The Art of Stakeholder Interviewing: Asking the Right Questions to Get the Insights You Need

Stakeholder interviews are a crucial part of any project or initiative. By interviewing key stakeholders, you gain valuable insights that can shape your approach and lead to better outcomes. However, simply sitting down with stakeholders isn’t enough. You need to ask the right questions to eliciting meaningful information.

In this article, we’ll explore best practices for stakeholder interviewing and provide sample questions to guide your conversations. With thoughtful preparation and strategic questioning you can conduct interviews that provide actionable insights.

Why Stakeholder Interviews Matter

Stakeholders are individuals or groups who have an interest in your project. They include both internal team members and external partners, vendors, or customers. Stakeholders have valuable perspectives to share given their vantage points. Interviewing stakeholders:

  • Gathers diverse insights to inform planning
  • Builds understanding of needs and priorities
  • Allows you to identify risks, blockers, and dependencies
  • Strengthens stakeholder buy-in through engagement

Incorporating stakeholder feedback lays the foundation for success. You make more informed decisions and create solutions tailored to your stakeholders. Interviews also foster collaboration by making stakeholders feel heard.

Preparing Effectively for Stakeholder Interviews

The key to extracting maximum value from stakeholder interviews lies in thorough preparation. Follow these tips:

Identify your core stakeholder groups – Brainstorm all project stakeholders and segment them into groups like senior leaders, project team members, end users, vendors, etc.

Prioritize your interviews – Given limited time, determine which stakeholder perspectives are most important to engage initially.

Customize questions for each group – Tailor questions and conversation focus based on the stakeholder group. For example, end users care most about features, while executives want updates on progress towards business objectives.

Set interview goals – Define the specific insights you hope to gain from each stakeholder or group. This gives focus to guide questioning.

Send questions in advance – Share your core questions with interviewees beforehand so they can prepare thoughtful responses.

Allot enough time – Schedule at least 30 minutes for stakeholder interviews to allow for relationship building and rich discussion.

10 Key Questions to Ask During Stakeholder Interviews

While each interview requires customized questions tailored to the stakeholder, certain questions provide useful insights no matter who you’re speaking with. Here are 10 go-to questions for stakeholder interviews:

1. Tell us more about yourself and your role related to this project.

This open-ended question allows stakeholders to share their background, perspective, and involvement with the project. It also builds rapport.

2. What excites you most about this project and what concerns do you have?

This two-part question uncovers both the potential value stakeholders see along with any apprehensions or risks they perceive.

3. How will you and your team interact with the solution we’re developing? What features or capabilities are most important?

For stakeholders playing hands-on roles, dig into specifics around how they’ll use the end product and what matters most in their workflows or processes.

4. What metrics are most important for determining success for you? How should we measure impact?

It’s essential to understand how stakeholders define success and what data points they care about most when judging outcomes.

5. What potential roadblocks or risks do you see with this project and what would you suggest to avoid or mitigate them?

Stakeholders often spot landmines you may miss. This question surfaces risks and elicits ideas to navigate challenges.

6. Which other groups or individuals should we engage to help guide this project? What insight could they provide?

Stakeholders know key experts or champions to involve. This surfaces additional perspectives to incorporate.

7. What technical, compliance, or policy considerations should we keep in mind based on your expertise?

Stakeholders may offer important constraints, standards, or precedents to factor into planning.

8. Imagine it’s one year from now, and this project has succeeded wildly. What does success look like to you?

This question provides color on stakeholders’ vision of success and desired end state.

9. What advice do you have for my team as we work to launch and execute this project?

Stakeholders share on-the-ground wisdom to apply based on their vantage point.

10. Is there anything else we should know or you’d like to share?

An open-ended closing question allows stakeholders to offer miscellaneous guidance or collateral you may find helpful.

Use this list of 10 stellar questions as a starting point when planning your stakeholder interviews. Tailor and expand it with customized inquiries for each audience based on your project’s specifics.

Best Practices for Conducting Interviews

Once you’ve prepped your interview plan and questions, it’s time to conduct the actual discussions. Follow these best practices for smooth stakeholder interviews:

  • Establish context – Give interviewees background on your project aims, timeline, and their role.

  • Take detailed notes – Document stakeholders’ responses to glean key insights and action items.

  • Ask strategic follow-up questions – Dig deeper into their initial answers to uncover more detail.

  • Clarify next steps – Be clear on expected actions from the interview and next touchpoints.

  • Capture quantitative data – Supplement narrative responses with numerical ratings around importance, likelihood, etc.

  • Manage time – Keep the conversation focused and gently redirect tangents to fit the allotted window.

  • Show gratitude – Thank stakeholders for their time and emphasize how their input benefits the project.

Approaching interviews deliberately using these tips results in productive conversations. You gather robust qualitative and quantitative information to drive strategic analysis.

