Once upon a time, a team of rainmaking sales leads were landing big sales. And the company would ring a loud bell to celebrate every close.
But over time, the culture leaned harder on their “close at all costs” style. Downstream, operations was drowning in promises no one had checked, stuck playing “the bad guy” with furious clients.
Those rainmakers were under big pressure to keep revenue flowing, so they’d take the shortest path they knew. That meant skipping reality checks. Resentment grew, scalability tanked. Growth stalled on these few irreplaceable stars.
It’s a common tale: rainmakers making it rain, everyone else mopping up the flood. In this episode, learn simple ways to speak up from the ops seat—bravely, tactfully, and without blowing things up, starting today.
The Hidden Cost of Rainmaker Culture for Ops Leaders
You know this rainmaker culture well from the inside. The sales leads, account managers, business development folks who’ve been doing it their way for years and don’t get questioned much. They bring in the money the company runs on, but the way they work can leave everyone downstream in a bit of a wreck.
The tricky part is that this “close at all costs” approach doesn’t usually stop to ask, “Can we actually deliver this without frying people or breaking trust?”
When the landscape is changing with—new products, new markets, customers who want everything yesterday—the pressure of that just gets louder. The drumbeat turns into, “Just get it done.” There’s barely any room to say, “Wait a second, what’s actually workable here?”
From your chair in operations, it can feel pretty boxed in. Speaking up feels risky when the culture rewards speed over sanity, and when questioning the deal sounds like you’re just being difficult instead of helpful.
How Ops Leaders Challenge the Status Quo with Tact
But here’s the thing: in a rainmaker culture, ops is often the voice that understands the whole system. That’s kind of the job.
Having the courage to say the uncomfortable thing—with a bit of tact—is how the company stops lurching from deal to deal and starts building something that can hold up. When ops leaders step into that role, you’re not just cleaning up the flood anymore; you’re helping everyone see where the riverbanks really are.
Here are a few things that might help:
First, build your situational awareness. Notice who really has pull, who can handle nuance, and when people have enough breathing room to hear a different point of view. You don’t need to make a big speech. Sometimes a well-timed question—like, “What happens if we can’t staff this in 60 days?”—is enough to bring context.
Second, tie everything to shared success. Instead of “this won’t work,” try, “I want us to deliver something the client loves and wants to renew, so here’s what I’m concerned about.” So, you’re not blocking the deal; you’re protecting the win.
Third, don’t do this solo. Build a small circle of allies upstream and downstream—people who see the strain of what’s going on and care about delivery that actually satisfies. Compare notes before the big meetings. Agree on the important points to make. When more than one person names the risk, it starts to sound more like wisdom, and less like resistance.
I see ops leaders using these small, steady moves—courage, tact, partnership—to nudge rainmaker cultures back into balance. Not trying to be heroes, just asking better questions, naming the tradeoffs, and staying in the room when things get tense.
A Coaching Challenge for Your Next Conversation
So here’s a challenge for you this week: What is one conversation where you’ll risk being a little more honest than is comfortable, in service of a better outcome? Take a small step toward that, and see what happens.
And if you tend to hold back because you don’t feel “ready” or fully sure, listen to Episode 95 for practical ways to move decisions forward even when you don’t have all the answers. You’ll find it at YourFutureRealized.com/95.
Remember, you can’t stop the chaos, but you can change the game — and I’m in your corner.