Just Figuring It Out Podcast · Episode 10

Why Your Team Keeps Coming Back to You (And How to Fix It)

When every decision routes through you, it's usually a leadership problem, not a people problem. In this talk from one of our live client sessions, we cover clear asks, the three buttons your team needs to feel safe pressing, and how to stop carrying what's theirs to carry.

With Will Boyd, Alex Engar, and Ian Hogan · 61 minutes · September 23, 2026

The Short Answer

Your team keeps coming back to you because, somewhere along the way, they learned it was the safest or fastest option. Most performance problems are really clarity problems: people don't know what done looks like, what standard you expect, or what they're allowed to decide without you. Then your reactions teach them the rest. If you fix every problem, rescue people when they're stuck, or shut down new ideas, they stop bringing those things on their own. To change it, ask fully for what you want, spell out decision rights, respond with questions instead of answers, and let people carry their own problems with your support.

Signs Every Decision Still Routes Through You

Most owners don't notice this happening until they're buried in it. Here's what it tends to look like when leadership is missing:

  • Every decision, big or small, ends up on your desk.
  • The same problems keep coming back, even after you try to automate them away.
  • Meetings are quiet. The real talk happens afterward, and usually not with the person who needs to hear it.
  • You hear about problems late, or you hear about them from a customer.
  • Good people leave, and others stay and coast.
  • Nobody brings you new ideas anymore.

It shows up in your own head too. "Why does nobody care as much as I do?" "It's faster if I just do it." You can't take a real week off without checking every notification. And the one that stings: I built this, so why don't I like being here?

None of that means you hired the wrong people. Usually it means your team has adapted to how things work around you. That's actually good news. If you set it up, you can change it.

Most Performance Problems Are Clarity Problems

"Can you handle the invoicing?" sounds like a clear request. It isn't. When someone keeps missing the mark, check whether you've actually asked for the full thing you want. A clear ask has five parts.

PartThe question it answers
OutcomeWhat does done actually look like?
DeadlineWhen does it need to be finished?
StandardHow good is good enough?
ReasonWhy does this matter?
AuthorityWhat can they decide without you, and how should they bring you the rest?

If you're vague about a deadline, ask yourself why. Often it's because you'd have to commit to something too.

Outcome can be as simple as a picture. Years ago we had a shared kitchen and office space that got left differently depending on who cleaned it. Someone finally took a photo of it clean and hung it on the wall. Before you leave, does it look like the picture? It sounds silly, but anyone can answer yes or no.

Authority is where most owners get stuck. If you've never said what someone can decide on their own, or how to bring a decision to you (with three possible solutions, after trying a few things, after checking with a coworker), the safe default is to bring you everything.

A few more habits help. One of our CFOs ends every request with "Is there anything you need from me to get this done?" Most people won't volunteer that on their own. If it's something new and you don't know the standard yet, say so and plan a tight feedback loop for the first couple of weeks. And when you're throwing out half-formed ideas in a meeting, say that too. When the owner says something, the team often hears an order.

The Three Buttons Your Team Can Press

Picture three buttons every person on your team can press: something's broken, I need help, and I have an idea. Each one carries a risk for the person pressing it. How you react the first few times decides whether they ever press it again.

ButtonWhat it risks for themReaction that switches it offReaction that keeps it on
Something's brokenGetting blamed"Who did this? Why didn't you think to do it the other way?""Thanks for bringing that up. Walk me through what you saw."
I need helpLooking like they can't do the job"Don't worry about it, I'll handle it.""What have you tried so far? What do you need from me?"
I have an ideaGetting brushed off"We tried that already. Here's why it won't work.""Tell me more. What would it take to make that happen?"

Even if you have tried that idea before, hear them out. You learn how someone thinks, and you show them that thinking is welcome. Some people won't press a button because of how a past boss reacted, which has nothing to do with you. You may have to model it first by asking for help yourself.

"Your culture is a sum of your reactions."

From this episode of Just Figuring It Out

If you feel like your team never gives feedback, ask yourself how often you ask for it directly. It's usually less than you think.

How Owners Accidentally Train Their Team to Come Back

Most owners don't set out to create a team that can't decide anything. It happens through habits that feel helpful in the moment. Each one quietly switches off a button.

