Key Insights From “Good Leaders Ask Great Questions”

Artem Gurnov
Apr 12 · 9 min read

Growing as a leader means constantly challenging yourself to help raise your team to even greater heights. For my own self-improvement, I’m always on the hunt for books — which, unfortunately, often don’t draw a distinction between leadership and management. Many of these books have general information on what makes a leader, but supplement it with examples of management. Although the information is valid, it doesn’t always correlate with what’s expected from a leader.

Since the early days of my professional career, I felt that there was a big difference between leadership and management and that the latter has very little to do with titles. That’s why I started looking for authors who had personal experience with not only being a leader but also with developing a new generation of leaders.

Recently, I found a book by John C. Maxwell who checked all the boxes I was looking for. He has several decades of experience in developing leaders and helping them be the best at what they do. The book is titled “Good Leaders Ask Great Questions.” Here’s a list of insights I noted when reading it.

  1. Asking the right questions is more than half the battle

My manager helped me understand this one. Most of the time when I’m stuck and need assistance, instead of offering solutions she asks questions. Honestly speaking, it took some time for me to get used to this piece of advice, but now I greatly appreciate it, since I’m able to approach any problem from different angles and come up with creative solutions. I try to replicate this approach with my team members — when they ask for help I start with asking the right questions to help them get to the solution themselves.

2. When you’re stuck, ask yourself these 3 questions

  • Why do we have this problem?
  • How do we solve it?
  • What steps should we take to solve it?

It’s important to go back to the first question to confirm that your initial answer is still valid. No, “We do it because we always did it like this” isn’t a good reason. This three-step approach will help you move beyond a surface-level understanding of the problem to its root cause and how to solve it. As someone who loves breaking down complex problems into simple checklists, this approach is definitely something that resonates with me. It’s also critical that these questions are asked in time. Fixing a problem that’s likely repeatable results in duplicate work. It can also be difficult to come up with a step-by-step solution without a general understanding of the problem, and dissention on an exact plan can either delay a solution or even make it impossible.

3. Invite the right people to your brainstorming workshops

In a brainstorming workshop, no idea is considered “bad.” But imagine how much more productive the process would be if most (or all) attendees had the right expertise to tackle the problem. That means you’re more likely to get to a working solution easier, faster, and with more confidence. So, asking the right questions is important, but make sure you’re asking the right people, too.

4. Miscommunication is rooted in assumptions

Many of the mistakes I made in my early days as a customer success manager (CSM) were due to making incorrect assumptions. This often led to wasted time during my client calls and less value for my clients. I learned this the hard way, so I do my best to help my team avoid similar mistakes. Maxwell emphasizes that asking simple questions at the beginning of any conversation — from discussing project details to delegating responsibilities to your team — reduces the likelihood of miscommunication by a significant margin.

5. Successful people ask better questions and get better answers

A core idea throughout the book is that asking questions is a skill that can be trained and, as a result, improved. Great questions can open new perspectives and get people thinking. I loved the example that Maxwell shared about a question that his colleague once asked him, “Why do you write books?” What seemed like a simple question challenged him to dig deeper into his motivations. After some time he replied, “I write books to influence people that I’ll never meet!” I completely agree that a leader can help their team learn effective questioning. We actually do group practices on discovery questions from time to time, which helps everyone better understand their clients’ challenges and what tailored solutions to offer.

6. Ask this question every day: “How can I make my team better?”

Continuous growth helps teams deliver amazing results in an ever-changing environment. While you may have outstanding talent on your team, it’s your job to help them identify areas to improve, so they can do the best work of their lives. It can be something major like a change in work processes or something minor like giving the team an extra day off after finishing a complicated project. You can also help the more stressed team members by enrolling them in training/coaching courses to boost their confidence in areas that they want to work on. And, going back to #4, don’t make assumptions. Ask your team for their opinions on what can be done to make things better.

7. Know what your team’s strengths and weaknesses are

A big part of being a leader is doing everything in your power to help your team succeed and, crucially, putting the right people up to the task. But how do you define who’s “right” for a specific type of job? Obviously, when a team member has more expertise in a certain area, it’d make sense to leverage their experience. Now, how do you find out your team’s strengths and weaknesses? Sometimes just asking them about their previous experience is the easy answer, but according to Maxwell, there’s no better way of finding out than getting them to try new things — a lot of them. You may realize that one team member is good at preparing analysis while another does an amazing job with presenting the results in an engaging way.

8. Take care of relationships today and you’ll be successful tomorrow

Business success comes from the relationships you build with your clients, partners, and — of course — employees. A relationship takes time and effort to build and maintain, which means that to reap the rewards of a meaningful relationship tomorrow, you first need to commit the effort it takes into building it today. Take care of your team members. Treat your clients with respect. That’s the recipe for success.

