How To Get Your 1st Scrum Master Role

Strategies, paths and why, how, what of getting your 1st break as a Scrum Master

Apr 02, 2023

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I’m Vibhor, and welcome to my weekly newsletter, the “Winning Strategy.” Each week I explore one question from you about agile, product, roles, processes, frameworks, career growth, working with humans and anything else that’s stressing you at your office. Send me your questions here, and in return, I’ll offer actionable, down-to-earth, and simple advice.

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Q: I am a business analyst working with a SaaS company in Singapore. I am interested in exploring the role of a Scrum Master as my next career move. Is there a set path that I need to follow? Is this the right career choice? How do I get my first Scrum Master role?

Thanks for the question.

Scrum Masters play a pivotal role in the success of a product/project and often find their careers to be rewarding and fulfilling. If you are considering a transition into the Scrum Master role, this article is designed to guide you through the process, from evaluating if the role is right for you to acquire the necessary skills and ultimately landing your first Scrum Master position.

Let me start by saying that there isn’t a rule of some kind that you can follow to become a Scrum Master. Like any other career, the way you get your 1st break is to work deliberately toward getting your 1st break. There are a number of myths that are associated with getting your first Scrum Master job. I am listing the most popular ones below.

Myth#1: You can become a Scrum Master by getting a certificate (CSM, PSM).
Scrum Master is a role that requires a great deal of understanding when it comes to dealing with people (human side), products (technical side) and yourself (spiritual side). Scrum Masters are responsible for facilitating effective communication, ensuring that the team stays Agile amidst the chaos. To understand what I mean by “Agile,” read this post.
Myth#2: You don’t need any experience to get your first Scrum Master role.
Scrum Master is not an entry-level role. You need experience. Having said that, I do not mean you need experience as a Scrum Master. You need the experience to bring individuals together to work as a team, resolve conflicts, help the team solve/workaround impediments, interact with executives, make them understand the team’s point of view etc. So the chances of anyone getting into this role without relevant experience in implementing the above skills are quite low.
Myth#3: Anyone can become a Scrum Master.
More than a “role,” Scrum Master is a set of characteristics that you must have to survive in this role. Therefore it is important to know about your inner engineering, how you function, what gives you pleasure and what you resent before pursuing this role. So to get started, you need to figure out “WHO” you are.

Start with WHY “WHO” you are

15 years ago, I made the decision to transition from my role as a software development lead at IBM to pursuing a career as a Scrum Master in a tech startup.

This transformative experience allowed me to gain insights into the challenges and rewards of embracing this role, and I have since (now an Agile Product and Executive Coach) dedicated myself to guiding and mentoring others who seek to follow a similar path.

I survived this role because my inner engineering aligned with the characteristics required to thrive in a rather (for lack of better words) “hostile” work environment.

Through experience, I discovered that I survived this role because:

I loved helping others to succeed
I loved guiding others through Agility
I loved facilitating communication and collaboration
I loved resolving conflicts
I loved being curious and finding ways to improve
I loved teaching, mentoring and coaching
I loved problem-solving
I loved navigating ambiguity
I loved learning about new skills
I loved transparency

I would have failed miserably if I preferred:

Authority
Control over decisions
Appreciation
Working in a silo
Always being right
Building things myself
Avoiding meetings
Strict plans
Avoiding challenging situations
Avoiding people

If the above resonates with you (give or take a few), then proceed to the next step, which is all about the “HOW.”

Work on a strategy, the “HOW.”

There are only 3 paths (tried and tested) you can take to land your first Scrum Master role. Depending upon what your current situation is (in terms of your current job and number of years of experience), your path will differ from others.

Below are some roles that most commonly transition to the Scrum Master role due to their overlapping skills and experience:

Developers (most common)
Testers/QA Specialists
Project Managers
Business Analysts
Product Managers
Tech Leads
IT Managers

For the above roles, below are the 2 most common paths to transition to a Scrum Master role based on my experience and the experience of those I have hired and worked with.

