“The most powerful advisors are those who speak the fewest words, but the most meaningful ones.” – James Lukaszewski
We were waiting for our military aircraft to arrive at the VIP terminal at Joint Base Andrews, and I was making the most of a freshly baked cookie from the kitchen while the boss and I reviewed the bidding for the next leg of our trip. He asked me something, but my attention was elsewhere. I recognized a protection detail when I saw one, and the people entering the terminal were even more serious than most.
Then I understood why.
Once the detail cleared the area, Vice President Joe Biden strolled into the lounge. He saw us sitting at our table and came over to visit. I wasn’t sure exactly what to expect, but what followed was an hour-long discussion that ranged from the quality of the cookies to the state of affairs in Afghanistan and Iraq. He was frank, he was blunt, and he was utterly genuine.
Before he left, we gathered for photos and a final exchange of pleasantries. But what struck me most about the encounter was the level of trust the boss had in me. While some senior leaders might have cleared the staff for that type of dialog, mine didn’t. He trusted me not only to stay but to be an active participant in the conversation.
You don’t get a seat at the table unless you’re in the circle of trust.
the Trusted Advisor
Leading the commanding general’s initiatives group – the first of several tours where I led similar teams – came with a fair amount of autonomy. If I wasn’t traveling with the boss, I would be moving independently, engaging other senior leaders, coordinating engagements, and building a network that helped to support our efforts. Being a trusted strategic advisor wasn’t a role I sought, but it was one that I earned.
When I first found myself on the cusp of the circle of trust, James Lukaszewski’s 2008 book, Why Should the Boss Listen to You?, proved to be an invaluable resource. Although his advice was largely directed to a business audience, the parallels were impossible to ignore. Serving in a strategic advisory role is essentially the same whether you’re in the C-Suite or the E-Ring.
Drawing on decades of experience in crisis communication and executive consulting, Lukaszewski outlines a clear path for gaining influence — not through authority or technical expertise alone, but through disciplined behavior, emotional intelligence, and strategic insight. The focus of his message is on the seven disciplines that underpin a successful strategic advising.
1. Be trustworthy.
Build a reputation for integrity, discretion, and reliability.
2. Become a verbal visionary.
Speak in clear, compelling language that resonates with leadership.
3. Develop a management perspective.
Understand and align with the broader organizational goals and pressures.
4. Think strategically.
Focus on the long game and account for the fog of war.
5. Be a window to the future.
The senior leader’s job is always about tomorrow; that’s where your focus needs to be.
6. Advise constructively.
Provide counsel that is actionable, respectful, and timely.
7. Show courage.
Stand firm when the heat is on, even when it risks personal discomfort.
Trusted advisors are defined by their ability to listen deeply, speak wisely, and act with integrity; they earn influence through consistent, reliable behavior, not position. Their ability to lead from behind is a discipline of service, foresight, and emotional maturity.
Leading from Behind
Once the Vice President left to board Air Force Two, we took stock of the conversation and the chance drive-by nature of our encounter. It was remarkable and made for some great storytelling in the aftermath. But it was hardly a unicorn. Similar encounters followed in other roles, all of which helped me to be a better advisor to different senior leaders. Along the way, I catalogued some useful knowledge for others who served in similar positions.
1. Provide value.
No matter who you are, what you do, or where you work, you want to be perceived as someone who provides value to the organization. To be successful, you have to be value added.
2. Live the values of the organization.
The values of an organization are the mortar that binds the institution. As long as you are a part of the organization, you should live those values.
3. Be honest.
The truth is a powerful, if often misunderstood, tool. It isn’t just being honest; it’s having the courage to tell the truth when others might not want to hear it.
4. Be loyal.
Trust and loyalty are inseparable. Demonstrate loyalty, and you are likely to be seen as a trusted member of the organization. Violate that trust, and bad things happen.
5. Be humble.
You are a supporting actor in a much bigger cast. Know your role and play it well.
6. Embrace risk.
Risk creates opportunities, which in turn bring value. If you really want to be value added, then you need to be comfortable with embracing risk.
7. Be your best.
To truly be your best, you have to challenge yourself. That means setting a bar that pushes you to your limits, then setting it again when you hit it.
8. Be a team player.
Be positive, be proactive, be reliable. Be the “go-to” person everyone trusts and respects.
9. Be a change agent.
Change is inevitable. You can either be part of the change or watch it pass you by.
10. Hold the moral high ground.
Be polite, be professional. Always. It’s non-negotiable.
On the flight out, a message landed in the boss’s inbox on his BlackBerry. It wasn’t good news. Someone he trusted, someone who he relied upon had violated that trust. People make honest mistakes, and good leaders underwrite those mistakes. But this wasn’t an honest mistake, it bore the mark of hubris, of disrespect. It wasn’t a mistake he could ignore. He didn’t get angry, though: “Learn from this. Remember this. We’re all on one big team here. If you can’t play by the rules, you won’t be on the team for very long.”
