Nobody likes being told they are wrong. That applies to your client’s CFO, your client’s IT director, and the new partner you are trying to expand. It also applies to you. The problem is that an MSP seller’s job sometimes requires telling somebody that what they are doing is putting their business at risk, or that the investment they made last year was in the wrong place, or that the security posture they believe they have does not match the reality.
How you have that conversation decides whether the client stays or walks. Heather, a Cynomi partner account manager who spends her days coaching MSPs through these moments, has a move she uses almost every week. She calls it flipping the script. It is a small reframe with a large payoff, and it rests on a distinction most sellers get wrong: the difference between sympathy and empathy.
This piece is for MSP sellers and leaders who can feel the tension in a client conversation and know they need to push, but are worried about pushing too hard. The answer has less to do with softening your point and more to do with changing whose work the client is looking at.
Sympathy Makes You a Spectator. Empathy Makes You a Partner.
Sympathy sounds like “I’m sorry to hear that.” Empathy sounds like “That’s awful. What can I do?” Both responses are well-intentioned. Only one of them gets you closer to fixing the problem.
Sympathy keeps you outside the situation, offering commentary. Empathy puts you inside it with the client, working on the same side of the problem. When you are building a case for a security investment the client has been resisting, or pointing out that their incident response plan will not survive a real incident, empathy is the only stance that earns you permission to keep talking. Sympathy politely ends the conversation.
The shift shows up in small language choices. You stop saying “you should” and start saying “here’s what I’d do with you.” You stop telling the client what is broken and start asking them what they think is broken, and then building on the answer they give you. Clients will forgive a lot from somebody they feel is in the work with them. They will forgive almost nothing from a person who sounds like a judge.
The Flip: Turn Your Problem Into Their Consult
Here is where Heather’s script move pays off. When you need to challenge a client’s approach but do not want the conversation to turn defensive, do not present the problem as theirs. Present it as yours.
The language sounds something like this: “I’ve been doing X this way and getting Y result. It isn’t working. If you saw me doing that, what advice would you give me?” Then you lay out, in plain terms, the exact problem the client has. Same situation, same missing controls, same unanswered questions. The only difference is the subject of the sentence.
Two things happen. The first is that the client stops protecting the choice they made and starts analyzing it. They are no longer looking at their own work, so the defensiveness drops. The second is that they get to be the expert. Most people do not enjoy being told they were wrong, but they enjoy coming up with the right answer. When the client tells you what the solution should be, and the solution happens to match what you were going to recommend anyway, the plan becomes theirs. Ownership shifts. Implementation gets easier. You do not have to convince anybody of anything because the client already convinced themselves.
Think of it as structure rather than manipulation. You are rearranging the conversation so the client can think clearly, which is hard to do when your ego is in the room. Strip the ego out, and most clients get to the right answer within a few minutes.
Outcome-Oriented Framing Without the Fear
A common failure mode when MSP sellers try to push is that they slip into fear-based language. The threat is the ransomware, the regulators, the cyber insurance renewal that will not get approved. Fear works for about twenty minutes and then the client pushes back, either by minimizing the risk or by cutting off the conversation.
Heather’s alternative is what she calls coming from a place of power rather than a place of fear. You do not tell the client what could go wrong. You ask them what happens if it does. “If ransomware hits tomorrow, what is your response? Who pays for the downtime? Who answers to the board? How long can you operate without the systems you rely on?” These are the same facts, phrased as questions the client answers out loud. You are not predicting a disaster. You are walking them through a scenario and letting them draw their own conclusion. That is a different posture, and it is the one that gets movement.
Notice that none of these questions assume the client is stupid or unprepared. They assume the client is capable of thinking through the scenario once somebody slows them down enough to do it. That posture is empathy in operating form.
When the Client Is Not Performing, Start With You
Heather’s third move is the one that takes the most discipline. When a partner is missing meetings, failing to convert trials, or generally underperforming, her first instinct is to look at her own work before she critiques theirs. “Something I haven’t done correctly. Let’s meet. I’m obviously not doing my job.”
That phrasing is strategic. It is also, when she means it, true. Most of the time, an underperforming partner is underperforming because the plan the two of you built together had gaps. Leading with your own accountability opens up a conversation that a lecture would shut down. The partner drops their defenses, tells you what is going on, and the two of you can troubleshoot the real problem. You keep the relationship intact, and you make progress on the thing that was stuck.
The same move works with clients. If a security program is not landing, ask where the plan you built together missed. The client will tell you. Their answer almost always points to the real issue faster than an audit would.
One Thing to Try This Week
Pick a single hard conversation you have been putting off. Before you have it, write down the problem as if it were yours, not the client’s. Rehearse how you would ask for advice on that problem from a peer. Then have the conversation with that script in your head.
Small change. Large difference in how the other side responds.
Cynomi’s GTM Academy Sales Kit includes conversation guides, discovery templates, and objection scripts designed to help MSPs have these exact conversations without resorting to pressure tactics. If you want frameworks for the harder moments in client work, you can find them here.