(1) Internal transition

This is by far the easiest, fastest, most reliable and most common route. But for this route to work, you must have 3 key elements to align:

An internal transfer process
An opportunity to demonstrate your SM skills
A supporter. An internal champion who supports your transition (usually your current or new manager.

If you don’t have these elements (all of them) in sight, consider other paths. If you have these elements aligned, do the following:

Participate in a Scrum team
Volunteer to conduct daily standups
Be friends with other Scrum Masters
Express your interest in the role to your team and your “manager”

Building strong relationships with your team members, demonstrating your Scrum (and Agile) knowledge and expressing your willingness to pursue this role will help you get considered for this role.

Here’s a handy email template you can use to inform your manager about your interest and ask for support.

(2) Joining a startup with a burning need

You can join a startup with a need for Agile expertise. This path relies heavily on your networking skills. It requires you to make connections with startup founders and showcase your willingness to hustle and prove yourself.

Attend local meetups, conferences and workshops on Scrum and Agile ways of working. Apart from existing Scrum Masters and Agile Coaches, a lot of startup founders attend these events to self-learn Agility and the art of pivoting. Network with these professionals, learn from their experiences and discover job openings.

Although this path is full of challenges, it is a sure-shot way to learn all the necessary skills (listed below) you need to run a business, let alone be a Scrum Master. Here are a few startups looking for a Scrum Master.

(3) Entry-level role in a big company

This route is limited to companies with internship programs. This route is getting popular among MBA graduates, though I do not prefer this route. The Scrum Master role requires the development of a certain mindset that a fresh graduate does not have. So my advice for fresh graduates is to get some experience in other roles before making a decision about pursuing this role.

6 core skills to build to help you thrive.

The role of a Scrum Master requires you to build numerous skills. All of those ten thousand skills can be divided into 2 categories:

Tactical skills
Strategic skills

Tactical skills are those that you need to get the job:

Knowledge of the Agile Manifesto
Knowledge of Agile frameworks (Scrum, Kanban…)
Knowledge of tools (Jira, Confluence…)
Knowledge of software development process (for tech products)

But these are not the skills you need to survive on the job. For that, you need strategic skills. In my experience, the following 7 skills (in order of importance) are the most crucial to building early in your SM career.

Along with a short overview of each skill, I’ve included a set of concrete suggestions for how to develop that skill, as well as links to my all-time favourite writing on each topic from industry experts. Don’t worry about being a genius at all of these instead, double down on your strengths and fill in the gaps.

Click image to see high resolution version

1. Communication

Being a Scrum Master is all about bringing people together, helping them work effectively as a team, and making sure everyone is on the same page. Good communication is at the heart of all that!

Great Scrum Masters create an environment where everyone feels comfortable sharing ideas and working together. The team, in such cases, is like a well-oiled machine, with each team member contributing their unique skills and perspectives to achieve a common goal.

But that's not all!

You, as a Scrum Master, will need this skill to:

bridges the gap between the team, the Product Owner and other stakeholders. By communicating clearly and actively listening to feedback, a Scrum Master makes sure everyone's on board with the plan and keeps expectations in check.
teach, coach and mentor the team to embrace continuous improvement.
clear the path for the team by helping them identify and remove any obstacles that might be slowing them down.
make people understand your point of view. As a Scrum Master, you’re in a tough spot. You are regarded as a “process keeper,” which most people translate as “scrum police.”

Some recommendations for developing your communication skills:

Join a Toastmasters club
Record yourself speaking or giving a presentation
Learn improv techniques
Read The Ultimate Communication Skill: Learning When to Keep Quiet by Michael Thompson
Watch The Best TED Talks To Level Up Your Communication Skill
Buy and read Unleash the Power of Storytelling by Rob Biesenbach
Buy and read Five Stars by Carmine Gallo

The most important thing in communication is to hear what isn’t being said.

- Peter Drucker

2. Facilitation

Great Scrum Masters with good facilitation skills are able to create a welcoming space where everyone feels heard, at ease and ready to share ideas. This helps the team collaborate more effectively and make the best decisions together.

If you are a good facilitator, the team is less likely to resist attending the Scrum events.

