The 3-Person Advisory Board: Small Group, Big Shift

Most companies have blind spots.
Not because they’re careless—because they’re busy.

Serving customers.
Chasing growth.
Managing teams.
Keeping the wheels on.

In the middle of all that, strategic thinking gets pushed aside.

What are we not seeing?
What’s changing outside our four walls?
What bets should we be making?

Here’s the missed opportunity:
You don’t need a full board of directors.
But you do need outside perspective.

That’s where an Advisory Board comes in.

An Advisory Board is:

• Private
• Flexible
• Free of governance obligations
• Built for clarity, not control

It exists to think, ask, push, and challenge—without slowing you down.

How to Structure It

• One meeting per quarter
• One-page prep sent in advance
• Two-hour focused conversation
• Professional compensation that respects their time
• One point of contact to coordinate

No layers. No decks. Just high-leverage insight.

Why It Works

An Advisory Board solves for isolation.
It brings perspective from other industries.
It sharpens your thinking.
And strengthens your company.

Start with Three

One operator who’s scaled.
One financial strategist.
One sector-savvy voice who sees what’s next (think AI, regulation, shifts in talent).

That mix alone can change your trajectory.

The Real Benefit?

It doesn’t just help your company grow.
It helps you grow.

As a leader.
As a thinker.
As a decision-maker.

You don’t need twelve directors.
You just need the right three voices in your ear.

Thinking about building one?
We’ve created a simple checklist for structuring your 3-person Advisory Board.
Comment “Advisory” and I’ll send it your way.

Drop us an email.

How to Secure Your First Board Seat

Have you ever wondered why certain executives seamlessly transition into coveted board positions? Breaking into the boardroom isn’t about waiting for an invitation—it’s about strategic positioning and deliberate preparation.

When I first began exploring board opportunities after 15 years in business, I quickly learned that the path requires both patience and precision. Here’s what makes the difference:

Clarify Your Value Proposition – Boards seek directors who bring distinct expertise to enhance governance effectiveness. What unique insight do you offer—digital transformation, regulatory compliance, international expansion, or financial restructuring? Craft a compelling narrative that translates your functional excellence into governance impact. Boards look for directors who complement existing skill sets, not duplicate them.

Be Realistic About Where You Add Value – Your first board seat likely won’t be with a Fortune 500 company. Private companies, PE-backed firms, and growth-stage businesses often seek directors with hands-on operational expertise, deep industry knowledge, or transactional experience. Identify sectors where your background provides immediate credibility.

Cultivate a Strategic Network – Board roles are rarely filled through formal postings. Build relationships with sitting directors, governance professionals, and investors, particularly in private equity and venture capital, where board seats often arise. Offering industry consulting to PE firms investing in your sector is an effective way to demonstrate value—many of these engagements naturally lead to board opportunities.

Understand Time Commitments & Compensation – Board service requires 200–300 hours annually per board, including preparation, meetings, and committee work. Private company boards typically offer a mix of retainers, meeting fees, and sometimes equity. For context, the average total compensation for S&P 500 directors (excluding independent chairs) is around $327,096, with a blend of cash and equity. Understanding these practicalities signals your seriousness about board service.

Develop Governance Experience – Board dynamics differ from executive leadership. Serving on nonprofit, advisory, or private company boards builds governance acumen, broadens your network, and signals your commitment. These roles also teach the critical skill of influencing without direct authority—a key distinction between operational and governance roles.

Deepen Your Governance Knowledge – Effective directors understand fiduciary responsibilities, risk oversight, and board strategy. Programs like NACD’s Directorship Certification or Harvard’s board excellence programs enhance credentials. Mentorship from experienced directors provides valuable insights into the realities of boardroom decision-making.

Engage with Board Search Firms – While networking is essential, specialized firms like A-Street Advisors increasingly focus on broadening board diversity and matching directors with the right fit. Developing relationships with search consultants specializing in your industry can create additional pathways.

Be Intentional & Patient – Breaking into the boardroom is a marathon, not a sprint. Keep refining your positioning, deepening governance expertise, and engaging with the right circles. When the right opportunity emerges, you’ll be prepared—not just with the skills, but with the connections and credibility to make a meaningful contribution.

I’ve found it incredibly rewarding to work on a company, not in a company, and to partner with influencers who shape industries and drive meaningful change. - M.A.

