August 2025 Newsletter
Burning Questions from the C-Suite
From a Right Hand: Should I Be Talking to the Board and Investors?
Right Hands often ask, what role should I play with the board and investors? It’s a good question because any misstep at that level is risky.
There is no one-size-fits-all answer. What matters is alignment. Do you both know who’s doing what? Are you in sync? In some organizations, the CEO handles all interaction with the board, investors, and any outside financial person. In other orgs, the Right Hand plays a big role. It’s whatever works for the two of you and the business.
Here are three ways to approach the question:
Know Your Place. When it comes to boards and investors, the RH is always the second, never the first. Don’t lose sight of this! Your job is to help the CEO win with these key relationships, not build your own credibility. You should be asking, What does my CEO need from me here? Everything you do in this arena should edify and support the CEO. (Note: We are not referring to those rare exceptions when CEO performance is risking the survival of the company.) You may be gathering or creating reports, building the board packet, arranging logistics, prepping the CEO, and capturing to-dos. Even when you’re invited to be an active participant in strategy discussions, remember you’re there to help the company get maximum benefit from these capable outsiders who’ve agreed to lend their wisdom. Listen more than you talk.
Clarify Context. Not all boards are the same. A fiduciary board is legally accountable to the owners of the business. It ensures finances are managed, the law is followed, the top exec is performing, and valuation is there. Fiduciary boards are in play when someone else’s money is involved: private equity, venture capital, bank covenants that require oversight, non-employee shareholders who want protection. An advisory board is completely different. It has no enforcement authority and is created by a CEO to help the company navigate major opportunities and threats. Your role as Right Hand will change based on the type of board and your level. Presidents and COOs may be formal members of an advisory board, but will hardly ever be voting members of a fiduciary board. A President will often report to either type of board quarterly or annually. A COO may do the same. A VP or other C-suite Right Hand may report on their specialty area, but infrequently and only by request.
Remove the Mystery. Sometimes the CEO’s interaction with the board or investors feels like a black box mystery to the RH. You could probably help more if you understood more. With your CEO’s permission, consider digging in. Ask the CEO about their goals with the board and investors. Read past board reports, research the expertise and background of each board member or investor, and learn which issues your CEO is working on with them. Then you and the CEO can decide together if there’s something you should do to make the CEO’s investor/board life easier. Caveat: Realize that not every CEO will want their RH involved in this part of their life. Board and investor relationships are often highly personal and vulnerable. These people can function as the “boss” for the CEO, and the CEO may want to keep any critiques or feedback private. Sometimes the black box remains opaque, and that’s okay. Respect the CEO’s choices.
Famous Right Hands—“You get a Right Hand! You get a Right Hand! You get a Right Hand!”
Are you old enough to remember Oprah Winfrey bestowing a car on every person in her studio audience? Maybe not. But I bet you’ve heard about the Oprah Winfrey and Gayle King friendship. The two met as young journalists in Baltimore in the mid-1970s and have maintained a continuous personal and professional bond for decades.
Here's what jumps out to me about this CEO/RH pair:
Alignment with Autonomy. Gayle retains her independence with roles at CBS and as Editor-at-Large for Oprah Daily. Oprah supports and elevates her but allows editorial freedom. Each brings her strength: Gayle’s credible voice, Oprah’s brand and reach, but aligned around shared values.
Mutual Respect, Deep Trust. It seems like decisions, both strategic and creative, occur in an atmosphere of candor and emotional safety. This enables bold authentic projects, and probably smooths negotiations at every level
Clear Role Definition. Roles and boundaries are known. Gayle leads the journalism content and commentary. Oprah leads strategy for the brand. This likely minimizes turf wars, amplifies each person’s talents, and creates seamless cross-platform messaging. It’s high-impact collaboration without overshadowing either party.
Sources: Oprah Daily, Prevention, This Day in History
News
New Client Portals Are Here!
We’re excited to announce that Practical PhD has launched a brand-new client portal experience for our Level Up, LAUNCH, and Right Hand Coaching programs.
These secure, streamlined portals give you on-demand access to program materials, personalized progress tracking, and a centralized hub for updates, assignments, and deliverables. Each portal is secure and completely custom, so your team sees exactly what they need when they need it.
Recommendation
Heather is a big believer in advisory boards for startup and scale-up businesses. They keep CEOs and Right Hands from “navel-gazing,” which is spending all your time looking down at yourself instead of up at the rest of the world. Setting up an advisory board is often a good next step for a CEO who recently handed off daily operations to a trusted Right Hand. Because how do you translate the CEO’s new job of working on strategy into a tangible to-do list? You implement systems that require that CEO to engage in strategic thinking consistently. An advisory board does that. You will be forced 2–6 times a year to pull your head out of the weeds and defend your vision to smart people who care far more about markets, valuations, and finance than they do the problems of Joe in manufacturing. It’s a great way to elevate your game.
We’re not experts in setting up and running advisory boards, though we’ve done it ourselves and strongly recommend it for most CEOs with executive level Right Hands. Here are some resources to get you started. Reach out if you want to hear Heather’s personal advisory board story.
Video with lots of specifics about boards, including recruiting and compensation.
Quote of the Month
"I thought I hired an employee, and a human showed up." --Andi Bailey, Founder of Alliance Nursing
This wisdom was shared by Eric Bailey, Vistage member and Owner/President, who reports that Andi posted these words on the backside of her office door for years. She could see the quote, but unless the door was shut, no one else could. Just a gentle reminder for the boss to take a deep breath when people around her did the unexpected.
What can we do for you?
At Practical PhD, we help companies Get the Right Hand Right so they're ready for top leadership transition in 1-3 years:
Find and hire a Right Hand
Onboard a new Right Hand
Teach an aspiring Right Hand the job
Performance-manage a struggling Right Hand
Create a phased leadership succession plan