9. The greatest result a leader can achieve is another leader who takes their place when they’re finished

Maxwell emphasizes the importance of growing leaders internally with the necessary skills, knowledge, and experience to eventually take over your position. Many people tend to exaggerate the second part of the statement and worry too much that these young leaders will take over earlier than they expect. But as long as your team is happy about what they do and achieve amazing results under your leadership, the probability of that happening is close to zero. Also, according to Maxwell, a leader needs to understand when it’s their time to leave the team and/or organization in good hands.

10. Pay attention to your listening skills

Maxwell presents three levels of listening and highlights the importance of continuous development and growth to attain the third level. The three levels of listening are:

  • Internal listening: The most important thing for internal listeners is how they’re affected by what the other person says and what it means for them.
  • Focus listening (also called emotional intelligence listening): The most important thing is what impact their reaction will have on the speaker. People who are focus listeners are usually good conversationalists and friends.
  • Global listening: Those who are global listeners are intuitive and mindful of action, inaction, and interactions between people and the environment.

11. Listen to the answers you receive

When you listen to others you demonstrate that you value their opinion. Listening to new perspectives can lead to a learning opportunity, so make sure you don’t interrupt the person you’re speaking to. Interrupting them sends a message that you believe what you’re saying is more important than what they’re saying.

12. “What do you think?” is a great opening question

Being able to come up with insightful questions that can guide your team member to find the solution on their own is an amazing skill. However, in many cases, it’s fine to keep it simple and ask, “What do you think?” It doesn’t influence the person you’re talking to one way or another — you’re simply asking for their opinion. As a result, they won’t be concerned about providing the “wrong” answer, but instead, they’ll share their unbiased perspective, which may be an eye-opener for you and your team.

13. Decisions should be made as close to the problem as possible

Usually, upper management (e.g., C-level executives, VPs, and directors) has a great understanding of the company’s processes and challenges, which helps them make informed decisions. However, they can’t be expected to know every detail about their teams’ minute-to-minute activities. So, to make important decisions, they need to gather these details by speaking directly to team members who have a closer experience with the problems on hand. While this can be done, it’d require additional time, which is always a limited resource. That’s why Maxwell recommends delegating the decision-making process to team members who are as close to the problem as possible. Of course, they should also be encouraged to ask upper management for input, if necessary.

14. People who wait for one great opportunity often keep waiting

What’s the key for finding a great opportunity that has the potential to change your and your team’s careers, or even the entire organization? Some people may say that it’s all luck and timing. While some indeed get lucky, anyone can find more opportunities by putting themselves out there. The “do nothing” scenario won’t get you anywhere, but being willing to experiment and innovate has the potential to net you a big win.

15. Successful people practice daily

To achieve amazing results, successful leaders implement daily routines into their lives. They’re not doing anything completely unique; they simply have the discipline to commit to daily practice. So if you’re not there yet, the first step is to identify the daily practices that will help you achieve your goals, and then do them! And a general habit that Maxwell recommends is keeping a positive attitude.

16. You don’t need a title, position, or formal education to lead

Many people tend to associate leadership with a title. While it’s true that many leaders do have a title, not every person who has a title is a true leader. Maxwell states that leadership starts with influence, which in due turn is a choice. You can choose to care about people and try to positively influence them. And at that point, you’re already showing leadership material.

17. You either delegate tasks or dump them

Delegating is giving your team members tasks with a clear explanation of what needs to be done and how. It doesn’t mean that you need to provide detailed instructions within multiple pages of steps. But it does mean that you should be capable of performing the task yourself, and help out if needed. “Delegating” work that you don’t know how to do yourself (especially with a dismissive comment such as, “Figure it out”) is called dumping. Take into account your team’s skills and interests, which will guarantee high-quality work, since your team members will actually be passionate about them. Now, how do you figure out when it’s a good time to delegate? Maxwell provides a simple tip: If someone in your team can do the task at 80% of how you can do it, you shouldn’t be doing it yourself anymore.

18. It’s OK to operate in some uncertainty

In many books on management, we often encounter the idea that if you have 100% of the information, you’re already late. You need to decide internally what level of ambiguity (and risks associated with it) would be acceptable for you to operate in. What you can’t afford as a leader, though, is being unclear. You always need to be able to communicate to your team members why you chose that route, what they can expect, and that they have your full support.

I hope that this list of insights motivated you to read “Good Leaders Ask Great Questions” and learn even more valuable takeaways.

CX@Wrike

Customer Experience in Wrike

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