Episode 72: Answering Questions About Panicked Startup Founders, Aligning Executives, and Vetting Startup Jobs
In this Dear Melissa segment, Melissa answers subscribers’ questions about wishing startup founders were able to see the value of being more product-oriented and how to influence them in that direction, organizing executives across multiple business units to align on product strategy, and how to gather evidence that a startup is the right place to work (and whether or not it’ll stay in business if you do decide to take the job).
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Q: How do I help my leadership be more product-oriented? [2:06]
A: When things go wrong [is] a really bad time to start shaking things up. They don’t want to listen to you because they’re panicking, and it's really hard to take people who are panicking and get them to change their ways. It’s a psychological thing…our minds go ‘oh, let's stick to what we're used to doing,’ and that's why you see a lot of companies in crisis unable to pivot out of it because they started when they were in crisis… Let's think about empathy with these founders. If [you go] in there and [say] ‘we have to change things’ or ‘how could you be thinking about it that way?’ it might feel scary to them… Let's say they want to try something now… if we believe that by doing x, y and z, and putting the solution out into the world, what do we think will happen? And then maybe from there if they're receptive to that, get behind their ideas… and then try to pull it back into the assumptions. [3:01]
Q: How would you go about getting alignment or endorsement from your executive group with multiple business units on product strategy? [9:45]
A: This is something that I do all the time and here's what I would start with: you have to go in there knowing that people probably don't know the same jargon as you. They don't quite understand product, so you've got a lot of different backgrounds, a lot of different people coming from different places. Start from a perspective of ‘these are not all product managers.’ Now when you're talking to them, you want to first align on what success looks like… what outcomes you’re trying to achieve; that is really important… Present yourself from the beginning about what you’re trying to do as a business, and how technology can enable that or do things that you never thought were possible before - start with those questions that help set up your product strategy as something that's more business minded. [10:19]
Q: What would be your strategy to evaluate if a product management role in a startup is a good fit? What questions should I ask in the interview? [15:44]
A: ‘How do I know it’s not going to shut down in three months?’ That’s a great question you should ask in an interview, and if a startup won’t answer, you do not go there. You can ask how much their runway is at their current burn rate, how much money they currently have in the bank, what’s their cash flow, how long they can survive at their current burn rate, if they have any anticipation of making that burn rate higher over the next year, etc… These are questions that you're allowed to ask, do not shy away from them - this is your job, this is your livelihood, so don’t feel weird about that. And if people are shady about answering you with that, do not go there… You will not have a good time and I guarantee you it's probably not going to last as a company. Also, evaluate for yourself. You're a senior product manager; make sure the problem makes sense to you and do a little research outside of the interviews on the company. [16:38]
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Transcript:
Melissa:
Hello, and welcome to another episode of dear Melissa. Today. We've got three questions for you. One about transitioning from a really large company into a startup. Another one about taking founders and helping to make them a little bit more product led. And the last one is about organizing executives across multiple business units to align on product strategy and all of that wonderful stuff, especially in an organization where you don't traditionally do product management. Well, so we're gonna dive into those, but I wanna remind you first that you can submit all your questions to me at dearmelissa.com and I'll answer them every other week on this podcast. So make sure that you go over there, let me know all the questions. It can be very, you know, it can be very specific. It can be very broad, but let me know all your burning questions and I'll get to them.
Also, if you're worried that I already answered one of your questions, um, we have the whole back catalog of the product thinking podcast listed on our website at products, labs.com. Make sure you go back and look through those dear Melissas. We also summarize some of those answers for you too. So you can quickly search and find out if I already answered your question. So with that, let's dive in first question, dear Melissa, my company is a seed round SaaS startup, and we currently have a few customers, but as we approach series a our revenues stop moving, the founders are all engineers and are feeling the pressure. And the result is no proper user discovery, validation, or even clear idea of what we try to learn. We definitely are in the build trap. I sense my founders, the CEO and CTO are freaking out. I believe that having more control over the product in their own hands is the way to go because my company was founded by four engineers.
The product culture has been weak since the beginning. I feel that a good product culture is not something on the forefront of leadership's minds because their answer to product related challenges is always, let's try more things faster. I want the product to succeed, but I feel the foundation is very weak and I wanna help my leadership, but how they're not very open to new ideas in high pressure times like this. Well, I definitely feel your struggle here. And you know, when things go wrong is usually a really bad time to start shaking things up. So I will say they don't wanna listen to you because they're panicking. And it's really hard to take people who are panicking and get them to change their ways. Honestly, it's, it's a weird psychological thing, right? Because when things aren't going well, we should probably shake it up. So that things start to go well, but our, you know, our minds go, oh, let's stick to what we're used to doing.
