Make Your Sprint Retrospectives Awesome—Here’s How (with Alexa Huston from Crema)

Ben Aston: Thanks for tuning in. I’m Ben Aston, and this is the Digital Project Manager Podcast. Today I’m joined by Alexa Huston, one of our resident DPM Experts at the Digital Project Manager. Alexa, thanks so much for coming on the show again.

Alexa Huston: Thanks for having me back.

Ben Aston: Well, do you feel like your team is making the same mistakes over and over again? And it’s probably not just because you feel like they are. It’s probably because they are making the same mistakes, and it’s probably because you’re not helping them change, but there is a helpful tool in our DPM Toolkit that can help us change this, and it’s the Sprint Retrospective. Done properly, these are the agile meetings that can highlight opportunities for change, they can generate some process improvements, and ultimately help move the team in the right direction. Done badly, though, they’re the worst kind of blame game ever. So, keep listening to discover how you can use the Sprint Retrospective as a vehicle to drive positive change. We’re going to talk about some of the practical applications to making Sprint Retrospectives as productive as possible.

So, just on the off chance, though, that you’ve missed the last podcast with Alexa, let me introduce her. Alexa is awesome. She’s a PM turned new biz girl, and she’s currently working at Crema. Did I say it right that time? In Kansas City.

Alexa Huston: It’s Crema, but at least you didn’t call it Crema Labs. It could be worse.

Ben Aston: So, you are a PM turned BD, so, can you tell us, what does that look like? What does a PM turned BD person do in BD?

Alexa Huston: She looks like your regular person. No, it was a pretty natural progression, for me at least. I work at a small agency, we’re a little under 25, I believe, as of today. And I had been working as a DPM for the last couple years, and there’s just a natural overlap, as most of us know, between sales and project management. Over that time I’d got really interested in more of the sales side of things, and after a few conversations with Biz Dev and some of our operations people, it naturally came up as an opportunity at the end of last year. I spent the better half of the first quarter transitioning my projects over to our amazing project managers here, and now I’m full blown on the business development side of things, but with a unique twist of managing many, many projects in my pasts, so I feel like I have a good grasp and ability to talk about the ins and outs with some new prospects and opportunities.

Ben Aston: Yeah, I think one of the big criticisms or pet peeves of PM’s is typically that, hey, sales has done this, awesome job at securing a new client, but somehow they engineered their own estimate and statements of work and timeline that’s unrealistic. Are you transforming the BD world from the inside out? Do you find that now you’re the one that’s responsible for giving these crazy estimates and timelines to clients and then handing them over?

Alexa Huston: No, I know what you’re talking about. Thankfully, here, we don’t have a huge gap, but there still is one. With any sort of handoff between departments, there might be some things lost in translation. I’m trying to do my best to highlight where there might be gaps and fill them in from an operational standpoint. One of those easy, off the cuff examples was, we weren’t doing a great job at identifying, which resources were pegged for future projects. Who was tentatively booked? We do duration and price agreements. At the end of March, for example, we had someone coming off a project and they weren’t properly indicated on our forecasting software where they were going to be next. I’m just trying to find those opportunities to plug the holes.

It’s not just me, we have a really strong sales and operations team that come together every couple of weeks to identify where we can get better. I hope I’m not making anything worse. Trying to get better. Definitely, I do know it does help me coming from a PM background first, to be able to speak into some of the battle scars of product development and have a lot of things in my back pocket that I can refer to.

Ben Aston: In your new role, then, what are some of the unique challenges that you feel like you’re encountering now that, as a PM, you always kind of look to BD, like, oh, I can’t understand why they don’t get that right. Now, you’re in there, you’re like, oh, I understand now why they get that wrong.

Alexa Huston: Yeah, oh, that’s a good question. It’s interesting because I think every person we speak with has a unique challenge and we really try to focus on the value we can provide versus the capabilities that we have, because we’re one of many product development shops in the country. Where, I think I might be able to answer your question with an example, I’m trying to think of one, is maybe where timelines come into play. I mentioned earlier, we do duration and price agreements and I had heard, prior to me moving into this new role, in sales conversations quoting maybe too short of a duration. Oh, we can get to an MVP in two months. I would challenge that now and say, we probably need more like three or more, just realistically. It’s all about setting expectations as we all know. That’s a really simple example of where I’m trying to get a little bit more in tune and provide examples of projects that I’ve personally worked on. That’s been super helpful.

Ben Aston: Yeah, that sounds really helpful. In your new role, do you find that there are parts of your skillset that you need to improve? What are you trying to get better at now that you’ve transitioned into this more BD role?

