What CRITICAL Questions to ask at the start of a project?

👉 Develop the Right Skills to Become a Great IT Project Manager

I'm starting a new IT project. Now, it's time to meet project sponsors for the first time. However, I don't want to waste time. Therefore, I prepare to ask the correct questions to the project sponsor, which will help me create a project charter. Likewise, I will try to assess high-level risk and start controlling the expectations.

✅ Get My Book to Systemize Your Project Management Knowledge
(Even If you have little to no experience)

00:00 | Intro
00:44 | Preparing Project Charter
01:55 | Conversations with Product Sponsor

[ITProjectManagers]

🔥 There’s one skill that separates great IT Project Managers from everyone else—project tailoring.

Most project managers get stuck trying to learn every new tool and process out there. They dive deep into theories but still struggle to deliver projects on time and within budget. It’s frustrating.

The truth is, great project managers don’t try to do it all—they focus on tailoring simple processes and tools that work best for their team and projects. That’s what creates transparency, predictability, and results.

But here’s the thing—tailoring isn’t just guessing what might work. It’s about knowing three critical components:

1) Understanding project management on a deeper level.
2) Knowing exactly what to tailor.
3) Applying it effectively in real companies with real people.

That’s why I created the Professional Development Plan for IT Project Managers—to help you master project tailoring and finally become the project manager who delivers every time, no matter the challenge.

✅ Click the link below to get your development plan now and take the next step toward mastering project management.

[rajatsharma]

Brilliant bit of explanation Dmitriy, it really sets up the exact conversation skills required to deal the external stakeholders initially. Please do keep posting such kinda scenario..it really helps onboarding PMs to reach a comfortable stage...

[KingaHanyecz]

Thanks so much, Dmytro, you are great - so pragmatic and clear - and the llama lady was a really refreshing element :) we are more than happy to see and learn more from you :)

[kalpanasiddharth]

Thanks a lot for wonderful mock session Dmitriy !! Your videos are very motivating for aspiring project managers !! Please keep doing more of them

[itsmechicpalak]

First question should be to understand the detailed requirements from the client.

[chlovado]

😂😂 Had me laughing so hard I needed to rewind a few times. Nice job

[itsmechicpalak]

00:03 As a project manager, setting boundaries and goals at the start is crucial.
01:14 Asking critical questions for project charter
02:16 Understanding the context and purpose of the project
03:19 Discussing project scope and initial plans
04:21 Key questions to uncover project constraints
05:25 Always ask about constraints and dependencies
06:37 Clarifying detailed project requirements is essential
07:44 Smooth transition from meeting to project setup

[ritapalanjian]

Thank you, Dmitry, @IT Project Managers, I need to relisten again. Super helpful.

[bmk]

Also how to deal with clients who order something innovative which requires Research and development, and both of the sides don't know what the result be, but the client still pays despite of the result. Something that technically might be not feasible. But still worth researching, which requires developer's time. Thank you in advance!

[bmk]

Hi Dmitriy, thank you for the videos. Do you have a video for composing detailed technical specification document ( if it's called like that, in russian I meant Техническое задание). Thank you in advance!

[AKSHAY]

To client: can you please provide us the brief about the project and how this product benefited to your company