After a few years at my current company, I felt like I was ready for a new challenge! I wanted to bring it up to my manager, but I knew I had to prepare well and stress test how ready I was in terms of my competencies and the responsibilities that I may have to pick up in the transition.

Here’s what I did.

Before scheduling the one-on-one with my manager, I prepared an agenda to structure my thoughts and for my manager to get a heads up of what’s coming. I jotted down the following.

Establishing clarity about the Senior PM role.

I looked these up on Google, but you can also base it on your company’s career ladder or note down observations from Senior PMs you know.

  • The day-to-day of a Senior PM
  • The responsibilities of a Senior PM
  • The top challenges of a Senior PM, generally and personally for me
  • The top priorities of a Senior PM
  • Things to look out for when transitioning
  • Stakeholders I will have to work with as a Senior PM
  • The aspects of this aspiration that excites or fulfils me to stress test whether this is actually the right role for me


  • My top 3 strengths that would come into play as a Senior PM
  • My top 3 weaknesses that may challenge me in a Senior PM role
  • Why the company would benefit from having me as a Senior PM

My proposed plan on achieving this aspiration

  • The North Star: Becoming a Senior PM
  • The milestones or objectives I’d have to achieve or things I need to improve on
  • The timeline: includes progress timeline, check-ins
  • What happens if the milestones don’t get met? Would I like to be transitioned to another role?
  • If you are already doing the responsibilities of a Senior PM and you feel like you’ve been doing your job well, this portion of the agenda becomes a discussion on what will happen next for this transition to happen, along with a timeline.

Establishing my role and my manager’s role in this process

My role

  • Keep my manager updated on the progress made on my proposed plan
  • Prepare an agenda for our fortnightly check-ins

My manager’s role

  • Aligning discussions and expectations with promotion decision-makers
  • Keeping me in the loop if there’s anything that’s hindering me from achieving my aspiration or objectives, i.e. feedback loops

Then I scheduled the meeting with my manager and asked him to read and comment on the agenda so by the time the meeting happens, everyone is on the same page. I scheduled it for an hour, but if you suspect that you’d need more time to brainstorm ideas with your manager, you should consider booking a longer slot or schedule a follow-up, whichever is most effective for you and your manager.

During the meeting, I

  • Opened up with something casual and made sure both my manager and I are comfortable. Smiling helped lighten up the mood, as both parties knew this would be a long conversation. I tried to create an environment where both parties can be honest with each other.
  • Asked my manager if he agreed with everything I’d written, and if not, discuss which definitions or plans should be changed or added in accordance to the company or my manager’s standards.
  • Asked my manager what his honest thoughts are about my aspiration. If your manager doesn’t seem to be too supportive, this is the time to talk about why. Really listen to what your manager is telling you from verbal and non-verbal cues. You want to make sure that everything that needs to be discussed has been talked about. If your manager doesn’t think you’re ready, welcome the disagreement and incorporate his concerns into your proposed plans. Maybe your manager may not be aware of what happens backstage and you may need to prove your contribution to the team or company.

After the meeting, I

  • Set calendar reminders of milestone deadlines
  • Brainstormed plans on how to achieve the milestones in the given timeline. What do I need to do? Who can help me?
  • Created a roadmap on those plans
  • Reflected back on the meeting and re-read the meeting notes. Were there any milestones I missed or were there any that are not necessary in helping me to become a Senior PM? Since the agenda has been shared with the manager for them to read and comment on, you may choose to keep your personal notes on a separate document.
  • Sent a calendar invite, with the previous meeting notes attached, for the agreed-upon check-ins to my manager.

In these check-ins, I

  • Reported the progress I’ve made. This is the time to provide proof on how you’ve been working toward your milestones, e.g. a screenshot of how you’ve improved on given feedback.
  • Discussed feedback from my manager and other decision-makers
  • Noted down any changes to the plans or timeline due to the feedback received.


  • Keep in mind internal processes that may support or hinder you, e.g. certain promotion guidelines or timeline from the People Team.
  • If your manager is not sure of the company benchmark or procedure, add this as an action item on the meeting notes and circle back to this offline. Not every decision has to be made in the meeting.
  • You may choose to set up a reminder for yourself 1-2 days before the discussion or check-in to remind your manager of the upcoming discussion, the agenda you’ve prepared, and the action items that were agreed upon in previous discussions.
  • Create multiple backup plans! Are there other roles in the company that supports the core, underlying reason why you wanted this promotion? Can you fill this role in another company?

Best of luck with your meeting! This may be a hard conversation to have for many, but preparing well will give you more confidence. If you know what you want, go after it! Cheers!

Please send any feedback you may have to