I don’t know about you, but I always hated those questions in school that would begin with ‘why?’ or ‘can you explain...’ I always thought to myself, why do I have to explain myself? I know the answer. Those questions are one of the main reasons why I leaned towards math at a young age. 2+2 = 4… no questions asked.. It just is. Let’s move on and focus on the important stuff.

As I started my career, I learned just how important ‘why’ and ‘explain’ are in the real world. As a Product Manager, I had 10+ people a day coming to me across the organization, acting as if the building was burning down. We needed to build a feature, address this customer issue, or change our roadmap. At first, I wanted to help everyone as much as I could and went with it. A few months into my first PM role, I realized that most of the questions and asks people were coming to me with really weren’t that important or were simply wrong (in the case of the feature that needed to be built, as an example). So, I started asking why? And then I would get a response and ask why again. By the third ‘why’ people usually broke down and said OK, it’s not that important, or we don’t need to build the entire feature.

As a Product Manager, you have finite resources: your time, engineers, designers, and more. You should be smart about how you leverage your resources and aim to have the highest output, whether it be aligned with revenue or customer impact. There are many important PM traits, but being comfortable pushing back and asking why ranks near the top of my list these days. When I started my first PM job, my VP of Product told me ‘You have finite resources. The best Product Managers find a way to leverage the resources they have for the most impact, not complain and ask for more resources.’ Whenever I reflect or spend time thinking about strategy, I always come back to that line.

It Doesn’t Come Naturally

Early career PMs and founders (I have experience in both) always jump the gun and want to do everything to impress their boss, get their first customer, or just make people happy. I became good at asking ‘why’ as a PM, but I hit reset when I became a founder. We didn’t have anything; we didn’t know anything. So, we took everything we heard from users and potential users and took it at surface level. We were so happy that they’d even bother talking to us, let alone try our product that we didn’t want to question them. Unfortunately, we started doing that too much and it was taking us in a million different directions. I took a step back and decided to be the ‘bad guy.’ My other co-founders and people within the company would come to me saying they got feedback that we need to build this feature, and I’d ask why? They said because they wanted it? I asked why again… ultimately, they would get flustered because I was never ‘sold’ that we needed to build that feature or change the color of the button. This behavior was typical while I was a Product Manager. Everyone wants what is best for their customer or their team. It’s your job as a Product Manager to determine what is best for your product, the business, and the company. Some people are naturally good at this, but most people need some practice and though I hate to say it, even the experience of being burned a little in order to learn.

Customer Interviews (Discovery)

When you’re doing a customer interview and someone tells you they have a problem, ask them why they have that problem. Then, when they give you a response, ask them why they haven’t tried to solve it yet or why the current solution isn’t solving it. One of the critical things here is understanding how vital or painful that problem is for the customer. Remember, you have finite resources, you don’t want to spend them on something that annoys your user, but they deal with it. You want to make sure the pain you’re addressing is not only in that customer’s top three problems, but also for five or ten other customers too. Too often, as Product Managers, you hear that a customer has a problem, and you’re excited to go and solve that (it’s natural). Then, you spend all the effort with UX to design it, engineering to implement it, marketing and sales to promote it, and no one uses it or cares. It’s most likely because it wasn’t that big of a pain point, and you didn’t do enough to vet it.

If you focus on the why and ask the customer/user to explain, you’ll truly understand how big of a pain point it is and why it’s a pain for them. They’ll also tell you how to solve it at the surface level (e.g., a feature request), but if you dig deeper and understand the problem by asking why, you’ll build a better solution than the feature they initially requested. This way, you can make an informed decision on whether or not you should proceed, and if you do, you have a better sense of direction and can tell your engineering team and other teams why you’re pushing for resources because they’ll ask why too!