Alexa Huston: Definitely, always, always room for improvement. I think my biggest focus, especially in this quarter, as I’ve gotten my feet under me, is focusing on more consultative sales. We’re not a turnkey. We don’t sell widgets. We’re trying to consult our prospects along the way in solving their unique business issues. I’ll be honest, there’s times where people, I’m speaking with them and they have such strong expertise in their industry, and it can be a little intimidating for me to understand what they’re talking about. There are common business applications that I can inquire about and get to the core issue, or how are you going to make money out of this product, for example? Or, what is your business model? How do you intend to skill your business or improve your productivity by investing in technology.

What I’m trying to get better at, in short, is being more confident in those early conversations and identifying things that we can help with that maybe aren’t as apparent on the surface.

Ben Aston: Yeah, and I think those are useful skills whether or not you’re in BD or you’re PMing as well. It’s all I think about, having that confidence to ask what you think might be stupid questions.

Alexa Huston: Totally, and they’re typically not. People want to be understood and I think there’s hesitancy sometimes to ask questions in the fear of acting stupid, but I would venture to guess that any clarifying question is worth asking, if you’re not totally sure.

Another thing I’ve been focused on is growing our existing accounts. We don’t have an account management layer here, which some agencies may, but it kind of falls on the shoulders of the product team to identify where we can keep moving, but I’m trying to also play that role as well, in client appreciation, client hospitality, and trying to identify new ways in which we can work with our clients that we love working with. That’s another area where I feel like having the PM background and getting systems set up here to be incorporated into projects, even as a BD person now, it’s proven to be effective, just as we think about growing accounts within our company.

Ben Aston: Sounds good. Client hospitality, does that mean taking them out for lunch? Is that what you mean?

Alexa Huston: Yeah, maybe a little bit of that. Some opportunities to interact with the clients outside of the weekly rituals, which we’ll get to one of those in this podcast. Since I’m not in the ground with projects anymore, I don’t want to come in later and be, hey, I’m the sales girl. Do you want to talk about more money you can spend with us? Just trying to build those relationships along the way, even after I pass, so to speak, the project off to the project managers.

Ben Aston: Yeah, no, I think that’s a really important point. That handover between sales and account or account and project management. I feel like it should never be like, okay, well, I’ve done my job and goodbye. Good luck guys.

Alexa Huston: Yeah, exactly and it can feel that way sometimes. I’m trying to, yesterday I sent cupcakes to one of our client teams just for being awesome and I was thinking about them.  I suppose it’s not hospitality, more appreciation, but just keeping a pulse on things and knowing that we’re thinking about them. Things like that.

Ben Aston: Let’s talk about your article. Alexa’s written a stonker of an article and it’s called “How to Run a Sprint Retrospective That Actually Leads to Change.” Go and have a read if you haven’t yet. If you’re new to Sprint’s and Scrum, you’re in luck because the article actually starts off explaining all of those basics about what a Sprint or a Retrospective is, why you should run them and what the difference is between a Sprint Review and a Sprint Retrospective. We cover all those kinds of things and then Alexa tackles some of the challenges, what are some of the things you might run into?

For those who aren’t doing retro’s or retrospectives yet, help make the case for us. Do these really help?

Alexa Huston: Yes, they do. I know they might seem like they can either drone on or they’re not being effective but we’ll talk about ways you can mix things up and maybe rally for more participation. I truly believe it’s important to take a step back in the course of a project, even in the course of your personal life, not to say you need to do quarterly retrospectives on yourself, but there’s some sort of benefit to reflecting on what had just occurred and then putting things in place to help make things better in the future.

I’m a huge proponent, obviously, like you mentioned, if you’re doing agile processes, you’re likely to having these types of conversations already, but yeah, I’m kind of a fan girl. I love them.

Ben Aston: I’m going to play devil’s advocate here. I have been on longer projects, or where you’re kind of in the same part of the process in the product development. You can sometimes find, and we’ll talk about this, but you can sometimes find that you get to the end of the sprint and it’s like, well, yeah, it’s pretty much the same as last time. Like, what’s going well? Well, we’re kind of tracking along okay. What’s not going so well? We’re just a bit slower than we thought we’d be. What should we do better next time? Well, we should try and be faster.

For me, the big thing is kind of inertia on the status quo and then the kind of getting people engaged. Let’s talk about how we can actually make them effective. That first thing, I think, for me, is one of the things that you mentioned in your article, which is all about fighting apathy. Tell me, what are your kind of ways that you think we can fight the routineness of a scheduled meeting? I’m all against meetings, for meetings’ sake.

