***This article is inspired by chapter 5 of “Leadershift” by John C. Maxwell – “Pleasing People to Challenging People” ***

Leadership is about people. Regardless of what business you’re in, you’re in the people business. If you don’t like people, then you’re better off staying away from leadership roles because “people issues” dominate the time of leaders. And every person is different, so you must learn to customize your leadership to fit the personality and needs of each of your followers.

One temptation most leaders face is to be a people-pleaser in order to keep everyone happy. The truth is that it’s rare for everyone to be happy. And the happiness of everyone doesn’t equal organizational success. Leaders are responsible for specific outcomes. These outcomes must be done with and through the skills of others. Leaders can’t control the emotions of their people and make them happy, but they can control the skill of challenging people to grow and perform at their best.

If you find yourself falling into the people-pleasing trap, how do you get out and become a leader who courageously challenges your followers to succeed?

Consider John C. Maxwell’s 7 tips on how to shift from pleaser to challenging leader:

1 – Change Your Expectations Toward Leadership

Begin with realizing that you can’t be everyone’s buddy. In fact, as leaders are promoted, some of their relationships can sour with coworkers who now view them differently. That’s normal, but not always easy to deal with. Leadership can be lonely at times. Your relationships with people who once talked with you as a peer may now treat you differently. It’s natural, so expect it.

Realize that leaders are responsible for sharing the vision, raising the bar, challenging others, showing the way, asking for commitment, and taking courageous action with or without consensus. If people don’t want to move into the future with you, let them go their own way without expending your precious time and energy trying to win them back. Your job is to help your people succeed, improve the organization, and achieve the vision.

2 – Value People as Much as You Value Yourself

To get the best out of your followers you must believe the best about them. If you devalue yourself, you will probably devalue others. You must develop self-confidence and self-worth and then pass that along to those you lead. When you value people and they know it, they will work diligently to assist you to achieve the vision of your team or organization. If you devalue people and make them feel like they’re simply a means to an end, they will not perform at their best nor will they help you be successful. People matter, so make it a priority to express regularly that you care and recognize how important their contribution is.

3 – Work to Establish Expectations Up Front

Unmet expectations are often the cause of damaged personal and professional relationships. Assumptions can be deadly in any environment. They almost always lead to unfulfilled expectations and create disappointment. In order to establish healthy expectations, make it a habit to have clear up-front conversations that get everyone on the same page. When things get off-track, work to regroup and reset expectations. This is not a one-time effort, but must be continually reinforced. This is why consistent one-on-one touch-base meetings and reviews are important. The more you meet face to face and deal with real-time issues, the better. An annual review is not enough. It can be a great tool to set goals and review overall growth and performance, but it is inadequate to stay on the same page with your followers. Commit to consistent face-to-face meetings so you can address challenges and take advantage of opportunities in real-time. These upfront expectation-setting conversations will save you much heartache and frustration long-term.

4 – Ask Yourself the Hard Questions Before Any Potentially Difficult Conversation

This is where many leaders fall down on the job. It’s easy to lead when everything is going smoothly, but our leadership mettle is tested when we must have difficult conversations about performance issues. In order to prepare well, ask yourself the hard questions to understand the situation best so you can address it well. Determine what the problem is, what the source is, and then evaluate your engagement level with the person you must address. Have you invested in the relationship? What part of the problem is your fault versus theirs? How can you resolve the issue together? Are you clear on your expectations and ready to express them in a conversation? Do the upfront work of preparation so you can make the difficult conversations as peaceful and effective as possible.

5 – When a Tough Conversation is Needed, Do It Right

This step piggy-backs on #4. Remember that the person you’re confronting is a valuable individual. Care enough to confront them in a healthy way and then commit to helping them overcome their challenges to be successful. They must do their part in the end to address problems, but you must commit ahead of time to helping them as they need. One option is to replace people who make mistakes, but the more challenging (and most rewarding) option for leaders is to invest time, energy, and resources into people to become better. Use wisdom in how you handle the tough conversations. If you attack, expect people to be defensive. If you approach situations with a coaching and problem-solving mindset, great outcomes are possible.

6 – Understand the 25-50-25 Principle

Leaders naturally want everyone to be on board with their vision and decisions, but it’s unrealistic to believe that everyone will be. When you expand an old vision or cast a new one for the future, you will have various responses. Some people are early adopters. Some are late adopters. Others are resistors and will need to move on. This principle states that 25% of people will support your efforts, 50% will be undecided, and 25% will resist change altogether. People are all wired differently. As a leader, your job is to help the middle 50% join the first 25% and accept that the bottom 25% rarely will join you. That’s when you’ll need to make difficult, but necessary decisions to help them transition to other areas of the organization or leave for a better fit somewhere else.

7 – Balance Care With Candor

Care without candor creates dysfunctional relationships. Candor without care creates distant relationships. Care balanced with candor creates developing relationships. Consider the following aspects of both care and candor:


  • Values the person
  • Establishes the relationship
  • Shores up weaknesses
  • Offers comfort
  • Makes the team pleasant


  • Values the person’s potential
  • Expands the relationship
  • Brings out strengths
  • Offers a challenge
  • Makes the team productive

As a leader, both care and candor are vital. How you communicate to each person needs to be filtered through their personality type and how they best receive information. If you will take the time to care for the person before there are challenges or problems, then being direct with them is built on a solid foundation of trust that creates respect and motivates the person to respond positively.

Leadership is both hard and rewarding simultaneously. If you will learn to shift from pleasing people to courageously challenging them to grow and do their best, everyone can win – you, your followers, and your organization. That’s the best-case scenario that all leaders should strive to achieve.

You can make this shift. I believe in you.

Until next time…make today GREAT!

P.S. If you’d like some help with navigating personal or professional challenges and opportunities, click HERE to learn about my coaching services.

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