Asking the right questions relevant to Stakeholder Personas

Sidd Member Posts: 32 Expert
edited October 2023 in CS Conversations

Hi Team - I'm curious to learn more about how I should differentiate my outreach/communication based on the people I'm meeting with, let's assume there are 3 types

  1. Product Champion - ( I assume we can focus on all things product)
  2. Executives - CEO, CIO, IT Director, etc ( This is where I need help )
  3. The middlemen - Finance, product users, etc ( Again not sure)

What are the questions we can ask - mainly to Execs and what are the metrics that matter?

I'm trying to pool in all possible Questions from here and make a list and send it across :)


  • Alex Tran
    Alex Tran Member Posts: 38 Expert
    First Anniversary
    edited July 2020

    I can speak on behalf of Product Champions since I work primarily with Product teams :)

    The questions you can ask to product people include:

    • What are your product adoption goals?
    • How many monthly/weekly/daily active users are you aiming for?
    • Which features are most sticky? Less sticky? This is a good convo starter for product simplification.
    • Where do your customers need most guidance?

    For executives, somehow tie product metrics to business results. Many times it has to do with MAU/WAU/DAU (monthy/weekly/daily active users).

  • Archive User
    Archive User Member Posts: 24 Thought Leader
    edited July 2020

    Questions for executives (directly or indirectly) might include:

    • What was the single biggest frustration for you with the past solution (if one existed)?
    • What do you expect to get from this product? (what makes it valuable for YOU?)
    • What business measures will you be monitoring to evaluate the impact of this investment? (client measures, not CSM measures - this helps you think about how to line up  CSM measures)
    • What upstream or downstream process activities could be improved with this product?
  • Naveen Nair
    Naveen Nair Member Posts: 5 Seeker
    edited July 2020

    Executive "questions" are always tricky, ask the wrong ones and you'll lose their interest right away. Good generic question themes i've used in the past:

    1. What are you hoping to achieve with your program in the next 12 months? (Business outcomes)
    2. Where are you expecting delays and roadblocks in the next 3-6 months? (Tactical challenges)
    3. If you could really dream, where would you like to be as an organisation? (White space - caution, this ALWAYS needs to be deep into an engaged conversation to get a real response)

    The other thing I try to maintain is the mindset you approach the discussion with, it shouldn't be about technical capability or solutioning (unless specifically requested), it should be about business needs and drivers. 

  • Andrey Tirel
    Andrey Tirel Member Posts: 15 Thought Leader
    First Anniversary
    edited July 2020

    @Sidd Great question. Happy to share insight.

    Re #1, you can ask questions like:

    • Help me understand the challenges you have faced with XYZ competitor product? Our product? 
    • Have you run into limitations or roadblocks when trying to solve [xyz product feature your company offers}
    • What is your 2021 roadmap/plan for [your company product]/rollout plan?
    • Have we documented a mutually agreed-upon success plan? If not, when can we sit down, here is what I had in mind?  


    • How much [insert product value statement] saved/reduced over the last few months?
    • How often has {product champion, other you interact with as a CSM] provided updates about XYZ product use
    • Are you aware of XYZ use cases I built with #1 (see above)? What are your thought on [insert success and some challenges]? 


    • Describe some of the challenges you and your team have run into, if any?
    • Have you had a chance to [attend a webinar, review white papers, other content you might have sent the users]? 
    • Whom do you engage with when XYZ fails? Does your team engage with [insert product champion/executive sponsor] for ongoing updates? 
  • Matt Vadala
    Matt Vadala Member Posts: 47 Expert
    edited July 2020

    Great query @Sidd 

    I'd like to follow through more on @Andrey Tirel's response on reaching the users. I think you have some great input on executive buy-in from others here, so I'd like to help you approach the service's users who could be your loudest fans or foes. 

    I'd definitely ask about use cases and their workflow. That can help you to understand if your product is aligned with their use cases well, or not. You would also be receiving this info from Execs: asking about hoped outcomes and business goals. However, the key to remember is that the users can express the loudest grief if the functionality doesn't allow for the overall business mission to be achieved. 

  • Mahesh Motiramani
    Mahesh Motiramani Member Posts: 21 Thought Leader
    Photogenic First Anniversary
    edited July 2020

    @Sidd  - Great question!

    There have been a good amount of questions shared in responses above already. I'd like to suggest that you can take prior to asking or selecting/crafting questions to ask -- which is "what does each persona care about".

    C-Level Execs care about:

    1. Business Value at Company/LoB level
    2. Business Outcomes at Company/LoB
    3. Competitive Advantage

    Senior-Level Execs (VP/Dir) care about:

    1. Overall Success of the initiative where your product/service is being used
    2. Speed & Agility
    3. Delivering what the business wants
    4. ROI
    5. Adoption (can our people adopt, and how expensive will it be to adopt a solution)
    6. Quality, Governance & Security
    7. Talent (do I have ability to execute on this initiative)

    Product Champions care about:

    1. Successfully deliver & maintain
    2. Ease & quality of delivery
    3. Making life easier

    Enabling Functions (Procurement, Legal, Finance) care about:

    1. Level of internal demand and support for your solution
    2. Staying clear of any traps, gotchas such as cost inflation YoY or when crossing tiers
    3. Adequate legal protection (liabilities, risks, solvency)
    4. Pricing and terms

    I wouldn't look at "end-users" as middlemen. They may not have decision-making powers but each individual has the power to accelerate or impede adoption, so knowing what motivates them (resume-building!) and what creates friction or poor work-life balance will be tremendously important.

    Bear in mind that the list (or "cares") above under each category is not exclusive to that category, and you'd find that some things that Enabling functions care about surfaces in your interactions with other personas. 

    As you'd go through this list, you can start thinking of questions that help you uncover these needs and concerns.

    Good Luck!