Think Like the Boss to Become the Boss
People need things from the boss. They show up to ask, explain, and justify. You want the boss to support you. Learn to think like the boss so you can thrive.
Dig deeper than polite conversations and task lists. Understand their expectations, preferences, and needs. Your success hinges on theirs.
Learn to think like the boss:
#1. Watch the boss work.
Learn their habits, routines, and interaction styles. Pay attention to their tone in meetings, how they respond to challenges, and how they make decisions.
Don’t be the person who frustrates higher-ups. Notice when the boss bristles. Avoid those behaviors.
You build a foundation for mutual success when you think like the boss.
#2. Have wooden toothpicks ready.
Show up thinking about your boss’s needs.
Captain Mark C. Fava Ret. was an Admiral’s aide part of his career. He writes about wooden toothpicks in, “Lessons from the Admiral.”
The Admiral’s aide that Mark replaced handed him three individually wrapped wooden toothpicks. Sam briefed me, “When the Admiral finished a meal, he would sometimes ask for a wooden toothpick.”
Toothpicks might be irrelevant, but how does your manager like to work? What communication method works best? What causes frustration?
#3. Adopt your leader’s priorities.
List your boss’s top three priorities. If you don’t know, ask. Include one priority about their career. Ask, “What does success look like to you?”
Don’t wait for clarity—seek it.
Think about what the boss prioritizes and focus on things they care about.
#4. Learn from others.
Seek insights from people who have worked with your manager. Ask about her work style and what has helped her succeed. Secondhand observations expand your understanding.
I can always spot people ready for advancement. They think like the boss.
How can you think like the boss today?
What concerns you about the ideas in this post?
Thank you to Captain Mark C. Fava Ret. for sending me a copy of his new book, “Lessons from the Admiral.” The ideas in this post are inspired by his work.




This post does not resonate with me. I feel that it is asking the reader to be a professional kiss up to the boss. That person, who “thinks” like the boss will get promoted and move up – and that is why we have so many failed leaders and managers.
Thanks for jumping in today, Andrew. I thought it might rub some the wrong way. We all adapt to others. It’s impossible to live in any community without surrendering something.
It’s a mistake to equate adapting to incompetence. Although you are right. Some incompetent people earn promotions because they kiss up. Don’t reject adapting because some bosses promote kiss ups.
I suggest that abrasiveness isn’t very useful. Thanks again for joining the conversation. Frankly, I enjoy a contrarian viewpoint even if it is wrong. 🙂 Cheers.
Your goals and priorities should align with your boss’s goals. Their goals should support and align with the organization’s strategy.
The more you understand how your boss likes to operate (communicate, make decision, use toothpicks, etc.) the more prepared you will be to influence their focus and decision making.
Thinking like a boss requires you to:
1. Understand customers needs and wants
2. Understand the strategy and the company’s competitive advantage
3. Make sure the structure, systems, and people are supporting the strategy
Thanks for your insights, Paul. The people who influence the leader are the people who row-with. If we can’t align with organizational mission, vision, and values, the best way to adapt is to find a place where we can.
It is advisable to think like the boss so you know how to work with/for the boss. Your behavior should still be your own. You can work with a jerk hole without being a jerk hole. Emulate behavior you agree with and help mitigate behavior you don’t agree with.
Thanks, Stephen. Adapt, but don’t lose yourself. Do it sincerely. It’s hypocrisy otherwise. Adapt in service to a greater cause.
Your illustration of a jerk hole is powerful. Don’t use someone else’s poor behavior to be an excuse for your own. It’s challenging. We demonstrate character when we bring our best in imperfect situations.