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How To Lead When Your Boss is a Workaholic

Updated: May 28

The hospital room is sterile, bathed in the cold, fluorescent glow of medical equipment. Johnny lies on the bed, his face ashen, weakened by the bleeding ulcers that have brought him to the edge of life. The rhythmic beeping of the monitors provides an eerie soundtrack to the silence that envelops the room.

At the same time, in his factory across town, the bustling world of business continues, seemingly indifferent to Johnny’s suffering. He is CFO and minority partner in the business. Johnny’s CEO, known for being a workaholic, has just settled into his corner office when his phone rings. Johnny’s wife’s voice trembles on the other end of the line.

“It’s Johnny. He’s in the hospital. The ulcers... they’re really bad,” she says, her voice laden with worry. “He won’t be working for a while.”

The CEO feels a sudden jolt in his heart, a stark reminder of the vulnerability of life. Despite his busy schedule, he knows he has to see his longtime friend and employee. Without a moment’s hesitation, he rushes to the hospital.

As the CEO steps into the dimly lit room, he sees Johnny lying there, weak and fragile. Gently, approaching his bedside, he tries to find the right words to convey his concern. “I’ve never had ulcers,” the CEO begins, “but I hope you get well soon.”

Johnny turns his weary eyes towards the CEO, a hint of a smile tugging at the corners of his lips. “You don’t have ulcers,” he replies, his voice faint but resolute, “but you are a carrier!”

The words hang in the air, heavy with meaning. Johnny’s statement strikes the CEO like a bolt of lightning. He realizes that in his relentless pursuit of success, he unknowingly carries the burden of deadly stress and pressure, infecting those around him with his own intensity.

The gravity of Johnny’s words sink deep into the CEO’s soul, sparking a profound realization. As he drives the company forward, his employees pay the price.

As the days pass, Johnny slowly recovers, and he regularly challenges his boss to converse. They speak about life, happiness, and the importance of finding balance in the chaos of work. His boss begins to entertain the idea that being successful doesn’t have to come at the expense of one’s health and relationships.

With continual input from Johnny, the CEO begins to change his ways. He starts to delegate tasks, slowly trusting his team to handle more responsibility, and encourages a healthier work culture. He prioritizes spending time with his loved ones and learns to cherish life’s precious moments.

Johnny’s words have been a wake-up call, one that saves not only his life but also the CEO’s soul.

Step three in the Cultivating Impact Succession Planning Method is to build your team to maximize impact.

But how do you do that when a workaholic leads your company?

Like with Johnny and his boss, it begins with conversations.

Subordinates who work for a workaholic need to have conversations about the team they are building. Thoughtfully, they must express their concerns and propose a plan for building more self-efficient teams.

It will be hard for the workaholic leader to see how performance can be maintained in a balanced life. To engage workaholics in solutions, wise leaders use non threatening questions. The workaholic will have to be shown–not just told–how this new thing will work. This is not a simple process but a doable win-win for everyone.

Here is an outline for those conversations:

1. Choose the right time and setting: Find an appropriate time when the owner is relatively relaxed and not overly focused on work. Arrange a private meeting away from the office, where both parties can have an uninterrupted discussion.

2. Express appreciation and understanding: Start by acknowledging the owner’s hard work and dedication to the company.

Workaholic entrepreneurs often need this encouragement.

3. What are the concerns that should be addressed? Gently raise the concern that the owner’s constant involvement in every aspect of the business might hinder the team’s growth and ability to take ownership of their responsibilities. Mention that the owner’s constant presence may inadvertently discourage team members from growing.

4. What is the vision? Present the vision of building a strong, empowered team that can efficiently handle their tasks and make informed decisions without the owner being present. Emphasize that this approach will create a more sustainable and productive work environment.

5. Should there be any new training? Outline any training programs that will give the owner added confidence in the team. Mention any specific training sessions or workshops that will be conducted to develop their decision-making abilities.

6. Assure the owner: Reassure the owner that building this self-sufficient team doesn’t mean neglecting the business. Explain that the goal is to create a balance where the team can handle most tasks effectively, allowing the owner to focus on higher-level strategic decisions.

7. Propose a trial period: Suggest starting with a trial period to show the effectiveness of the fresh approach. Encourage the owner to delegate tasks to team members gradually and stay connected with them by offering guidance. Be open to feedback and suggestions.

Challenge the owner to take one day away without calling in or checking their email. After that, challenge them to do it for two days; then three and more. Afterwards, discuss the results. Giving people the chance to succeed and fail is important and inspires growth.

8. Maintain open communication: Stress the importance of ongoing communication between the owner and the team during this time of growth. This ensures that everyone is on the same page and can address any challenges that arise.

Remember, this conversation should be approached with respect and understanding. The goal is to foster a positive and collaborative work environment that benefits both the owner and their teams.

Remember, there is no success without a successor. When your leader is a workaholic, prayerfully look for the time for strategic conversations.

What you are doing is rare, and amazing. Email me at and let me know how you are doing.

Speaking of something that is rare. I am doing something rare! We are offering six free one hour masterclasses on succession planning, based on the proven Cultivating Impact 6-Step Method for Succession planning. You will learn how to:

  • Step 1: Recognize Your Impact Tuesday, September 26, 11 a.m.

  • Step 2: Develop Your Business as Mission Tuesday, October 10, 11 a.m.

  • Step 3: Build Your Team to Maximize Impact Tuesday, November 14, 11 a.m.

  • Step 4: Exchange the Baton Tuesday, December 12, 11 a.m.

  • Step 5: Multiply the Impact Tuesday, January 9, 11 a.m.

  • Step 6: Finish Well Tuesday, February 13, 11 a.m.

You can reserve your spot in the first class, Tuesday, September 26, 11 a.m. EST now. The masterclasses are free, my gift to you. Space is limited. You can sign up for the first class now here.

I believe in you!

Harry T. Jones

P.S. While you are thinking about it, CLICK HERE to sign up for the first of my six-part masterclass, Tuesday, September 26, 11 a.m. EST, on The Six Steps to Succession Planning.

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