And that's why you see a lot of companies in crisis. Not able to pivot out of it because they started too late. Right. They started when they were in crisis. So you're definitely starting from a really hard place. And I feel for you because you know, it's gonna be, uh, it's gonna be hard to actually make this transition, but let's, let's try to think of a couple things that you could try, um, by starting this with, Hey, we should change our ways or we should try something new or we should do this, or you're not doing product management. If you're approaching any of the conversations like that, I can tell you that they're probably gonna shut down because they're scared. So let's take a couple steps back, put on our, you know, you are a senior UX researcher I can see, but you're also the UX lead, you know, half a product manager, cuz you're the only UX person welcome to seed round SaaS startups like totally get it.
You are the everything person, but from your background, I know that you like to think about empathy with users. Let's think about empathy with these founders. All right. So if I'm coming in there and going, oh, we have to change things or how could you be thinking about it that way? And even if you're not doing it in the tone that I just suggested, it might feel scary to them. So can we bring it back and make it not scary to them? Good ways to not be scary is let's let's think about what they're trying to do. Try more things faster. Okay. So let's take another idea. Let's say they wanna try something now. How can you ask questions about it? Great. That sounds like a fantastic idea. I'm really on board with that idea. Can we write down before we launch it? Just like what you think will happen or what you think will change when we put it out there, that way we can compare it to what actually happens.
So if we believe that by doing X, Y, and Z and putting the solution out into the world, um, what do we think will happen? And then maybe from there, if they're receptive to that and like, like get behind their ideas, even if you think it's the worst idea in the world, um, telling somebody that in the moment is probably not the best idea, like get behind the idea and then try to pull it back into the assumption, right? Try to pull it back into what do we think success is gonna look like? What do we think? Um, good will look like in this situation. Uh, how do we know that this will work and maybe just casually talk to them about that and see if it opens any new ideas at the same time. Can you go out and do some, you know, some user research on this too, like figure out why the revenue stopped moving if it's a sales problem, which it sounds like, is it, you know, it sounds like you you've got a product that might not be solving the appropriate problem, but can you go back to your customers?
Talk to them, be like, Hey, I am the user researcher. Like, let me go talk to your existing customers and find out like what the special sauce is. Right. Are we targeting the right people? Are we, um, going after the right personas? Do we have to, are we not solving things completely? Are people going to different companies because we don't have the full feature set. Can you know those questions to ask? I can tell just by the way that you're phrasing some of this, can you go do of that and then bring it back to the team to help point it out? Um, sometimes in this situation, you know, it's let, let them keep doing what they're doing, but can you take an approach of, Hey, like that's a really great idea. I think that what we should do as well is like go talk to X, Y, and Z person about this.
Um, like they might be able to give us some more, you know, more eye opening ideas about how to do this well, right? Like don't phrase it as like product culture or, you know, product thinking or anything like that. Like not discovery validation, like take the buzzwords out and just try to make it about the work that you're trying to execute now and pull it into how it's gonna help you do what you're currently trying to do. That's gonna make it less scary for them. Um, but I will say like with all of this suggestions and you may have tried this and it may not have worked. Like, I totally recognize that as well. All these suggestions you're in a really hard place. Um, and if they're not receptive to actually, you know, digging into why and getting in there, it's gonna be hard. I will also say that if you're a seed round startup and you have some advisors in your purchase series, a like you should probably have some advisors, um, hopefully they should be asking the same questions.
So they, it may be the quality of the advisors that you have on the company too, if they're all engineering minded as well, they're not gonna be asking these questions. Um, but you might wanna like say, if you, if you do know who's the advisors or people there, you might wanna say like, Hey, maybe this person like might be able to help us with this. Or maybe that can like help, you know, shed some light on this. Uh, that's what startup advisors are there for. I advise startups, um, I've been on boards, like that's the whole point. We're there to help round out a team that's not fully formed yet and help ask the hard questions. So if you know who those people are, and you can convince the CEO or the CTO to go talk to them, like, that's literally what they're there for.
