7/9 Critical Conversations You've Forgotten to Have With Your Team: Assumptions Part 2

[00:00:00] Welcome to the Convergence Podcast. I'm your host, Ashok Sivanand.

[00:00:05] How do we kind of transition those big wins and big sad faces down to sort of micro wins and micro sad faces where the emotional turnaround time when we find what we're wrong about something is way less.

[00:00:19] On this show, we'll deconstruct the best practices, principles, and the underlying philosophies behind the most engaged product teams who ship the most successful products.

[00:00:36] This is what teams are made of.

[00:00:39] Welcome back, folks.

[00:00:40] This is part two of two of the Crucial Conversations series number seven about what assumptions we're making as a product team.

[00:00:50] I am delighted to be joined once again by Bailey O'Shea, who is now the Director of Product at TransImpact.

[00:00:57] Bailey is also someone that I've had the pleasure of leading product teams alongside for over five years.

[00:01:02] On part one of this conversation that we shipped last week about assumptions, Bailey and I talked about product stories from the field and how facilitating this conversation through workshops and other methods led to our teams building better products a lot faster.

[00:01:19] Today, we'll get deeper into the how of this.

[00:01:24] We'll get deeper into the information.

[00:01:25] We'll get more information about how bringing the team together and giving everyone permission to poke holes in the plan can surface hidden risks, as well as a mindset of vulnerability and trust on your team.

[00:01:37] We talk about what types of assumptions we're typically looking to address the most, some tips on facilitating a good assumptions generating exercise, and how you can get started today with some sticky notes and sharpies.

[00:01:51] By the way, if you're curious about the other crucial conversations like this one, check out the summary episode that we did from April 23rd, 2024, where we talk about all nine conversations at a high level, as well as an ebook that you can get for free that's linked in the show notes.

[00:02:09] Make sure to also subscribe to the podcast to be notified when we launch episodes about conversations number eight and nine, which are about target audiences and the highest priority problems that we're solving as a team.

[00:02:22] Subscribe to the podcast to get future episodes as soon as they're published.

[00:02:26] If you find this helpful, give the podcast a five-star rating on your podcast app or hit that like button on YouTube.

[00:02:33] Here's part two of two of Bailey's conversation with myself.

[00:02:41] You talked about a plan there, Bailey, but I think we know that, you know, plans are useless, but planning is indispensable in this case.

[00:02:49] And so what do you think about that?

[00:02:52] Planning is indispensable because what you're trying to do when you're making a plan is that that whole plan is a hypothesis, a giant assumption.

[00:02:59] This is what we think is going to work.

[00:03:02] The plan allows the team to all row the boat in the same direction.

[00:03:06] But when you're talking in assumptions, it gives everybody permission to pivot and also to challenge each other's assumptions along the way.

[00:03:14] So you don't feel like you just have to do the plan because it's the plan.

[00:03:18] So it really does invite more like purpose-centric conversation and collaboration.

[00:03:24] And it also takes away kind of maybe like asking a question and getting an answer rather than asking a question, having somebody own that answer or own the outcome of it.

[00:03:40] So I just I really like using assumptions to pull apart a plan.

[00:03:48] It gives everybody permission to poke holes in, which is what you need in order to have like the collected brain trust of the team be leveraged and ultimately move faster.

[00:03:58] And you were talking about speed to market with getting your solution up as soon as possible.

[00:04:04] And I think it's also speed to pivot to use some of your favorite language.

[00:04:09] You mentioned that when we talk about assumptions, it's a less emotionally loaded conversation, maybe.

[00:04:15] Yeah, that's a good way to do it.

[00:04:16] Where we can collectively just kind of agree like, hey, this is our best guess on this working.

[00:04:19] And if it works, we're all going to be, you know, way more successful and so forth.

[00:04:24] But if it doesn't work, it's going to be big sad faces.

[00:04:26] And how do we kind of transition those big wins and big sad faces down to sort of micro wins and micro sad faces where the emotional turnaround time when we find that we're wrong about something is way less.

[00:04:42] And so there's just less disheartening and other things like that that you have to worry about collectively on your team around the overall energy that everyone has to show up and do really great and try really hard.

[00:04:55] Where if we talk about it as assumptions, I think we kind of buy ourselves some level of safety net for getting back up quickly when we realize that we were wrong about an assumption and then solving for it versus when it gets really big and the risk is really big and we find out really late.

