The Journey: #82 Competitors Don't Need Permission

Early in my career as a CSM, I was working in a genuinely competitive market. Not the fake kind people throw around in a QBR deck to sound strategic. The real kind, where one competitor in particular was aggressively going after our customer base, and doing it well. Good for them, honestly. That's a strategy, and it was working.

Here's where I went wrong. I assumed that if I was doing my job well, if my customers had strong adoption, strong usage, a good partnership, that was enough to be defensible. That the relationship itself was the moat. So I led with assumptions instead of information, which is exactly backwards, and I know that now because I lived it.

So I started teaching myself how to get over the fear of asking. Not just what to ask, but how to ask it, because there's a real difference between a question that puts your customer on the defense and one that opens a door. I didn't want my customers to feel like they owed me an explanation for looking around. They don't. What I wanted was enough safety in the relationship that they'd just tell me the truth about what they actually needed, competitor or no competitor.

I got good at this. Good enough that I became the official competitive overlay for our entire customer base. When a rep or another CSM knew a competitor was in the mix on an account, I was the one who got pulled in, to navigate the conversation, run the demo, walk the account through to the other side of it. Not because I had some secret sales gift I'd been hiding. Because I'd stopped being afraid of what I might hear.

That's the whole shift. Knowing a situation was competitive didn't create the risk. It just meant we could finally do something about it, instead of finding out after the renewal already slipped through our fingers.

Here are the questions that got me there:

→ Is it your intention to renew your subscription with us? → Are you evaluating any alternative solutions at this time? → Are there any specific gaps or challenges you're experiencing that may cause you to consider another solution? → As the market continues to evolve, are there any other products you've come across that you've found interesting? → What's your internal philosophy on build versus buy, and is there any discussion around building your own version of this?

The Takeaway: Adoption and a good relationship aren't a competitive strategy. They're table stakes. Your competitors aren't asking your customers for permission before they show up in the account, and your sales team can tell you exactly how often they're calling back into deals they lost eight months ago. The only real choice you have is whether you find out early, from your customer directly, or late, from a churn notice with your name on the account.

The Resource

Steal this. Starting four to five months before renewal, work these five questions into your regular check ins, one at a time, not all in one meeting like a competitive risk audit:

→ Is it your intention to renew your subscription with us?

→ Are you evaluating any alternative solutions at this time?

→ Are there any specific gaps or challenges you're experiencing that may cause you to consider another solution?

→ As the market continues to evolve, are there any other products you've come across that you've found interesting?

→ What's your internal philosophy on build versus buy, and is there any discussion around building your own version of this?

The goal isn't to interrogate your customer. It's to give them permission to be honest with you before the renewal conversation turns into a save.

AI in CS

This is exactly the kind of blind spot AI is starting to help close, if you're willing to use it that way. Most CS teams are sitting on a mountain of signals that could point to competitive risk long before a customer ever says the word "evaluating" out loud, and most of it is going completely unread.

→ Support tickets with comparison language. → Usage patterns that echo what churned accounts looked like right before they left. → A meeting note where a customer casually mentions a tool their team is "also looking at," said in passing, then never brought up again because nobody flagged it.

Tools like Gong, Fathom, Granola, Planhat, and AI-powered platforms can now flag competitor mentions automatically across calls, emails, and tickets, so you're not relying on a CSM to catch it live and remember to write it down three meetings later. Some teams are building simple AI prompts into QBR prep that scan account history for competitive keywords and surface a risk flag before the call even starts.

The tactical move here isn't complicated. Pick one AI tool you already have, your call recorder, your CS platform, or even a basic prompt into an LLM with your notes pasted in, and ask it to flag any mention of alternative solutions, build versus buy language, or budget scrutiny across your top twenty accounts this month. You'll be surprised what's already been said out loud that nobody thought to write down.

Closing with Kristi

Asking these questions won't feel comfortable the first few times. That's fine. It's not supposed to. Comfort was never the goal, clarity was. The best defense really is a strong offense, and you can't play offense on a threat you've refused to name out loud. So go ask the uncomfortable question this week. If you want help building this into your renewal motion, that's exactly what we work through in Advisory, or just hit me up and let's talk it through.

See you next Tuesday,

Customer Success. Revenue Follows.