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The Last 120 Days: How CS Leaders Decide the Year

A line chart running from September to December showing the final 120 days of the fiscal year, with a dip in the middle and a climb to a December endpoint, and an icon of one person helping another up a set of steps.
What you do in September shapes December. The dip in the middle is the part nobody plans for.

You can see it just ahead.


Others may overlook it. Not because they don’t care. But because they’re preoccupied with getting things done, today, this week, this month.


You’re staring at one date on the calendar: fiscal year end 2026. The date the books close and the scorecard is final.


Not next week. December. Which is exactly why we’re talking about it now. What you do in September shapes December, and September is when most teams are just coming out of the summer daze.


Your job is not just to hit the monthly targets. It’s to make sure the fiscal year objective gets across the finish line too.


Net revenue retention. Net promoter score. Time to onboard. Gross margin. You name it, you own it as the leader of Customer Success.


It’s stressful. You’ve had a plan. You’ve executed your plan. And like all plans, it’s had bumps and pivots along the way.


How do you keep your head on straight? How do you keep others focused on today’s mission while ensuring they’re driving towards the big picture? How do you finish the year strong?


If you’re waiting until Q4 to think about how you’ll finish the year, you’re already giving away options. So let’s dig in.


The school of hard knocks


I’d like to say all the memories are fond. That’d be a lie.


I was stressed because I knew the numbers and the general trajectory. The team was stressed because they knew they were ultimately going to be judged against a target they perceived not to have much say in or control over.


And we were all annoyed because despite vigorous planning, focused efforts, and a customer-first mentality nothing ever worked as planned. Let me repeat that: nothing ever goes as planned.


Frustrations set in because some of those barriers were never ours to fix. They lived in someone else’s department, someone else’s budget, someone else’s priority list. And you know you’ve already done everything you can to move them.


So, one-on-ones became tedious, and not much could move the needle. Or so I thought.


What took me a while to figure out was that I didn’t need another nugget in the data or another way to get even “more ahead of it.” I needed to change how I was helping leaders and their teams think and act, so they could get themselves out of unintentional stagnation.


Blanket incentive programs worked for some, but not all. It wasn’t until I layered in longer-term upside that my best people pushed past the line, while the ones who needed a nearer finish line finally got over the hump.


The mistake I kept making was pulling one lever for everybody.

The people who were behind needed a closer finish line. The people who were ahead needed a reason the finish line wasn’t the end. Figuring out how to say both of those out loud, to both groups, in the same room, was more art than science.


Years later I found the study that puts numbers on it. Take the quarterly bonus away and the weakest performers lose about 6% of revenue while the top performers barely feel it, around 2%. Take the overachievement pay away instead and it flips: the top performers drop close to 15%, and the weakest hardly notice.


The other interesting thing: it felt like the account picture wasn’t changing month to month. It was. What moved was who sat in red, yellow, and green, and who was genuinely likely to renew or expand.


A better question than “what changed this month” would have been: who’s fast-growth and who’s slow-growth? Where are we a critical part of the customer’s strategy versus a valued functional partner who just needs to do the job?


Fast-growth companies felt it more acutely, and not only because more things happened outside our control. Pivots simply happened more often. The right move was to see that and use it: forecast better, get ahead of the change, and respond instead of react.


The headline for me was this: I was strong on the data and workflow. I could build the mechanisms for success. Where I needed to grow was aligning those mechanisms with the talents and uniqueness each person brought to the table. That human element gap narrowed my vision and, ultimately, stifled the team.


One-on-ones with a set agenda are great for structure. But they’re bad for value if you’re not empowering and coaching people to use the time to solve problems instead of repeatedly reviewing why an account is red and what to do about it.


Had I built that skill earlier, I would have helped the business move on from a lost cause sooner instead of grinding away while accounts we could actually grow went underserved.


We’ve all been there. Get this last unit or dollar across the finish line. Every customer is sacred. But you can’t save them all.


As long as you’re confident you executed to the best of your ability and it still didn’t work, then say so and move on. Give that customer the best possible exit you can. That’s what buys you the room to shift to accounts you can actually win.


It’s hard to let it go.


It’s hard to tell the team it’s time to move on.


But if you don’t, you increase the risk of losing more than just this account.


Getting on with it is just as important as trying to salvage it.


Weighing the subjective vs. the objective


A two-column comparison. The left column, labeled "What the dashboard sees," lists login frequency, feature adoption, ticket volume, survey score, and days to renewal. The right column, labeled "What the CSM hears," lists things a customer says out loud, such as a champion job hunting or a budget moving elsewhere. Below both: don't pick a winner, half model, half manager.
 Do you lean in on the CSM's POV?