Analyzing Interview Results for Actionable Insights

Conducting stakeholder interviews is only step one. To derive value, you must compile key findings from your interviews and analyze them to identify actionable insights.

Review notes and recordings – Refresh yourself on the full stakeholder input to identify major themes.

Extract major themes – Look at the interviews collectively to pinpoint areas of emphasis, alignment, and divergence.

Identify insights and actions – Determine what insights will actually shape your plans and document next steps based on stakeholder feedback.

Prioritize conflicting views – Where stakeholders disagree, assess who to consider more heavily based on project impact and influence.

Update plans and materials – Incorporate stakeholder perspectives into your approach, requirements, messaging, and any deliverables.

Circle back with stakeholders – Share how you’ve addressed their input and ask if it resonates.

Thoughtful analysis of stakeholder perspectives drives an inclusive, insight-driven approach. You incorporate diverse vantage points while still maintaining focus on core priorities.

From shaping product requirements to mitigating risks, stakeholder interviews unlock immense value in any project through diverse perspectives. They are well worth the time investment required. Prepare diligently, create strategic questions, conduct interactive discussions, document thoroughly, analyze insights systematically, and update plans accordingly. This process results in holistic solutions supported by those they impact most. Master the art of stakeholder interviewing, and your projects will reach new heights.

To succeed with your project, you need to gain a deep understanding of others’ motivations

stakeholder interview questions

The project manager had sold the interviews to the client and set them up, so I did my first round of them. I wasn’t sure what I would get out of it, and since I only had a short time for this project, I thought it was a waste of time. Most of the people involved, I assumed, had already been present during previous meetings. There’s no way that another conversation with them could lead to anything useful for the project. I’ll be proven wrong very soon. I now LOVE this activity and believe that interviews with stakeholders should always be a part of any immersion phase.

Depending on how much time you have, who you talk to, and what you ask, they can help you with many parts of your project. On a basic level, they are crucial for three things:

  • To connect with the people you are interviewing and get them (and make them feel) involved, use these skills. Everyone who has an interest in the project is involved, and you will need their help at some point. They might do this to get other people to come to a workshop, give you data, or be a project champion in their company. There can never be too many people working on something at the same time.
  • On the other hand, listening to the people whose business you are about to change and their problems, needs, and hopes can really motivate you. Many likely got into this business because they want to make things better for those people. They’re part of the reason you’re here, and hearing about their hopes in person always makes me feel like slamming the table or something. Let’s do it!
  • Inspiration and insight: They give you ideas that are hard to get any other way. What can and can’t you do? What are the real issues at every level of the business? Who can help and how? What does everyone want to achieve? Why are you doing this project in the first place?

Tips for your preparation

Stakeholder interviews don’t require an awful lot of preparation, but you’ll want to hold them very early on in the project. Before going into a stakeholder interview, be clear on who you are going to talk to (ideally you cover every department that touches the domain of your project), what their responsibilities are, and what you want to learn from them (If you would like to go deeper on this, the team of wrote a thorough guide). Based on these factors, you then prepare your question catalogue.

To give the conversation some structure, I split it into sections. If you have to do a lot of interviews in one day, give yourself a lot of time for each one and plan breaks in between. Your agenda could look like this:

  • Introduction (1 min) Introduce yourself and why you are here. Help them understand that the talk will be kept private and that there are no right or wrong answers.
  • For the 13-minute interview, have your partner explain in their own words what they do and who they are in charge of. Try to figure out what drives them and what worries them.
  • In this 13-minute section, you can learn about the practical parts of the project, find out what your interview partner wants to get out of it, and find out how they feel about it. You can also learn about the relevant dynamics and what might get in the way of the project.
  • Follow-ups and a wrap-up (3 minutes): They can help you decide what to do next. Ask open-ended questions that you don’t know the answer to (this is what I mean by “unknown unknowns”).

Stakeholder Interviews 101

Why did you Hold Your first stakeholder interview?

I held my first set of stakeholder interviews because the project manager had sold them to the client and scheduled them in. I wasn’t sure what I was going to get out of it, and in a project with very limited amounts of time at hand, I viewed it as a bit of a waste of time.

What questions do you ask in a stakeholder management interview?

General stakeholder management interview questions typically focus on your traits and soft skills. Here are 10 examples: Can you describe yourself in a few words? What interests you in this role? Can you highlight a few of your weaknesses? Can you tell me what you consider to be your most significant strengths?

Why should a project have a stakeholder interview?

Stakeholder interviews can facilitate communication and collaboration among stakeholders, which can benefit the project. Stakeholder interviews are a valuable tool for gathering the information and context needed to ensure the success of a project while also building support and commitment from key stakeholders.

How many questions do you ask a stakeholder interview?

Review 39 general, background and in-depth stakeholder interview questions and explore three example answers for a position in collaboration management.

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