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Episode 16:

How do we self-organize if our boss is on our team?

Today’s question come from an anonymous source. “Stifled Scrummer” says that their boss is on their team, which makes self-organization difficult. Stifled is wondering what tips I have for helping them deal with this organizational impediment.

Mentioned in this episode: 

  • Free chapter of Agile Antipatterns 

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Adam: Welcome to Agile Answers. I’m Adam Weisbart, your Certified Scrum Trainer and agile coach. Each week, I get your questions about Scrum and agility, and I answer them, here on Agile Answers.

Well, after a bunch of shows and a ton of good questions submitted, someone finally submitted an anonymous question. As you know, you can go to and you can record a question that I might answer here on the show. It’s great, because now, everybody gets to hear from you. The downside is maybe you don’t want everyone to hear from you. Maybe you’d like to remain anonymous. Well, the question that we got today falls in those lines, really. The person who submitted it sent it by email and asked me not to reveal their identity. Let’s give a listen and see if I can help.

Stifled Scrummer: Hey, Adam. Please keep my personal information private. I’ve got good reason for remaining anonymous which I think you’ll discover in a moment. I work on a Scrum team with my boss. Everyone on the team reports to her and it makes it really hard since I don’t feel like we’re free to figure out our own estimates or the technical direction we’d like to go. She’s always directing us, in one way or another. What are some ways of dealing with this? Thanks, Stifled Scrummer.

Adam: Oh, Stifled Scrummer, you are in a difficult situation. When organizations have people’s bosses on their Scrum teams, I think they’re setting their teams up for a fool’s errand. Their telling the teams, “Hey, teams, go ahead and self-organize.” And then nobody can, because they’ve got somebody on the team who’s used to organizing them. And whether this person is super altruistic and doing their best to be a good Scrum Master or a good Scrum team member, it’s pretty hard for anybody else in the room to set aside their previous command and control approach to management.

Even if they’re the nicest person in the world and they were a great mentor, and not so command and control-ly, it’s still pretty difficult, still pretty difficult. And the reason for that is every manager walks around with an invisible gun. You might not know this, but I bet, intuitively, you do. They’re walking around with an invisible gun, because they have a say over your job, over your livelihood, I guess, or if you can feed your family, at least for the next couple of weeks. And very benevolent bosses walk around with smaller guns and less benevolent bosses carry big shotguns. I know because I’ve been in this situation. I was an engineering manager who switched to being a Scrum Master. I thought I was doing a great job helping with the agility at our organization, but it turns out, everybody looked to me for solutions, how they should approach doing work.

As a new Scrum Master, I didn’t know that this was a big problem, until I just realized, “Wow, my teams are not self-organizing so well. I thought this self-organization thing was supposed to work.” It turns out self-organization can only work if you give it room to work. And if you are the boss of the people on your Scrum team, and they have to work with you every day, you are not giving room for self-organization to occur, no matter how nice you are. I like to think that I was carrying around a little pea-shooter, not much of a gun. I don’t know what it appeared to be to other people, but it certainly was an issue.

It’s cool that you’re asking how to deal with this. Unfortunately, I think it’s a pretty simple solution. I say unfortunately, because even though it’s simple, it’s not always easy. I would say that your boss should not be on your Scrum team. If you’d like to do Scrum, you’d like to self-organize, well then, don’t have them be on your team. It sounds like an impediment that you can give to your Scrum master. Oh wait, your Scrum master is your boss, which makes it very hard to remove, doesn’t it? Ah, it’s a slippery slope.

Well, I would have a conversation with them one on one, about how them being on the team is affecting all of your work. And maybe better than having it one on one is to have it as a retrospective with your entire team. I guess this would depend on your relationship with your boss, if you’re close to your boss, you felt like you can speak with them freely, you spoke with them one on one, maybe you can have a conversation. Or maybe, you can hold a retrospective about your Scrum Master, which is not an uncommon thing. It might be an uncomfortable thing, if that person is your boss, but I bet you can help surface some useful things.

