Waiting for the client call means firefighting. Strategic advisory means starting the conversation and preventing problems before they flare up 9. Advisory time gets wasted chasing data. Prep and analysis should happen before the meeting, so the meeting can focus on better questions and strategy 10. Clients don’t buy numbers, they buy outcomes. If advice isn’t tied to their goals, it won’t stick. Linking back to goals is what drives action 11. Firms wait too long to train their team. Too often advisory stays in the partners’ heads. The earlier you build skills across the team, the faster it becomes consistent and scalable 12. Advisory isn’t a bolt-on. It’s not another service line it’s a cultural shift in how the whole firm thinks and operates. My biggest reflection is that Accountants already have the skills to be great advisors. The gaps aren’t in knowledge, they’re in structure, confidence, and human connection. When advisory stops being about partner instincts and becomes a trainable, structured process, firms unlock consistency, scalability and impact. Which of these resonate most with your experience? Leaders in Business CPA Australia #businesssdvisory

So many people are told to “be more strategic,” but few are told how. Here’s my advice for where to start: shift your attention from content to context. Content relates to your responsibilities, your tasks, your expertise—‘what’ you do. Context is about the environment and the factors driving demand for the content—the ‘why it’s needed.’ Let me illustrate with a few examples: For a product manager, feature specs, user stories, and the product roadmap are content. Context is found in the users—what they need, the challenges they face, and what drives their priorities. For an analytics professional, data, analytical methods, reporting tools form content. The organization’s goals, the problems it needs solved, and how decisions will use those insights define the context. For a C-suite executive, annual goals, business strategy and budgets are content. Context lies in the external environment—shifts in customer expectations, competition, emerging technologies, and the broader business landscape. Focusing too much on the ‘what’ of your job and neglecting the ‘why’ limits strategic thinking. Context reveals hidden problems, shifting needs, root causes, and opportunities. Over time, you’ll see how the pieces connect and instinctively know what deserves the most focus. To be strategic is to see the whole and understand its relationship to the parts. #StrategicThinking #ProfessionalDevelopment

I recently shared a viral post that said accountants shouldn’t just forward financial reports without explaining them.  Some responded:   👉 “𝘉𝘶𝘵 𝘐 𝘥𝘰𝘯’𝘵 𝘬𝘯𝘰𝘸 𝘸𝘩𝘢𝘵 𝘵𝘰 𝘤𝘰𝘮𝘮𝘶𝘯𝘪𝘤𝘢𝘵𝘦.”  If that’s you, here’s a simple framework that makes your reports valuable:  ✅ 1. WHAT ✅ 2. SO WHAT ✅ 3. WHAT’S NEXT --- ✅ 1. WHAT (The Data)   → What happened?   → What do the numbers show?  ✅ 2. SO WHAT (The Insight & Impact)   → Why does it matter?   → How does it affect the business?  ✅ 3. WHAT’S NEXT (The Action Plan)   → What should we do about it?   → What are the next steps?  Real-World Example:  📌 WHAT:   📊 𝘙𝘦𝘷𝘦𝘯𝘶𝘦 𝘧𝘰𝘳 𝘘1 𝘸𝘢𝘴 ₦150𝘔, 𝘶𝘱 20% 𝘧𝘳𝘰𝘮 𝘭𝘢𝘴𝘵 𝘺𝘦𝘢𝘳, 𝘣𝘶𝘵 𝘱𝘳𝘰𝘧𝘪𝘵 𝘥𝘳𝘰𝘱𝘱𝘦𝘥 𝘣𝘺 5%.  🤔 SO WHAT:   📉 𝘌𝘷𝘦𝘯 𝘵𝘩𝘰𝘶𝘨𝘩 𝘴𝘢𝘭𝘦𝘴 𝘨𝘳𝘦𝘸, 𝘰𝘶𝘳 𝘤𝘰𝘴𝘵𝘴 𝘪𝘯𝘤𝘳𝘦𝘢𝘴𝘦𝘥 𝘧𝘢𝘴𝘵𝘦𝘳, 𝘴𝘲𝘶𝘦𝘦𝘻𝘪𝘯𝘨 𝘱𝘳𝘰𝘧𝘪𝘵 𝘮𝘢𝘳𝘨𝘪𝘯𝘴.  ✅ WHAT’S NEXT:   🔎 𝘞𝘦 𝘯𝘦𝘦𝘥 𝘵𝘰 𝘳𝘦𝘷𝘪𝘦𝘸 𝘤𝘰𝘴𝘵 𝘥𝘳𝘪𝘷𝘦𝘳𝘴—𝘦𝘴𝘱𝘦𝘤𝘪𝘢𝘭𝘭𝘺 𝘭𝘰𝘨𝘪𝘴𝘵𝘪𝘤𝘴 𝘢𝘯𝘥 𝘳𝘢𝘸 𝘮𝘢𝘵𝘦𝘳𝘪𝘢𝘭𝘴—𝘵𝘰 𝘱𝘳𝘰𝘵𝘦𝘤𝘵 𝘱𝘳𝘰𝘧𝘪𝘵𝘢𝘣𝘪𝘭𝘪𝘵𝘺 𝘪𝘯 𝘘2.  See the difference?  Now, instead of just being “the accountant,”   You become the finance leader who guides decisions.  Sending numbers without insights is like giving someone a map without directions.  Next time you send a report:   ✔️ Don’t just forward numbers.   ✔️ Add the narrative.  That’s how you go from a functional role to a strategic advisor.  Cheers,   Ajibola Test this approach and let me know how it changes the conversation!

Your clients don't need data providers. They want strategic advisors. So share your perspectives on key takeaways. Highlight risks, challenges, and chances to improve. Translate data into insights that tie back to client goals and priorities. Make data-driven recommendations. Ask hard questions to extract the story behind the data. Turn conversations with clients into strategic discussions, not just reports. Data alone isn't valuable. Real impact comes from advisory that blends analytics with critical thinking.