Are You a “Should-Head”? The Danger of Giving All the Answers

September 12, 2025

“Great leaders don’t tell you what to do. They ask you what you think.” – Coach John Gallagher

Happy Friday, Brew Nation!

Public speaking is consistently ranked as one of the world’s greatest fears, but for leaders, there’s a different kind of fear we need to face: the fear of silence. The fear of not having the answer, of not being in control. This can turn us into “should-heads.”

What’s a should-head? It’s a leader who, when a team member comes to them with a problem, immediately says what they “should” do. Instead of trusting their people to think for themselves, they jump in and provide the solution. This happens for a couple of reasons. Maybe you think it’s faster just to give them the answer. Or, in the worst-case scenario, you feel they couldn’t come up with a solution as good as yours.

The result is that the individuals you hired to make a change in your organization become passive. They learn not to think because they know that if they just bring a problem to you, you’ll make the decision for them. It takes all the risk off of them. If something goes wrong, they can simply say, “Well, you told me I ‘should’ do it this way.”

I love the illustration of a former CEO who told his team not to bring a bag of dog poop into his office and put it on his desk. Instead, they could bring a problem, but they also had to bring two or three ideas about how they believed it could be solved. This simple rule forces people to take ownership and responsibility.

The most powerful tool a leader has is not a command, but a great question. You have to be willing to give your team the space to answer. If you don’t, you risk creating a workplace where people simply wait for you to tell them what to do, and that is a surefire way to stunt the growth of both your people and your organization.

The Coach’s Questioning Method

This shift from “should-head” to coach doesn’t happen overnight. If you’ve spent a lifetime giving all the answers, the first step is to admit that you’re a “should-head.” Then, you need to be aware of when you’re about to do it and stop yourself.

Here is the coaching or questioning method I work to employ myself and teach others to use when they bring in a problem:

What is the target? Help them clarify the desired outcome.
Where are you today? Encourage them to define the current state and the gap between where they are and where they want to be.
What is the biggest thing standing in your way? This gets them to identify the primary barrier to progress.
What’s one thing you can do to eliminate that barrier? This forces them to come up with their own first step.
When can you show me? This is the accountability piece, which puts the responsibility back on them.
How can I support you? This is the crucial final question. It shows them you’re on their side, but it doesn’t take the problem off of their plate. You’re offering a hand, not an answer.

The Jesus Principle: The Master of Questions

If you want to learn from an expert in this method, look no further than the New Testament. Jesus asks 307 questions. He is asked 183, of which he only answers 3. Asking questions was central to Jesus’ life and teachings. In fact, for every question he answers directly, he asks—literally—one hundred.

It would seem the questions Jesus asked were far more important to him than the answers he gave. When we look at the questions Jesus asked, we see that he is helping the people he’s interacting with evaluate their lives and set a better course. Answers are overrated. We think we need them, but in many cases, they don’t give us what we’d hoped. He also seemed to be more interested in questions than answers. When people asked Jesus a question, he often gave them a question back. In fact, he hardly ever gave a direct answer to anything. Jesus liked to share his thoughts through parables that required his audience to go away and figure out the answer for themselves. He was undoubtedly the ultimate “anti-should-head.”

Ultimately, your task is to grow leaders. And when you simply tell them what and how to do things, they do not grow, and your team’s performance will be stunted. Your job is to be a mentor, not a crutch.

Quote of the Week

“Good leaders ask great questions that inspire others to dream more, think more, learn more, do more, and become more.” – John C Maxwell

Being effective as a leader means consistently choosing discipline over distraction. It’s about deeply reflecting on what’s working, humbly learning from what hasn’t, and courageously course-correcting in relentless pursuit of uncommon growth. Leaders don’t just drift into success—they evaluate, decide, and act. At Growing Champions, we equip leaders with the precise tools and vision to do just that—because real leadership is about consistent, deliberate alignment between your values, your habits, and your desired outcomes.

What’s a leadership lesson you’ve learned in an unexpected place?

Email me at coachjohngallagher@gmail.com with the subject line “ANSWER” and share your story. I’m excited to read all your messages!

What you need to do:

Your Call to Action: Ditch the “Should” and Ask

The biggest barrier to growth is the one we allow ourselves to build. It’s time to take ownership of your personal and professional development by mastering the art of coaching.

Do you want to become a Champion of empowerment? Are you ready to stop being a “should-head” and start developing the leaders around you? This week, when a team member brings you a problem, instead of giving them the answer, use the six questions above to help them find their own solution.

You’ve got the time. You’ve got the tools. Now it’s time to make this year your most intentional, inspiring, and uncommon year yet.

It’s an honor to be your trusted Friday Coffee Guy. Each week, I bring what I’m learning and living in the trenches of leadership. If this edition challenged or encouraged you, share it with someone who leads, stays faithful, or learns alongside you, then click subscribe. Let’s grow Brew Nation together!