UpTrajectory Review

HBR's latest episode of its coaching podcast features executive coach Muriel Wilkins working with a senior leader who has a clear vision for her department's future but cannot get the CEO to endorse it. The format is a live coaching conversation: Wilkins probes the leader's assumptions, reframes the problem, and pushes her toward a more effective approach. The available text is minimal, but the scenario is instantly recognizable to anyone who has run a team inside a larger organization. You have done the analysis, you know what needs to change, and the person with budget authority and final sign-off remains unconvinced or simply noncommittal.

For a small-business operator, the dynamic may seem foreign at first. There is no layer between you and final authority. But the underlying problem, how to get a skeptical decision-maker to commit to a plan they did not create, shows up constantly. Your 'boss' might be a key investor, a co-founder with equal equity, a bank lender, a major client whose contract funds your next hire, or even a spouse or family member whose support you need to take a risk. The skill Wilkins addresses, translating your vision into terms the other person can actually hear and act on, is the same regardless of the org chart.

What makes this piece worth attention is not the premise, which is well-worn territory in leadership literature, but the coaching format itself. Wilkins does not hand the leader a checklist. She asks questions that expose the gap between what the leader wants and what she is actually communicating. That gap is where most internal pitches die. The leader often presents a fully formed plan and treats the CEO's hesitation as a flaw in the CEO rather than a signal that the pitch missed something the CEO values, whether that is risk mitigation, speed to result, or a connection to a broader company priority.

The second-order effect of weak upward persuasion is not just a stalled project. It is a leader who retreats into frustration, starts disengaging from the executive team, and eventually either executes the plan half-heartedly or leaves. For a small business, the equivalent is the operator who cannot get a lender to extend a line of credit or a key partner to co-invest in expansion and responds by scaling back ambition permanently. The cost of a failed pitch is rarely the pitch itself. It is the quiet recalibration of what you believe is possible.

The practical takeaway is to treat any high-stakes internal pitch as a listening exercise before it becomes a selling exercise. Before you present the full plan, find out what the decision-maker is actually optimizing for right now. Then frame your strategy as the answer to their problem, not yours. If you are a small-business owner preparing to ask a bank, investor, or partner for something significant, do a dry run with someone who will push back the way Wilkins does. The goal is not to polish the slides. It is to find the objection you have not anticipated and build your response before you walk in.

“Muriel Wilkins counsels an ambitious leader who needs to convince the company CEO to support her vision for her department's future.” — Harvard Business Review

Takeaway: Before pitching any decision-maker, find out what they are optimizing for and frame your plan as the answer to their problem, not yours.