I guarantee you, they're gonna start talking to them anyway. when they start telling them revenue's not moving and it could be jeopardizing their series a they'll start asking the hard questions. It might be a waiting game, um, which is just a hard position for you to be in at where you're at. But, um, that's, that's the hard part is like in high pressure times, it's really, really hard to pull people back. And those are my best suggestions on how to do that. It may not work. It sounds like your team, wasn't really your founding team. Wasn't really well rounded, which is fine. That usually happens. But they have to have the foresight to hire in for their skills that they don't have. And one of those sounds like product, like usually it's a product like a CEO or the CTO is gonna be the product leader at the beginning.
Um, at this juncture, maybe, maybe it starts a conversation about how you get a great product manager in there to help them ask those questions too. Like, I know you are trying to do it. Um, it's hard sometimes to see what we have right in front of us when you're part of the team, which is really sad, but like, that might be why they're just really not receptive to new ideas. It might be like, oh, you know, but you're here. You don't understand. Um, which I hate, I don't like that mentality. It might take an outside perspective to kind of like shake them out up a little bit. Um, but the best thing that you could do is probably suggest how do they get help from different places and start asking like, questions that don't, don't come off as like challenging or were doing it wrong or anything like that.
Just keep it very simple, be energetic and make it sound like, like you're behind them and what you're doing, but then poke, poke a little bit, but don't poke too much cuz I will put their reactions up. So that's the best thing I could suggest. But they at, at the end of the day, they're the leaders and they have to see that they have a problem and they have to want to correct it. There's only so much you can do. And that's, what's so challenging about not being in the position yourself. All right. Next question, dear Melissa. Thanks for the awesome work you do. I get so much outta your podcasts. Well thank you very much. I'm glad you enjoy them. How would you go about getting alignment or endorsement from your executive group with multiple business units on product strategy, your vision objective squads example of work in organizations with low product maturity.
Historically tech has been an order taker here. I have a workshop booked with the relevant GMs heads of product heads of everything to review product strategy and reference to business unit OKRs and identify alignment or misalignment. Um, and I have to say I'm a little nervous thanks. All right. So this is something that I do all the time. Um, and here's what I would start with one. You have to go in there knowing that people probably don't know the same jargon as you. They don't quite understand product. Um, maybe some of them do, but not all of them, especially if you have it like sounds like your business unit heads, an executive group is all coming. So you've got a lot of different backgrounds, a lot of different people coming from different places. So just start from a perspective of these are not all product managers.
Um, I see that you are the head of product. So cool. Now when you're talking to them, you wanna first align on what does success look like? Uh, what does success look like for our business? What are the outcomes we're trying to achieve? Uh, that is really important. So make sure that you are aligned on that first start there and then start at the highest level of the OKRs, right? Like get rid of the, how at the beginning and talk about the why. So when you talk about the vision brainstorm, right? Like I run little things where we start individually and then we bring it all back together and then we brainstorm and we look at it and we say, why, why, why, why, why, why? Um, it's really important too. I don't know. Who's gonna be the person in this group of people, but um, you need to have like a decision maker.
So like, are you bringing this back to the CEO? Are, is there one person who is like the, the end game, right? Who says like, this is the way that we're going, because everybody can have inputs at the end of the day, but you need, uh, if there's like wild disagreement, you need to have somebody who's going, okay, cool. Like you can all dissent, but we're gonna go this way. Like this, this is the way that I wanna go. So identify who that person is. Um, and if they're not in this meeting, you are, you may come to a full, you know, alignment on things, which would be fantastic. But if you don't, that's the person that you go to next. And then I would say, don't make the objective of this workshop to come out with like a consensus building, make it to come out with, okay.
Here's like two, two different options of what we could do. Let's bring it back to the CEO and figure out what they wanna do. Right. Something like that. So that's really the hard part about this is like, uh, you don't wanna just make it consensus, building across all the GMs and the heads you wanna be aligned, but somebody needs to really be the one who's sticking to their expertise and being like, I own this and I want your inputs. And uh, you know, whoever owns it gets to have the final say, but everybody else gets input. So remember that for every specific part of this like squad organization, if you're the head of product, uh, you and the head of technology own the squad organization. Like I don't really care. Not that I don't care. I get the inputs from the GM, but at the end of the day, I'm gonna organize it the way that it works for me.
