How Do Leadership Teams Identify and Fix Their Biggest Problems?

board room strategic planning meeting

Introducing What's Your BIG Problem?™: A Card Game for Strategic Conversations

After years of remote work, leadership teams are rediscovering the value of being in the same room. Whether on-site or at an off-site retreat where daily distractions can’t derail strategic thinking, physical presence makes difficult conversations easier. But here’s the reality: people enter these sessions with mixed feelings. They want productivity, but dread eight hours in a conference chair. They want to voice concerns, but some hesitate to raise uncomfortable topics, while others charge ahead without filter. The tension exists before anyone even speaks.

Leadership teams are great at identifying symptoms. They feel the friction. They see when things aren’t working. What they struggle with is uncovering the root causes behind those symptoms, prioritizing what to tackle first, and aligning on solutions without politics or personalities derailing the conversation.

After nearly 30 years as fractional CMOs, we’ve worked with more than 300 companies across thousands of projects, listening to frustrations from business owners, executives, and leaders across all departments. We’ve conducted countless SWOT analyses and facilitated hundreds of candid conversations about what’s actually holding organizations back. Now we’re sharing those learnings to help others.

Introducing, What’s Your BIG Problem?™ (WYBP),  a strategic card game that helps leadership teams raise critical issues, align on solutions, and fix their biggest problem(s).

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The BIG Problem with “Problems”

The word “problem” itself has a negative connotation because it’s associated with something (or someone) that is difficult.

Another way to define it is “the gap between the current state and the desired goal.” That takes the edge off a bit. But what happens when there’s more than one problem across multiple departments? Not to mention multiple people with different perspectives and motivations. Does the squeaky wheel get the grease?

Inevitably, teams wind up having the same vent sessions quarter after quarter, year after year. The loudest voices dominate the conversation, tactical challenges and symptoms distract from root causes, and the obstacle or source of stress widens the gap instead of closing it. 

AI Can’t Solve Your Biggest Problems

It’s 2026, and AI has dramatically changed how organizations operate. It handles administrative tasks, analyzes data, supports content creation, automates processes, and resolves tactical challenges faster than ever.

But AI alone can’t fix your BIG problems.

The challenges that truly hold companies back aren’t technical; they’re human. They involve understanding how people dynamics, external factors such as daily economic shifts, supply chain issues, immigration policies, and individual fears, hopes, and dreams impact decisions across organizations, large and small.

These are the problems that require facilitated conversations, honest dialogue, and alignment among people who may see the world very differently, but need to run a business harmoniously.

That’s why we created What’s Your BIG Problem?™ (WYBP)—a card game that brings teams together on an even playing field, for a fun, interactive experience with productive outcomes.

What’s Inside the Box?

Over years of listening to clients describe their challenges, we identified patterns that cut across industries, company sizes, and business models. We’ve since distilled those insights into six core categories. Within each category are eight timely business issues—48 total problems reflected in the WYBP deck.

The categories include:

  1. Revenue: Unpredictable cash flow, pricing challenges, customer acquisition struggles
  2. Growth: Talent attraction and retention, scaling obstacles, capacity constraints
  3. Brand:  Inconsistent messaging, unclear value proposition, weak market position
  4. Competition: Crowded markets, price pressure, differentiation challenges
  5. Performance: Unreliable data, ineffective processes, poor measurement
  6. Alignment: Communication breakdowns, internal friction, conflicting priorities
WYBP Category Card

What’s Your BIG Problem™ is Much More Than a Game

WYBP is a strategic facilitation tool disguised as a card game.

Playing cards feels familiar, even comfortable. Teams aren’t staring each other down across a conference table while someone lists problems on a whiteboard. With WYBP, they’re holding cards, discussing scenarios, and building consensus. The tactile experience and familiar format shifts the dynamic from confrontational to collaborative. It makes hard conversations easier to have.

Instead of pointing fingers or making accusations, teams are reacting to cards, discussing scenarios, and building consensus through a structured process.

As we say, “What’s inside the box is what’s holding you back.™”

WYBP helps teams move past symptoms, tools, and tactics to identify actual root causes. It surfaces critical issues that everyone knows exist, but no one wants to name. It creates alignment on what matters most right now—not someday, not eventually, but right now!

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How Do Teams Incorporate WYBP into Existing Processes? 

WYBP is designed for self-facilitation with teams of 2 to 15+ people. The process is straightforward but powerful:

  1. Choose: Each player selects cards that personally resonate across the six categories.
  2. Share: Without debate or comment, individuals explain their selections and perspectives.
  3. Align: The team reaches consensus on the most critical issues.
  4. Commit: The group prioritizes action, plans the quarter ahead, and has the next quarter’s ideas ready to go.

Beyond the Leadership Team

While WYBP was designed primarily for executive teams, it’s a valuable exercise to run across all levels and departments.

What does your sales team think are the biggest problems? What about operations? Customer service? HR? Marketing?

Using multiple decks across departments reveals critical insights. You’ll discover where dangerous disconnects are creating friction, and you’ll bring attention to strengths, weaknesses, opportunities, and threats that might otherwise stay hidden in silos.

This cross-departmental perspective often reveals the root causes that purely leadership-level discussions could miss.

The beauty of What’s Your BIG Problem?™ is its flexibility. It works alongside your organization’s existing planning methodology or provides structure if you don’t yet have one.

Professional Facilitation Available

WYBP is built for self-facilitation. However, if you prefer professional guidance or are tackling particularly complex organizational challenges, Incite Creative, Inc. can facilitate WYBP sessions. We’ll guide your team through the process and ensure you walk away with an actionable game plan.

As fractional Chief Marketing Officers, we typically apply WYBP concepts within the first 30 to 45 days of marketing research and strategy development for new clients.

What’s Your BIG Problem?™ has become an invaluable resource in our own work, and we’re excited to make it available to leadership teams tackling their biggest challenges.

Why NOW Matters

We’re living through a time of significant change. Teams that worked remotely for years are coming back together. Organizations are rediscovering the value of collaborative, in-person experiences.

But simply being in the same room isn’t enough. You need productive frameworks for having difficult conversations.

WYBP provides that framework. It’s a fresh, fun, functional approach to replace tired vent sessions and one-sided leadership monologues with genuine dialogue and consensus-building.

Ready to Tackle Your BIG Problem(s)?

What’s inside the box is what’s holding you back. The question is: are you ready to open it?

About Incite Creative, Inc.: Incite Creative is a marketing advisory firm that provides fractional CMO services. In short, we become your company’s chief marketing officer and do so virtually and efficiently — saving you time and money. Since 1999, we’ve built and boosted brands across a core set of industries. Our thoughtful process, experienced team, and vested interest in our clients’ success have positioned us as one of the Mid-Atlantic’s most sought-after marketing partners for those looking to grow their brand awareness and bottom line. Stop paying for digital and traditional services you may not need. Our retainer, no-markup model means our recommendations don’t come with any catch or commission. Our guidance aligns with your needs and fits within your budget. For more information, contact us at 410-366-9479 or [email protected]