The Journey: #85 Collaboration or Compliance

I saw a pattern repeat itself at all 5 companies I worked at as a CS Leader. We ran a ritual every quarter that we proudly called cross-functional planning. This is exactly how this played out. Sales leadership walked in with a few slides to present their plan. They would start with their revenue number, present their plan to hit it, and then say “here’s what we need from each of you.” Marketing got asked to run a campaign, CS got asked to move up three renewal calls, and Product got asked to make sure a roadmap slide said the right thing to one specific prospect. Everyone said yes. We had a shared number, a shared meeting, a shared Slack channel and called it One Team. Here’s what we never did. We never asked marketing what they were actually seeing work in competitive deals before the plan got built, even though they had real intel on why prospects picked us over the alternative. We never asked CS what new use cases or wins were sitting in call notes that could reshape how sales pitched the next thirty days, even though we were on those calls every single week. Nobody asked product if anything on the roadmap could realistically get pulled forward to save a deal, or asked finance if a smart end of quarter offer could do more work than another round of discounting. One function built the plan in a silo, and the rest of the team got handed “homework” and were expected to be enthusiastic about it. It looked like collaboration. But let’s be honest, it was compliance. I didn’t see it then. I couldn’t; I was too close to it. I was too busy hitting my own number to notice the room had never actually been a room. Funny thing about forests: you really can’t see the forest through the trees. It took stepping outside as a consultant, watching this same scene play out at company after company, to see the actual shape of the problem. The most senior, most capable leaders in a building will run through a wall for a plan they helped design. Those same leaders will slow-walk, resent, or half execute a plan that got handed to them, no matter how many times you tell them it’s a shared number. If I was a CS Leader today, instead of presenting my plan and giving orders, I’d present my target and goals, I’d share what I am thinking and how I want to get there, but then I would open the floor to my peers and with a lot of trust and vulnerability ask them these questions:

1. What can we do that you’ve seen work that I haven’t thought about?

2. How can you and your team help us get there faster?

3. What holes do you see in the plan I’ve put together?

4. Of what I have proposed, what do you think will have the greatest impact and why?

If the thought of doing this causes a visceral reaction, it’s because your ego is too big, you don’t trust or respect the voice of your peers, or you’re not allowing yourself the time to really collaborate. Remember, just because someone has an idea or recommendation, doesn’t mean you have to take it. Maybe they lack perspective or experience in your domain, and you can use this opportunity to educate them and start an honest dialogue. But there is also a likely chance you will walk away with something new to do, a different perspective and a better plan to execute. The Takeaway: If your planning process starts with one function’s finished slide and ends with everyone else’s task list, you don’t have a cross-functional plan. You have a cross-functional to-do list with extra steps. Real planning starts with the target on the table before any plan exists, and one honest question to every leader in the room: given this number, what would you do, and what do you need from the rest of us. Sequence that correctly, target first, real input before execution, and you get a plan people helped build instead of one they were assigned.

The Resource

The Four Questions Framework Next time you’re about to present a plan instead of build one, stop right before the “here’s what I need from you” slide. Ask your peers these four questions instead, in this order:

1. What can we do that you’ve seen work that I haven’t thought about?

2. How can you and your team help us get there faster?

3. What holes do you see in the plan I’ve put together?

4. Of what I’ve proposed, what do you think will have the greatest impact, and why

Ask them out loud, in the room, one at a time. Let people actually answer before you react. You don’t have to take every suggestion, some will miss context you have and they don’t, but you do have to sit with all of them before you decide. Use this at your next QBR, annual planning session, or even a stuck 1:1. The goal isn’t consensus. It’s making sure nobody in the room could honestly say later they never got asked.

AI in CS

Here’s where this gets practical fast. The four questions in that story only work if the person answering them has something real to bring, not a gut feeling. Most orgs already have the raw material sitting in disconnected tools. Your CS platform has churn signals, Gong has the actual language prospects use in competitive deals, product analytics has usage patterns nobody’s synthesized. The gap was never the data, it’s that nobody translated it into a point of view before someone asked them a hard question in a room full of peers. This is exactly where AI can help right now, and it’s not glamorous. Teams are using call transcript tools to surface, in plain language, what CS is actually hearing from at-risk accounts before the planning meeting, not during it. Marketing teams are feeding win-loss data into a simple AI-built brief on what’s working in competitive deals, so when someone finally asks “what have you seen work that I haven’t thought about,” they’ve got a real answer instead of a shrug. The reframe: stop using AI to answer questions leadership already asked. Use it so every function walks in ready to answer the harder ones.

Closing with Kristi

None of this needs a new framework or a laminated One Team poster in the breakroom. It needs a leader willing to ask honest questions and sit with answers that don’t always flatter the plan they already built. There’s an old saying about going fast alone and going far together. Turns out quarterly planning runs on the same math, speed without the room just means you rebuild the plan in week three anyway. I’ll be talking through a version of this exact tension in more detail in the coming weeks so if you want to keep the conversation going, I’m around.

See you next Tuesday,

Customer Success. Revenue Follows.