Right. That's, that's something to keep in your mind. So you don't want to make this just like full on consensus, driven, like organizations that are just full on consensus, consensus driven. Like that's not great strategy. Like you have specific functions in there. You want alignment, you want buy-in. Um, but you also want to agree to dissent on something things, but they're gonna commit. Right. So keep that mentality in here now. Um, I would say another piece of it too. Start high level. Start with the vision. Start with why start with where you came from review, like current metrics, review, current status review, things that are going well right now, things that are not going well right now, and then start really high and then get more specific. Like that's, that's the order of that this should be going on. Um, and if you are feeling like a lot of, if you are feeling like a lot of people aren't agreeing or there's like tension or whatever, um, you know, don't try to get to one answer by the end of this workshop, just try to get to a narrowed down set of things.
I will also say it's really hard to get to one answer out of a workshop. You should look at it as it's narrowing down my options to like two or three options, and then we're gonna go run some numbers on them and then figure out what's next. Right? You're probably gonna have to do a series of these workshops too. Especially if they haven't done this before. Um, with the tech being an order taker, you want to show that as the head of product and with, I hope you're head of technology is in this conversation as well. Um, you guys are asking the right questions that are business oriented. So present yourself from the beginning about what are we trying to do as a business? How can technology help enable that or do things that we never thought were possible before. start with those questions, right?
That helps set up your product strategy as something that's more business minded, right? Like it's more connected to the business than just like, Hey, tech is over there, just like, you know, fixing databases. Like we don't know what they do, right. Start with the conversation of what does technology do to drive this forward? What are things that we wish we could do that we never thought were possible? And then can we do that with technology, right? Like those are the conversations you need to be having with people who don't understand quite how technology could've worked. Um, when tech is an order taker in most companies, it's because people don't understand how business and technology come together and how technology can be part of the business. So you need to bridge those gaps in this workshop and really start talking about that so that they all see you as part of the business and as part of the business strategy as well, not just the product strategy.
And also remember like you, since you're the head of product in your other head of product people, right? You guys are responsible for the product strategy. At the end of the day, the GMs have input. They're responsible for the business strategy, but you are responsible for the product strategy. So you've gotta be where that ends, right. And if you're doing it across units and you're trying to come up with a holistic product strategy, this is why I advocate for CPOs to sit in that function. But a lot of times we don't have it. Then you guys have to be the team that makes up the CPO, you and your other head of products to kind of create that common platform strategy or that common product strategy across business units. All right, last question, dear Melissa. All of my professional experience has been in big international companies, including the last couple of years as a senior product manager, as I'm preparing for my next career step, I'm considering exploring the startup world, especially around creative industries, art NFTs, all that stuff. However, I'm not sure how to evaluate a given startup is a good fit for me. I'm also uncertain of what questions ask or what data to look at, to understand if the startup won't shut down in the next, say three months as a PM, I enjoy and have experience in early stage of product development, namely ideation, and building a VPs. What would be your strategy to evaluate if a product management role in a startup is good fit considering this context? What questions should I ask during the interviews? Thanks in advance.
All right. Great questions. I started laughing because I, I went through this same question when I joined open sky many, many, many moons ago, um, because I had an offer from Amazon and I was like, do I go to Amazon where it's nice and safe? Or do I go to a startup that I was like, employee number 35 at, and I asked the same question, how do I know it's not gonna shut down in three months?
And I asked it in the interview and they were like, don't worry. We have money , which is great. But like, that is a question that you should ask in the interview. So like these are legitimate questions. And if the startup will not answer, you do not go there. if they do not answer you on these types of things. Um, and I think every other startup person would tell you the same thing you can ask. How much is our runway at our current burn rate? Like how much money do we currently have in the bank? What is our cash flow? And how long can we survive at our current burn rate? Do you have any anticipation of making that burn rate higher over the next year? Right. So a company should be able to come back and say at the moment with the cash in the bank, we have a three year runway.
Um, with our current burn rate, we do not anticipate hiring like crazy over the next three years. So we think that burn rate will stay very similar. But what we are trying to do is go for our series a and, um, we're actively starting to recruit for that. We should be able to lock that down with in the next year and a half. In that case, you know, we'll be raising a big round and we'll be able to hire more and we'll be able to grow faster. These are questions that you're allowed to ask, do not shy away from them. This is your job. This is your livelihood. So don't feel weird about that. And if people were shady about answering you with that, do not go there. That's some shady people, you should not be working for them. Uh, you will not have a good time.