[00:05:14] Where it's just a lot harder to kind of bounce back from, I think, as a team and causes a bunch of sort of political, cultural rifts on the team that ends up requiring a lot more management effort that could have been spent towards solving business or customer problems otherwise.

[00:05:33] Yeah, for sure.

[00:05:34] What are some of your favorite ways to facilitate that conversation?

[00:05:38] I mentioned one with like just the stickies example and we can use that or pull that apart, but I'm curious kind of your thoughts there.

[00:05:45] And what are the questions that you ask yourself for your team?

[00:05:50] I think the myself question, I like that you phrased it.

[00:05:53] The first one is, have I given the team enough context to for their brains to start generating those assumptions?

[00:06:00] Right.

[00:06:00] And you gave us the answer key to that.

[00:06:02] We want to make sure we're highlighting to the team.

[00:06:05] Hey, this is where we're today.

[00:06:06] Number two, this is where we want to get to.

[00:06:08] Number three, this is how we think we're going to get there.

[00:06:13] These are the reasons that we want to get there.

[00:06:15] These are the and then, you know, this the next thing is these are the assumptions we're making along the way or these are the problems that we anticipate we need to encounter along the way.

[00:06:24] Yeah.

[00:06:25] And so what do I ask myself first?

[00:06:29] I think it's have I given the team enough context where they're energized and they're, you know, their brains are starting to fire out ideas on how they're going to win and maybe what's going to get in the way.

[00:06:40] And then the second thing I think is another thing we mentioned is have we had a conversation across folks who advocate for the business and the business model across folks who advocate for the customer and their problem across folks who advocate for the technology we're building.

[00:06:56] Our business people are design and product people are engineering folks all in the same room having the same conversation around assumptions.

[00:07:03] If you're assuming that it's going to take three times as long to have this conversation, you're right.

[00:07:09] It might take even longer in the short term during that first week where you need to pull everyone together and have them change their schedules.

[00:07:16] But I guarantee you it's going to help you with firing in all cylinders and moving a lot faster and saving way more time than the upfront investment when the team is able to communicate with each other.

[00:07:27] When they understand that, hey, none of us are perfect here and we can ask for help and lean on each other.

[00:07:32] We can share problems that we see around the corner early versus feeling like we may get reprimanded for bringing a problem to bear.

[00:07:41] And that overall sort of trust and vibe in your culture can also be formed by having the conversation together.

[00:07:49] You mentioned the sticky note thing.

[00:07:50] I think that, you know, it's tried and tested.

[00:07:53] It's fairly simple.

[00:07:54] Sometimes folks do need prompts, right?

[00:07:56] The word assumption, I remember the first time I did it, I had to really remember what it meant as much as it's a word that we use colloquially all the time.

[00:08:04] And so what are some prompts that maybe help get the brain juices flowing when you're getting folks to write down their assumptions and sticky notes?

[00:08:11] Yeah.

[00:08:12] So I'm going to try not to use the word assumption when I'm thinking about these.

[00:08:16] It's hard.

[00:08:18] What are some qualities about our customers that we like?

[00:08:24] What are some actions that we think our customers are going to take?

[00:08:28] That is a way to say it without saying assumption.

[00:08:30] That means what do we assume our customers are going to be doing?

[00:08:35] I think you're what must be true that you said earlier.

[00:08:39] Maybe like a good start to them, right?

[00:08:41] Yeah.

[00:08:41] Yeah.

[00:08:42] So if we were talking about putting together like an ice cream delivery service, like what must be true in order for this ice cream delivery service to succeed in today's marketplace?

[00:08:54] At the top, you're thinking of the customer experience.

[00:08:57] Does the customer want ice cream delivered?

[00:08:59] When they get it delivered, is it of good quality?

[00:09:02] How much do they want to pay for it?

[00:09:05] And we're going to make a lot of assumptions about what our customers are willing to do to even like,

[00:09:11] move forward.

[00:09:12] And those are the things that we want to write down and we want to go validate with little experiments.

[00:09:16] That can be as simple as conversation.

[00:09:18] It could also be, you know, putting a prototype out there and seeing if people start to interact with it.

[00:09:26] From the technology element, what must be true in order for this ice cream delivery service to work?

