Navigating the twilight zone
Transitioning from Founder lead product to first Product Manager
Based on a talk given at Product Tank Brighton. The recording and slides are available at the end of the article. Many thanks to Chloé Hajnal-Corob for her contributions.
I’ve been doing a lot of coaching of product managers, founders and other early stage leaders. During this process I’ve realised that most of the content that is written about product is for established companies. There’s very little out there about the often perilous transition between founder lead product and product manager lead product. This transition is often long, emotionally fraught and full of starts and stops. I call it the Twilight Zone.
The Twilight Zone sits between what Nikhyl Singhal calls the “Drunken Walk”, where effectively the company is walking into walls, trying all these different ideas, and not really quite hitting the spot, and the moment where it finally finds product-market fit and brings in the first product leader.
If you’re in the Twilight Zone yourself, I hope this article provides some tips to help you survive and even thrive in this transition. If you have never been in this weird zone before, this article will give you some insight into what it feels like to be the first product person at a seed stage or Series A company. And help you consider whether this is something that you’d like to try some day.
The first product leader
In her talk The Product of You, Melissa Perri describes the first product leader as someone who is good at going from 0 to $20MM. They spend time coaching teams and setting up processes, while still executing. She emphasises that at this stage it’s less about defining a perfect strategy, and much more about rapid experimentation to see what works quickly.
There’s another characteristic that first product leaders have: they are masters at navigating founder dynamics. This is the critical skill that enables them to ultimately be successful and true strategic partners rather than be stuck delivering whatever the founder asks them to build. But what are founder dynamics? And how do you master them?
Founder-PM Fit
When looking for a role in an early stage company, it’s not enough to vet whether the product is interesting, and the industry is growing, you need to figure out if the founder is someone you can work with. Lindsey Jayne, CPO at FT and ex-VP Product at Monzo, calls this “shopping for founders”.
So what should you optimise for when shopping for founders? There’s two key aspects you need to vet to ensure Founder-PM fit: functional fit and values fit.
Functional Founder-PM Fit
Functional fit is all about ways of working. Can the two of you be productive together without stepping on each other's toes?
Ken Norton interviewed Slack’s VP of Product Noah Weiss and Senior Staff Product Designer Anna Niess, and they described two archetypes of how CEOs, in this case Founders, get involved in product development.
In the first example the Founder says “I totally trust you, you’re the product expert, do whatever you want”, and as you’re just about to ship, they come along and are completely shocked to find what you built is nothing to do with what they expected or wanted. They panic, cancel your launch and you have to start again.
The second example is how Slack founder and CEO Stewart Butterfield works. This type of founder joins you at the beginning of a project to set a vision, agree on goals and then leave you and the team to find the best way to achieve the goals. They come back when you’re close to launch to provide feedback, like make sure it matches the brand, or that it’s aligned with the marketing efforts, whatever is needed to make the launch successful.
When shopping for founders, it’s important to tease out which one of these modes the founder will default to, so you can avoid the sad swoop and poop style behaviour.
Ultimately you’re after some sense of where your role ends and the founder’s starts, and where you’ll work together. One technique I’ve had success with is playing delegation poker with the founder, by applying it to core product management activities.
Delegation poker is a tool by Management 3.0. It helps codify delegation into seven distinct levels. It spans the fully directive “(1) Tell — I will tell them” all the way to “(7) Delegate — I will fully delegate”, going across a beautiful rainbow of shared decision making including Selling, Consulting, Agreeing, Advising and Inquiring. It’s a very powerful tool to make explicit how a task will be delegated, and how the manager will be, if at all, involved.
It extends beyond tasks, in this case I applied it to areas of responsibility when it comes to managing and building products. For each product management activity, from Product Vision, all the way down to Delivery Execution, the founder and I each scored our comfortable delegation level from (1) to (7).
This enabled us to figure out where there was misalignment, and discuss a middle ground that would be productive. For example the founder wanted to keep Product Vision as a (1) e.g. they would tell me the product vision. I would have preferred to get to a point where we were operating on a (4) and both agreed on the vision together. This helped us make a plan for the first year of ramp up being a (1) to a (2), and then over the next six months we would slowly progress closer to a (4).
Values Founder-PM Fit
Functional fit is not enough to get a good working relationship with a founder. Some people call this second axis of fit “chemistry”. I think of it as whether you have the same values. Do you believe in the same things? Or are you going to clash on something that has nothing to do with product management?
Lack of value fit has popped up in my “founder shopping” as not valuing work life balance in the same way. But you might bump against differences in valuing psychological safety differently, or co-location vs remote cultures, sync vs async work styles, or anything else that one of you values that the other doesn’t and that neither of you is willing to compromise on.
The following questions can help you tease out your values. Being clear on what is important to you, and helps you articulate it clearly to founders you might be considering working with.
“What are my values as a leader?
What am I strong in?
What am I committed to?
What do I believe in?
What won’t I compromise on?”
— Questions by Paul N. Larsen, Sarah Froning Nodarse and Lori Liddell as interviewed by Brandyn Campbell.
