Escalation Levels: A Framework for Better Sales Conversations
I work as a Tech Advisor to CXOs, and this post is about sales conversations, which are conversations we have before an agreement is signed and my advance is paid. These conversations can drag on for hours, fortnight after fortnight, which is frustrating. One important tool to fix this is escalation levels:
Sometimes a conversation can get stuck. When this happens, I don’t repeat myself in different words. I need to shift to a different level and try a different approach or communicate a different message. Just as driving a car in only one gear regardless of the situation doesn’t work, neither does sticking to one escalation level in sales.
Asking which escalation level is right is like asking which gear is right — all of them are, depending on the situation. You start at level 1, and shift up as needed.
At higher levels, I’m more firm. If I were this firm at all levels, I’d be an asshole. I used to be soft regardless of how the conversation is proceeding, but I was taken advantage of and felt frustrated many times. That’s why multiple levels are needed.
Once I escalate, the problem may get resolved, in which case I drop back to a lower level. Escalation is not one way. I may have to escalate more than once to resolve a problem. And if even the final level doesn’t work, I reject the lead.
Now that you’ve understood the concept, here are the specific levels I use:
Level 1: Gather information
I begin at this level. I want to learn about the lead’s problems, desired outcomes, team, maturity, budget and so on.
At this level, expressing opinions is not allowed. Why? Because I’ll lose the plot of trying to understand the lead’s situation. Trying to understand and express opinions at once is like trying to drive a car in both forward and reverse at once.
I can ask clarifying questions. And follow-up questions. I just need to ask them in a neutral and calm tone, not demanding, frustrated, or incredulous, which are really opinions, just as “Can you pass the salt?” is only grammatically a question. It’s also better to ask questions that assume less, like “Have you considered hiring another engineer?” rather than “Why haven’t you hired another engineer?” The former will help me learn whether the lead is able to even recognise that recognise that hiring could have fixed his problem.
A coach said, “Every time the prospect speaks, give yourself one point. Every time you speak, subtract one point.” I used to jump in1 too quickly, eager to help — only to realise later that I missed important information. Maybe it sounded like a familiar problem before I got to the details. Or the details gave me other valuable insights, like an insufficient budget.
Level 2: Explain what to do and why
At this level, I may share insights, or recommend a course of action. I address concerns I’ve identified at the Information Gathering level.
If I’m unsure about a recommendation, I may phrase it as a question — but the intent is still to explore a particular course of action. That’s different from information gathering questions I ask at level 1. For example, when I ask “Have you tried Kanban?”, it might come from a desire to understand (level 1), or it might be a gentle nudge toward a solution (level 2). Same phrasing — different intent. It’s the intention that matters, not the form.
I’m not salesly like “Buy my service! Buy my service! Buy my service!” The tone I try to strike is a professor discussing with a student.
Here’s an example of something I’ve said at this level:
Don’t interrupt engineers when they’re working on a task. Instead, when they’re done and have time to pick up another task, then assign to them whatever you think is most important then.
Engineers need focused time. If you interrupt them, they’ll waste a good part of the day context-switching. Their productivity will be low and they won’t be able to get as much done at the end of the month. So don’t interrupt them. Wait for them to have free time.
This communicates three points:
what not to do2
what to do instead
why (second paragraph)
Level 3: Clear instructions, no rationale
At this level, I repeat the what from the previous level, without the why3:
Don’t interrupt engineers when they’re working on a task. Instead, when they’re done and have time to pick up another task, then assign to them whatever you think is most important then.
The general format is:
Don’t do X. Instead, do Y.
Some leads were overwhelmed with too much information, and understood when I told them the what without the why.
Level 4: If [desired outcome], then
If [desired outcome], you need to Y, not X.
For example:
You said that you want faster delivery. If you want to achieve that, you need to stop interrupting engineers mid-task. Instead, assign a new task only when they have bandwidth.
This is same as the previous level, but we’re directly connecting it to an outcome the lead desires, because he didn’t understand that my advice was related. You can never be too clear. If there’s one thing people care about the most, it’s their own goals.
Level 5: If, then
Here, I redirect the focus from the lead’s goals to my immediate goal, which is getting clarity on whether to invest more time in this lead4:
If we’re to work together, you5 need to [have a reasonable budget]…
or
If we’re to continue this conversation, you need to [respond thoughtfully rather than mindlessly]…
Final level: No
Then you can’t work with me.
I use this as the last resort, when the lead insists on something that doesn’t work and responds to the earlier level mindlessly:
If we’re to continue this conversation, you need to respond thoughtfully rather than mindlessly.
Lead: I’m just trying to keep the discussion moving forward.
Then you can’t work with me.
This may seem similar to the previous level, but depending on how the conversation unfolded, I may need this level of clarity.
Notice the word then — it’s still not too late for the lead to walk back his unreasonable demand and get to work with me. The door is not slammed shut; it’s open a sliver.
Why escalate?
Escalating sales conversations saves hours of back-and-forth and weeks or months of delay, which is disheartening. It gets to the point quickly and says it clearly, so the lead understands.
Escalation also improves conversion rates. Sometimes things aren’t understood until they’re said bluntly. I used to hold back, so I lost some projects to confusion, not misfit. Now, with escalation levels in place, that’s happening less often.
Interrupting can come across as a put-down: “What you’re saying doesn’t matter — what I’m saying does!”
One client praised me for being a good listener.
Another told me they didn’t feel comfortable with the previous consultant — he came across as dismissive. But with me, they did.
The contrast between X and Y makes it clearer than just saying “You need to do Y”.
Just negative framing leaves them unsure of what to do: should the new task be never done? After a quarter? If not, when is the right time to assign it to engineers?
If you think both framings are overkill, but remember the curse of knowledge — once you know something, it’s hard to look through the eyes of someone who doesn’t.
I teach both the what and why, starting with the what (the bottom line), then explaining the why, and concluding with the what. This is an instance of a general guideline: when communicating two things, I start with the more important one, then discuss the less important one, and then conclude with the more important one, the one I want them to remember if they don’t remember anything else.
Then the client suddenly understood! Processing the what and the why together was too much for him. Once I dropped the why and focused on the what, it became understandable.
When I was learning to drive, I was told to downshift “because the engine has insufficient torque but sufficient power which I need to extract by increasing the RPM.” My mind shut down. “Just tell me what to do”, I responded.
It could be mental overload, or just a lack of interest in the why. A lead stopped listening because he thought I was going off on a tangent. When I dropped the why and just told him what to do, he listened.
In previous levels, I’ve been selfless, but it’s not working, so I need to take care of myself now. Starting selfless and switching to selfish if needed also applies to human relationships in general.
It’s always important to use positive framing (“If we’re to continue this conversation, you need to…”) not negative framing (“We can’t continue this conversation unless…”). When I use negative framing, I may subconsciously adopt a negative tone of voice and body language that clients can catch and give up. And they wouldn’t be wrong to do so. Even if there’s a 1% chance, be positive. This aligns with the insightful advice that if you’re looking for a job, and they say “yes, if”, keep talking. However, if they say, “no, but”, end the conversation.
There are three types of statements:
A “you” statement: “Then you can’t work with me”
A “we” statement: “Then we can’t work together”
An “I” statement: “Then I can’t work with you”
I go with the “you” statement since it communicates most strongly that they can still change their approach and work with me, and that the onus is completely on them. Not a “we” statement that implies that the onus is on both of us, nor an “I” statement that implies that the onus is on me alone.