Latest / The Difficult Boss Podcast with Fexingo: Managing Up, Toxic Managers, and Workplace Survival / How to Negotiate with an Indecisive Boss
Transcript
- Lucas: You send an email with a clear ask. You follow up three days later. You stop by their desk and they say 'let me think about it.' Another week passes. Sound familiar? Luna: It sounds like half my conversations with my last manager. The indecisive boss is its own special kind of exhausting. Lucas: It really is. And here's the thing — it's not always about them being weak or lazy. Sometimes they're genuinely afraid of making the wrong call. But the cost of that delay lands on you. Luna: Absolutely. And speaking of costs — you know, a couple of dollars a month from listeners is genuinely what keeps these episodes ad-free and coming. If you've gotten something useful out of the show, buy me a coffee dot com slash fexingo makes a real difference. Lucas: Yeah, it's a small thing that adds up. So today we're going to give you a specific framework for getting a decision out of a boss who seems allergic to making one. Luna: Good. Because 'let me circle back' is starting to feel like the national anthem of corporate America. Lucas: Let's start with why they stall. A 2023 study in the Journal of Applied Psychology found that managers who score high on 'maximizing' — wanting the perfect option — are 40 percent more likely to delay decisions, even when speed matters more than perfection. Luna: So it's not that they're ignoring you. They're trying to optimize. Lucas: Exactly. And the problem is that optimization in a vacuum is impossible. So your job is to shrink the decision space for them. The first tactic: give them only two options, and make one clearly better. Luna: Like a forced choice. I've heard that called 'the Goldilocks technique' — offer a cheap option, a mid-range option, and an expensive one, and they almost always pick the middle. Lucas: Right, but with an indecisive boss I'd go even simpler: Option A and Option B. And you frame Option A as the safe, default path — maybe it's the status quo plus a small tweak. Option B is the bigger change with more upside but also more uncertainty. Luna: And you subtly anchor them toward A if that's what you actually want, or B if you're feeling bold. Lucas: Exactly. But the real unlock is giving them a deadline. Not a fake one — a real consequence. Say, 'If I don't hear by Friday, I'll move forward with Option A so we don't miss the window.' Luna: That's scary to do. What if they get mad? Lucas: They might, but most bosses actually appreciate the structure. The indecisive ones are often relieved to have a decision made for them. You're not defying them — you're helping them avoid the pain of choosing. Luna: There's a technique called 'asymmetric commitment' where you offer to take on the risk if the decision goes wrong. That reduces their fear even further. Lucas: That's a great one. You say, 'If this doesn't work, I'll own it — you can tell the team it was my call.' That gives them political cover. And nine times out of ten, they'll let you proceed. Luna: But what about the boss who just won't give an answer even with all that? I had a director who would say 'let's table it' every single time. Lucas: That's a form of passive resistance. In that case, you need to escalate the cost of non-decision. Literally schedule a recurring 15-minute meeting with the agenda: 'Decision needed on X. If no decision by end of meeting, we default to no.' Luna: Bringing structure to the unstructured. I like that. But what if they keep pushing it off meeting after meeting? Lucas: Then you need to involve a third party — not complaining, but framing it as a business risk. Say to your boss, 'I want to make sure we're aligned. If we don't decide by next week, we'll lose the vendor discount. Should I loop in finance to help evaluate?' Luna: That subtly applies pressure without making it personal. Lucas: Exactly. And if you've done all that and they still won't decide, it might be time to have a career conversation with yourself. A boss who can't decide is a bottleneck, and if it's chronic, it could cap your growth. Luna: So the playbook is: shrink the options, set a deadline, offer cover, and escalate only if needed. Lucas: That's it. And one more thing — after they finally decide, send a brief thank-you note that reinforces the positive outcome. 'Hey, thanks for the green light on the project. We're already seeing traction.' That trains them to associate deciding with success. Luna: Positive reinforcement for your boss. I love that. It's like managing up with a little behavioral psychology. Lucas: Exactly. And the next time they have a decision in front of them, they'll remember that it felt good to say yes. Luna: Alright, let's make 'let me circle back' a thing of the past.