Ask most managed service provider owners what they charge per user and you will rarely get a number. You get context first: the methodology, the assumptions underneath it, the three ways it could go wrong, and somewhere near the end, if the prospect is still listening, the price. The owner is not being evasive. He is credentialing himself, and he believes the explanation is what earns the trust. It usually does the opposite. The order of selling every MSP must know puts selling yourself ahead of selling the service, and the sales call that felt like it went perfectly is usually the one where the owner did most of the talking. The same habit shows up in how leaders read their own team's communication style.
Andrea Lipton has spent thirty years watching this pattern from inside corporate learning, and she has a name for the fix. On this episode she walks Josh Peterson through AEIOU: answer, explain, inquire, onboard, update. It is a small discipline with a large surface area. Applied in a discovery call it shortens the path to trust. Applied at the service desk it changes what a client concludes about your competence. Applied by an owner it removes the most expensive habit in owner-led sales, which is continuing to talk past the moment the buyer had already decided. None of that requires a new tool, a new script, or a new hire. It requires deciding that the answer goes first.
Andrea Lipton grew up in a school where getting the right answer on a math problem was not enough. You had to show your work. Decades later she was sitting in investment banking rooms with people who measured their days bell to bell and their success in basis points, and they did not want the work. They wanted the number, and they would ask for the reasoning if they needed it. She describes the gap between those two worlds as a paradigm shift, and it is the same gap an MSP owner falls into on a discovery call. The instinct to show the work is not laziness or ego. It is training, reinforced by every environment that rewarded thoroughness over clarity, and it does not switch off just because the audience changed.
Josh describes a call he had the same day we recorded. A prospect asked him a direct question about per user pricing. Josh knew the answer, knew he should give it, and instead heard himself say that he wanted to contextualize it first. He could tell the man on the other end just wanted the number. Andrea's answer to that moment is AEIOU, a piece of self-coaching she built after being told to get to the point and now teaches to her teams. Answer the question as it was asked. Explain, but only if asked. Inquire whether the answer landed. Onboard whatever comes back rather than retreating into your own head. Update your response accordingly. It is deliberately unglamorous, and that is the point: it is a checklist you can run mid-sentence.
Josh runs strategic planning sessions that start with what do you want, and then push with why do you want that, again and again, until something real surfaces. Andrea's response reframed it in one sentence: why invites a defensive answer. Not defensiveness in the emotional sense. Why invites the other person to make a case, and making a case is not the same as telling you the truth. Her substitutes are what and how. What had you say that. What has that be a priority for you. Josh worked it through live: when an owner says he wants to sell for a million dollars, "why do you want that" makes him wonder whether you think he is greedy, while "what happens when you sell it for a million dollars" gets you to the same place with the defenses down. Same destination, different toll.
Andrea's sharpest observation for this audience is not about sales at all. It is about a technician resetting a password for the third time. People who are deeply skilled become unconsciously competent, she says, and then forget that they are. The technician stops registering that the client cannot see what he sees, and the question starts sounding stupid. It is not always said out loud, but clients hear it anyway. Her instruction is blunt: answer it, even if you think it is a stupid question, and only then inquire whether they would like to know how to stop needing you every week. Every MSP owner already knows which engineer is brilliant and impossible with clients. Very few have ever given that person a framework to practice instead of a performance review that says be nicer.
Answer, explain, inquire, onboard, update. Answer the question as it was asked. Explain only if the other person wants the explanation. Inquire whether your answer gave them what they needed. Onboard their response rather than returning to your own train of thought. Update your answer based on what you just heard.
Andrea Lipton built it as self-coaching after receiving feedback to get to the point. It is her own framework, not a published methodology, though it grew out of the pyramid principle she was trained in early in her career.
A presentation methodology developed by Barbara Minto. Most people funnel information downward and arrive at a conclusion at the end. The pyramid principle inverts that: lead with the conclusion, then supply the analysis if the audience asks for it.
The fear that it will is exactly what drives over-explaining. In practice the opposite tends to hold. A direct answer followed by an offer to explain signals confidence, while a long preamble signals that you are still building your case.
Because an MSP's client relationship runs through hundreds of small conversations a year, most of them handled by technicians rather than the owner. Surveys consistently find client experience, not technical failure, is the leading reason clients leave. Communication is one of the few levers that costs nothing to pull.
Andrea trained in game theory and uses it to map a buyer's utility curve: what that person values, how they rank it, and which decision nodes matter. In the bonus segment she and Josh connect it to poker, where the technically optimal play stops being enough once everyone at the table is running the same solver.
Andrea Lipton is Director of Delivery for Training as a Service at ISG (Information Services Group), where she leads the design and delivery of training that turns enterprise technology transformations into measurable workforce performance. She has spent thirty years in talent development, learning, and training, starting at JP Morgan as what she calls the accidental trainer and later working at Harvard Business Publishing and NIIT. Alongside that she has run an executive coaching and facilitation practice since 2013. Her academic background is in political science, statistics, and game theory, which shows up in how she thinks about business conversations. AEIOU began as a piece of self-coaching after she was told to get to the point, and it has since become the framework she teaches to her own teams and clients.
Connect with Andrea on LinkedIn →
Josh Peterson is the CEO of Bering McKinley and host of The BMK Vision Podcast. Since 2004, Josh has worked with hundreds of MSP owners to build operationally sound, profitable businesses through consulting, peer teams, and direct coaching.
Connect with Josh Peterson on LinkedIn →
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