I used to be the guy with all the answers.
Team member hits a roadblock? I’d swoop in with the solution before they finished explaining the problem. Someone struggles with a client issue? I’d take over the call. New process causing confusion? I’d just handle it myself.
Felt productive. Felt like leadership. Felt completely wrong.
Here’s what actually happened: I created a team of professional question-askers. Every decision, every challenge, every tiny hiccup sent them straight to my office. Zero growth. Maximum dependency. And me? Working 70-hour weeks because I’d become the bottleneck for everything.
The worst part? I knew better. But watching someone struggle when you have the answer feels like watching someone use a manual can opener when you’re holding an electric one.
Stop it.
Your need to be helpful is killing their development.
Why we can’t help ourselves
Let’s be honest about why this happens.
First, it physically hurts to watch inefficiency. When you see someone taking three hours to do something you could knock out in 20 minutes, every fiber of your being screams “JUST LET ME DO IT.”
Second, we’re rewarded for having answers. Our whole career progression probably came from being the person who solved problems fast. That dopamine hit from fixing things? Addictive.
Third, there’s ego involved. Being the expert feels good. Having people need you feels important. Admitting someone else might find a different (maybe better) solution challenges that identity.
And fourth, short-term thinking rules. Letting someone fail today means slower progress today. Never mind that it means faster progress forever. We optimize for this quarter, not next year.
BTW – this is where even experienced leaders stumble. They intellectually understand delegation but emotionally can’t handle the messy middle part where things aren’t perfect.
Signs you might be holding the team back
Before we go further, let’s get honest. These behaviors mean you’re probably the problem:
- You’re exhausted but can’t let go of control
- People ask for help before they even try
- You dread taking time off because no one else can handle things
- You say “It’s faster if I do it” more than once a week
- Your 1:1s are mostly you talking
- Every decision still routes through you
- You’re proud of being “the person with all the answers”
Recognize yourself? Good. That’s the first step.
How do you stop being the bottleneck as a leader?
I used to track my “helpful” interventions. Averaged 20+ per day. Each one trained someone to need me more.
Every time you jump in with the solution, you teach your team that thinking is optional. Why develop problem-solving skills when the boss will provide the answer? Why take risks when playing it safe and asking for help gets rewarded?
You’re not building leaders. You’re building really expensive task-executors.
I’ve seen this pattern destroy companies. Not dramatically, but slowly. The founder/CEO/leader becomes the single point of failure. Every decision routes through them. Growth stalls because the leader’s capacity becomes the company’s ceiling.
Vacation? Forget it. You’ll spend the whole time on calls because no one can function without you.
Promotion opportunities? What’s the point? You haven’t developed anyone capable of stepping up.
Scaling? Impossible. You can’t clone yourself, and you’ve trained everyone to need you for everything.
The irony kills me. We think we’re being good leaders by having all the answers. We’re actually being terrible leaders by preventing anyone else from developing answers.
What’s the right way to let your team fail?
Letting people fail doesn’t mean throwing them off a cliff and yelling “figure it out!” That’s not leadership. That’s abandonment.
Here’s the approach I use now, after learning this lesson the painful way.
Start with stakes assessment
Not all failures are created equal. Before you decide to let someone struggle, ask yourself:
What’s the worst realistic outcome here? Lost time? Unhappy customer? Damaged relationship? Legal issue? Understanding the stakes determines your involvement level.
Low stakes = let them own it completely. High stakes = stay closer but still don’t solve it for them.
Master the art of questions (with examples)
When someone comes to you with a problem, resist the urge to solve. Instead, become curious. Real curious, not fake “I’m asking leading questions to get you to my answer” curious.
What most leaders say:
- “Here’s what you need to do…”
- “The answer is obviously…”
- “Just do X, then Y, then Z”
- “Let me handle this for you”
- “I’ll show you how it’s done”
What to say instead:
- “What have you tried so far?”
- “What’s your instinct telling you?”
- “If you had to decide right now, which way would you lean?”
- “What information would help you feel confident about the decision?”
- “Walk me through your thinking on this”
The magic happens when they realize they had the answer all along. That builds confidence in a way your solution never could.
Set clear boundaries upfront
People need to know when they can struggle and when they need help. I tell my team:
“I want you to own this completely. Try everything you can think of. But if you hit X point, or if Y happens, loop me in immediately.”
This removes the guesswork. They know they have permission to fail but also know when to escalate.
