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  • 6 min read

10 Strategic Questions To Ask Your Clients

Strategic success planning is vital for CSMs when engaging with their high touch clients. In today's market, where client-vendor relationships are under scrutiny, being strategic and collaborative is indispensable. The winning vendors are those who offer maximum value.

Adopting a strategic approach to success planning is vital, especially when dealing with your high touch clients. We find ourselves in a place where client preferences and priorities are in a constant state of flux with budgets tightening, the role of a CSM has never been more important.

In this article I want to help you find that all important and strategic position that places you as one of the most important vendor relationship your client has. A utility and not a nice to have.

There are two things we need to get there. A great set of questions to help you uncover the key outcomes your clients care about and a well thought out success plan to help you deliver those outcomes to your clients.

10 Strategic Questions To Ask Your Clients

Lets run through a set of example strategic questions you can start using in your client meetings today.

  1. What are the key business objectives you aim to achieve this year, and how do you see our solution contributing to those goals?

    Guidance: This question helps align your understanding of the client's overarching goals and how your solution fits into their strategic roadmap.

  2. In what areas do you feel our solution is currently falling short of fully meeting your needs or expectations?

    Guidance: Use this question to pinpoint specific pain points or gaps in your solution's performance, enabling targeted improvement efforts.

  3. Can you elaborate on any challenges or obstacles your team is facing in fully adopting and leveraging our solution across your organization?

    Guidance: By exploring adoption challenges, you can identify barriers to usage and devise strategies to enhance user engagement and product adoption.

  4. How does our solution integrate with your existing workflows and technologies, and are there any compatibility issues hindering seamless adoption?

    Guidance: Understanding workflow issues helps tailor solutions to fit seamlessly within the client's existing ways of working, ensuring smoother implementation and usage of your solution.

  5. What specific metrics or KPIs are you using to measure the success and impact of our solution within your organization, and are there any gaps in performance or outcomes?

    Guidance: This question helps you gauge the client's expectations for success and identify areas where your solution can better align with their measurement criteria. It's more direct but definitely worth asking!

  6. Are there any additional features or functionalities you would like to see added to our solution to better address your evolving business needs?

    Guidance: Soliciting feature requests allows you to prioritize development efforts based on client needs, enhancing the value derived from your solution.

  7. What feedback have you received from key stakeholders or end-users regarding their experience with our solution, and are there any recurring pain points or areas for improvement?

    Guidance: By gathering feedback from stakeholders and end-users, you can identify recurring issues and opportunities for enhancing user experience and satisfaction.

  8. How effectively are you currently utilizing the resources and support services provided as part of your subscription, and are there any areas where you feel additional assistance or guidance is required?

    Guidance: What is their health score and how can you help them unblock obstacles to improve their product adoption.

  9. Can you share any insights into how our solution is impacting your overall business strategy and competitive positioning within your industry?

    Guidance: Another direct question is around understanding the broader impact of your solution and how it may enable you to tailor your support and engagement efforts to support the client's strategic objectives.

  10. Looking ahead, what are your strategic priorities and initiatives for the upcoming year, and how can we align our roadmap and offerings to better support your long-term objectives?

    Guidance: By aligning your roadmap with the client's future priorities, you can foster a long-term partnership focused on mutual growth and success.

By asking these strategic questions, the CS team can gain valuable insights into their clients' business challenges, adoption barriers, and future needs, enabling them to proactively address issues, drive value, and strengthen the partnership for the foreseeable future.

How To Write A Strategic Success Plan

Firstly, lets define a success plan:

A success plan outlines initiatives and actionable strategies to ensure clients achieve their desired outcomes with a product or service. It typically includes clear goals, milestones, and metrics tailored to individual client needs, with the aim of fostering a proactive and collaborative approach to achieving mutual success.

To put it simply, success plans are a vehicle to deliver value for your clients and to make your CS teams life easier when it comes to ensuring usage is up, benefit is gained and renewals are a simple walk in the park.

So, how do you structure a well defined success plan?

A well-defined success plan begins with a comprehensive understanding of the client's objectives, challenges, and key metrics for success. If you read through the strategic questions in this article, asking the correct strategic questions will help you get the understanding and content you need to create your success plan.

Your success plan needs to be specific and have measurable goals aligned with the client's business outcomes. Initiatives are established to track progress, with assigned responsibilities and timelines. Regular checkpoints or assigned actions with due dates allow for adjustments and alignment with evolving needs.

The success plan needs to incorporate actionable strategies, leveraging the product or service's features to address client needs effectively. Continuous communication and collaboration between the customer success team and the client ensure transparency, accountability, and a shared commitment to achieving desired outcomes.

To help convey this well, we'll use Retentional's success planning solution to build out our own success plan.

Below is an example success plan we would make as Retentional for a client using Retentional:

Success plan Title:

Deliver Net Revenue Retention Growth


Achieve 10% NRR growth across all our Top tier accounts by implementing strategic success plans with Retentional.


  1. Define Strategic Outcomes

    • Act 1: Identify key strategic goals

    • Desc1: What are your clients trying to achieve with your product? What business outcomes?

    • Act 2: Map your clients strategic goals 

    • Desc 2: Identify ways your clients can use your product to meet their goals

  2. Strengthen Client Relationships

    • Act 1: Key Stakeholders 

    • Desc 1: Identify key stakeholders who will collaborate with you to produce your success plans

  3. Improve Product Adoption

    • Act 1: Identify feature adoption goals

    • Desc 1: Which features do your clients need to adopt to help them meet their strategic targets?

We've included the above example in every new account created in Retentional to serve as an inspiration and a place to get started. It's also free to get started with Retentional today.

Becoming strategic moves you away from reactive problem-solving and instead, pushes you to become proactive in addressing your clients' needs. By deeply understanding their goals and challenges you can tailor your approach and your product to perfectly align with their objectives. This alignment shows exactly where your efforts directly contribute to their success, positioning you as a trusted advisor rather than just a service provider.

Strategically aligning yourself with your clients' goals not only enhances the value you bring but also cultivates long-lasting partnerships built on mutual understanding, trust, and shared success.

If you haven't doubled down on this yet, then you should get started today.