Take 10 minutes to write down the answer to these questions. Not only will it help you to find founder fit, but also refine your leadership voice.
Shared vision
Once you have found founder fit and you’re done shopping, your first job once your start working together is agree on a vision.
This is the number one thing leading to founder-PM disfunction. It comes up over and over again when I’m coaching product managers in founder led businesses: the founder doesn’t think the product manager understands the vision.
This is very common because most founders have never had to explain the vision to anyone in a repeatable and sharable way. Technical founders in particular struggle with this. They have always been able to build the product themselves. They haven’t had to explain the vision to a designer, a product manager or another engineer, the vision poured out of their fingers straight into functioning code.
Critically, if the founder doesn’t think the product manager understands the vision they’re never going to move away from telling the product manager what to build. They are never going to engage in a conversation about how to get to that vision together. If the founder doesn’t think the product manager understands the vision, they simply don’t trust the product manager.
Without founder trust, no product person can be successful, so the number one job is to get the vision out of their head, and make it something sharable and repeatable.
In order to get to a shared vision, you first need to share language. Just like product needs to speak the language of engineers, and designers, and other cross-functional peers, the product manager needs to speak the founder’s language. Take the time to learn how the founder speaks and thinks, as well as teach the founder about product management terms.
Getting the vision out of their head
One way to start to speak the same language, and uncover the vision, is to dig into the things that have been built before. Often founders are seeing five steps ahead into a distant future. They bake this into what they are building. It might be visible in the initial database architecture, or in the choices of values for the brand. By just asking them to tell you why they chose to build something in a particular way, you might uncover a bit of the vision.
Another way to tease out the vision out their head is to ask questions that get to the meaning of their vision:
“What change in the world do you hope this product will bring about?
What makes you proud/will make you proud to work on this product?
What’s the most rewarding part of what you get to do?”
— Questions by Claire Lew as quoted in Vision Sprint
Or questions that focus on the impact they hope the vision will have:
“What is the product’s significant purpose that will motivate team members on a deeper, intrinsic level?
What impact will our product have on affecting positive change in the world, or reducing negative change?
How might our product be remembered by our grandkids’ generation? What mark will we leave?”
— Questions by Kelsey Shanahan et al in Vision Sprint
These questions help you tease that inspiration and impact. Once you manage to articulate an answer to these questions in a credible way, that you yourself truly believe, imagine how inspired you’ll be to go to work, and how you’ll be able to inspire the rest of the company.
These questions come from a process called the Vision Sprint. They have a similar format to a Design Sprint. A Vision Sprint is exactly the same thing, but attempting to get a vision out in the end, rather than a design. It’s really focused on getting things out of founders and product leaders’ heads and into a format that’s externalizable, shareable, repeatable and inspiring. It takes a whole week, and the time investment more than pays for itself. But if you struggle to get buy-in to run something like this for a whole week, start by taking 10 minutes to interview your founder with the questions above. They should give you a really great start.
Visiontypes
So what does a vision look like? How do you make it shareable and repeatable? Marty Cagan coined the term visiontype: a prototype of your vision. And like any prototype, a visiontype can be in various levels of fidelity and artefacts. There are many formats to pick from, ranging from simply writing it down, all the way to producing a high quality video.
If you prefer text you might want to consider a Press Release FAQ. It’s a simple template with prompts that enables you to tell the story of how the product will impacts its customers in x years.
Drawing is also a great story telling medium. Airbnb hired an animator from Pixar to draw vision storyboards.
Though it really doesn’t need to be this fancy. Particularly if you’re an early stage company. All you need is just pen and paper to draw your customers’ world in x years once you’ve realized our vision.
A video is also a great way to tell your vision’s story. You can go as polished as Google’s Tilt Brush vision video, or as simple as Sabrina Rzepka’s approach at BWM: filming her hand drawing a stickman.
The value of visiontypes
A visiontype is not only useful to build trust with the founder.
Cagan argues that it enables you to do demand testing with customers, the same way you’d validate value on a single feature prototype. Though you can’t validate feasibility and usability, as the work to make the visiontype a reality is multiple years in scope. The product teams will do that work at a smaller scale, focusing on smaller chunks like epics and features.
It also helps you sell the vision to investors. It makes sure that investors are excited about the future you are building, and makes it easier for them to stay aligned on the future direction of the company.
Particularly for software as a service (SaaS) business, customers are not only buying your current product, they are buying into your vision, and trusting that over time you’ll get there. So often rather than a roadmap, showing a customer or prospect the visiontype is a much more compelling well to sell them on this future.
Finally a visiontype is very useful for engineering and architecture leadership to ensure the technical foundations of the product match the direction of travel.
If you don’t have a visiontype today, I’d strongly encourage you to experiment with some of the formats above. Cagan and his team at SVPG have compiled a list of examples of visions which might give you some more inspiration.
Surviving the ride
Early stage start ups are chaotic by nature. Having a strong visiontype is a solid start, but in no way guarantees success. Due to the nature of the drunken walk to product market fit there is no one blueprint to follow. There are however some common themes in companies at this stage. Being aware of these and embracing the chaos is a key ingredient to successfully navigating the Twilight Zone.
