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, and stay here as much as possible in the first meeting. I want to learn about the lead’s problems, desired outcomes, team, maturity, budget and so on.

A coach once 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.

I ask questions, both clarifying and follow-up. I also have a list of questions I ask all leads. And if I’m concerned about something, I dig deeper.

At this level, I’m not allowed to express an opinion². Trying to do two things at once results in neither done well.

Level 2: Teach

At this level, I shift from listening to teaching. I may share insights, or recommend a course of action³. I address concerns I’ve identified at the Information Gathering level. For example, if the concern is insufficient budget, I may say, “To get the outcomes you want, you need a million-dollar budget.”⁴

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.

I teach⁵ both the what and why, starting with the what (the bottom line), then explaining the why, and concluding with the what⁶.

All this is anchored by what the founder says he wants. If he says he wants his app to be reliable, then I’ll teach him what to do to get there. To do this, I may identify what he’s doing wrong, like interrupting engineers mid-task to assign another, and tell him, “Engineers need focused time to work on a task. If you interrupt them when they’re working, they’ll do both tasks poorly, resulting in unreliable software. So from now on, once you assign some tasks, don’t interrupt engineers till they’re done.”

Level 3: Identify the critical fix

Founders often resist change, and we end up talking past each other. When this happens, we need to focus on the critical fix, the one change we can make that will produce the greatest impact.

The 5 whys technique is a tool for this:

1. “The app is buggy and keeps crashing.” Why? You may ask the lead this, or yourself.

2. Maybe because the CEO isn’t giving enough time for the tech to be built properly. He’s always interrupting and assigning another task. Why?

3. Maybe because there are a lot of things to do — features, mobile app, desktop app, UX, scalability, reliability … — and not enough engineers. Why?

4. Maybe the founder hasn’t hired enough engineers. Why?

5. Maybe he has a low engineering team budget like 1 crore.

The critical fix⁷ is “You should have a budget of $1m.”

In other words, suppose I listed all the fixes I could make in their company:

1. Switch from scrum to kanban.

2. Make your app servers autoscale

3. Reduce time wasted in repeated arguments about the same thing.

4. Have an engineering team budget of $1m.

5. Hire a customer service rep.

I then ask myself, “Which of them has the highest leverage? If there was only one thing I could fix in this company, which would it be?” That would be the budget.

Conversations tend to drift from one topic to another, and before you know it, you’re debating something that’s not the key fix. If that happens, refocus on the key fix.

The key fix can also be about changing a personal belief. For example, if he’s always giving insufficient time to engineers, it may be because he believes that’s how to get better results. In fact, given this belief, it’s rational for him to give insufficient time to engineers!

Though this be madness, yet there is method in it.

- Shakespeare, Hamlet

These unstated beliefs are like a puppeteer pulling the founder’s strings. Trying to influence the puppet doesn’t work — you need to influence the puppeteer.

Level 4: Instruct the lead

At this level, I say

You’re doing X. Instead, do Y.

Leave out the why:

Don’t interrupt engineers when they’re working on a task.⁸

They 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 till he’s done.

Final level: Ultimatum

At this level, I say

You can’t do X. If you want to work with me, you need to do Y.

For example:

I’m not your assistant, to do what you say, how you say it, and when you say it. I work as an advisor. I educate non-technical people like you who are lacking in tech skills on how to run a startup. If you want to work with me, you need to hire me as an advisor.

When I say this, I interpret any response other than Yes as No. For example, “Yeah, but…” or “At the same time we need to…” Some people don’t say no directly. Others are not clear themselves. That’s why anything but an unqualified yes is no.

No lead reached this escalation level and converted into a paying client, so if a lead reaches this level, my is on saving my time rather than getting the gig.

Sometimes the ultimatum isn’t for the engagement but to continue the conversation:

You’re rejecting what I’m saying without understanding it and repeating the same thing mindlessly: I want this! I want this! I want this! If you want to continue this conversation, when I say something, you must leave aside your opinion and listen. Then think about what has been said. Change your plan based on what I’ve taught you. Only then respond to me. Is that clear?

