When you are about to work under a new boss, there is always a tinge of anxiety and apprehension even though you want to put the best feet forward. It’s called FOMU — the fear of messing up. It takes a long gestation period for both your boss and you to get to understand each other, adapt to the working styles, and understanding each others’ expectations. It is such a delicate phase that one should tread the path with utmost care to avoid any unintended misreckoning. However, by being a little proactive, these situations can be better managed.
Inspired by the very popular post by Jay Desai who proposed writing a user guide to make it easier to work with you reportees, I thought of writing a similar user guide to work with a new boss. According to Jay, the goal of a user guide is to set blindingly clear expectations on how to collaborate without extra second guessing. The user guide helps prevent unnecessary second guessing and imagining and misunderstanding things. It also helps establish trust must faster that the due natural time it would otherwise take.
But since all bosses may not have a user guide for you, you could proactively take charge and come up with your own list to share it with him when you formally meet him the first time. So, after a bit of reflection, I came up with my own list. Make sure you send it out to your manager a few days before your first 1–1. This will give your manager time to prepare for these questions and also compel him to add more of his own.
1. Help create a job map:
Seek help of your manager to draw a job map of everything you are supposed to do as a new PM. Sometimes your boss may not be very clear himself and the nature of PM discipline is such that it is difficult to define a scope. But you must still draw out a map to align with his expectations of you and help you prioritize your tasks.
2. Org structure
Ask him to lay bare the organizational structure.
3. Learn about the product and the business
Ask for receiving a demo on the product, learn about the architecture and the technology stack that builds it.
Also, are there more reading material than you have already provided?
Internal product videos
Presentation materials currently in use
Win/loss analysis data
Customer proposal template and signed contracts
Available competitive information
Customer data sources
Product cost information or a product P&L
Existing product-related materials
What would be your preferred style of communication with me?
Would email be the most common way?
Would you also call or text me ?
Is a call or text more important or urgent than an email?
Do you not appreciate emails or chat messages after office hours/weekends? What are the boundaries?
Here’s what I promise to do?
I would give you a fast turnaround and acknowledgement on written communication. You can expect a quick “got it” or “on it” type acknowledgement notes so that you know things that we’re discussing are moving. I wont respond if it’s an FYI.
In the early days as we are building trust, I would communicate a little more than usual. I will ask a lot of questions and over-communicate. Once, I find my bearings and we both have established some trust, I would normalize the extent of our communication.
As we begin to work together, I would appreciate direct and quick feedback if any that you observe in day to day work. I thrive on constant feedback to be able to see any blindspots that I may have missed in a new organization.
5. 1–1s and meetings
How frequently do we have our 1–1s and for how long?
What do you expect to cover in 1–1s?
Do we keep the 1–1 minutes in a shared location? Wiki?
I also like to use the 1–1s as a means to seek feedback on an identified personal improvement goal or a goal identified by you.
Do you want me to share weekly reports?
What would you like to see in the report?
I would like to plan my quarterly efforts in the form of OKRs. I will embed it in my revised 100 day plan for your to review. The OKRs will contain my learning goals, quick wins etc. Do let me know if that works for you.
How often do we document our performance?
Would you be letting me know the goals and success metrics for my performance? Quarterly, bi-annually?
8. Culture and dynamics
I would like to understand the culture and dynamics of the org. Any inputs in this regard will be helpful.
9. 100 day Plan
Commit to share your first 100 day plan with your boss. Write your 100 day plan in a document or email and send to your manager before you meet again. That would give him some time to review it. In all probability, your 100 day plan might not have been fully fleshed out. And that is okay. Take help of your boss to flesh it out. More often than not, your boss will have more accurate sense of how best you should spend your first 100 days according to his expectations of you. Take notes of his expectations and send an updated plan later to him.
I had written another post on how to plan the first 100 days:
Meeting with other stakeholders in the organization
After your boss has sent you a list of people to meet in the organization, schedule an hour long meetings with each of them in the coming weeks. Because the conversations could go in all directions, it helps to have a structure. Usually I have a few questions like these:
Ask them to share with you everything they think you should know. Take copious notes. Only stop them to ask about things you don’t understand.
Ask them to help you understand their area of work. A brief background on the project and the team helps you gain perspective.
Ask them about the biggest challenges the team has right now.
Also ask what can I do and how can I be helpful to you.
Ask them who else you should talk to. Write down every name they give you.
These were some of my thoughts. Do let me know if you have more ideas to add to the list?