Then the question becomes well, if our boss was our Scrum Master, who’s our Scrum Master now? Now, I think a lot of organizations default to having bosses be Scrum Masters because they think, “Oh, the Scrum Master is somebody who manages the team.” Well, we know that’s not true, but people often think it’s true when they initially adopt Scrum. They don’t realize that well, the Scrum Master just needs to be good at facilitation. They don’t need someone who is of high organizational authority. In fact, it works best when they’re not.

So here’s the trick. Anybody on your team can be the Scrum Master. They just need to be excited about being a Scrum Master and be good at facilitation or be decent at facilitation, be interested in getting better. There’s no need for your boss to be the Scrum Master, no need at all.

I suspect the next question that would come up, if you share with your boss that having them on your team is hurting self-organization, if they haven’t noticed this already, is what the heck your boss does when they’re not on your Scrum team? Well, I think the good bosses, good managers are good mentors. And you can be a mentor from outside of the team. You can be there for your direct reports to answer questions, to help them with career development, if they need more training or need a deeper understanding of a particular methodology, for example. You can do that from outside of the team. And as a manager, you have the power to remove impediments that nobody on your team can remove.

That is the stuff I would focus on if I was a manager of an agile team. Your team still self-organizes. They figure out their estimates. They figure out technical directions, and you figure out how to remove impediments that they report to you, impediments that they don’t have power to remove. And when they come to you asking about career development, about how to take the next steps in their development, you can help them with that as you would any direct report, really, at any organization, agile or not.

So I, as an engineering manager, would step out of that role, at least on the team level where I was trying to manage day to day things like, again, as amidst technical direction, etc., and I would focus more on what I think it’s important for which is to be a really strong and good mentor. I say this from experience. I, with my first Scrum team, was a manager previously and then switched to Scrum and then was the Scrum Master and engineering manager, thinking, “Well, I’m super altruistic, I can do both of these things.” I failed miserably. I failed miserably because it’s not really possible to wear two hats. You might think you’re wearing two hats as the manager, but everybody on your team, because of your invisible gun, knows that you are not.

Stifled Scrummer, I hope that was helpful and you feel a little less stifled. If you’re stuck on how to introduce this idea to your manager, a couple thoughts, you could give them a link to this podcast, they could give a listen, that might introduce things. And hey, listen, bosses, if someone just sent you a link to this episode, you just listened to it, and you thought, “Hey, that’s the guy who submitted the question, this guy who reports to me,” it’s not necessarily you. It could be anybody. So, you know, maybe they just stumbled upon this podcast. I didn’t make it just for one person.

Or if, Stifled Scrummer, you think it’s a little weird to give him a link to this podcast, you could go to my website and get a copy of one of the chapters of my upcoming book, “Agile Antipatterns.” That chapter is all about having your boss on your team, and how that can be damaging to an agile initiative or to self-organization. You can get a copy of that in the show notes or just by going to That’s W-E-I-S as in Sam-B as in boy-A-R-T as in Thomas-dot-com-slash-book. I bet you know how to spell book. You can get a copy of that, print it out, and just leave it on their desk. They don’t even need to know who it came from, if you wanted, who knows.

Well, if anybody else out there has a question about Scrum or agility that you’d like me to answer on a future episode, well, you can submit it at Right there on the home page, there’s a little link if you’d like to email me anonymously of if you’d like to record a question that I’ll answer on a future show using your own voice, you can do that with the little widget there on the home page. If your question gets selected by me for a future show, just like Stifled Scrummer’s did, you’ll get a deck of my Agile Antipattern Cards. In fact, Stifled Scrummer, yours is coming in the mail to you. You’ll get a deck of Agile Antipattern Cards. One of the antipaterns in the Agile Antipattern card deck is “My boss is in my team.” Heck, Stifled Scrummer, you can just hand your boss one of those too.

All right, well, until next time, stay agile. Never change.

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