It's almost midnight. You're at the kitchen table, laptop open, staring at the screen willing it to give you an answer you haven’t yet found in your podcast library, spreadsheets, or doomscrolling.
You have a history of making good decisions and don’t hesitate to listen to your gut. But the decisions are getting bigger, information is more imperfect than ever, and the stakes keep getting higher.
It’s getting harder to know when to say yes or no.
You’ll run some ideas by your spouse but they count on you to make the ‘right call’ when it comes to things like this. The nagging thought you have is “What am I missing?” when trying to decide whether to
You run the numbers again. You reread the email. And somewhere around midnight, you collapse into bed determined to make the decision in the morning.
As I said in The Difference Between a Plan and a Decision, when you make a decision you’re sayings: this is the direction, this is the call, and I’m prepared for what happens next as a consequence of that choice.
You’ve probably lived with lots of consequences over the years, so you might just need a good night’s sleep.
Then again, it may be time to invite people into your circle of trust. Confidantes with whom you can have owner-level conversations about personnel, finances, risk and reward, family dynamics, long-term goals, and the assumptions influencing your decisions.
If I asked you ‘Who helps you make big decisions - a peer group, legal and financial advisors, a business coach, or an advisory board?’ you might say:
“I don't know who I'd even ask.”
“I don’t have the time.”
“No one understands this business like me.”
“I don’t want others to know my business.”
I understand why you might feel this way. It takes time to meet with people and build trust. You may have invested in personal development before and not gotten the results you want. You might not know what kind of expertise you need for this particular situation.
And sometimes the hardest question is simply: Help me do what, exactly?
Other people can’t make the decision for you. They can help you see what you may not be seeing.
They can listen without judgment. Share experiences. Explain nuances that aren’t obvious from a spreadsheet or an AI prompt. Challenge your assumptions. Call you out when you’re operating under false urgency and make you face facts when something really does require your immediate attention.
Sometimes we’re conditioned to only ask for help in a crisis or to downplay our need to feel seen, understood, and supported as a leader.
But when your plan is to grow with intention, the decisions get bigger and the stakes get higher. Knowing who to bring into the conversation and when becomes a critically important ownership skill.
I had a client who joined a peer group, hired a fractional CFO, and called me later saying the peer group wouldn’t shut up about ESOPs and they still don’t know what jobs are profitable.
The problem wasn’t that these weren’t smart, experienced people. They simply weren’t helping the owner solve the right problem at the right time.
Unsurprisingly, not all advisors, consultants, and peers are the same or the best fit for every owner or situation. Sometimes you won’t find the right thought partners and experts on the first try. Other times, you may be asking really talented people to weigh in on something outside their wheelhouse.
That means you need to be clear about what counsel and advice you need when asking for help. With context and clarity the people you trust can gauge their capacity to be of assistance and connect you to the people they trust as needed.
These are four different sources of support and how they can be most valuable.
A Vistage CEO group, an EO forum, or a roundtable of owners in your industry can give you regular opportunities to brainstorm and problem-solve with people who’ve lost sleep over similar issues.
Peers can provide a gut check, challenge your assumptions, share what worked for them, and often inspire you to keep going. They don’t have to know everything about your business to be useful and supportive. In fact, seeing the commonalities across businesses and industries can help you look at your own situation differently.
A peer group is particularly valuable when the question is: What have other owners experienced, and what might I learn from them?
Your CPA, attorney, banker, wealth advisor, insurance professional, and other specialists can go deep in their respective lanes. They can help you quantify a problem, understand the implications of a decision, or design a specific solution. There are some decisions you should never make without their counsel.
These advisors often deliver the greatest value when they work together in a coordinated way on your behalf. They can also help you identify expertise you don’t yet have. A CPA once introduced me to his client because she needed help improving revenue and net income, something he knew was outside the scope of work he provided.
Subject matter experts are particularly valuable when the question is: What are the legal, tax, financial, or technical implications of this decision?
