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How to Make Your Boss Like You: A Personal Story and Guide to Winning at Work

When I was hired at the digital marketing agency, my responsibility was to deliver content marketing services to our clients. However, it wasn’t long before I began noticing patterns and anticipating challenges not just in my department, but across the ...

When I was hired at the digital marketing agency, my responsibility was to deliver content marketing services to our clients. However, it wasn’t long before I began noticing patterns and anticipating challenges not just in my department, but across the company as a whole. 

Our CEO was juggling a lot, still working on sales and leading accounts instead of using his time and energy to focus on growing the company. I could see cracks forming in areas that could significantly impact our growth. 

Instead of waiting for someone else to fix things, I made it my responsibility to find solutions.

I didn’t limit myself to just content-related tasks. I took the initiative to dive into projects that fell outside of my official job description. Whether it was streamlining processes, suggesting new marketing strategies, or handling sales calls myself, I became a proactive problem solver. 

For example, I led a company-wide project to pinpoint and document our core values, something we now rely on for hiring and promotion decisions. Next, I created onboarding templates for new clients, so we didn’t always need to start from scratch. Similarly, I created sales “playbooks” so anyone who took a sales meeting would know what needed covered. 

I communicated openly with my boss, always framing my suggestions as ways to alleviate his workload or help the company move forward.

My efforts not only streamlined operations but also freed up our CEO to focus on high-level growth strategies. This shift in responsibilities demonstrated my leadership potential and ultimately led to my promotion to Vice President of Operations.

Here’s how you can do the same, with actionable steps to make a positive impression at work:

1. Get in Sync with Your Boss's Goals

Why it matters: Your success is often linked to how well your boss does. Understanding his or her priorities lets you focus your energy where it counts most. 

Take Action: Set up a one-on-one chat with your boss to really dig into what’s on their mind. This isn’t about self-promotion—it's about figuring out how you can genuinely help. Ask questions like, "What's on your radar right now?" or "How can I be most helpful to you?" Show them you're all about making things easier for both of you.

2. Be the One Who’s Always a Step Ahead

Why it matters: Waiting for problems to come to you is a missed opportunity. If you can spot and solve issues before they blow up, you’re not just helpful—you’re invaluable. 

Take Action: Look around and find one thing in your area that needs fixing. Maybe it’s a messy process or a recurring issue. Come up with a plan and bring it to your boss as a time-saver or efficiency booster. For instance, if deadlines are always a scramble, propose a new system to keep things on track.

3. Keep the Communication Flowing

Why it matters: Regular updates keep everyone in the loop and build trust, making it clear that you've got things under control. 

Take Action: Start sending a quick weekly email or schedule a brief check-in with your boss. Highlight what you've accomplished, what’s coming up, and any potential issues with your ideas for solutions. This shows you're proactive and on top of your game.

4. Deliver, Deliver, Deliver

Why it matters: At the end of the day, results are what count. Being reliable and consistent makes you someone your boss can count on. 

Take Action: Set clear goals for yourself at the start of each week or month, and track your progress. Share these goals with your boss so they can see your commitment. When you hit a milestone or achieve something significant, don’t be shy—let them know!

5. Be the Problem-Solver, Not the Problem-Bringer

Why it matters: Nobody loves it when someone just points out problems. But if you can bring solutions to the table, you’re showing real initiative. 

Take Action: When a challenge pops up, don’t just drop it in your boss’s lap. Think of at least two potential fixes before you bring it up. Present the problem and your ideas for tackling it, and then get your boss’s input. This shows you’re resourceful and ready to take on whatever comes your way.

6. Build Strong Relationships Across the Board

Why it matters: How you get along with your coworkers can shape your boss’s opinion of you. Collaboration and teamwork can make a big difference. 

Take Action: Be proactive in working with your team. Offer help when you can, share the credit when things go well, and handle conflicts professionally. Being a team player not only boosts your own rep but also reflects well on your boss.

7. Lead, Even Without the Title

Why it matters: You don’t need a fancy title to show leadership. Taking charge when needed sets you apart and shows you’re ready for more. 

Take Action: Look for opportunities to lead, even in small ways. Whether it's running a meeting, mentoring someone newer, or managing a project, these small steps can lead to bigger opportunities down the line.

 

Making your boss like you isn’t about being a yes-person or overly flattering. It’s about building a relationship based on trust, respect, and mutual success. By following these actionable steps, you’ll not only make a positive impression on your boss but also position yourself as a key player in your company’s success.

Are you ready to unlock your potential? Get Your Path to Independence Guide—a comprehensive roadmap to career growth, financial literacy, and emotional well-being—and start your journey to independence today!

 

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