Alexa Huston: Totally.

Ben Aston: If we’re not careful, that can just be, at then end of our, it’s in our calendar’s, everybody knows it’s happening at the end of the sprint, we then finally do the sprint retrospective before we start the next one. How do you fight that apathy?

Alexa Huston: That’s a great point. I, too, hate meeting for meetings’ sake. There’s a couple things I would say to that. Prepare people, and I might have a sunnier disposition than some, but just encourage the positives and maybe pimp the value of what a retrospective can provide. You mentioned kind of these longer-term projects where things just kind of hum along and yeah, there might be some things to talk about, but mostly, we need to pick up the pace. To that, I would encourage the suggestion that people be collecting thoughts along the way of the sprint, versus just waiting to recall at the time of the retro, because it can be, at that point, maybe null and void, at least at the point of the question.

What I try to do is just, along the way, collect feedback that I’ve heard from the team, gripes, or high fives, and use those as talking points to start to generate the conversation. That way, you can not have to rely on your memory at that point of …, what could be improved? That might be a good way to get started is just, offer up the suggestion that people be collecting their thoughts throughout the course of the sprint and then we’ll get into some more details later, but mixing things up, you don’t always have to ask the same questions and you don’t always have to secure 90 minutes for a meeting when it might just take 15 or 20 on those more routine projects. Be cognizant of the type of project and schedule that you’re in. It doesn’t require all hands on deck all the time.

Ben Aston: Yeah, I think that’s really solid advice. I think what you’re talking about preparing in advance, I think is really useful as well. I think, with any meeting, what we want to do is to send out an agenda in advance and tell people what we expect of them. I think, for a sprint retro, one of the things, in order for it to have any value, people need to have thought about it beforehand. It’s great if we ourselves are keeping track of all those things, but what I sometimes find is that I’m the one in the retro and I’m telling everybody what went well, what didn’t go well, and what should be changed for next time. Everyone else is just sitting there and noting and I’m like, come on guys and challenge me. Tell me something I don’t know. Actually giving them the say, hey guys, I want to come to this prepared, I think is really important.

Alexa Huston: Yeah, and again, focusing on what the outcome should be because DPM’s are more than likely and probably shouldn’t be contributing to the working product. They’re just helping to make sure that all the trains are running on time. The value isn’t necessarily on the project manager, it’s really more on the development team. There could be some PM learnings there. In fact, I have adjusted processes several times because of suggestions made in the retro. It really is sort of a holistic view of the project from DPM all the way through the whole team that is contributing to that. Yeah, I agree, just getting prepped and making sure that the team members know that this is in their best interest too.

Ben Aston: Yeah, and in your article, you talk about a couple of the things that we can do to elicit stuff for when we have people who aren’t talking or aren’t contributing. What are the kind of things that you’d suggest that we can do to actually help people? One thing is preparing but then help them contribute in the meeting itself.

Alexa Huston: Right. There’s a lot of different ways you could do that in terms of asking different questions, as I mentioned, or sort of going around in a circle and almost requiring, this might not sound ideal, but almost requiring that everyone has an answer. Don’t just throw it out and wait for someone to pick it up like a hot potato. Just say, all right, we’ll start to my right, or we’re going to start with you, John, and go around, and that way, everyone ought to contribute before moving on to the next person.

Ben Aston: Yeah, no, I think that’s really helpful. The other thing I found really helpful is when you know you have a team that’s usually reluctant to say anything. Saying, let’s start by everybody just take some post-it notes, write down three things, across all three categories, and you give them two minutes to do that. Then, they can’t not say anything. I find that helpful too.

Alexa Huston: Totally. That’s a great example and it takes the pressure off a little bit. Sometimes it might feel, especially if something is particularly sensitive or maybe a little bit of a risky suggestion, for whatever reasons, it maybe makes this person feel a little more safe. Again, the retro shouldn’t be a blame game. It should never feel like people are pointing fingers at each other. It should really be constructive and help offer up both things that work great and things that could be improved. That idea of putting it pen to paper might make people feel more comfortable.

Ben Aston: Yeah, so one of the things that you cover from your article is, how we elevate them. How we make them better. Let’s talk about some of those. One of the things that you mentioned in making our retros better, and I love this is incorporating some novelty into it. We’ve kind of covered that just now, like when we talked about, okay, just get everyone to write something down, but what are some of your favorite games or way that you actually get people thinking about things so that we stop it from being so routine?

