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How do I start in a new agile coaching role?

The Agile Coach & Scrum Master industry (note industries, not roles) have become bloated due in part to the fantastical number of traditional organisations undergoing some form of agile transformation or simply just trying to apply some agile principles. These organisations need support, so when they tell the world they are looking for it, they are engulfed by a mountain of applicants.

What are organisations, at least the ones I am speaking to, looking for in applicants?

  • Experienced Scrum Masters, those with only a certificate need not apply
  • Professional Scrum Master and Certified Scrum Master Badges – Funnily enough, this base level of certification is now seen as a base requirement, not a differentiator.
  • Experience in Agile Training and creating training courses. People would rather train the basics in-house and outsource the more specialised training such as Agile Coaching & Facilitation.
  • In the larger organisation they often do not want to see a clean slate when it comes to the words “Agile adoption”, “Agile Transformation” or even, dare I say for the more senior and lofty of agile coaches the term “Enterprise agile” (for the record, I dislike all of these terms and the mental models that create them. It doesn’t change the fact that some large organisations will want to see this)
  • So if you you are one of the lucky ones and you have ticked those boxes and landed a new gig it proves that you are doing something right.


But the high of getting the new role soon wears off. In the days and weeks leading up to the first day as Agile Coach or Scrum Master, minds turn to what you are going to find when you start. Have you been sold a dream story of an agile transformation only to find out it’s more like a nightmare with the only sudo-agile with the odd Daily Scrum? How you are going to be perceived? How can you make a positive impact? Am I going to be made responsible for some kind of Culture shift? 

An unknown status quo means scary times indeed!

Isn't a great agile coach someone who goes in and convinces teams, managers and product owners to live by agile principles?

Ha ha. No.

That is so far from the truth. It is much, much more than just speaking a good about agile practices, Product Backlogs and getting an agile coach certification (no matter how good it is).

A small portion of the gig may be helping a Product Owner, and some Development Teams get their head around the agile manifesto. Some of your time might even be spent helping people understand what User Stories are not (as most people still don’t seem to truly understand them, which is why I take any opportunity to share the TRUTH about them 😘 ). 

It is very unlikely that you will be in this position, say, with just an individual team and a handful of regular meetings.

If it is, you can stop reading, you have landed a nice easy Scrum Master/Agile Coach gig, and you can go and put your feet up.

If this is not you, read on and find out how to not crash and burn on day one.

Man in a suit pointing and shouting at a lady who does not care

What can I do to make a great first impression on day one?

I have been in the agile community for a good few years. Over that time, I have been involved in everything leading full-scale Agile transformations where I was involved in hiring and managing agile coaches and Scrum Masters through to supporting single cross-functional teams and their Product Owners as a Scrum Master (this was not a Scrum Team btw, rather a Product Owner Team and Teams in a LeSS Huge Adoption).

I have learnt from all these experiences that there are some habits and behaviours that great Agile coaches and Scrum Masters apply from the very beginning of their time in new organisations that so frequently have set them apart from the crowd and led them to make a significant impact.

This article will give you six practical tips that will help you have the same success, so here goes.

Agile Coach & Scrum Master Performance = What?

Any coaching role has to some degree, a responsibility to improve performance. I don’t think that this is a difficult one to argue. People hire coaches because they want to get better at what they do. Traditional Organisations and agile ones alike should be hiring into Scrum Master and Agile Coach roles to increase the performance of an entire team, numerous teams and ultimately the organisational system as a whole.

Sometimes this means supporting the evolution of an organisational design and culture. Other times, you may have work cut out for you with an individual team. Whatever the situation you find yourself in, great agile coaches are well-tuned into what performance means for that company culture at that time from day one. 

What if what they believe performance means for me is not what I think it should be?

That’s tough. The easy and somewhat arrogant answer is to say, “just walk, find another position” but that it crazy talk for many people as (of time of writing, January 2023) the job market for Agile Coaches and Scrum Masters is not as good as it has been. 

I see that you have a few options.

The classical super confident approach. I have seen this work, but I have more often than not seen it fail.

  • “I will accept what they say and prove that it should be something different. I’ll show them!” 

Or the more reserved approach. But for many, this is too much to bear:

  • “I will accept what they say and change who I am to pay the bills.”

My preferred approach. As it speaks more to the agile principles, I can start role modelling. Of course, they can say no, but then I have to question my life choices.

  • “Can we set a date and a clear objective or two and then have a retro with the team, you and me?”
A ranked list of grades ranging from Poor through to excellent

Sadly not every culture perceives performance in ways which are helpful to achieving agility 

An organisation’s culture will be intertwined with its structure. For many, this means that performance means an individual’s performance rather than a balance between individual performance and the performance of a self-managing team as an entity.