Speak Up—But Do It Right

We’ve all been in meetings where someone talks just to fill space. And we’ve all seen moments when someone stays silent when their voice is needed.

Knowing when to speak and how to do it matters. Here’s a quick guide:

Listen before you speak. Conversations aren’t competitions. Pay attention, process what’s being said, and respond with intention—not just to be heard.

Say what you mean. Get to the point. Be clear. Don’t bury your message in fluff or qualifiers.

Know when to hold back. Not every thought needs airtime. If you’re adding value, speak. If you’re just echoing or venting, reconsider.

Add, don’t repeat. If you agree, say why or build on the idea. “I agree” doesn’t push the discussion forward.

Pick the right setting. Big ideas? Address them at the right level. If it’s a peer discussion, keep it there. If it’s a leadership issue, raise it at the right table.

Be constructive. Pointing out a problem is easy. Offering a solution makes you part of the fix.

Read the room. Different groups have different dynamics. Some reward bluntness, others expect diplomacy. Adapt accordingly.

Confidence is good. Overconfidence isn’t. Speak with conviction, but stay open to other perspectives. The best voices in the room leave space for others.

Speaking up well is a skill. Master it, and people will listen when it counts.

What’s your take—how do you decide when to speak and when to hold back?

The Art of Board Participation

Effective Contribution Timing

When to Speak

• When you have unique expertise relevant to the discussion

• After listening to initial perspectives to build on ideas

• When you notice a critical risk or opportunity that others haven't mentioned

• To ask clarifying questions that will benefit the whole board

• When you can offer a different strategic perspective

When to Listen

• During the initial presentation of new information

• When others are sharing specialized expertise

• During complex financial or technical discussions outside your expertise

• When emotional tensions are high

• When multiple viewpoints are being shared rapidly

Reading the Room

• Observe body language and engagement levels

• Notice if the discussion is moving toward or away from a resolution

• Pay attention to time constraints and agenda progress

• Watch for signs that others want to contribute

• Be aware of the chair's cues for discussion flow

Maximizing your impact

Quality of Contributions

• Be concise and specific

• Link comments to strategic objectives

• Support points with relevant data or experience

• Acknowledge and build on others' input

• Focus on forward-looking solutions

Active Listening Techniques

Take notes on key points

• Observe others' reactions

• Consider implications before responding

• Look for patterns in discussions

• Think about unasked questions

Balancing Participation

Finding the Right Balance

Contribute to every significant decision

• Allow space for others' expertise

• Save detailed questions for offline discussions

• Focus on strategic rather than operational matters

• Support board unity after decisions

Meeting Dynamics

Follow the chair's lead on the discussion flow

• Respect time allocations for agenda items

• Keep contributions relevant to the current topic

• Know when to take discussions offline

• Support inclusive participation

Special Circumstances

Challenging Conversations

Choose timing carefully for complex messages

• Frame concerns constructively

• Focus on issues, not personalities

• Suggest solutions along with concerns

• Support board cohesion

Remote Participation

Signal your intention to speak clearly

• Be more concise than in-person

• Use chat features appropriately

• Minimize background distractions

• Stay visibly engaged

Remember:

• Quality over quantity in contributions

• Timing is as important as content

• Support collective decision-making

• Maintain professional courtesy

• Focus on board effectiveness

The Interview: Mastering the Art of the Two-Way Conversation

The interview has evolved far beyond the traditional interrogative format into a sophisticated dialogue that reveals mutual fit and potential. Success lies not in merely answering questions but in orchestrating a compelling exchange that demonstrates value while gathering crucial insights. Here's how to master this nuanced art.

Reframing the Interview Dynamic

The most successful interviews transcend the conventional question-and-answer format to become strategic conversations between potential partners. This transformation begins with a fundamental shift in mindset:

From Interrogation to Dialogue

Traditional interview preparation often focuses exclusively on anticipating and crafting responses to expected questions. While important, this approach misses the broader opportunity to engage in meaningful discourse that reveals mutual value alignment.