And I guarantee you, it's probably not going to last as a company. So ask the questions, get into that. Right. Um, also evaluate it for yourself. You are a senior product manager, like make sure the, the problem makes sense to you do a little research outside of the interviews on the company. Like make sure it's solving a problem that you think is an actual problem. Um, if it has VCs backing them, look at who's backing them, right? If somebody, if a big VC gave them a seed round it's because they usually believe in them, wanna see how it plays out and then they'll do their series a, um, if it's just like friends and family money, that's fine. But like, it also works out. But like if it's, if they do have any big names backing them, um, you know, it's a good sign. Uh, it's not always a guarantee though.
Sometimes people just throw money at stuff and see if it hits. But, uh, you know, there was something that they saw there something enough to make them go, Hey, this is interesting. Right. So do the due diligence there, ask the questions about the runway, um, and then make sure it's solving a real problem. Right? That's, that's the big thing. And especially if you're getting into things like NFTs, I mean, everybody's into NFTs right now. Um, but I don't know if it's gonna be a fad or not. People will probably freak out if I say that , but like, I, I don't, I don't know where this stuff is going. Um, I think they could be used in, in ways that do solve a problem and make sure that the place that you're at is not just hyped up social media type stuff. Like it is actually solving a problem.
And I do believe NFTs are insane for the art business. Um, I know a lot about the art world. Um, and I will say NFTs right there, uh, probably are game changer. So like, if you are actually solving a real problem with them and helping in that area, like it could be great. It could be a fantastic place to land. So, you know, just do the due diligence and make sure that it's solving a problem. Uh, second, is it right for you now? That's a bigger question, right? Uh, if you are moving from a really large international company to a startup, the first thing that you need to know is that it's messy as hell, right? Like characterized by pure chaos. That is the startup world. Uh there are no set processes. Usually there is usually no structure. There's like no career ladders. It is like all hands on deck, just do what you wanna do, roll up your sleeves and get in there.
That doesn't mean it won't change, but like, that's what you're walking into. And as it starts scaling, you get the processes, you get the standardization, you get the HR teams, right? Like that's, that comes later. So if you are not okay in pure chaos, if you do not like uncertainty, a startup world is not for you go to a growth stage company where you'll get a little bit more of that. If you wanna go smaller. Um, but do not go for a very early stage startup. Now that's something to really think about because I've seen a lot of people go, oh, I love startups are really cool. I came from the enterprise and now I wanna try it. And they just are like, what, what in the fresh hell is this like, is a mess here. Um, nobody's doing what they're supposed to be doing all of this different stuff, right?
Like, uh, just be aware, be aware of that. Now. Let's say you love uncertainty. You love playing like four roles instead of one very well defined senior product management position. Uh, that's great. And that's the startup world for you now also ask them what your role is gonna be like on a day to day basis. Now, a lot of people in startups hire in product managers and they do not know what they do. They do not know what the job of a product manager is. I educate founders on this all the time. We always talk about your first product management hire, um, in my class at Harvard business school for the founders, uh, sometimes they don't know what it is, so they might be hiring for a position. They don't really understand. So ask them specifically, what do you see my day to day looking like, what do you see my week to week looking like, what activities do you need me to do?
Um, what if I ju like, if I take this role, what does success look like for me, I'm here for a year. What, what makes you think I did a good job? What did I do? So that's gonna give you a lot of insight into what they think the role of a product manager is. And if it aligns with your expectations, like cool, you're, you're great if it doesn't run, right. So really ask them about what you should be doing. And then also ask them, you know, ask them about their strategy, ask them about their vision, all that wonderful stuff that you typically would, but like, make sure you ask them about what you are supposed to be doing on a day to day basis. Don't assume that they know what product management is. That is my biggest piece of advice there.
All right. That's it for dear Melissa this week. And if you have questions, make sure that you please submit them to dear melissa.com so that I can answer them in an upcoming episode next week, we're kicking off a really cool series, all about pivoting in product management during COVID. So we are talking to startup a growth stage company and an enterprise company all about what they did during, COVID, how they pivoted and then how the company really succeeded and worked through those pivots and what led to those ideas into that success for them.
So I'm very excited for that. So make sure that you tune in for the next three weeks. Um, every Wednesday, when we release a new episode to hear all about how they succeeded during COVID, we'll see you next time.