Written by James Chae — Co-Founder, Expert Sapiens
Korean Licensed Administrative Attorney (행정사)Reg. No. 220-06-06463 · 대한행정사회
Platform expertise: Business strategy & consulting · Reviewed March 2026
Session Prep
Business consultants are most valuable when they're challenged to go beyond diagnosis and into prescription. These questions push for concrete thinking, test how well they understand your specific situation, and make sure you leave with more than a list of considerations. This guide is structured around three phases: diagnosing the actual problem, developing strategy and prioritization, and defining execution and next steps. Before your session, write down the one or two business problems you most need to make progress on. The best sessions are focused, not broad — resist the temptation to cover everything. Come prepared with key context: recent performance data, the decisions you're facing in the next quarter, and any previous attempts to address the problem. The more prepared you are, the more specific and actionable the advice you'll receive.
1.What do you think is actually causing the problem I described — and what's your confidence level in that diagnosis?
Pushes past surface-level observations into root cause analysis. The confidence qualifier matters.
2.What information would change your view of my situation if you learned it?
Reveals how they're thinking and what they consider the critical unknowns.
3.What are similar companies doing that I'm not — and should I be doing it?
Gets you cross-industry or competitive pattern recognition that's hard to see from inside your business.
4.Is the problem I described the real problem, or a symptom of something else?
Forces a reframe. The best consultants often redefine the problem before solving it.
5.If you could only fix one thing in my business this quarter, what would it be and why?
Forces ruthless prioritization. Consultants who can't answer this clearly haven't done the diagnostic work.
6.What's the highest-risk assumption my current strategy is built on?
Strategy always rests on assumptions. Finding the fragile ones before they break is the point.
7.Where are my competitors beating me, and is it something I should care about?
Not all competitive gaps matter — this question separates signal from noise.
8.What's the most common mistake companies make when trying to execute on what you're recommending?
Surfaces implementation pitfalls before you hit them — not in hindsight.
9.What does success look like in 6 months if we do this right, and how would we know?
Forces definition of outcomes and measurement — not just activity.
10.What would you do first if you were me, starting tomorrow?
The 'what would you do' question is the best test of conviction. Vague answers mean vague thinking.
Written by James Chae — Co-Founder, Expert Sapiens
Platform expertise: Business strategy & consulting · Reviewed March 2026