But that’s not all.

By being a good facilitator, you’ll be able to help the team quickly sort things out when a conflict arises within the team.

Some recommendations for developing your facilitation skills:

Read How a Kinesthetic Approach Builds Better Teams by Douglas Ferguson
Buy and read Collaboration Explained by Jean Tabaka
Buy and read Facilitator's Guide to Participatory Decision-Making by Sam Kaner
Buy and read Training From the Back of the Room by Sharon L. Bowman
Read Developing Facilitation Skills
Read How to Improve Your Facilitation Skills by Robert Cserti

Leading is about learning to be a facilitator

- Ashif Shaikh

3. Assertion

Assertion upgrades your communication skill. When you are assertive, you communicate your thoughts, ideas and needs confidently without sounding aggressive.

Here’s an example.

Imagine you're a Scrum Master working with a team that's consistently struggling to complete their work within the sprint. During the sprint retrospective, the team members share their concerns about the unrealistic workload and tight deadlines.

As an assertive Scrum Master, you decide to have a discussion with the Product Owner about the team's capacity and the need to refine the sprint backlog. In this conversation, you might say,

"Based on our recent retrospective, the team has been consistently struggling to complete the work within the sprint. We need to ensure the team can deliver high-quality work without experiencing burnout. I suggest we work together to reassess the sprint backlog and prioritize items more accurately based on the team's capacity."

By confidently and respectfully expressing your thoughts, you advocate for the team's well-being and work to create a more balanced workload.

There’s a fine line between being assertive and being aggressive. The table below highlights that difference.

Click on the image to see it in high-resolution

Some recommendations for developing your assertion skills:

Read Standing up for yourself doesn’t mean putting others down by Diren Alexander
Read How to Boost Your Assertive Communication Style by Suzanne Marie
Read Six C’s to Assertive Communication by Darlene Lancer
Read Why do some adults fail to learn assertiveness skills?
Buy and read The Keys to Being Brilliantly Confident and More Assertive by Richard Banks
Buy and read The Assertiveness Guide for Women by Julie de Azevedo Hanks
Buy and read The Art of Everyday Assertiveness by Patrick King

The basic difference between being assertive and being aggressive is how our words and behaviour affect the rights and well-being of others.

– Sharon Anthony Bower

4. Observation

Engineers code, designers produce designs, and Scrum Masters… observe. Observation is another name for being “situationally aware.”

For example, let’s say you’re observing a daily standup as usual.

You notice that Alice, a developer on the team, has been quiet during the meetings for the past few days. She typically contributes enthusiastically and provides insightful input. However, now her updates are brief. She doesn't engage in discussions as much as before.

It’s your observation skills that help you pick up this change in Alice’s behaviour.

Instead of ignoring it, you decide to have a 1:1 conversation with Alice to understand the underlying issue. During the conversation, Alice reveals that she's been struggling with a particular task and feels overwhelmed. She's hesitant to speak up during the stand-ups because she doesn't want to hold the team back or appear incompetent.

Armed with this information, you can now take action to support Alice. You might:

facilitate a discussion between Alice and other team members who can offer help on the task
help her break the user story into smaller, more manageable parts
discuss the situation with the team and help them reallocate tasks

Some recommendations for developing your observation skills:

Read Improving Observation Skills by MiT
Read 9 thinking routines to improve your powers of observation by Claire Bown
Buy and read The Power of Now by Eckhart Tolle
Read Look: A Practical Guide for Improving Your Observational Skills by James Gilmore

To acquire knowledge, one must study; but to acquire wisdom, one must observe.

Marilyn vos Savant

5. Influence

As a Scrum Master, you’re a leader without any authority. As simple as it sounds, it is quite tough to implement.

Influence helps you build trust within the team. Trust is the foundation of any successful collaboration and keeps morale up no matter what’s going on. The best SMs quickly become the leaders of the team, not because of any authority, but because they help everyone on the team do the best of what they do.