[00:09:33] Well, you know, customers need to know time of delivery.

[00:09:37] They need to probably be able to track it.

[00:09:39] Like, do we have that real-time experience in mind?

[00:09:43] Is there a way that we can do that with less effort?

[00:09:46] Also, from the business model standpoint, what must be true for this ice cream delivery service to succeed?

[00:09:51] How are we going to make money?

[00:09:53] What are the margins?

[00:09:55] What margins do we need to sustain the continued investment into the technology?

[00:10:00] So that's the way I think in terms of prompts.

[00:10:06] Yeah, and I think, you know, folks from the product schools of thinking that have embraced lean, agile, and so forth

[00:10:12] have probably come across that Venn diagram from design thinking, right, around desirability, feasibility, and viability.

[00:10:19] Yeah.

[00:10:20] And as much as we look at those as checkboxes of things that have to be true, it's a slight reframe to understanding the assumptions of what must be true

[00:10:31] for all of those three circles to overlap enough for you to feel like you have a viable, sustainable product or a sustainable business.

[00:10:39] And I think most of the time it's around those three things that we identify things that cause issues where is this a desirable thing for the customer, enough for them to engage?

[00:10:51] Can we sustainably build this in the long term?

[00:10:55] Like you said, not just for the technology now, but also a sustained investment into the technology that we know tends to be the case for how software works today.

[00:11:07] And the third one's around, you know, we maybe go specific to technical feasibility, but I prefer kind of solution and service feasibility.

[00:11:17] Because especially in the early days, you're going to have a combination of manual and automated components coming together where you have operations teams or employees plus the software.

[00:11:30] And thinking about them together, I think also allows us to ask questions about, do we have the right team composition?

[00:11:36] Do we have any technology components that we need to go and outsource?

[00:11:42] And does that work?

[00:11:43] And the spikes that you talked about and so forth.

[00:11:45] So, yeah, going back to those three is another way where if your team's feeling like the sticky notes are not firing off in the beginning,

[00:11:51] those are some sub prompts that you can feed into your team to get things firing off.

[00:12:00] Fostering an engaged product organization and aligning them with the principles around lean, human centered design and agile will more than likely lead to successful business outcomes for your organization.

[00:12:14] But getting started or getting unblocked can be hard.

[00:12:16] This podcast is brought to you by the player coaches over at Integral.

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[00:12:40] During this session, the integral team will facilitate a problem solving exercise that gives you clarity and confidence to solve a product design or engineering problem.

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[00:12:55] Now back to the show.

[00:13:01] And then once you got all the sticky notes, what do we do?

[00:13:05] Well, then we want to see which ones are common across all the different perspectives.

[00:13:11] And then you want to get to the point where you're prioritizing or ranking them against each other.

[00:13:16] Thinking about risk is a great way to do that.

[00:13:22] So, you know, what is what is the impact of this isn't if this doesn't come true?

[00:13:26] This specific element.

[00:13:28] If the Costa Roll will not pay $10.50 to have their ice cream delivered, what is the impact of that?

[00:13:34] It's pretty huge.

[00:13:37] And so I would then, you know, prioritize the biggest risks first and try to minimize the impact of those risks using experiments.

[00:13:49] Yeah, I've gotten pushback on sort of the stack ranking or relative ranking that you mentioned there because item number one could be few orders of magnitude bigger than item number two.

[00:14:01] But really, like, it's a pragmatic approach to end up with just a few sticky notes compared to 20 so that our team is allocating towards those top four.

[00:14:10] And so the relative stack ranking, I think, is a quick way to get out of that conundrum or dilemma.

[00:14:18] And then, of course, as you start to zoom in further, you're starting to ask yourself, you know, maybe assumptions in the business model of we need to capture this percentage of the market who's willing to pay a minimum of X dollar amount while also servicing this for less than X amount of cost.

[00:14:37] And, you know, you go away from just sticky notes to opening up the spreadsheets or other ways that we need to get a little bit more precise.

[00:14:47] But we reasonably can't afford to do that for all sticky notes.

[00:14:50] So the stack ranking, I think, is really helpful in helping us whittle down even our experiments and de-risking effort.

[00:14:56] And then really, like, the two by two, if you will, in terms of what are the riskiest assumptions, I think, are what are the things that could really hurt you the most that you also know the least about?