Product strategy
Don’t expect there to be a product strategy in place. In fact in early stage SaaS, product strategy is the business strategy. If the business is e-commerce or particularly operationally heavy there might be a separation between business strategy and product strategy, but generally they are one and the same.
The delegation poker exercise discussed above can help you tease ownership, but do expect it to come out as a solid (1) i.e. the founder will tell you what the strategy is. With growth and as you find product market fit, you might start to see separation between the business strategy and the product strategy, at which point you are more likely to take make contributions to it and eventually take on some degree of ownership.
Timing
In early stage, time is always running out. The main driver of this is funding. Start ups are not born profitable, which means that at any point you might run out of cash. This is a forcing function on how fast you need to go, and how rushed everything feels. The only advantage a start up has against the incumbents is speed.
As the first product manager or product leader, it’s important you get comfortable with this. Beautiful roadmaps that extend into a one or two year horizon have no place in early stage.
Inherently there a huge amount of uncertainty about what is the best strategy. The sooner you can de-risk it the better. The main priority should be optimising for speed of learning.
Given that product strategy and business strategy are likely one and the same, you need to co-create the roadmap with the founder. Going away and creating the perfect roadmap by yourself is unlikely to succeed. Founders need to trust that you understand the vision, and they know the priorities for the business as a whole. Co-creation ensures the business strategy and vision are baked in.
Keep your roadmap shot. When placing bets be clear on the timeframes and amount of risk the founder is willing to take. Do you need to execute on a high certainty item in time for the next fundraising? Or can you go for a less certain bet that could have really high returns? Be as clear as you can on timeframes for bets. Founders lose patience very quickly.
Disagreements between founders
Multi-founder businesses have one added layer of complexity: the founders might not agree. I’ve seen product people twist themselves in knots trying to resolve founder conflicts.
It’s not your job to make sure the founders are aligned. It’s your job to make sure they know they are unaligned and ask for clarity. Let them fight it out between themselves and get them to tell you the decision.
Don’t become their therapist: you’ll lose hours and your mind trying to do this.
Expect the founder to change their mind
Founders will change their minds. Many product people struggle with this. They perceive their job is about saying no, protecting the team from change and staying focused. This works if you’re focusing on to a winning strategy, but in early stage you have no idea if the strategy is the right one, because you haven’t yet found product market fit.
Rather than say no, have as much curiosity towards your founder’s decision making process as you do towards your customers. Because more often than not, the founder has a really good reason to change their mind.
Approach it like you would a discovery call. Discover what insight they have, what change they have perceived, what they are optimising for, what information you might be missing.
Start ups are extremely vulnerable to signals of what the market finds valuable. Founders are constantly thinking about the proof points the market needs to enable further financing. These could be year on year growth, margins, frequency of transactions, proof of success in a larger total addressable market (TAM), etc. If investors suddenly decide that growth is no longer everything, and that margins are king, then your start-up will need to change course, and fast.
Make peace with the fact that change is inevitable, and that a few roadmaps will end up in the bin. And remember to approach your founder’s decision making with the curiosity of a discovery process, you’ll learn a lot, and make better decisions as a result.
Proof point work vs Core vision work
This vulnerability to what the market finds valuable means that you’ll often need to do proof point work.
If a venture capital firm (VC) or angel investor needs to be reassured that your transaction frequency can be very high, or that you have the potential to have really low customer acquisition costs, then you need to prove that. Quickly and cheaply ideally.
When doing proof point work, be in hacky scrappy experimental mentality. This is not production long lived durable product. This is just to prove a point and raise that next round of financing.
When you’re executing on core vision work, on the other hand, you should invest in proper execution that supports live traffic, and sets up the right foundations to continue to build on.
Being able to switch between these two different ways of executing is critical to managing founders changing their minds, and the short-term nature of the proof points required by investors.
Closing thoughts
Early stage companies are exciting, fast paced and full of potential. It’s exhilarating to create something new from scratch and watch it grow. Joining early also gives product people a huge amount of influence and a large surface area, they wouldn’t be able to get in a more established company. With high speed growth also come high speed promotions.
So much of whether you’ll enjoy and thrive in a particular start-up is down to the founders. So invest in shopping for founders and finding PM-Founder fit. Find a founding team that you gel with not only from a functional and ways of working point of view, but go deeper. Check cultural and values alignment. Do you value the same things? Will you compromise on the things you disagree on?
Remember that your number one job is to get the vision out of their head. This is the key ingredient to enabling trust. With trust you can elevate yourself from delivery work, to contributing to the strategy.
Once you understand the vision turn your attention to understanding the business strategy. It’s not your job to create it, but it is critical to your job to be clear on what it is.
Co-create the roadmap with the founders, keep it really short term and be ready to bin it at any time, because things change very quickly in this world.
Here’s hoping this either resonated, and gave you tools to succeed in your current early stage role or excited you to join one. It’s certainly a high risk, high emotion job, but the rewards are also huge.
If you ever want to chat about this reach out via DM on Twitter or get in touch via susanavideiralopes.com.
The slides are available on susanavideiralopes.com/writing.