Scrum Masters should know how to use their influence without having to resort to the “because I say so” style. The ideal Scrum Master should come with a degree of corporate political skills, know-how decisions are being formulated in an organization, and, most importantly, be an asset to the company.
- Dan Martin

Some recommendations for building your influence:

Watch other Scrum Masters and observe how they get things done without any authority
Request your Scrum Master to let you run the events for the sprint
Build a personal brand
Read How to Increase Your Influence at Work by HBR
Read Six powerful hacks for Scrum Masters to Gain Influence without Authority by Kamlesh Ravlani
Read The Qualities of Good SCRUM Master
Read Top Strategies For Building Influence & Persuasion by Shelley Seale
Buy and read The Business of Belief by Tom Asacker
Watch my video on building Gravitas

Your influence is determined by your ability to get people to take action.

— Sally Hogshead

6. Always being prepared

Embrace the "I got this" attitude!

It's all about making your team feel confident that you'll not only get the job done but also do it brilliantly.

To develop this mindset, just follow these simple steps:

sharpen your attention to detail,
come prepared for meetings and tasks, and
set the bar high for yourself and your team.

I'll be honest - I wasn't great at this in the beginning. But once I focused on these skills, my Scrum Master career truly took off! So, give it a try and watch your team's confidence soar!

Some recommendations for being proactive:

Keep a high bar for everything you do — re-read the recommendations in the #1 skill above (Communication).
Develop situational awareness — re-read the #4 skill above (Observation)
Do you know people who are very well organized? What are they doing to stay on top of things? Don’t wait, just ask them.
Read 11 Productivity Tips that Help Me Stay on Top of Things by Ewelina Adamczak

Luck is what happens when preparation meets opportunity

— Seneca

Community Wisdom

Below are some skills suggested by the members of the Agile community on Linkedin.

Bonus: Skills you’ll need to build over time to continue to excel

Vision — Work with the PO to determine your team’s north star, articulate it clearly, and help your team to commit to it
Business value — Understand what drives the business, and help your team and build the right things in the right order
Obsess with impact — Connect everything you/your team is doing to the impact it will have on the business value and end users
Agile/growth mindset — See everything around you as a seed that has the potential to become a full-grown tree with fruits and flowers.

Where to go from here

The journey to becoming a “great” Scrum Master might have its twists and turns. Remember, a Scrum Master's main goal is to "Guide the team forward." So, what's next on your path to mastering Scrum?

Here's a friendly tip. Focus on building the 6 core skills we've talked about above. Stay eager to learn, absorb new ideas, and use your creativity to tackle challenges (after all, resourcefulness is part of the job!).

Keep your eyes peeled for opportunities, and be prepared to seize them. As you grow, try out one or two of the career paths we've mentioned.

This adventure might take a year or two, maybe even three. If things aren't going as planned, switch it up and try something new. Connect with fellow Scrum Masters, listen to their stories, and put their advice into action.

If you're truly passionate about becoming a Scrum Master, stay persistent and make your dreams a reality!

This post contains a great deal of information, so don't worry about attempting to remember it all.

Consider it more of a reference guide or a source of inspiration for when you're generating ideas. And when you do come up with brilliant ideas, hit me up!

I am always open to suggestions and feedback. Pls, let me know if I missed something or if something seems odd.

Have a fulfilling and productive week ahead 🙏

📌 Things I loved this Week

📚 Book - Doing Agile Right by Darrell

If you're looking to dive into the world of agile or level up your current approach, "Doing Agile Right" is your new best friend. This easy-to-read book is filled with practical tips and real-life examples that help you navigate the agile journey with confidence. The authors are like friendly guides, teaching you how to strike that sweet spot between flexibility and stability.

🔥 Remote job openings

Questrade: Release Train Engineer (Toronto)
Questrade: Senior Scrum Master (Toronto)
Questrade: Senior Product Owner (Toronto)
Telus: Scrum Master (Vancouver)
EXL: Agile Delivery Lead (NY)
Metlife: AVP, Agile Marketing Lead (NY)
CBrands: Agile Domain Coach (US-Remote)

“I share things I wish I knew in the starting years of my career in the corporate world"

Vibhor Chandel