My colleagues in our most recent series of columns made a compelling case for surrounding ourselves with the right advisers.
Teresa Rhyne reminds us of the importance of getting the right people “in the room where it happens.”
Michelle Herting makes the case for recognizing when we need specialized expertise rather than expecting one trusted professional to know or do everything.
And Teri Parker shows us the value of having those professionals operate as a connected advisory team.
All of which raises another question: Once we have the right people in the room, what makes collaboration actually work?
In my work with executives, leadership teams and family businesses, I have seen highly capable people struggle to collaborate. It is rarely because they lack expertise or good intentions. More often, it is because collaboration asks something more of us. We have to listen beyond our own point of view, make room for competing perspectives, navigate disagreement, and keep coming back to what we are collectively trying to accomplish. And sometimes that is harder than it sounds.
Are we solving the same problem?
Each professional naturally sees a situation through a different lens. An attorney may be thinking about protection and risk. A CPA is considering tax implications. A financial adviser may be looking at the long-term financial picture. As an executive coach, I may be paying attention to something different: the people involved, how decisions are being made, and whether those who will ultimately carry out the plan are prepared to do so.
We need those different perspectives because no single one gives us the whole picture. But I have been in conversations where everyone was working hard toward a solution, only to discover that they did not share a goal or actually agree on the outcome they were trying to achieve.
Imagine a family business whose owners say, “We want to successfully transition the business to our children.” What does “successfully” mean? Maximizing the parents’ financial security? Keeping the company in the family? Treating the children equally? Preserving the culture? Giving the next generation genuine authority to lead?
Before asking, “What should we do?” we may need to ask a more fundamental question: “What are we ultimately trying to accomplish?”
We don’t have to agree
We sometimes confuse good collaboration with harmony. Yet some of the best collaboration happens when smart, experienced people see a situation differently and are willing to say so.
After all, that is one reason to assemble people with different expertise. We don’t need five people around the table to give us the same perspective. We need them to help us see what we might otherwise miss.
The challenge comes when I interpret your questioning of my recommendation as questioning my competence. It is easy then to become defensive, protect our territory, or listen for the flaw in someone else’s argument rather than becoming curious about what they may see that we don’t.
Two of the most useful questions we can bring into a collaborative conversation are surprisingly simple: “What am I missing?” and “Tell me more about what concerns you.” Those questions don’t require us to agree. They simply keep us open long enough to learn from one another.
Listen to all of the conversations
Whenever people come together to make important decisions, I find there are often two conversations taking place. There is the financial, legal, strategic or business issue everyone came to discuss, and then there is what is happening between the people while they discuss it.
Who dominates the conversation? Who routinely defers? Who seems reluctant to challenge the person with the most authority? Is a founder expecting the next generation to step up while continuing to hold tightly to every important decision?
I have worked with business owners who genuinely wanted to prepare the next generation to lead, and yet they struggle when that next generation began making decisions differently than they would have. On paper, the issue might have been succession. In the room, we were also dealing with trust, identity, control and what it means to let go. Those dynamics matter. Sometimes what appears to be a financial, legal or business problem is also a people problem. Solving one without addressing the other rarely produces the best outcome.
Then, who owns what?
Collaboration can create another challenge. When many people are involved, responsibility can become surprisingly unclear. Everyone may leave a meeting believing something was decided, only to discover later that they had different understandings—or that everyone assumed someone else was taking the next step.
At some point, good collaboration must move from discussion to clarity. What are we deciding? Whose perspective do we need? Who ultimately owns the decision? And what happens next? Not everyone needs the final say in every decision. But the right people need the opportunity to contribute, and everyone needs to understand what happens once the conversation ends.
Don’t lose the person at the center
Perhaps most importantly, collaboration among advisers should never become so sophisticated that the client gets lost in the process. There is an important difference between asking, “What should we do?” and asking, “What are we trying to accomplish, and which of these options best supports that?” Sometimes the answer requires more than technical expertise.
A founder may say she wants to retire while struggling with the prospect of no longer being needed. Parents may want an equitable succession plan without ever discussing whether equitable means equal. A couple may agree that they want to leave a legacy without exploring what they actually want that legacy to be. No adviser can answer those questions for them.
We can bring our expertise, ask good questions, surface consequences and help people think more clearly about their choices. Ultimately, though, the client’s values, priorities and definition of success need to remain at the center.
The best collaboration isn’t measured by how many smart people we have around the table, or even by how well they get along. It shows up in our willingness to listen, question, disagree thoughtfully, stay curious and set obtainable goals – and keep returning to what we are ultimately trying to accomplish.
When we can do that, the room becomes more than a collection of experts. It becomes a place where better decisions can be made.
Patti Cotton serves as a thought partner to CEOs and their teams to help manage complexity and change. Reach her at Patti@PattiCotton.com.