You can also engage a C-suite-level thought partner who specializes in executive coaching, business growth, leadership, operations, or another area relevant to what you’re trying to accomplish in your business.
Some clients call me their fractional COO. Others say management consultant, business coach, or strategic advisor. The titles matter less than understanding what someone actually does and whether their approach complements your own. This kind of relationship can be especially valuable when the decision crosses multiple parts of your business.
Hiring a CFO, for example, isn’t only a people decision. It impacts your finances, organizational structure, responsibilities, leadership team, growth capacity, and your own role as owner. A strategic advisor can help you connect those pieces, determine what you may be missing, coordinate input from other experts, and translate a decision into action.
They are particularly valuable when the question is: How do all these pieces fit together, and what do we need to do next?
An advisory board — not to be confused with a governing board — can include peers, subject matter experts, consultants, and other people whose judgment and experience you value.
Instead of turning to different people when you have a problem, you invite a group to meet regularly and give you perspective on your numbers, team, industry, opportunities, risks, and major decisions. An advisory board can also help you look beyond revenue and profit to whether you’re building a more valuable, transferable business over time.
Forming an advisory board can be an important evolutionary step for an owner who wants to change their relationship with the business and begin separating the roles of owner, CEO, and manager.
An advisory board becomes particularly valuable when the question is: How do I create an ongoing structure for making better decisions without everything depending on me?
If you’re not sure where to start, think about the problem you’re actually trying to solve.
Peer group: You feel isolated more than uninformed. You know your business and industry, but you don’t have enough people around you who understand the weight of leading and growing a business the way another owner does.
Subject matter expert: You have a specific decision with legal, tax, and/or financial complexity, and you need someone‘s professional, expert opinion on that exact question.
Coach, consultant, or strategic advisor: You’re wrestling with a decision that crosses multiple parts of the business, or you need help turning a decision into coordinated action and follow-through. You need someone to dig in with you and help you do some heavy lifting.
Advisory board: Your goals require ongoing, iterative decision-making that benefits from multiple perspectives. You want a more structured decision-making process and may also be preparing the business for a future in which ownership, governance, and management are more clearly separated.
You can also use the Owner’s Compass to help you identify which options make sense based on what you want and what’s true about your business today.
If you want or need to engage more than one kind of support system, that's normal. Most owners use a combination of all four at one time or another. Start wherever you feel most comfortable knowing you can change the groups, advisors, or experts on your team as your needs change. Don’t assume one advisor, peer group, or expert can do the job of all the others.
For years, being the person who could make the call may have been one of your greatest strengths. Now, as your business becomes larger, more complex, and more valuable, the answer isn’t necessarily to become even better at making every important decision yourself.
The shift is to get better at knowing which decisions require other perspectives and whose perspective you need to make strategic decisions quickly. That’s part of the evolution from building a business for you, by you, to building an enterprise designed to fulfill your goals, create transferable value, and perform without you wearing all the hats all the time.
In the next article, we’ll explore another part of that evolution: intentionally designing a future organizational chart on which your name no longer appears.
An advisory board gives you perspective without authority. Its members can challenge your thinking, share expertise, and hold you accountable, but they have no vote or legal power to override your decisions.
A governing board, sometimes called a fiduciary board or board of directors, has legal responsibilities. Depending on how it is structured, the board may have authority over major transactions, executive compensation, CEO selection, and other significant decisions.
Many owner-operated businesses start with an advisory board. Businesses transitioning ownership across generations or formally separating ownership from management may eventually establish a governing board.
It depends on the kind of support you need.
Peer groups typically require a membership fee and regular meetings. Individual subject matter experts generally charge hourly or project rates. Coaches, consultants, and strategic advisors may work on a project basis or monthly retainer.
A small advisory board might meet quarterly for two or three hours, with additional preparation beforehand.
You don’t have to choose.
You might use a peer group for shared experience and pattern recognition, individual experts for technical decisions, a coach or consultant to connect strategy to action, and an advisory board to bring multiple perspectives together on a recurring basis.