If this balance is not correct, people who believe in, and love working in teams, won’t want to stay. They will see no career progression (if it is too team focussed) and, to add insult to injury, won’t perform well as a team over the long term as there is little financial or reputational reward in doing so (the balance is too much to the individual). 

In my opinion, a truly agile organization or at least one well on the way to agility “transition” nirvana will, across the entire organization, have an increased awareness and appreciation of the balance between recognising team-level performance alongside individual performance.

Agile Coaches & Scrum Masters should have their performance judged on how they can help teams improve themselves. Not how well they can make individual rockstars

As an agile coach or Scrum Master, I think that we are at our most valuable when we are coaching teams as an entity in addition to the individuals, as well as acting as management coaches when the opportunity arises.

If the performance balance is not optimal, I think it will be hard for a great agile coach to thrive.

Should the balance be there, then I think that both agile coaches and Scrum Masters can help to evolve a company culture to be one where teams and their coaches are truly respected. Who knows, in time, those organisations may also see the value in technical coaches (that can help with development practices which are sadly often overlooked).  

Understand what is Agile Coach & Scrum Master performance in relation to the organisation's goals

Before you begin, spend some time getting a good grip on the business context and organisational purpose (more on that below) and how you could contribute towards it. There is nothing wrong with asking the question during your interview or before you begin.

“In your business context, what doe’s success look like for an Agile Coach/Scrum Master”.

If they turn around and say

“Well, it’s 100% about Project Management. You will be working with one of our Project Managers to get some agile methods into their way of working. Basically, we need you to get the project manager to drive the project over the line using agile sprints and agile methods. Your job is to convince the project manager and everyone else agile will work. That is success to us.”

Hopefully, you remember where the door is, be polite as you leave, and never come back.

Creating alignment on how your performance will be judged and getting clear in your mind whether you want to be

  • a convincer (with no coaching responsibility to help others improve their performance)
  • or a coach (with coaching responsibility to help others perform better)

This is a critically important decision. If what you decide is different to what you think they want, well you have a tough decision to make.

Now of course, some of us get lucky and just waltz in without having made these considerations. They tune in and play the role of Team Facilitator, Coach and Mentor to a tee.

They knock it out of the park.

The rest of us go to hit the ball and end up hitting ourselves in the face a few times before we are swinging and winning. This is why I think it’s probably best to follow this advice, at least until you are one of the blessed few.

If you are wondering why I mention Team Facilitator, Coach and Mentor, go ahead and check out the videos on this page to learn a little more or even take a look at what a bit of support on the role of an Agile Team Facilitator can achieve.

System Education - From the Teams to the Tills

A couple buying groceries at a Supermarket self-service checkout.

The organisation is going to be much more than the sum total of all the Product Backlogs you can hunt out (although, really, the number of Product Backlogs we have should be few, so maybe that will be a quick task)

It is easy for us to want to dive and help Product Managers, Product Owners and Teams, but without a broader understanding of the larger system they are part of, we run the risk of helping in the wrong way.

The tip here? Get a deep understanding of the organisation, its purpose, competitive landscape, mergers, acquisitions, damn, that feels like a lot of things!

Why? Read on.

Engaging Senior Stakeholders as an Agile Coach or Scrum Master

You may think this is overkill, “do I really have to delve that deep?“.

From experience, I have consistently found that knowing this information can help you come across as credible when engaging the senior leadership or management in an organisation. The really good leaders and successful managers I have always found are deeply connected to the DNA of the group and/or organisation. Being able to display an understanding and attachment to these quickly builds respect. How? They see you as being in their “In-Group.” Whilst I would love to explain this in depth now, it’s not the time :-). In short, think of fans of sports teams, that is, an in-group.  This in-group, Team A fans let’s call them, are not that keen on Team B fans as they view Team B fans as an out-group. If you want to learn more, I would recommend this study In-group favouritism and out-group discrimination in naturally occurring groups

As an interesting side note, in Large Scale Scrum, there is a subtle yet important change to the Scrum Master’s role articulated in the LeSS Rule that I think relates heavily to this tip

Scrum Masters are responsible for a well-working LeSS adoption. Their focus is towards the Teams, Product Owner, organization, and development practices. Scrum Master's do not focus on just one team but on the overall organizational system.

Let’s say, for example, you are working with a few teams (traditional Scrum Teams, Scrum-but teams or just plain old teams using Scrum) and notice that their Sprint Backlogs are full of related items.

Great, we may think.

But what if a merger is on the horizon with a business that already excels in that area? Is it really a good idea to duplicate this functionality?

These moments for me, are golden. It’s the best invitation to show that you have a grasp of the organisation beyond the teams by engaging Product Owners or whoever is closest to setting the direction of the Product to explore further and create some transparency. 

