The Struggle of the Scrum Master: Balancing Agile Advocacy with Team Realities in Medium Sized Companies

Being a Scrum Master can feel like herding a bunch of cats through an obstacle course. You’ve got the Agile principles etched into your frontal lobe, and you know they work—but then there’s reality. And reality is opinionated.

Medium-sized companies (we’re talking 100-500 people here) come with their own unique blend of chaos: teams with different skill levels, people wearing multiple hats, leadership demanding miracles yesterday, and the eternal struggle of “we’ve always done it this way.”

If you’re a Scrum Master (or other Agile practitioner) navigating this storm, welcome. Let’s talk about balancing Agile ideals with what actually happens in the trenches.

The Ideal Scrum Master (in a Perfect World)

In an ideal world, the Scrum Master is a mystical guide. They:

• Run smooth Scrum events.

• Coach teams on Agile principles like a motivational guru.

• Shield the team from distractions like a bouncer at an exclusive club.

That’s what the Scrum Guide says, anyway. But let’s be honest—how often does “ideal” actually happen?

Welcome to Medium-Sized Mayhem

Here’s the deal with medium-sized companies: they’re not startups, so they’ve already got some structure (and maybe a fair bit of baggage). But they’re also not huge enterprises with dedicated Agile departments and endless resources. That middle ground is where things get dicey.

You might have:

• Teams still figuring out what “Scrum” or "Agile" actually mean.

• Stakeholders asking, “Can’t we just skip the retrospective?”

• A product owner who’s so swamped they can’t even spell “backlog.”

• People with multiple roles, because "we're really great at multi-tasking"

Add to that a sprinkling of legacy systems, a dash of siloed teams, and a whole lot of “but we’ve always done it this way,” and you’ve got a recipe for challenges that don’t fit neatly into the Scrum Guide.

Advocating for Agile Without Being “That Person”

Let’s be real—nobody likes the “Scrum purist” who quotes the Agile Manifesto like it’s gospel (does anyone else leave it up in a browser tab all the time?). But as a Scrum Master, it’s your job to steer the ship toward Agile values. So how do you do that without becoming a walking eye-roll?

1. Pick Your Battles: Not every principle is worth dying on a hill for. Maybe your team isn’t ready for daily standups at 9 a.m. sharp. That’s fine. Start with what works for them and build from there.

2. Frame Agile as a Solution, Not a Rulebook: Instead of saying, “We have to do this because Scrum says so,” try, “Here’s how this practice can make your life easier.” People like things that solve problems—not things that create extra work.

3. Be OK with Progress: Rome wasn't built in a day and your not going solve all of the teams agile adoption issues in a single sprint. Be ok with making iterative gains every sprint (I mean its one of the agile principles after all).

   
   

Making Scrum Work for Your Teams

Let’s talk Scrum events. Sure, the book says you need sprint planning, daily standups, reviews, and retros. But in reality? Maybe your retros have turned into complaint-fests, or standups feel like a waste of time.

Here’s what you can do:

• Retrospectives Feeling Stale?: Mix it up! Use fun formats like “Super Hero Retro” or even a simple “Start, Stop, Continue”. Change the vibe to keep things engaging.

• Standups Dragging On?: Keep it tight. Standups are the kick off of collaboration for the day. 15 minutes max, and stick to the basics: What did you do? What’s next? What’s in your way? If your team pair programs, "Dido" is a perfectly acceptable answer.

• Low Stakeholder Engagement: Have an engaging demo as part of your sprint review. Talking your way through the sprint backlog, telling the stakeholders what you did in the last sprint, is a surefire way of see lower turnout at future reviews. Instead, put a small amount of time into show and tell. The feedback you gain will be well worth it.

  
  

Dealing with Stakeholders and Leadership

Ah, stakeholders. They mean well, but sometimes they’re the biggest challenge. Here are two common scenarios and how to handle them:

1. “Can’t You Skip the Retrospective?” Explain why retros matter. Frame it as a chance to improve delivery speed or quality—things they care about. If all else fails, just say, “Trust me, it’ll save us time in the long run.”

2. “We Need to Add This to the Current Sprint” Oh, the dreaded mid-sprint scope creep. Politely but firmly explain how introducing new work disrupts the team’s focus (context switching kills productivity). Offer alternatives:

   • Add it to the backlog for prioritization in the next sprint.

   • If it’s truly urgent, discuss what current sprint item can be removed to make space. (Spoiler: They rarely want to give something up.)

     
     

Scrum Master Survival Tips

If you take away one thing, let it be this: progress > perfection. Agile isn’t about doing everything “by the book.” It’s about delivering value, improving over time, and keeping your team sane in the process.

Here’s a cheat sheet for surviving the chaos:

• Be Flexible: Adjust Scrum to fit your team’s needs (but don’t lose sight of the principles).

• Communicate Like a Pro: Speak the language of your audience—whether it’s developers, stakeholders, or leadership.

• Celebrate Small Wins: Did your team actually stick to timeboxes this sprint? That’s a win. Celebrate it.

  
  

The Takeaway

Being a Scrum Master is a balancing act. You’re the champion of Agile, but you’re also the team’s ally in the messy, real world of medium-sized companies. The good news? You don’t have to be perfect. Start where you are, work with what you’ve got, and keep moving forward. Agile is a journey, not a destination. And hey, if all else fails, there’s always coffee. Or chocolate. Or both.