Agile7 minute read

5 Questions a Scrum Master Should Ask Before Joining a Startup

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The scrum master role has been gaining popularity with the widespread adoption of Agile. Startups adopt Scrum at an ever earlier stage and look for professionals to help them out. There are some simple questions a scrum master candidate can ask to find the right startup company for their skill set.

Toptalauthors are vetted experts in their fields and write on topics in which they have demonstrated experience. All of our content is peer reviewed and validated by Toptal experts in the same field.
Vytas Butkus

Vytas Butkus

Projects Blog Editor

Vytas is a professional project and product manager leading products and projects in education, 3D graphics, eCommerce, and adtech.


The scrum master role falls within 2018’s top 20 highest paying jobs in the US and is ranked 10th in Linkedin’s most promising jobs for 2019. With the increasing popularity of the Agile methodology and Scrum, these results are not surprising.

The adoption of Scrum in small-to-medium companies is becoming popular. 34% of scrum masters work in companies with less than 1,000 employees according to the 2019 Scrum Master Trends report.

A lot of startups that are moving beyond the seed stage find themselves with a need for a professional scrum master. Sometimes this is due to friction and miscommunication between software developers and business stakeholders.

Not all startups are created equal and scrum masters should be able to pick apart the ones that will suit their professional experience. Below are five questions that a scrum master should ask during an interview to garner the most realistic environment and expectations for potential employees.

Why Are You Hiring a Scrum Master and Not a Project Manager?

By asking this question, the scrum master applicant will get a better understanding of the expectations for the role. For example, a newly formed company might need guidance on how to implement Scrum in order to deliver their minimum viable product (MVP). It is vital for the scrum master to know the scope of the work and the level of Agile maturity of the startup as early as possible﹣ideally even at the interview stage.

An experienced scrum master is usually needed to level up the performance of a startup team. They need somebody to point out how they can improve and develop into a well-performing team. The discussion can go further by asking about the level of cohesiveness of the team. Are they self-organizing? If not, why?

The interviewer’s answer to these questions will define their expectations for the scrum master position. The scrum master is not a manager who dictates what to do but a servant leader who provides an environment where the team collaborates autonomously. The scrum master role involves optimizing the individual strengths for the team to perform at its best and achieve their goals.

Sometimes people who lack experience with Scrum, mix up the two positions. If founders feel that the development process is slow, opaque, or disorganized, it may mean that the startup needs an agile project manager to organize the work and collaborate with other teams or even a product owner to prioritize the development work instead.

A scrum master might determine that a project or product role needs to be filled for the development team to function effectively and for the Agile transition to be successful.

This question will help scrum master applicants to identify these situations early on and to avoid unrealistic expectations. An agreement to hire a project manager or a product owner can be made before signing the contract.

Scrum Master is not equal to project manager

What Is the Leadership Style of the Startup Founders?

It is crucial that the applicant understands the leadership style of the core group within the startup. The scrum master will need to collaborate with the management of the startup at least on a weekly basis. Figuring out how the founders deploy their vision on a practical level will make the applicant more prepared in terms of stakeholder management.

The discussion can start by asking how the company started and what some of the early challenges were. Most founders are eager to share their experiences, but they may focus only on the resolutions and end-results. With follow-up questions, nudge the interviewers towards highlighting how they actually solved those challenges. What were the alternative solutions discussed? Who suggested the final solution and who made the call?

Founder Traits to Look Out For

Some startup founders are very technical and focus more on the architecture and design of the product, but lack organizational skills. If it’s an early stage startup, some of the founders may still be doing some development work themselves. In some scenarios, they may be protective over their coding practices and potentially develop some resentment towards the scrum master, who is suggesting some uncomfortable changes to their approach.

Scrum masters may also run into non-technical founders, who may be concerned more with “getting things done.” They know the vision of the product and sometimes take on the responsibilities of a product owner. However, not being professionally trained in Agile practices, non-technical founders may make various mistakes, like introducing new items during a sprint or not spending time to validate product assumptions.

The scrum master should become aware of these potential traits as early as possible to understand how to best tailor its approach in the future.

Importance of the Founder Sign-On

Agile emphasizes team collaboration, continuous learning, empowerment and customer interaction. It does not adhere to the hierarchy-style of management; people are empowered to make decisions and not rely on managers. Scrum masters should clearly communicate that adopting Agile requires some cultural change within the company. Gauge the founders’ reaction to the possibility of exchanging some level of control for more empowerment for the team.

What Is Your Current Software Development Process?