Why escalate?

Escalating sales conversations saves hours of back-and-forth and weeks or months of delay. 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.

1. 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.

2. Some things phrased as questions are really opinions, such as when someone asks “Why can’t you do X?” in a demanding tone. It’s a question only syntactically, just as “Can you pass me the salt?” is really a request, not a question, as Paul Graham pointed out.

Genuine questions are asked in a calm tone, not demanding, not frustrated, not incredulous.

Before asking, stop and reflect:

What’s my intention?

Is my tone matching that intention?

3. 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.

4. See how they react to unpalatable truths: snapping “nooooooo!” is a red flag. “Yes” and “Let me think about it” are good responses. Once I told a founder that his team would need 10 crores a year. He didn’t say anything, so I asked an open-ended question: “What do you think?” He said, “That sounds high, but you’ve done this before and I haven’t, so I won’t argue with you.” That’s an intelligent response.

5. I’ve had moments where something I said didn’t land. When I rephrased it, it suddenly did. But it sounded the same to me! You never know which phrasing will resonate with the next person you meet.

To be a good teacher, you must be a good listener, willing to leave your opinion aside:

1. Meet people where they are.

2. Understand their worldview. If you can’t state it back to them clearer than they can, you haven’t really understood their perspective.

3. Inhabit that worldview for a short while

4. Bring them forward.

Imagine a group of people on a hike, and one person falls behind. The leader has to walk back to where that person is, then bring him forward. He can’t stand where ahead and yell, “Why aren’t you here yet?” Some of the bad teachers I’ve had growing up did exactly that — they were authoritarian, and didn’t give space for my objections or ideas.

As a teacher, I don’t hesitate to challenge my student with a direct “Why?”:

You should use React Native because it will decrease time-to-market and cost.

No, I’ll use Swift.

Why?

Some students need this level of directness.

6. People often don’t remember everything you say. They remember only the end. That’s why we need to put the thing we want the lead to remember — the what — at the end. So end with the what, even if you began with it. Redundancy is not bad — it’s how you reinforce the point.

7. The root cause is the problem; the key fix is the solution.

Teaching isn’t one-size-fits-all: I keep a variety of tools in my toolbox and pull out the one that fits the student’s maturity and mindset.

8. 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.

Let’s unpack this:

Both positive and negative framing are necessary. Just negative framing (“Don’t do X”) tells them what not to do, but leaves them unsure of what to do. Just positive framing (“Do Y”) often isn’t clear enough unless contrasted with the negative framing. As another example,

When I say things to you, you’re responding mindlessly. <— Negative framing

Instead, you need to leave aside your opinion and listen. Then think about what I’ve said. If you can’t do it on the spot, tell me you’ll need time. Then respond thoughtfully. <— Positive framing

You might 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.

Words like “mindlessly” are necessary. Yes, some people get angry — but this is the last escalation level before rejection, and I don’t want to lose a gig because of a misunderstanding. So the communication has to be black and white.

Now, about this line

If you want to work with me, you need to do Y.

The “If you want to work with me” is necessary. When I used to just say, “You need to do Y” some leads argued. They misinterpreted it as a general suggestion, like “You need to exercise every day.” “If you want to work with me” leaves no room for misinterpretation.

I phrase it as a “you” statement in “If you want to work with me...” to convey that the onus is on him to change his approach.

❌ Not an “I” statement like “If I’m to work with you…” which sounds like my obligation.

❌ Not a “we” statement like “If we are to work together…” which sounds mutual.

Finally, I don’t give a reason. Reasons dilute the message: when I say two things, the focus on each reduces. Reasons invite debate. Some leads thought that I was pleading with them and tried to dictate terms to me. At this escalation level, I’m giving an ultimatum. And ultimatums don’t come with reasons.