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:

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.

See you next Tuesday,

Customer Success. Revenue Follows.