Will it result in a change of direction? Perhaps not.

Will it show you are tuned into the bigger picture and earn you some respect? Most probably.

Spending time understanding an organisation, from the “tills” (metaphorical or actual) to the teams and a good portion of the influencing factors around it, for me, is a must.

Courageous Listening and Curiosity

It is 08:30 am on your first day with a new to you development team that you have been told is “cross-functional“. 

Someone during the interview mentioned that they have 15 teams using Scrum, and this one, your one, used to call themselves a Scrum Team (so you could assume some agile experience, maybe?). That was until their Product Owner & Scrum Master eloped, so they stopped calling themselves a Scrum team.

Needless to say, they still dutifully attended the Sprint Review, Sprint Planning and Retrospective yesterday, so you could not attend (remember, this is your first day).

You feel that your first option to get a feel for what this development team are all about is to go to what they call their “Daily Stand-up meeting” and see how this team uses it (or not, as the case may be).

The wrong thing to do is wade in with your “Agile Team Facilitators rule” t-shirt, watch them for 2 minutes, get annoyed because you do not feel this is how a self-organising team should behave in a daily standup, start giving them directives and facilitative “nudges”.

All this will successfully achieve is destroy any opportunity to observe the natural team dynamic.

Do this, and you will learn very little. Do this, and you will earn zero trust and zero respect.

A dog with huge ears

So what can you do differently?

First, you will not get far with this tip unless you learn to listen to and manage your self-talk. Your self-talk, as well as being a great companion, can sometimes be a little judgemental not only about yourself but about others too, and this can prove very constraining. 

In my example, this poor Agile Coach/Scrum Master had no mastery of their self-talk, and it suppressed all the green shoots of curiosity they had by shouting things like:

“no wonder this is not a successful “transformation”. Just look at these clowns.”

“Everyone is talking about having to wait for other teams to do stuff for them, cross-functional team, my ar*e”

“They are not even looking at their Sprint Backlog!”

In any environment, when we start to judge and our self-talk runs wild, our opportunity to apply our curiosity is lost. So we must learn how to manage it. 

Many great coaches rely upon self-reflection to master this art and to get you started on that journey, here is a self-reflection worksheet for you to try. We use it in our training with great effect. I even use it myself.

With the self-talk quieter and in check, you should now begin to make it all about them, not what agile practice they are using or how much of a self-organizing team they appear to be. Actually, them, as individuals and a team.


Ask to be invited to something, a stand-up perhaps.

When you ask, say that you want to be there to get to know them and the work. Avoid the word observe. It makes people feel like they are in a zoo.

If they say no, then take it on the chin and wait. Your time will come

If they say yes, brilliant, go, smile, relax, manage the self-talk and only verbalise your curiosity when asked or when you have offered, and it has been accepted.

So to recap, what should agile coaches & Scrum Masters do to be courageously curious:

  • Manage your self-talk through reflection
  • Make it all about them
  • Don’t judge, explore

Don't be a Show-Off, Be a Zero

an astronaut in outer space

Chris Hadfield, in his book An Astronauts Guide To Life On Earth, shares with us his thoughts on what it is to be a truly valued and esteemed team player.  What he shares is that we can be that esteemed team player if

  • We are not actively taking away from the team experience and performance (-1)
  • We are not trying our hardest all of the time to make a spectacle of how good we are (+1)
  • Oddly, it means being a Zero, not doing either of those things but instead helping other people to make use of their skills the best they can. 

So we have 

Minus 1: Convinced you got it figured out. Doesn’t listen. Unaware of blind spots. Doesn’t easily receive feedback

Zero: Competent and efficient. Learns quickly through observation and asking questions. Reliable. They are really good at what they do.

Plus 1: Tries to add value at every turn. Not in it for self-promotion. Always pushes the limit of what’s possible. Knows their environment and limitations well. Turns themselves into a minus one in one fell swoop by telling everyone how good they are

What does all this mean for an Agile coaches and Scrum Masters?

Remember, the Scrum Master and agile coach roles require a combination of technical knowledge and people skills. Whilst people skills should never be argued, technical knowledge is an often debated topic.

For the sake of this article, I will say that the level of depth and nature of the technical skills depends upon the context (think non-software environments as an example, technical knowledge here could be many things).

I will stand firm and say that as an agile coach or Scrum Master, some technical knowledge is a must if you are going to garner lasting trust and respect at speed consistently. Experts, at times, are less willing to give time to those who have no idea about the reality of day-to-day work.

Most of us can agree, I think that in software environments, to consistently and repetitively release a Product Increment, technical excellence is a must. 

