Four Questions for Leaders to Ask Themselves


I’m pretty sure Socrates would’ve liked my friend Jason Hodges.  

As you may recall, the Socratic method is named after the Greek philosopher who trained his followers to become critical thinkers—not by lecturing, but by asking questions. His queries exposed weaknesses in a person’s thought process and guided them into a more solid assessment of reality—and themselves.

Once a month, I’m blessed to sit down with a group of fellow StratOp facilitators (StratOp is our mutual methodology for strategic planning). As peers in strategic planning facilitation, we gather to encourage and challenge each other with new ideas and best practices. At a recent meeting, Jason Hodges shared four pointed questions that he said have changed him as a leader.  

As a coach, I spend a lot of time asking my clients questions. I do this to help build rapport and trust, while uncovering issues we need to address. 

However, after hearing Jason, I realized I don’t ask myself nearly enough questions—at least not the important, potentially awkward kind. Jason has graciously allowed me to feature his ideas in my blog. So, in the spirit of “Physician, heal thyself,” here are four big questions for leaders (including me) to ask themselves.

1. What’s It Like to Be on the Receiving End of Me?

I’ll be honest, I don’t like this question. That’s because I like to think I have it all figured out and that I deliver every comment and critique with grace and poise. I like to picture myself as a beacon of clarity and wisdom for all to enjoy. The reality is, though, I often stumble and misfire when communicating, especially with those I love. 

This is a great question to ask of others and solicit their honest feedback. Check with your spouse, children, colleagues, clients, and neighbors. If you’re a leader, check with those who report to you. If you’re a presenter, check with your audience. 

Personally, I was recently told that I often come across as intimidating. Now that I’ve heard this, I have a choice: I can ignore it, or I can seek to soften my delivery. (I’m thinking the second option will lead to better outcomes…whaddya think?)

Monitor yourself and evaluate your style of interaction. What’s it like to be in a meeting you run or on the other end of a phone conference with you? What’s it like to bump into you in the hallway or see you walk in the door? Do the people you do life with feel that you’re genuinely interested in them or that you’re indifferent? Do you come across as caring or cold? Compassionate or self-absorbed? 

Most of us have good intentions, but too often our outward behaviors don’t line up with our inner feelings. Watch your body language, tone of voice, and choice of words. They can make a huge difference in how you’re perceived.

2. Who Do I Need to Call Today?

I really needed this question. Throughout each day, the names and faces of countless people in my life pop in and out of my thought process. When they do, I nearly always feel an immediate urge to connect with them. But I seldom do. Again, I have good intentions, but I don’t follow through. I make a mental note to reach out, but because I’m so good at procrastinating, weeks and months can go by before I act on it.  

Maintaining and nourishing relationships is very important. I get that. And the truth is, I really, truly enjoy doing it! But much of the time, I feel like I’m just too busy (or at least I’ve convinced myself I’m too busy) to take a few minutes off and simply call or text. 

What makes this deficiency especially ironic for me, is that I often share the concept of the Five Capitals with my clients. As you may know, the second capital is relational capital. It’s defined as the quality and depth of your connection with other people in your life, measured in influence and impact. 

So, I have to ask myself, “Could I build more relational capital simply by making a call?” The answer is yes. This simple five-to-10-minute task could be a huge blessing to the one I call. That’s especially true in this season of quarantine and isolation. We never know what someone else is going through, and a text or email might make a world of difference. Just a quick call saying, “I’m thinking about you, and I’m always here if you need to talk” may be all they need to push through a tough day.

Next time you get the fleeting urge to contact a friend, relative, or associate—do it. Try contacting one different person a day for the next 30 days. The world will be a better place, and you’ll be a better person—and a healthier one. Connecting with friends via phone or video chat can actually reduce stress and relieve tension.

3. Am I the Best Person to be Doing This?

Mozart could have tuned his own piano. Rembrandt could have mixed his own paints. But devoting their time and talent to creating masterpieces was a better decision. 

The lesson is clear: Just because we can do something doesn’t mean we should. 

If you’re gifted in more than one area, this will be an uncomfortable question. If you love multitasking and “covering all the bases,” you’ll be tempted to skip it. It’s easy and habit-forming to spend your valuable (and limited) time on things that—although they are important—can be delegated to others. 

I recently introduced a client to the Eisenhower Matrix, a framework for determining the most effective way to get things done. One of the quadrants in the matrix forces you to ask, “Who else can do this?” At first glance, it might seem like a ploy to avoid doing tasks we don’t enjoy. Not at all. This is not designed to offload things we don’t want to do onto our minions. Instead, it’s an honest question that should drive us to focus on leveraging our strengths and using delegation to develop skills within our staff. 

If you don’t release tasks or projects to team members, you’ll not only be wasting your own time, you’ll also be stunting the professional growth of your followers. 

As leaders, we need to be continually re-evaluating the importance of our tasks, and be sure we’re spending time on things that matter most. An article in the Harvard Business Review says, “Research indicates that knowledge workers spend a great deal of their time—an average of 41 percent—on discretionary activities that offer little personal satisfaction and could be handled competently by others.”

By the way, as we think about assigning tasks to others, we should be asking the same question about them: “Are they the best person to be doing this?” This approach will make sure that everyone is fulfilled and energized by the work they do.

In a perfect world, we’d only do work we’re uniquely gifted to do—work that brings a sense of well-being and job satisfaction. But this is real life. In the meantime, look at each of your daily activities and decide which ones you can drop, delegate, or outsource. Stop clinging to work out of habit or because it makes you look busy or feel needed. 

As Queen Elsa sings in Disney’s Frozen, “Let it go.”

4. What Can I Do to Help?

Please notice this is not a yes or no question; it’s open-ended. 

We’re intentionally not asking, “Do you need any help?” When you frame it that way, 99 percent of people reply, “Nope, I got it.” It’s a conditioned reflex. A social norm. 

For some reason, people are wired to decline help even when they obviously need it. Maybe it’s pride or self-sufficiency. But if we present our offer to assist as an open-ended question, it gently compels people to identify places where we can help. 

Instead of being a rhetorical question that elicits an automatic answer, this different wording reveals our true motive (eagerness to help) and our true attitude (genuine concern). It helps people open up enough to admit they could use some help.

Most importantly, it casts those in management in the role of “servant leader,” which is the best position for any boss to be in. People naturally follow and commit themselves to leaders who serve versus leaders who demand to be served.

As a bonus, helping others often benefits you—emotionally and fiscally. Verbally volunteering to help others reinforces unity on the team and reminds every member that they’re all working together toward a common goal. And that breeds success. 

After Jason delivered these four gems, he followed up with two Bonus Questions:

  • Which of these four do I need to ask myself more often? 
  • Which of these four am I currently asking well?

In his 1936 classic How to Win Friends and Influence People, Dale Carnegie wrote, “Ask questions the other person will enjoy answering.” Today, I’m going a step beyond that advice: Dare to ask yourself questions you may not enjoy answering. 

Here’s the challenge: Ask yourself Jason’s questions daily, or at least weekly. Ask sincerely, answer truthfully, let the chips fall where they may. There’s no point in fibbing to yourself or sugar-coating your answers! 

Talk candidly to that person in the mirror, and join me in a little self-discovery homework. It just might have a powerful effect on how we lead.