The purpose of asking this question is to assess the level of technical agility of the startup. If the interviewers mention any scrum ceremonies, follow-up with questions that ask to describe those ceremonies in detail.

Cross-functional team expectation versus reality

Although Scrum promotes having cross-functional teams, the reality is often different. In large corporations, a scrum master sometimes has the ability to work with more than one team of highly skilled professionals. However, in small companies and startups, the scrum master often has to wear several hats. There are instances where the scrum master’s involvement is necessary for requirements analysis, functional testing, and other software development activities.

Also, ask about the current composition of the development team. The presence of a senior developer is key to creating a robust software product. Ask how the team ensures the quality of their code or what their code review and testing procedures are. This information will help a scrum master to understand how much time they will need to focus on the technical side of things and if that fits their experience.

Do Employees Get Any Regular Feedback?

An important part of the scrum master role is coaching the team members so that they can excel as agile professionals. However, it is common for startups to lack comprehensive feedback mechanisms. In such a scenario, more impactful team development will come from creating opportunities for team members to get feedback on their professional and soft skills. Discuss this during the interview process to set the expectations of the startup founders about what involvement might be needed from them or their colleagues to set up these feedback mechanisms.

Conversely, the candidate might find that there are some formal and informal feedback procedures in place already. Maybe the team goes out for drinks every few weeks to discuss how they are doing as a team. Maybe the CTO holds yearly or quarterly reviews with developers to boost their professional development. Whatever is the case, figuring out these initiatives during the interview process will make the applicant better prepared for implementing their own feedback processes. It is much easier to plug into an existing framework and suggest improvements then to build everything from scratch.

How Would You Define Your Company Culture?

This question is probably important in any job interview, but much more so for a scrum master candidate. Agile is a mindset and not only a project management methodology.

A transition to Agile means adopting a new mindset of interaction, customer collaboration, and being able to respond to unpredictable changes as embodied in the Agile Manifesto.

The scrum master is always at the forefront of this cultural change and there is no better place to start than the interview process. This question is less about gaining information about the exact company culture (which should be done nevertheless), but more about actually initiating the cultural change.

In adopting Agile, a startup’s culture does not need to be subverted. It might need to be slightly modified or at the very least, enhanced to incorporate some new values. Having this discussion as early on as the interview stage will help the scrum master in terms of keeping the record straight. Most startups are looking to hire a scrum master to become more agile and will agree on a theoretical level of change that will need to happen in terms of culture. If the scrum master joins the startup, they will always be able to refer back to the discussion during the interview if faced with opposition when actually implementing the changes.

Scrum for Startups to Match Your Skill Set

Before coming to a decision about whether to join a company, the scrum master should clearly evaluate the current situation of the startup with strategic scrum master feedback questions.

One of the most important responsibilities of a scrum master candidate is to make sure that the founders of the startup understand the concept of agility and know the areas where their involvement will be most needed. This will allow the applicant to see if there is a match between their skill set and the challenges at hand. Here is the list of the five most important scrum master questions to ask an interviewer:

  1. Why are you hiring a scrum master and not a project manager?
  2. What is the leadership style of the startup founders?
  3. What is your current software development process?
  4. Do employees get any regular feedback?
  5. How would you define your company culture?

The answers to these questions will give an overview of what to expect upon joining a startup company. A good scrum master should be able to identify the situations where a startup needs a project manager instead of a scrum master and not take on unnecessary responsibilities.

Discussing the development workflow will allow the candidate to evaluate the technical gaps and whether the scrum master has the right skill set to fill them. A review of current employee feedback mechanisms will reveal any low-hanging fruits for the team’s professional development. Lastly, talking through the leadership style of the founder and company culture will align expectations and prepare the startup for the mindset required during an agile transition.

Further Reading on the Toptal Blog:

Understanding the basics

  • What does a good scrum master do?

    A good scrum master makes sure the scrum team operates as efficiently as possible. They remove impediments, procure required resources, groom the backlog with the product owner and resolve team conflicts. A scrum master makes sure the team adheres to Agile principles.

  • Does a scrum team need a scrum master?

    Teams that are highly experienced in Agile may not need a scrum master. If the team members are able to self-organize and maintain a high level of agility, they can distribute the responsibilities of a scrum master among themselves. Less experienced teams will definitely benefit from having a dedicated scrum master.

  • What skills does a scrum master need?

    The scrum master role requires various soft skills. Scrum masters need to have great interpersonal skills as well as the ability to influence others without having direct authority over them. If working with software developers, technical knowledge is required to facilitate discussions.

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