So what about when you feel out of depth? Being a Zero means not trying to blag your way through a conversation on Development Practices or how to prioritise technical debt on a Product Backlog if you have never done it before. 

So don’t say,

“Just put some items on your Product Backlog that will reduce technical debt. It will be straightforward to prioritise them once they are next to potential features”.

When in reality, the causes of technical debt will be multi-faceted and much more complex than someone with no understanding of the product in question could know. Prioritising them is probably not as straightforward as you think.

Let's not forget working alongside your fellow coaches and Scrum Masters

Coming into an organisation as a new hire on payroll or an external coach has been known to “put the cat amongst the pigeons” as we would say in England.

Joining an existing team, an “army of agility coaches”, or pre-existing communities of practice of coaches and/or Scrum Masters is a daunting task.

By trying your best to be a Zero, you increase the chance of earning the trust and respect in double time. If they are not that greater team, you will probably be approached by each of them separately to test their judgements of your peers on you. Be strong, don’t get sucked in the gossip, and remain a Zero.

So what can Agile Coaches and Scrum Masters do to be Zeros?

  • Ask questions
  • Be thirsty for contextual information
    • Always delve into understanding who and what can affect, has been affected or could be affected by what the person is speaking about.
  • Be kind & compassionate.
    • I am not saying make friends, but I am saying show you are not a robot
  • Learn how to integrate without being disruptive
    • Experiment with how you can be involved in the day-to-day without disrupting the natural team dynamic (unless you feel the time is right, of course)

Bonus ChatGPT Content!

On my way to writing this, I thought I would ask ChatGPT what it’s advice would be for a new Agile Coaches or Scrum Masters starting a new role. Here is what is said. Enjoy!

Here are some tips to help you hit the ground running in your new role:

  • Understand Agile methodologies: Familiarize yourself with Agile frameworks such as Scrum, Kanban, and Lean. Understand the roles, ceremonies, and artefacts associated with each framework.
  • Learn the organization’s processes: Each organization has its own unique way of implementing Agile.
  • Learn the specific processes, tools, and terminology used within the company.
  • Build a rapport with the Scrum teams: Building trust and respect with your colleagues is crucial for success as an Agile Coach or Scrum Master.
  • Take the time to get to know each team member, understand their strengths and weaknesses, and communicate effectively with them.
  • Be a facilitator, not a dictator: Your role is to facilitate the team’s progress, not dictate it. Encourage team members to take ownership of their work and make decisions.
  • Be flexible: Agile is all about adapting to change. Be prepared to pivot when necessary and be open to new ideas.
  • Communicate clearly: Good communication is key to the success of any Agile team. Make sure everyone is on the same page and that all team members understand the goals and priorities.
  • Lead by example: As an Agile Coach or Scrum Master, you are a role model for the team. Lead by example and demonstrate the values and principles of Agile.
  • Continuously improve: Agile is all about continuous improvement. Reflect on the team’s progress, identify areas for improvement, and implement changes to help the team become more efficient and effective.

Not bad for a non-human, I would say!

In conclusion

Please don’t try and apply this all at once!

Pick one bit and try it. Get the benefits. Repeat. 

Or if you are a bit unsure about any of the advice, why not watch the video below. It was my first live stream of 2023 and was about about Starting Strong as an Agile Coach.

Or if you are really keen to go deeper on some of these topics with me, come to one of our courses, or join one of our Mentoring Circles to really up your game. 

Sheev Founder - Ben Maynard

Ben Maynard, Product Agility, Agile and LeSS Expert

Ben has coached, trained and been passionate about software and people since 2009, proving that it is possible to sustain change, and build relationships, trust and respect at all levels of an organisation.

The creator and host of the successful  LeSS Matters Podcast, the UK’s only Certified Large Scale Scrum Trainer and Certified Coach Ben brings unique expert insights to all agile or aspiring agile environments.

Ben’s focus for 2022 is to continue building awareness of the usefulness and power of Large Scale Scrum when blended with Professional Product Management Best Practices and the emergent field of Professional Team Coaching.

Ben’s clients range from Start-Ups scaling up their capacity to prominent household names who want to understand how to reduce their complexity to increase their focus and success with their customers, users, people and products.

As an experienced curator of organisational culture and design, Ben has helped organisations create value for their customers and their people by asking the following two questions, are we building the right product and are we building it in the right way.

The critical catalyst to all this has been an obsessive focus on coaching, mentoring and educating people at all levels of an organisation so that they can be effective and successful in achieving the organisation and their personal goals.

Ben is the UK’s only dual-certified Large Scale Scrum (LeSS) Coach and Trainer. He is also a Professional Executive & Team Coach, having graduated twice from Henley Business School on Europe’s only triple-accredited coaching course.