The modern interview requires viewing yourself as an equal participant in a strategic discussion. This perspective shift enables you to:

The Confidence-Humility Balance

Projecting the right level of confidence requires mastering a delicate balance. True executive presence combines self-assurance with genuine humility:

Verbal Communication

Master the art of confident communication through:

• Using decisive language while acknowledging alternatives

• Speaking in terms of "we" when discussing past successes

• Acknowledging team contributions while owning your role

• Addressing challenges directly without defensive positioning

• Expressing conviction in your approach while remaining open to other perspectives

Non-Verbal Presence

Project confidence through purposeful physical presence:

• Maintain consistent eye contact without staring

• Adopt an open posture that conveys both authority and approachability

• Use deliberate hand gestures to emphasize points without dominating

• Modulate your voice to convey enthusiasm while maintaining composure

• Enter spaces with purpose but without demanding attention

Balanced Self-Presentation

Navigate the fine line between confidence and arrogance by:

• Sharing accomplishments through the lens of learning and growth

• Discussing failures as valuable experiences without self-deprecation

• Acknowledging expertise while showing curiosity about new perspectives

• Demonstrating competence through questions rather than declarations

• Using humor judiciously to build rapport without undermining credibility

Knowledge Presentation

Display expertise while maintaining humility:

• Reference industry insights as observations rather than proclamations

• Present alternative viewpoints before advocating for your preferred approach

• Acknowledge the complexity of challenges before suggesting solutions

• Frame expertise in terms of continuing development rather than achieved mastery

• Use specific examples that demonstrate capability without self-promotion

Handling Disagreement

Show confidence in managing different viewpoints by:

• Acknowledging valid points in opposing perspectives

• Presenting counterarguments as additional considerations rather than corrections

• Maintaining composed body language when challenged

• Using phrases like "In my experience" rather than absolute statements

• Showing genuine interest in understanding different viewpoints

Additionally:

• Ask insightful questions that demonstrate strategic thinking

• Guide the conversation toward your strengths naturally

• Evaluate organizational fit from a position of mutual respect

The Art of Strategic Listening

Masterful interviewing begins with sophisticated listening skills. Beyond merely waiting for your turn to speak, strategic listening involves:

Active Engagement

Develop the ability to detect underlying themes and concerns in questions. Often, what appears to be a straightforward query about past experience actually seeks to understand:

• Problem-solving approaches

• Leadership Philosophy

• Change management capabilities

• Cultural fit indicators

Pattern Recognition

Identify recurring themes in the interviewer's questions and comments. These patterns often reveal:

• Current organizational challenges

• Unspoken role expectations

• Cultural priorities

• Strategic direction

Crafting Your Narrative

While spontaneity is valuable, successful interviews require thoughtful preparation in crafting your professional narrative:

Story Architecture

Develop a portfolio of experiences that demonstrate key competencies, ensuring each story:

• Illustrates multiple skills simultaneously

• Demonstrates measurable impact

• Reveals strategic thinking

• Shows emotional intelligence

• Connects to broader business objectives

Adaptive Storytelling

Master the art of modulating your narrative based on:

• The interviewer's background and role

• Organizational context and challenges

• Interview stage and objectives

• Signals received during the conversation

The Power of Strategic Questioning

Sophisticated questioning transforms an interview from a one-sided assessment into a mutual exploration:

Timing and Sequence

Structure your questions to build natural momentum:

Early-Stage Questions:

• Focus on role clarity and expectations

• Explore immediate team dynamics

• Understand near-term objectives

Mid-Interview Questions:

• Probe strategic direction

• Explore organizational challenges

• Understand decision-making processes

Late-Stage Questions:

• Address growth opportunities

• Explore success metrics

• Clarify next steps

Question Architecture

Design questions that serve multiple purposes:

• Demonstrate industry knowledge

• Show strategic thinking

• Reveal your priorities

• Create opportunities to highlight relevant experience

Managing Energy and Rapport

Interview success often hinges on intangible factors like energy management and relationship building:

Energy Modulation

Maintain appropriate energy levels throughout the conversation by:

• Reading and matching the interviewer's pace

• Varying your vocal tone and tempo

• Using purposeful pauses for emphasis

• Demonstrating enthusiasm through measured animation

Building Authentic Connection

Create genuine rapport while maintaining professional boundaries:

• Find natural points of connection without forcing familiarity

• Share appropriate personal insights that enhance your professional narrative

• Demonstrate cultural awareness and adaptability

• Show genuine curiosity about the organization and role

Closing with Purpose

The interview's conclusion presents critical opportunities for lasting impact:

