The Art of Asking the Right Questions: My 4-Decade Journey in Strategic Counseling 

Recently, a long-time client reached out about recovering seized assets – assets we’d spent years helping him protect before they were ultimately taken. Here’s the thing: he wasn’t calling because we’d succeeded in saving his property; he was calling because during those difficult years, we’d always told him the truth, treated his concerns with respect and found creative ways to protect what mattered most—his reputation and ability to continue doing business. 

This experience crystallized something I’ve learned over 40-plus years of counseling leaders through their toughest challenges: The foundation of great advisory work isn’t having all the answers. It’s knowing which questions to ask. 

Finding Common Ground Through Curiosity 

When a new client walks through our doors, my first instinct isn’t to showcase our expertise or rattle off past successes. Instead, I start with questions—lots of them. What are your pain points? What does success look like to you? What hasn’t worked before? 

I’ve discovered that clients sometimes don’t fully understand their own challenges. By asking enough questions, you begin to hear what’s really at the heart of their issue. More importantly, you find that common ground between what they’re concerned about, what they expect and what we can realistically deliver. 

One client came to us wanting to become “the most famous person in the world.” Rather than dismissing this as impossible, I asked: Would it be enough if you wrote a book cataloging your life’s work? Would being recognized as a leader in your industry satisfy you? Through these questions, we shifted from an impossible dream to achievable milestones that would make them feel their life was worthwhile. 

The Power of Defining Success 

In my experience, the most critical question is deceptively simple: what does success look like? Without a clear answer, you’re navigating without a map. 

I often share the story of a landlocked country that needed port access. The challenge was enormously complex, but the success metric was black and white—either they got access or they didn’t. Compare that to the client seeking global fame. One requires creative diplomacy; the other requires managing expectations and finding meaningful alternatives. 

When clients can’t articulate success, I throw out possibilities: what if we achieved this? Would that be important to you? It’s like identifying mile markers on a road—without them, you’ll never know how far you’ve traveled. 

Building Trust Through Honest Counsel 

Here’s something I’ve learned the hard way: You must be honest about difficult truths without being critical. When the client with seized assets first approached us, his assets were already “on fire.” We could have promised miracles; instead, we promised to explore every option and be transparent about the odds and costs along the way but noted that we’ve rarely seen this succeed.  

This approach does two things. First, it builds trust—clients know you’ll tell them the truth even when it’s uncomfortable. Second, it allows you to create what I call a “journey of small wins.” By delivering early successes that build confidence, clients become more willing to follow your guidance on tougher recommendations. 

Simplifying Complexity Without Losing Substance 

After decades of receiving both information overload and information drought, I’ve developed my own test: if I were the client, what five things would I need to know? What story connects these points? What might I be missing? 

I think about this constantly. Recently, while watching coverage of a presidential address, I switched between CNN, MSNBC and Fox News—not because I agreed with all perspectives, but because understanding different viewpoints helps me identify blind spots in my own thinking. 

The worst thing you can do is hand a client a 30-page memo when they need five clear bullets that tell a story and lead to a decision. It’s about respecting their time while ensuring they have what they need to move forward confidently. 

Looking Forward 

What’s changed most in my approach over the years isn’t the fundamentals—it’s the confidence that comes from lived experience. At nearly 80, I think differently than I did at 50. But that experience means nothing if you’re not still listening, still curious, still seeking to understand perspectives different from your own. 

The Middle East conflicts I witnessed decades ago inform how I counsel clients navigating today’s geopolitical challenges. The supply chain disruptions we helped clients manage taught us about “just-in-time” strategies before they became boardroom buzzwords. Each experience adds another layer to our collective wisdom at APCO. 

But here’s what hasn’t changed: great counseling is about building trusted relationships where clients know you’ll hear them, challenge them respectfully, and support them even when you disagree. Sometimes that means saying, “I don’t agree, but you’re the client. Let’s try it your way.” 

Because ultimately, our role isn’t to be right. It’s to help clients find their own version of success—whether that’s securing port access for a landlocked nation or finding meaningful recognition for a life well-lived. The questions we ask along the way just help illuminate the path.