(3) Questions Every New Manager Should Ask Their Boss

Corey Towe
4 min readJul 25, 2019

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So, you were just promoted to be a manager or just stepped into a new company as a manager. What do you do now?

There are many directions you can go to answer that question. Being a new manager is a challenge. The actions that made you successful as an individual contributor are not the same actions that will make you a great manager. Success is now defined differently and making that shift can make or break a new manager.

One of the keys to making this shift is to understand how to best interact and engage your new boss. They hired you. They believed in you. They brought you in for a specific purpose and you are highly motivated to validate their decision through your performance, but you cannot do this without some key clarifying information. Your new boss has information critical to your success and it is vital that you get clarity as early as possible by asking your boss a few questions to get you going in the right direction from day one.

I learned to ask these (3) questions through trial and error. I made mistakes. I made assumptions that proved to be invalid. I guessed and was sometimes right and sometimes wrong. Through this process I learned these are (3) important questions I need to intentionally ask and understand from day one so I can drive action based on direct information from my boss. It has proven to make a big difference when I see it applied and has helped remove noise and waste so managers can focus on other important actions they need to drive.

(3) questions every manager should ask their boss:

1. How would you define my success 90 days from now?

Understanding how success is defined is critical for a new manager. It is critical for all managers. Your boss has in their mind a definition of success. They hired you for a reason and have problems they are looking for you to help solve. The only way to understand the definition of success is to ask your boss to clarify it for you. Ask your boss to think ahead 90 days and help you understand what it would look like for her to give you a high-five because of the awesome job you did. What does that look like? That will give you indication of what success is so you can narrow your focus on the high impact actions.

2. What are the top problems you are currently working to solve?

Most likely, your boss has a lot on their plate. Take time to dig in and discern what the big problems are they are working to solve. What is keeping them up at night? What pressures are they feeling from others in the organization? What pressures are they putting on themselves to perform? Key in on this and make it a priority to help solve these problems on behalf of your boss. This will make you look like a rock star and open doors down the road. Focus on serving their objectives and what a win is in their lives.

Keep in mind your boss is solving both external and internal problems. The external problems are easier to notice. These are aspects like delivering on their numbers, driving better metrics, driving up quality, delivering a big project, etc. The internal problems to solve are more challenging. These might include aspects like your boss trying to build or rebuild their personal brand or overcoming their own insecurities and belief they have what it takes to do their job. These are important problems to discern and your ability to help your manager solve these problems is extremely valuable.

Key in on both and make it a priority to help your boss solve the problems important to them.

3. What is your preferred way to communicate?

Do not assume your communication preferences are the same as your boss. Take time to ask them how they like to receive information. Some like email, others like text or a phone call. You do not want to be in a situation where you are sending a lot of emails only to find out they are not being read and your boss is now surprised by something that happened they didn’t know about. Miscommunication can create a lot of noise or waste and make your first 90 days a little bumpy. Ask questions to figure out how your boss likes to get information and use that method when communicating.

The first 90 days of a new job are critical and can be chaotic. Asking these questions can help provide clarity so you know how to operate as a manager in your new role. Guessing or not asking can be detrimental and knock you off course but gaining clarity can set you up for success and create your path for future success.

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Corey Towe
Corey Towe

Written by Corey Towe

Leader. Storyteller. My passion is to inspire and instruct others on how to go further faster and live their purpose.

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