Strategic Summary

Create a compelling final impression by:

• Connecting discussion points to your value proposition

• Addressing any perceived gaps or concerns

• Reinforcing key strengths relevant to revealed priorities

• Expressing genuine interest with specific references to the conversation

Next Steps

Demonstrate professionalism and initiative in closing:

• Clarify the decision-making timeline

• Express interest in continuing the dialogue

• Propose specific follow-up actions

• Set expectations for next communications

Post-Interview Analysis

Transform each interview into a learning opportunity through systematic reflection:

Immediate Review

Document key insights while fresh:

• Unexpected questions and effective responses

• Organizational insights gained

• Areas for deeper research

• Follow-up opportunities identified

Pattern Recognition

Analyze recurring themes across multiple interviews to:

• Refine your narrative

• Enhance question strategy

• Identify preparation gaps

• Optimize energy management

Conclusion

Mastering the art of the two-way interview requires viewing each conversation as an opportunity for mutual discovery. Success lies not in perfectly scripted responses but in creating authentic dialogue that reveals alignment and potential. By approaching interviews as strategic conversations between equals, you transform what could be a stressful interrogation into an engaging exploration of mutual opportunity.

Every interview, regardless of the outcome, provides valuable insights for future opportunities. The most successful candidates are those who continuously refine their approach while maintaining authenticity and strategic focus.

How to Build a High-Impact Company Board from the Ground Up

Creating a company board from the ground up is critical in establishing the foundation for sound governance and long-term success. A thoughtfully composed board provides strategic direction, ensures accountability, and enhances the organization’s reputation. Here’s how to build a robust board from a blank slate:

Clarify the Board's Role and Objectives

Define the board’s role within your organization by determining whether it will be primarily advisory or assume fiduciary responsibilities. Align its objectives with the company’s mission, vision, and strategic priorities. This clarity will guide both member selection and the board’s operational structure.

Identify Key Skills and Expertise

Analyze your company’s needs to pinpoint the skills, experience, and perspectives that will add the most value. Essential areas include industry knowledge, financial expertise, legal and regulatory insight, technology experience, and diversity in thought and background. A skills matrix can help visualize gaps and ensure a balanced board composition.

Prioritize Diversity and Inclusion

Beyond demographic diversity, prioritize diverse professional backgrounds, geographic representation, and life experiences. A diverse board fosters innovation and improves decision-making, ensuring the board can consider various perspectives.

Define Board Members’ Responsibilities

Establish clear expectations for board members, including time commitments, meeting attendance, committee participation, and strategic oversight. A well-defined board charter is a vital reference point to ensure alignment and accountability.

Select the Right Candidates

Identify potential board candidates through professional networks, executive search firms, and industry associations—screen candidates for alignment with the organization’s values, expertise, and ability to contribute meaningfully. Conduct thorough interviews, reference checks, and background assessments to ensure a firm fit.

Balance Independent and Insider Perspectives

Strive for a mix of independent directors and those with deep knowledge of the company. Independent directors offer unbiased perspectives, while insiders provide valuable institutional insight. Avoid over-relying on insiders to preserve objectivity and fresh thinking.

Provide Comprehensive Onboarding and Ongoing Education

Equip new board members with the tools they need to succeed. A thorough onboarding process should cover the company’s operations, strategy, culture, governance policies, and opportunities to engage with key executives and stakeholders. Encourage continuous education to inform the board about industry trends, regulatory changes, and emerging risks.

Establish Effective Governance Structures

Implement regular meetings, transparent decision-making processes, and specialized committees (e.g., audit, compensation, and risk) to ensure robust governance. Define performance metrics to evaluate the board’s effectiveness and identify areas for improvement.

Foster a Collaborative and Accountable Culture

Cultivate a collaborative board culture grounded in mutual respect, open communication, and shared accountability. Encourage constructive debate while maintaining alignment with the company’s strategic goals. Building trust among board members and between the board and management is crucial for effective governance.

Assess and Evolve the Board's Composition

Periodically evaluate its composition and performance to ensure it evolves with the company’s changing needs. Consider introducing term limits or staggered rotations to bring fresh perspectives while preserving valuable institutional knowledge.