[00:15:08] We knew what it cost the business and the business wanted at least 2x that in terms of what the customer paid.

[00:15:18] And when we went to, in this case, Chicago and spoke to potential folks, we found that a lot of them were willing to pay even more than double what we knew it cost to service this.

[00:15:31] And they were looking at a variety of factors where they're adding up a new car and what it costs to insure a new car plus maintenance and everything else compared to us taking care of a lot of things in our own estimates and assumptions that went into the business model.

[00:15:44] Of course, this is a car company, so they had really good data on both insurance, given that in their case they were self-insured, and then also around what it actually costs to service this business in the long term.

[00:15:56] And so that was an area of innovation or area of opportunity because it was going to be way more accessible to the service provider in this case than what the consumer perception was.

[00:16:09] And so that was one big checkbox.

[00:16:11] On the flip side, the strategy brief we had gotten were millennials in urban populations, and that could mean anything.

[00:16:20] And as we did the research, we realized that, yes, there were a lot of folks that were millennials that lived in the city of Chicago, within the suburbs.

[00:16:34] And the folks who lived downtown didn't really care because they had a really high density of other options available to them.

[00:16:42] It's the folks who lived in sort of the midtown circle outside of downtown that had to take the L train all the way downtown and then take another L train from there maybe, that cared way more about it.

[00:16:55] So when it came down to which partners we wanted to find in dealerships to pilot this, we started targeting very different dealerships for our target cities because we knew that the downtown dealerships maybe wouldn't get the same traction as the midtown ones.

[00:17:12] And had a better story to go convince the dealerships to try this with us based on showing that we did some level of homework.

[00:17:19] And then I think the third thing that comes to mind for me was that the business model one, right?

[00:17:24] We were really shaky about like, hey, is this something that is a waste of money?

[00:17:29] Or is someone else, on the other hand, going to be spending 100x this amount of money and getting to market first?

[00:17:34] And in this case, it was enough for the car company's strategy team to say, hey, this investment that we thought we were putting in here, we're going to double down on it based on the level of validation we're seeing around our assumptions that the product team, surprisingly, was the one that were boots on the ground helping them learn more about.

[00:17:52] And we built very little tech in the first three months before they decided that, hey, we've seen enough about the customers you're able to generate and bring on to this using sort of strung together pre-MVPS tech.

[00:18:07] But the service offering itself was white glove.

[00:18:11] And they looked at that and said, hey, we should acquire the company that we're talking to.

[00:18:15] We think that our distribution channel is going to be plenty for thus, given this math now, for what they've already built and saves us 18 months of having to go out there and build it.

[00:18:26] And so I think there's different ways from prioritizing these assumptions across, hey, what is the stuff that we know the least about and also could hurt us the most?

[00:18:37] That counterintuitively, to your point, enabled us to go way faster when, don't get me wrong, there were folks who were thinking like, why don't you just build a database and start doing this versus doing this experiment?

[00:18:50] The experimentation is actually like how we built stuff and knowledge was the asset as opposed to lines of codes, lines of code.

[00:18:57] And it took a little bit of iterative thinking and going fast together with the more cynical stakeholders to show them that ultimately the business outcome they were looking for was to generate a new business model, generate new profitability and revenue streams.

[00:19:13] was getting there much faster as a result of knowing what the assumptions were, finding experiments and then taking actions based on the new information, as opposed to waiting the, you know, between six and 18 months, depending on your size of organization to get this solution out to market completely.

[00:19:31] That's wild. I love stories like that. When it, I mean, you ended up with a completely different, your plan and your outcome were completely different. Right. In that instance.

[00:19:40] Yeah. And I think we, you know, we, we did know the underlying thing that the, that the client was solving for, which was they wanted to find a new business model and new revenue streams to target this new customer persona.

[00:19:55] That was different from the previous generation of folks and how they engaged with them. So everyone, including the engineers, in this case was a relatable problem because most of the folks on the team had to figure out how they got from point A to point B, whether it's taking transit

[00:20:10] or buying their own car or leasing the car or leasing the car or leasing the car and everything else. So the ideas were a plenty and then prioritizing them was all we were doing as facilitators.

[00:20:20] Once we made sure that the context was there and don't get me wrong, the folks that we asked about the business strategy, weren't sure why we were asking them that in the first place, where we wanted to know about what would change in their business amongst all the things they could have funded.