Create learning loops, not failure spirals
The difference between productive failure and destructive failure? The learning that happens afterward.
BTW – none of this works if your team thinks failing means getting fired. They need to know it’s safe to struggle. Without that foundation of psychological safety, they’ll keep playing it safe and asking you for every answer.
When something goes sideways (and it will), schedule a real debrief. Not a blame session. A genuine exploration of what happened and why.
“Walk me through your thinking.” “What would you do differently?” “What did this teach you?” “How do we prevent this specific issue next time?”
Document these lessons. Share them with the team. Turn individual failures into collective wisdom.
When should a manager step in during failure?
The difference between productive struggle and drowning is subtle but critical. Miss the signs and you’ll damage confidence instead of building it.
Healthy struggle looks like:
- Trying multiple approaches
- Asking clarifying questions about goals, not solutions
- Showing frustration but not defeat
- Making progress, even if slowly
- Learning from each attempt
Drowning looks like:
- Complete paralysis
- Same failed approach repeatedly
- Emotional breakdown or withdrawal
- Missing critical deadlines
- Impact spreading to other team members
When you see drowning signs, don’t take over. Step in with scaffolding. Provide one piece of direction, not the whole solution. Give them a boost, not a rescue.
The mindset shift that changes everything
Here’s what finally clicked for me: My job isn’t to have all the answers. My job is to build people who can find answers.
That means redefining what good leadership looks like. It’s not about being the smartest person in the room. It’s about making everyone else smarter.
It means celebrating different solutions than yours. When someone solves something in a way you wouldn’t have? That’s not threatening. That’s exactly what you want.
It means getting comfortable with messy. Their first attempts will be rougher than what you could produce. Their second attempts will be better. Their tenth attempts might surprise you.
Most importantly, it means playing the long game. Yes, letting people fail their way to learning takes longer initially. But compound interest applies to skill development too. Six months from now, you’ll have a team that solves problems instead of a team that reports problems.
Common objections (and why they’re wrong)
Every time I share this approach, I hear the same pushback. Here’s why these objections don’t hold water.
“But my industry doesn’t allow for mistakes.”
Really? Every decision in your company is life-or-death? I call BS. Even in healthcare or finance, there are low-stakes areas where people can still learn. Start there.
“My team doesn’t want this responsibility.”
That’s learned helplessness talking. They don’t want it because they’ve been trained that you’ll handle the hard stuff. Start small. Build confidence. Watch them change.
“We don’t have time for people to learn.”
You don’t have time for them NOT to learn. How much time do you waste being the bottleneck? How much time do you lose when key people leave because they’re not growing?
“I hired junior people who need guidance.”
Guidance isn’t giving answers. It’s helping them develop their own answers. Even junior people can own decisions appropriate to their level.
Making it real: Your first week
Ready to try this? Here’s your week one action plan for shifting from solving to coaching.
Monday: Track every question you answer. Just observe. Notice how many could have been figured out without you.
Tuesday: Pick one low-stakes decision someone brings you. Instead of solving it, ask “What would you do if I wasn’t here?” Then let them do that.
Wednesday: Identify one process or area where you’re the bottleneck. Choose someone to own it. Give them context and constraints, not solutions.
Thursday: When someone brings you a problem, wait 10 seconds before responding. Often they’ll answer their own question in that silence.
Friday: Debrief with someone who struggled this week. Focus on what they learned, not what went wrong. This is where real coaching happens.
Small steps. Low stakes. Building the muscle.
The path forward
I still catch myself wanting to jump in with answers. The reflex doesn’t disappear. But now I recognize it for what it is: short-term thinking disguised as helpfulness.
Every time I bite my tongue and ask a question instead of giving an answer, I’m investing in my team’s future capability. Every time I let someone struggle through to their own solution, I’m building a leader.
The shift from “I have all the answers” to “My team can find the answers” transforms everything. Meeting dynamics change. People come prepared with solutions, not just problems. Innovation increases because different perspectives get space to develop.
Best part? You get your life back. When your team can think for themselves, you can actually take vacation. You can focus on strategy instead of tactics. You can work on the business instead of in it.
That team member who used to need your input on everything? They’re now mentoring others. The person who was scared to make decisions? They’re confidently owning entire projects.
And you? You’re finally doing the job of a leader: building more leaders.
That’s the lesson I learned the hard way. Sometimes the best thing you can do for someone’s development is to let them fail.
Even when it hurts to watch.
Especially when it hurts to watch.
Because that’s where the real learning lives.