Alexa Huston: Yeah, one of them, I’ve only done it once, it definitely mixed things up. It’s the Lego retrospective. You just find yourself a bunch of Lego blocks and you bring it in, and throughout the time box that you’ve set for the retro, you let people create shapes out of the blocks that represent the former sprint that you just completed. Then they also create a shape out of the blocks that should represent the future sprint. They have to talk about the differences and why they made what they made. It’s very abstract. People have to use their imaginations, but it gets the conversation going.

Ben Aston: How many blocks are you giving them?

Alexa Huston: However many you have one hand.

Ben Aston: How long was your time box? Was it a week?

Alexa Huston: Yeah, they created some amazing things with Legos. It was 45 minutes I think and it was really interesting because what we got out of it was just a unique conversations and again, abstracting from the day-to-day and mixing up the questions into more of an exercise where you’re using your brain creatively, which, if you think about it, I just put two and two together, code is kind of like a Lego block. It might help people think about the suggestions they make in a different way, if they’re trying to create it in a shape using Legos. I don’t know, that might be a stretch, but I’ll mention it.

Ben Aston: No, I think the point behind it is important and that is that, what we’re trying to do is just get away from the just making things feel routine. As soon as the team feels like, oh, yeah, this is just that meeting that we do after, the Sprint Review, I haven’t really got anything to add. What we’re trying to do is change that. We’re trying to make it actually valuable. That’s one of your other points about making it action orientated. How do you turn these kind of feelings and ideas into, how do you take them to the next step so that we can do something about it.

Alexa Huston: Totally. I think it’s important too, because you’ll hopefully have a very productive conversation where people are contributing, but it may not be a pain point felt by all, and that’s okay. You want to make sure you’re validating people’s thoughts and feelings. Oftentimes, I’ll ask, does everyone agree with what was just said? If there’s a resounding yes, then there’s an opportunity to create some sort of action item out of that.

As an example, we had a good conversation in a project around writing test cases. We were finding that the way in which we were incorporating those into the tickets wasn’t fitting right and it was brought up by our QA person, maybe obviously, but the whole team could understand that there were some issues with it. Point being, everyone agreed and then we created sort of a new step in our workflow to accommodate that and assigned it to the person who would be pulling it through. My point with that whole things is, if there’s something that can be changed, make sure to document it and then assign it with accountability for that person to, whether that’s to experiment with it the next sprint or report back in a month, or bring it up the chain to leadership, whatever that looks like, making sure that people know if they are responsible for taking action.

Ben Aston: Mm-hmm (affirmative). Yeah, I think that makes a lot of sense. One other thing that you talk about in your article is having an outside perspective. I’m curious as to, how outside have you got? Have you used people from another team or have you actually got a consultant in? How have you been able to do that?

Alexa Huston: Yeah, it’s a good question. Personally, I’ve relied on internal resources, to join retros occasionally. As Agile teaches us, the retrospective should be within the core team. You don’t need to have all the client stakeholders, or ancillary players involved. I’ve a couple times asked our COO, for example, who’s well ingrained in the company and the happenings of projects. I asked him to join once, as a kind of a neutral third-party, to make sure that we were identifying the right things and he’s really good at asking questions. He would kind of dig in when he noticed something was being spoken about to make sure that we were getting to the core issue.

I’m involved with a lean coffee group here in Kansas City, and we have an event every third Thursday where a bunch of DPM’s get together and talk about what’s happening with their projects with the organization’s that they’re in, some challenges they’re facing. A few of them have mentioned that they’ve brought in outside consultants to help with, I imagine, much more than just retrospectives, but that is an option that people have exercised in the past, I know, where they’ll bring in an agile coach to the whole Spring Ceremonies, including the Retro, to help them identify where things need to go. Perhaps that’s an output of conversations had in a Retrospective, but it can be helpful, maybe, to have someone else in there who’s not as familiar with the ins and outs to just come in as a neutral third party to say, well, that was interesting. Can you go into that in a little more detail? That might generate some new insights, just as an example.

Ben Aston: Yeah. Of all the things that kind of we’ve discussed and that you talk about in your article. What do you find is the hardest of all these things to do right? What can we learn from in terms of the things that actually probably the people are realistically going to find the most tricky?

Alexa Huston: I think it is, honestly, getting engagement, I have to say, and finding ways in which your team doesn’t just like, hm, this again. Really pushing for valuable outputs. I should mention, as a Scrum Master, as a DPM, you ought to be coaching the team, too, kind of in a servant leadership way, so you can’t will your excitement upon other people and you can’t will people to share their, share your enthusiasm. You can do simple things like, instead of opening up with the same questions every time, open up with a clip from The Office, and making it a little more fun and novel. Pull the old cookie card. Bring in some food. Make people feel like this can be a casual but productive conversation, things like that.