[00:20:35] Why were we sitting in that room talking about that specific thing? And I think those are things that sometimes we forget to do as product folks or delivery folks in terms of asking some more underlying assumptions that someone else has made that we are now carrying and maybe solving for those assumptions alongside them versus separating those duties saying, you know what, I'm going to take care of technical assumptions.

[00:21:02] You figure out the business assumptions. It's to your earlier point, it's a great way to bring the team together and engage and energize the team towards a very relatable problem, whether it's as an employee for this company that you want the company to succeed or on behalf of a customer who you would like to solve a problem for.

[00:21:22] We've been talking about this too from like a very strategic mindset around assumptions.

[00:21:27] But if anybody listening is on a product team today and maybe you're like, I would really love to try this next week.

[00:21:33] Like, what can I do? Right. And I just want to maybe share like a tactical way to get started.

[00:21:41] Like, if you are listening and you want to do this next week, look ahead on your roadmap, pull up a big epic or a goal, maybe next quarter, and write that at the top of your mural or mural board or your conference room.

[00:21:53] And then kind of sketch out that user journey as you would assume it to be.

[00:21:59] Just at a really high level, what is that customer journey?

[00:22:03] And then ask the group, what are our assumptions underlying?

[00:22:08] One, you're going to learn that not everybody's idea of that journey is the same.

[00:22:12] Then you're going to learn almost like a service blueprint technology.

[00:22:16] Maybe we're not so ready.

[00:22:18] But I tried this on the most simplest level for like an epic this past summer when I was working with a utility company.

[00:22:25] And we had people, again, from all different elements of the business.

[00:22:29] We not only talked about the journey, but we talked about the technology underlying it and also what are the potential integrations and the impact of the customer experience as a result.

[00:22:39] And what we started out with and what we ended up with were different at the end of the day.

[00:22:45] But it did allow the team to move faster.

[00:22:47] And everybody was shared, to your point, that same context as they were doing so.

[00:22:52] And they were bought into the mission of doing it.

[00:22:54] So you're not just doing a spike because the manager told you to do a spike.

[00:22:58] You're doing a spike because you actually care, because you know what's going to happen if you're wrong.

[00:23:05] And now you have the agency to change it.

[00:23:08] So, yeah, if anybody listening wants to do this next week, it's as simple as sharing that high level vision or goal,

[00:23:17] visualizing it in some way for the group and giving everybody some time to wrap their brains around it from their unique perspective.

[00:23:24] I'm so glad that you mentioned that point around visualizing.

[00:23:28] Going back to your question about what are the things that I think about,

[00:23:31] making sure that that's all out there and presented in front of the folks who have the sticky notes that are going to be ideating assumptions,

[00:23:39] is such a low-cost but highly effective way to get folks' creative juices flowing in alignment with the problem you're trying to solve

[00:23:49] or the experience you're trying to create.

[00:23:51] And it's so much easier for our brains to generate those assumptions when we're reacting or responding to something like a user journey

[00:23:59] compared to having it be something theoretical that they're holding in their head versus visualize out there.

[00:24:05] So I'm so glad that you brought that up.

[00:24:06] It's always a pleasure to have you on here.

[00:24:09] I've definitely heard from the guests too, that you're someone that they find very relatable and engaging.

[00:24:15] So thank you again for making the time.

[00:24:17] We will continue talking about the nine crucial conversations.

[00:24:21] We're getting closer to the end.

[00:24:23] The next one is going to be actually around who is the product for and the customer segmentation.

[00:24:29] And there's a ton of places where assumptions and experimentation from today come to play around in terms of highlighting who the customer is

[00:24:38] or the different segments of customers that we're targeting and what priority they are and everything else.

[00:24:43] So looking forward to speaking more about that.

[00:24:47] Don't forget to check the show notes for a link to an e-book that highlights all nine of these conversations,

[00:24:53] as well as some of the links of previous episodes in the podcast where we talked about all nine conversations,

[00:25:01] as well as individuals where we deep dive like this one into facilitation techniques and other lessons learned and stories from the field.

[00:25:10] Thanks again for listening, folks.

[00:25:11] We will be back on Tuesday with your next episode.

[00:25:15] Thanks for having me.

[00:25:22] Thank you for joining me on the Convergence podcast today.

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