How to Hire a Business Consulting Expert

1.Have you personally run a business at a comparable stage, and what specific decisions did you own that are relevant to what we're facing?

Why it matters: Operating experience creates a category of knowledge that external analysis cannot replicate: the experience of making a consequential decision with incomplete information and living with the outcome. Advisors who have been in the seat have a visceral understanding of the tradeoffs, the organizational resistance, and the practical constraints that make strategic advice either useful or theoretical. The more specifically their operating experience matches your current challenge, the more applicable their pattern recognition will be.

2.What is the most important thing that companies like ours typically get wrong at this stage, and what does the evidence for that come from?

Why it matters: This question tests both the depth of their pattern recognition and the honesty of their assessment. Strong business advisors can quickly identify the most common failure modes for companies with your profile — based on direct experience, not just frameworks — and can point to the evidence that informs their view. Advisors who give vague answers about common business challenges without connecting them to your specific situation or providing specific evidence may not have the depth of experience their positioning implies.

3.Looking at what we've shared about our current situation, what would you identify as the two biggest strategic risks or mistakes we're making right now?

Why it matters: Asking an advisor to identify your current mistakes directly tests whether they will deliver independent judgment or comfortable validation. The best business advisors are willing to tell you what you're doing wrong — specifically, not generically — and can articulate why it matters and what they would do differently. Advisors who struggle to identify anything you're doing wrong are either not engaging critically with your situation or are deferring to a preference for an agreeable interaction over an honest one.

4.What is the difference between outcomes you have personally driven and situations where you were in an advisory role — how do you distinguish your contribution?

Why it matters: Attribution in business consulting is frequently ambiguous: advisors who were present during successful periods of company growth often take credit for outcomes they observed but didn't drive. Asking advisors to be specific about what they personally owned versus advised on reveals the extent to which their track record reflects genuine contribution versus proximity to success. The willingness and ability to make this distinction honestly is itself a signal of the quality of their judgment.

5.How do you approach a situation where your recommendation is the right answer strategically but is very difficult for the organization to execute?

Why it matters: The hardest consulting situations are those where the right answer creates organizational disruption — requiring changes to team structure, culture, processes, or leadership. Advisors who can describe a specific situation where they navigated this tension — how they built the case for a difficult recommendation, how they helped the client work through the organizational resistance, and what the outcome was — are demonstrating the kind of practical execution experience that makes strategic advice actionable.

6.What would you not recommend for our situation — and why?

Why it matters: The most selective and thoughtful advisors are those who recognize what doesn't fit as clearly as what does. Asking what they would specifically not recommend — which strategies, frameworks, or approaches they would steer you away from given your current situation — tests whether they are thinking independently about your context or applying a standard framework. The answer also reveals whether their recommendations are genuinely tailored or drawn from a standard playbook applied to every client.

7.How do you stay engaged through implementation — and what does accountability for results look like in your engagements?

Why it matters: The most common failure mode in consulting is the disconnect between a strong diagnosis and weak implementation support. Understanding how an advisor structures their ongoing engagement, what they provide during implementation, and how they track and report on progress toward outcomes reveals whether they are outcome-oriented or deliverable-oriented. Advisors who disengage after providing strategic recommendations are providing advice, not accountability — and the two are very different in their impact on your business.

8.Can you describe a situation where your initial recommendation turned out to be wrong, and how you handled that?

Why it matters: Business advisors who can describe specific cases where their initial view was incorrect — and explain how they identified the error, what they changed, and what the outcome was — are demonstrating intellectual honesty and adaptive judgment that is genuinely rare. Advisors who have never been wrong, or who cannot describe a specific case of being wrong, are either telling you what you want to hear or have not done enough substantive work to have generated meaningful failures. Either is informative.