Feature Story
A few years ago, one of my CSMs was onboarding a new customer. We did everything right. The kickoff was strong. All the key stakeholders were in the room, we mapped roles and responsibilities, aligned on goals, and left that first session feeling genuinely good about where things were headed.
Then we hit a wall. A brick wall.
Progress stalled. We flagged it with our main POC and they assured us we were on track, and for us to keep going. So we kept going. Two more weeks passed and nothing moved. We escalated to the POC and the exec stakeholder together and laid out exactly where things stood. We were trying to complete the Salesforce integration, which was a complex one, with a lot of field mapping involved and we were stuck.
Our POC went back to discuss this internally and came back with a requirements document we had never seen before. Sales hadn't seen it either.
We asked for a call to get clarity. And that's when she showed up.
The Salesforce admin. Someone we had never spoken to, never heard mentioned, never seen in a single email thread. She got on the call and immediately told us this wasn't going to work. She had requirements and raised a ton of concerns she had. And then she said the thing that made everything click: she started talking about how one of our competitors handled it differently.
There it was.
This person had been quietly advocating for a competing solution since before we ever closed the deal. She never showed up in discovery, she wasn't in the kickoff, but she had been in the room the whole time. She was in every internal conversation we weren't a part of, and now that we had a hard dependency on her team, she had all the leverage.
We tried going to the executive and the response was soft. "Well, she knows better than me on this." There it was. The wall. Again. Bright red brick.
We eventually got through it. But not without a fight, not without new product development, and not without a timeline that stretched way beyond what anyone had planned. And we knew we'd face her again at renewal. The multi-year agreement we had in place is the only reason we had the runway to do what came next.
Because here's what we did. We stopped trying to go around her and started investing in her. We took the time to genuinely understand the impact our technology had on her workload and her role. We showed up for her specifically, not just for the account. Slowly, the resistance softened. Over time, she became a partner. And eventually, she became an advocate.
But that took time … a lot of time. And if we'd been on a one-year deal, there's no version of that story where we win the renewal. This is a reminder of the power of a multi-year contract … time.
The Takeaway: Map everyone. Not just the decision maker. Not just the exec sponsor. Ask about the people who will be affected by this implementation. Ask who has influence without a title. Ask who might have opinions they haven't shared yet. The stakeholder you can't see isn't a ghost. They're just someone you haven't found yet. Your job is to find them before they find you.
THE FIELD REALITY
The Hidden Stakeholder Checklist
Before your next kickoff, run through these questions … in the sales process, in your new customer survey, and in the kickoff itself:
Who will be directly responsible for implementation tasks?
Who owns the systems we'll be integrating with?
Does anyone have experience with a competing solution?
Who will be most impacted by this change in their day-to-day work?
Who has influence over this project that might not have a formal title or role?
Is there anyone internally who expressed hesitation about moving forward?
These aren't gotcha questions, they're protection questions. For your customer, for your team, and for your timeline. Add them to your pre-sales discovery, your new customer onboarding survey, and your kickoff agenda. Make it a habit, not a reaction.
AI IN CS
This is exactly the kind of problem AI can help CS teams get ahead of … before the brick wall appears.
Org mapping and research: AI tools can help CSMs research account structures before kickoff, surfacing names and roles that aren't on the intro call list. LinkedIn, company websites, and CRM data can all feed a more complete picture of who's actually in the org.
Pre-kickoff discovery prompts: Use AI to generate a tailored stakeholder discovery questionnaire based on the account's industry, tech stack, and integration requirements. If SFDC is in the mix, you should be asking about admins before you ever get on a call.
Sentiment and engagement signals: Platforms with AI-driven health scoring can flag when contacts who should be engaged simply... aren't. Silence is a signal. An admin who never responds to onboarding communications might be telling you something. Connect to your call recording software to listen for things you didn’t hear.
Handoff intelligence: AI-assisted account summaries during handoffs can prompt CSMs to identify gaps in the stakeholder map before they inherit a relationship blind spot from Sales.
The goal isn't to eliminate human judgment. It's to make sure you're not walking into a room without knowing who's already in it.
STATE OF CUSTOMER SUCCESS SURVEY
Planhat is running their annual State of Customer Success research and I want this community represented in it.
This is the data that actually matters. Post-sale performance, revenue trends, how CS teams are operating right now. The results shape how the industry understands itself and that only works if practitioners like you are in it.
It takes a few minutes. Your answers are anonymous. And when the report drops, you'll actually recognize the reality it reflects because you helped build it.
TAKE THE SURVEY HERE
POLL
Tell me about a stakeholder you never saw coming and how you handled it.
Hit reply. I read every response.
A FINAL NOTE
CLOSING WITH KRISTI
The people who can make or break your customer relationship aren't always the ones with the biggest title or the loudest voice on the call. Sometimes they're the ones who stay quiet until they have leverage. Your job is to find them first, understand what they need, and give them a reason to be on your side.
Map the room. Even the parts you can't see yet.
See you next week,
Customer Success. Revenue Follows.