Feature Story
Several companies ago, I had designed a renewal motion that looked good on paper.
90 days out, the CSM would kick off the process to get the renewal started. They'd send an email, get a call scheduled, and by the time everyone was on a Zoom together we were maybe 75 to 80 days from the renewal date. The CSM would walk in prepared, they’d follow the set agenda and talk through the next steps outlined. It was more of the CSM talking at the customer for 30 minutes. This definitely wasn’t a discussion.
What they weren't prepared to do was ask the hard questions.
And I get it. There's something psychologically uncomfortable about asking a customer "do you actually plan to renew?" It feels presumptuous. It feels like you're inviting a "no." So instead, we'd talk about our process, walk through timelines, and discuss what the paperwork would look like and who would need to sign. The customer would nod along and follow our lead. And of course we'd leave feeling like things were on track.
They weren't.
By the time the truth would surface, it was usually somewhere around day 30. And it wasn't coming up on a call, we were finding out through in an email. And usually a short one that was cold and felt like the door was closed. The kind of message where you can feel the decision has already been made and the person writing it just needs to get through the awkwardness of telling you.
The door wasn't just closing, it was already closed, and was a long time ago. We just hadn't noticed because we'd been too busy presenting our process.
This happened over and over. Churn after churn after churn.
And for a while, we blamed anything else. We’d point fingers at the product claiming it wasn't ready, highlight the fact that the customer's budget changed or discuss the impact of the champion leaving. And sure, sometimes those things were true, but the pattern underneath all of it was the same.
We weren't getting the information we needed, early enough to do something about it. And we weren't getting it because we weren't asking for it.
So I changed the motion entirely.
We started by pushing the first renewal conversation earlier and moved it from 90 days out to 120 days. We gave CSMs a clear set of questions to ask and gave them permission to actually ask them, not dance around them. We had to help navigate their fear and build their confidence so they would be able to ask the questions directly and clearly in the first conversation.
Once we did this the dynamic shifted almost immediately, and not because every answer was good. The reality was that sometimes the answers were hard to hear. But hearing the hard truth at 120 days allowed us to do something … the hard truth with 30 days left was basically closure.
The Takeaway: Avoidance isn't a strategy. The questions that feel uncomfortable to ask are almost always the exact questions you need answered. Ask them early, ask them directly, and give yourself enough time to actually do something with what you learn.
THE RESOURCE
The 5 Renewal Questions Worth Actually Asking
These aren't rapport builders, and they definitely aren't formalities. These are the five questions that will tell you everything you need to know about whether a renewal is a real probability or just a story you're telling yourself.
Ask them early. Ask them directly. Take notes.
1. "Is it your intention to renew your subscription with us?"
Simple, direct and informative. And most CSMs have never asked their customers this question.
This question removes all ambiguity from the conversation. You're not hinting or assuming … you're asking. The answer will either confirm your optimism or give you the information you've been missing. Either way, you win.
2. "Who will be involved in the decision-making process?"
Champions change, budgets shift, and there are influencers you may not have engaged with. Approvals that used to be automatic now require three signatures and a CFO sign-off.
This question maps the real decision landscape. You need to know who is in the room, who isn't yet, and who has the power to kill a deal that everyone else thinks is a sure thing.
3. "Are you evaluating any alternative solutions? And if so, is that your decision or is it being driven by procurement?"
This one matters more than people realize. A customer who is voluntarily exploring alternatives is telling you something about value versus a customer whose procurement team is mandating a competitive review.
These are two very different problems that require two very different responses. You need to know which one you're dealing with and understand that if your competitors are in the process this is going to significantly change things.
4. "Here's a full view of everything we offer. As you think about the next term, is there anything here that aligns with where you're headed?"
Renewal conversations should never be purely defensive. This question opens the door to expansion by framing it around the customer's future, not your quota.
Put your full product and services list in front of them. Walk through it briefly. Then let them tell you what resonates. You'll either uncover an expansion opportunity or learn something important about how narrow their perception of your value actually is.
5. "Is there anything that would prevent you from moving forward with the renewal if we were able to meet your timeline and requirements?"
This is the closer. The catch-all. The question that surfaces the objection that hasn't been said out loud yet.
Budget constraints, internal politics, a competitor who made a compelling pitch three months ago, or a stakeholder who's been quietly pushing for a change. This question gives the customer permission to tell you the thing they've been holding back, while there's still time to address it.
Ask all five. Write down the answers. Then build your renewal strategy around what's actually true, not what you hope is true.
COMMUNITY INVOLVEMENT
Interested in being a panelist for the SuccessHACKER CS Mastermind webcast series? Join me and Andrew Marks in one or more of our expert-led conversations!
We’re searching for industry pros who are excited to contribute their advice and expertise in lively, informative discussions on the impactful topics the industry is dealing with today!
Whether you've done this before or not, it's a great conversation with smart people. We’d love for you to take part in the discussion!
FROM MY WORLD
Quick updates … Events, podcasts, awards, news, etc.
EPS 10: Churn So Good: When Losing Customers Is Actually Winning
Not all churn is bad. Sometimes losing a customer is actually a win. Dannah Vaughan, Director of CS at Silverline Solutions, joins me to break down good churn -- what it is, why it happens, and why it might be your smartest retention move yet.
The Children's Book Author turned CCO at Point of Reference ft. Alison Bukowski
Allison Bukowski wanted to be a children's book author at age five. Today she's the Chief Customer Officer at Point of Reference. And the through-line between those two things is storytelling. Listen as Allison walks Kristi through a career built on writing, advocacy, and a fierce belief that customers deserve a seat at the table and not just a mention in the mission statement.
THE SERVICES
I work with CS leaders and organizations who are serious about getting Customer Success right.
Advisory
Strategic partnership for CS leaders who need a thought partner, not another framework.
Coaching
1:1 coaching for CS professionals who are ready to lead with more clarity and confidence.
Education & enablement
Workshops and programs built for teams who want to level up, not just check a box.
Speaking
Keynotes and sessions that challenge how your audience thinks about Customer Success.
POLL
Which of these five questions will help you uncover something you've not done a good job of surfacing in the past?
- "Is it your intention to renew your subscription with us?"
- "Who will be involved in the decision-making process?"
- "Are you evaluating any alternative solutions? And if so, is that your decision or is it being driven by procurement?"
- "Here's a full view of everything we offer. As you think about the next term, is there anything here that aligns with where you're headed?"
- "Is there anything that would prevent you from moving forward with the renewal if we were able to meet your timeline and requirements?"
A FINAL NOTE
CLOSING WITH KRISTI
Renewal risk doesn't usually show up as a crisis, it shows up quietly, in the questions you didn't ask and the answers you didn't have. The teams that consistently hit their retention numbers aren't just running better processes, they're having braver conversations.
The goal was never to avoid a "no." The goal was always to hear it early enough to do something about it.
If this issue was useful, forward it to someone who's managing customer renewals, they'll thank you later.
See you next week,
Customer Success. Revenue Follows.