1. Fixing Everything Yourself

"It's faster if I just do it." Maybe it is, today. But when fixing things is always your job, people stop noticing what's broken. Why would they?

2. Rescuing

"Here, let me." Do it a few times and nobody tries first anymore. They wait for you to swoop in. One of us calls his version of this habit saviorism, and still catches himself doing it.

3. Micromanaging

If you hear yourself say you need to "manage" someone, treat it as a signal that you've slipped from trust into obligation. The team's response is predictable: why suggest anything if you're going to redo it anyway?

4. Taking Over Every Idea

Owners are good at ideas and see the whole business from 30,000 feet, so it's easy to take over the room. If you want independent thinkers, let someone carry an idea all the way through and get the credit. Ask yourself honestly if you're okay with that.

When something goes wrong, look inward first. What about my instructions, the outcome I described, or my check-ins didn't set this up to work? That's more useful than deciding the person can't handle it. And remember you may be expecting someone to learn in a week what took you three years to figure out. The habits that got your business here usually won't get it to the next stage.

Coach Instead of Answering

There are four ways to handle a hard thing with someone: say nothing, drop hints, vent to someone else, or say it to them fully and kindly. Most of us stop at the third one. Treat the first three as signals that there's a conversation you're avoiding. A good question to ask yourself: if I couldn't avoid this, what would I have to feel instead?

When something didn't go the way you wanted, this structure keeps it a coaching conversation:

  • Ask what happened. If you hear a lot of defending, they're afraid. Don't punish them for being honest.
  • Say what you see. Share what you noticed, why it concerns you, and your own part in it.
  • Ask what would keep it from happening again. Let them come up with the fix.
  • End with "How can I support you?" Not "How can I do it for you?" They have to say out loud what they need.

When someone brings you a problem that's theirs, hand it back with support. "You've got this. I'm here if you need me, and I know you can figure it out." Ask them to come back with a few possible solutions. They can still ask questions. Your job is to keep pointing back to their ability to solve it.

Over time, the real sign it's working is that your team starts leading this way too, including holding up a mirror to you. That's uncomfortable, and it's exactly what you want. If you don't have a partner who does that for you, find a coach or mentor who will.

Try one this week

Ask completely for something you want. Have the conversation you've been rehearsing in your head. Thank the next person who presses a button, and tell them why. Or let one person carry their own problem while you support them instead of solving it.

Want a Team That Doesn't Need You for Every Decision?

This talk came from one of our live sessions with clients. Our coaching pairs the financial side of your business with the leadership side, so your numbers and your team both get clearer. Let's talk about where yours stand today.

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Frequently Asked Questions

Usually because they were never told what they can decide on their own, or because past reactions taught them it's safer to ask. If an owner fixes problems, rescues people who are stuck, or criticizes mistakes, the team learns to hand everything up. Spelling out decision rights and changing how you respond when people bring you problems is what breaks the pattern.

Start with clear asks that cover the outcome, deadline, standard, reason, and what they're allowed to decide. When someone brings you a problem, ask what they've tried and what they need from you instead of solving it. Ask them to come back with a few possible solutions. Then thank them when they handle something, so they keep doing it.

Notice the moment you want to say "here, let me" and replace it with a question: what have you tried, and how can I support you? Keep pointing back to their ability to figure it out while staying available for questions. It will feel slower and uncomfortable at first. That's normal, and it's how people build the confidence to stop waiting for you.

Quiet meetings often mean people don't feel safe saying what they really think, so the real conversation happens afterward. Look at how you react when someone reports a problem, asks for help, or shares an idea. If any of those has been met with blame or a quick shutdown, people stop speaking up. Ask for feedback directly and thank people when they give it.

Ask for it directly and often, more than feels natural. A simple question like "what was most useful today?" or "what's not working?" opens the door. Then react with gratitude, even when the feedback is uncomfortable. If you share your own mistakes and ask for help yourself, your team is far more likely to do the same with you.

Not entirely, and blaming yourself doesn't help either. But your reactions shape your culture more than anything else, so it's the part you can change fastest. When something goes wrong, ask what about your instructions, standards, or check-ins could have been clearer before deciding the person can't handle it. Then adjust and try again.

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