There’s a risk of leaning too far into “how are we going to close this” at the cost of the relationship you’re supposed to be building.


Yes, the renewal/upsell.


Yes, we need to find the path to growth for customers and the business alike.


But if we don’t dig into the why and use the power of the relationship between the CSM, their users, and the contract owner, we’ll miss it entirely.


And that’s the golden ticket.


So do you lean in on the CSM’s POV, lead them through a blind spot, or let the customer go?


Here’s the part that surprised me when I went looking at the research. When the CSM’s read and the health score disagree, the move isn’t to pick a winner.


The work on this is old, and it is specific. Across five different business forecasting situations, an even split between the model and the manager beat both of them on their own. Not sometimes. Every one.


Half model, half manager.

There’s a practical way to get there. People abandon a model the second they watch it get something wrong, unless they are allowed to adjust it. Give them that, and they will keep using it even knowing it is imperfect.


So let your CSMs override the score on the record, with a stated reason. Their judgment carries real weight, and the stated rationale gives you something concrete to coach when the override turns out to be the thing that was wrong.


What works


There is a lot to sift through as you head into the home stretch, and no shortage of advice on Q4 customer success planning. Overthink any one piece of it and you will burn the energy you need for the actual work.


Here are the four things I’d focus on if I were brought in to help a CS leader turn the remaining time into decisions and action.

  1. Be Declarative, Then Be Repetitive: Start by staying honest and grounded about where the team is, where it needs to be, what you believe needs to happen to get there, and what success means once the objective is achieved. Declaration is not a kickoff speech. It’s a standing weekly drumbeat. The hardest part isn’t stating the target. It’s being willing to say: “Here’s the part I’m not sure we can get. Here’s what I’m doing about it. Think through your part and come prepared to share it with me.”

  2. Name the Outcome You’re Trading Away: Q4 always forces tradeoffs. Margin for bookings. Expansion for retention. This year’s number for next year’s health. It can be maddening. The greatest risk is often not making a call at all. Stalling costs time, energy, and focus. You may get it wrong. But a wrong call you can correct in October beats an open question you’re still carrying in December.

  3. Spend Your Authority Where the Team Has None: By Q4, the window for new tools and training is usually closed. What’s left is you. Be the person who clears the blockers your team can’t clear on its own. Pre-grant the approvals you can, such as discount thresholds, escalation paths, and executive sponsor time, so nobody is waiting on you in December. A study of 7,600 managers across 262 companies found that 84% could count on their own boss and direct reports all or most of the time. Only 9% could say that about colleagues in other functions. That gap is your job. Your CSM doesn’t need another enablement session to save that renewal. They may need someone senior enough to get legal to turn a redline in three days instead of three weeks.

  4. Don’t Overlook Subjective Data, but Don’t Become Addicted to It: The great value of the CS role is the relationship, because it is the only thing that answers why. Why are you using the product this way? Why aren’t you? Why are we solving the problem you hired us for? Why aren’t we? Surveys, behavior mapping, and customer summits can tell you a lot. But a CSM with a real relationship with the main user and contract owner hears things those mechanisms never will. And that same relationship can create blind spots. Both are true at once. Trust the read. Then check it against the numbers. When they disagree, investigate the gap instead of automatically picking a winner.


Nobody gets a perfect year


Every company would love to build the ultimate customer experience workflow that creates universal upside. But there are too many variables, and too much change. Something will fail. A decision will have to be made.


In my experience, sitting on a decision often costs more than making the wrong one and correcting it. Make the call using the best information you have, from your people and from the tools in front of you. Then keep watching for evidence that tells you to adjust.


That’s the real goal. Not a perfect year. A balanced approach to constant change, clear tradeoffs, and timely decisions as you close the year out.


You have about 120 days left. Most of what shows up on the December scorecard gets decided well before December.


Wishing you, your team, and your customers well as you hit these final months of 2026.

 

One question before you go: what’s the cross-functional dependency that shows up in your Q4 every single year? Drop it in the comments. That’s where most years are quietly won or lost, and I’d like to see how much overlap there is.


I help SaaS and healthcare leaders get unstuck when the path forward isn’t obvious: clarify the tradeoffs, align the people who need to move, make the call, and lead the work through execution.


Cheers,




Sources


AI was used to support research, grammar, and structural clarity. All thoughts, opinions, lived experiences, and recommendations are my own.

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