Sep 21, 2023 4 min read

Make your Manager Love You

Come with Solutions, Not Problems

In 2010, while I was interning at a small Bay Area startup, I was in charge of DevOps and server administration. One day, while I was working on something, I noticed that our primary SSL certificate was expiring in 24 hours. I went into a full on panic mode because I knew the moment the certificate expires, all the connections to our backend will start failing for our customers.

I knew I had to alert others ASAP but I also knew time was of the essence. I spent the next 30 minutes quickly researching options, figure out how long it would take me to swap things out (remember I was an intern, so I wasn't really experienced). I collated everything, drafted an email to the CEO and a Senior Engineer alerting them about this and listed out the steps I was going to take in the next few hours. In a few minutes, I got a response from the CEO asking me to proceed with my proposal. But the engineer's response stuck with me throughout. He responded in the thread:

On another note, I love this email. I like how Vinoth not just came to us with the problem but also mentioned proposed steps to mitigate this.

As you progress higher up the ladder, your role tends to become less operational and more strategic. Put yourself in your manager's shoes - they are likely juggling a lot of context and responsibilities. As a reportee, you can get more out of your manager if you reduce their cognitive overload by providing options. This means not only identifying problems but also offering well-thought-out solutions. When you come to your manager with a problem, include possible solutions and the pros and cons of each. This allows them to quickly make an informed decision without getting bogged down in the details, freeing up their mental bandwidth for other strategic tasks.

This experience taught me the value of proactive problem-solving and how it can significantly ease a manager's workload.

Tell, Not Ask

I once had an excellent engineering manager reporting to me. He was a staff software engineer who was looking to become a manager so I decided to give him a shot and he exceeded all expectations.

During the annual appraisal review, he asked me for areas of improvement. I suggested something simple but powerful:

Instead of asking me if you can do something in a particular situation, tell me what you are going to do.

This approach demonstrates confidence and decisiveness. Managers appreciate team members who can independently assess situations and take appropriate actions. It shows that you are taking ownership and are capable of handling responsibilities without constant supervision. Moreover, it reduces the number of decisions your manager has to make, allowing them to focus on higher-level strategic initiatives.

But "Ask for Forgiveness" is Bad Advice

This common adage might seem bold and proactive. However, in practice, it can be risky and counterproductive. Acting without informing your manager can lead to misunderstandings, duplicated efforts, or worse, unintended consequences that could have been avoided with a bit of upfront communication.

Instead, aim for a balance. Keep your manager informed, but take initiative. Frame your actions in a way that shows you have thought through the implications and are prepared to take responsibility for the outcomes. This builds trust and demonstrates that you are a reliable team member who understands the bigger picture.

Happy Manager == Happy You

To make your manager love you, strive to make their job easier. Approach problems with solutions, communicate your actions confidently, and maintain a balance between independence and accountability. By reducing their cognitive load and demonstrating strategic thinking, you position yourself as a valuable asset to the team and an essential part of your manager's success.

One effective method to ensure your manager is always kept in the loop is the 5-15 method, a concise and structured way to communicate weekly updates. This was recommended to me by the head of our division at Hearst Magazines, and I religiously practiced it with my reporting managers. This technique involves spending 5 minutes writing a report that takes your manager 15 minutes to read. Here’s how it works:

Weekly Updates: Every week, spend 5 minutes summarizing what you have accomplished, what you are working on, and any issues or roadblocks you are facing.
Clarity and Conciseness: Keep your report clear and concise. Focus on key points and avoid unnecessary details.
Proposed Solutions: When reporting issues, include proposed solutions and potential next steps. This demonstrates your proactive approach and reduces the decision-making burden on your manager.
Consistency: Send these updates at a consistent time each week. This regular cadence helps build a habit and ensures that your manager can rely on your updates.
Feedback Loop: Encourage your manager to provide feedback on your updates. This helps you refine your reports to better meet their needs and keeps the lines of communication open.

The idea is that your manager will, in turn, do a 5-15 on all their reportees and share it with their manager (all the way to the CEO). By implementing the 5-15 method, you ensure that your manager is always informed about your progress and any challenges you are facing. This not only helps them stay updated but also builds trust and shows that you are reliable and proactive in managing your tasks.

By practicing these strategies, you'll not only gain your manager's appreciation but also foster a productive and trusting working relationship.