Engagement, I think, can be trickiest part. I’m not cracking any codes here but I’m realistic and I know that projects can kind of drum on for quite a while. I’ve always been on the agency side, so I can’t imagine what it’s like if you’ve been on a product for months or years. Even still, I can imagine that there can be incremental improvements that you can make along the way. Oftentimes, those are talked about in Retros.

Ben Aston: Yeah, in the article, in case you’re listening and thinking, yeah, that’s real cool but I need some ideas. Helpfully, in Alexa’s article, there’s a link to a whole bunch of games and they just go on and on and on. There’s a lot of things you could do. If you’re struggling to fight that kind of apathy and to keep it interesting, there’s a really helpful link in the article, so go and check that out. For those people who haven’t even ever done a retrospective before and are thinking, okay, well, you’ve talked about a lot of different things here. Where’s a good starting point, do you think? If we’re just starting simply and small, what’s the quick way and what’s the easy but most important thing for us to be doing?

Alexa Huston: That’s a great question. I think the simplest questions to ask are, what do we want to continue to do? What do we want to stop doing and what do we want to try? Those are three simple ones and another way to approach it is, what did we do well? What we want to improve? What we do want to keep doing? Getting the brass tax and just offering up the opportunity for people to reflect on the work that was just completed and kind if ideate on some suggestions to make it better. We’re not perfect, no project is perfect, and I’m not suggesting this the silver bullet that makes everything better.

There’s always going to be things we can improve and learn upon and there are things outside of the team’s control that I think will have impacts on the product, but definitely letting the team talk about those but doing your best effort to mediate and keep things as neutral as possible. I know it can be challenging to teams where there are outside factors that have limitations, or are putting limitations on their work. Maybe there’s ways in which the team can help direct change with that. I know there’s resources out there as well in how to make process improvements to drive change. My point with all that is, have people recognize that there’s a dedicated time at the end of every sprint for them to share their thoughts and offer feedback on what could be improved. That’s it. That’s the goal with the whole retro.

Ben Aston: Yeah, and I think your point there about positivity is important, right? Because so often there are external factors. There are always things that are going to suck on a project. Some of those things that you’re like, we should stop doing this. It’s like, well, sorry guys, but we can’t. That’s just the way it is. Somehow trying to turn it into a positive or trying to find a way that actually we can work around it. The focus has to be on improving rather than it just turning into a big whining session.

Alexa Huston: Totally.

Ben Aston: About how the client sucks and has changed their mind about the priorities again, or whatever it might be.

Alexa Huston: I might be an optimist, but I also have a healthy dose of realism. I know that there’s things that are terrible sometimes, that the team can’t directly control. I think, as the facilitator of these retros, it’s important to let people feel safe to voice that but then definitely, like I said, mediate and there’s a balance though. You don’t want to just put a blanket, like, oh, everything’s going to be great and everything’s fine and don’t worry about it because people don’t trust that. That’s not real. Finding the right balance between keeping things light but also trying to dig in to areas that really are challenging the team and finding ways in which to take that up the ladder. Find your allies within the organization, whether they’re on the team or outside of and see how you can help be impactful to make this better.

I would imagine if an organization, an agency has an agile team, or is building digital products, they are probably progressive enough and know the value that their team is providing. If those things do come up, definitely don’t brush them off. Note them and find ways in which you can find alliances within the organization to take them to discussion.

Ben Aston: Wise advice. Alexa, thanks so much for joining us. It’s been great having you with us today, again.

Alexa Huston: Oh, yeah, it’s been great. Thanks for having me.

Ben Aston: If you’ve enjoyed hearing Alexa’s wisdom, well, you’re in luck because Alexa is also going to be making an appearance on our upcoming course, mastering digital project management. If you’re not sure what I’m talking about, but you know you need some PM training, check it out. It’s a seven-week crash course that includes some interactive video, some weekly webinars, assignments, group discussions, and also the option of coaching sessions too. Head to digitalprojectmanagerschool.com and get yourself signed up before the course fills up as there are just a few places left.

Also, if you’d like to contribute to the conversation on retrospectives, than comment on the post and head to the resources section of the DigitalProjectmanager.com to join our Slack team and you’re going to find more than 1,000 other DPM’s there talking about this kind of stuff. There’s all kind of interesting conversations that you can be a part of, but until next time, thanks for listening.