Feature Requests

Depending on what type of product you’re working on (e.g., B2B, B2C, marketplace, etc.), you’re going to get feature requests from different sources. Most of my experience as a Product Manager (and founder) is on the B2B side. I had feature requests from sales, customers, customer success, support, legal, go-to-market, engineering, and other Product Managers. Every quarter my team and I went to the ‘sources’ to gather feature requests across the business. It would take 2-3 weeks just to gather and understand the feature requests.

When you have this amount of input, everyone is fighting. Support is getting yelled at by customers because we don’t have feature X or it doesn’t work ‘right.’ Sales folks are knocking on your door so they can close more deals, go-to-market is asking you to build features to support new markets, engineering is asking for bandwidth to address technical debt, the list is never-ending. How do you understand what’s truly important?

Tell the requester to explain, rather than send you a one-liner and then start asking why. Why does this customer need this feature? Why don’t they implement it in this way? Why hasn’t competitor X built it? Why do we need to burn down technical debt?

Another great question is, what if we don’t build it? What would you do? You’ll learn so much from the response. Are you going to lose the deal? Or will the customer just implement it differently? Is the backend going to tip over, or will we just be getting some failures that impact a small percentage of customers? Once you understand why the request is important, understand what would happen if you didn’t do anything. Knowing what would happen otherwise puts everything into perspective and helps you build your roadmap.

Conviction

All of this work of asking why and asking the individual(s) to explain themselves is for you to build conviction. The conviction that this thing (feature request, bug, product, etc.) is worth spending your finite resources on. When you bring it to the table (your boss, executives, engineering leads, etc.), they’re going to ask you the same questions. Your VP of Product will ask you why you’re spending 80% of engineering resources on technical debt for the next two quarters. If you don’t understand why and have no conviction around it, you’re going to be in for a not so fun conversation. The more conviction you have (by asking why), the less push-back you’re going to receive. You are on the front lines. You (should) know the customer and the problem better than anyone else in the room. You just need to build the conviction and show it.

Rejection

You won’t be able to build everything you want to build. It’s hard to swallow that, especially for new Product Managers and founders. When you do ‘reject’ someone, be it a salesperson, a customer, a support team, or another PM, have your reasons why. Early in my career, I was always worried about telling people no, or we can’t do it right now. When I started having those hard conversations and explaining why we’re not building that feature or spending our resources there, people were pretty receptive. Once you build that conviction and know why you are or are not doing something, make sure to tell others your decision and the why behind that decision.

You’d be surprised if you tell someone no, but instead share that we’re doing X, just how excited they may get. ‘Wow! I didn’t even know that was being considered, I’m thrilled that’s getting built’ was a typical response I received when presenting our roadmap and the why behind it.

Parting Thoughts

Asking why is not easy. At first, individuals might be turned off by the fact you’re trying to dig deeper. They may think that you don’t trust them. A good rule of thumb is to explain why you’re asking ‘why’ (ha, get it?). I’ve tried to preface the conversation with something like ‘Anne, I’m very interested in the problem you’re facing, and I want to understand the root of the problem so my team can best help. I’m going to ask several questions and keep digging, so be ready!’.

Ultimately, those questions in grade school that made us (well, maybe just me) mad helped us so much more than I realized in the real world. Ask why, ask the individual(s) to explain themselves, and build as much conviction around the problem/bug/feature request as possible.

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It’s December 2020. We’re roughly nine months into the pandemic. I quit my job back in March and I’ve been ‘trapped’ in the spare bedroom trying to build a company ever since.

If you know anything about San Francisco, extra space isn’t a luxury that many people have. I love our home. It’s right on the park in San Francisco and accessible to every part of the city by walking, biking, or public transport. When my wife and I moved into our place in 2019, we didn’t expect to be spending so much time in it, nor did I expect I’d be starting a company 25 feet away from where I sleep at night…

What I thought it was going to be like

When I jumped ship and started a startup with my two friends, I had envisioned that I would wake up every morning, go for a run, grab a coffee, knock out some emails, and head into the office with my co-founders and maneuver our way through startup life. It’s weird, but I had this vision in my mind that I’d try a new coffee shop every week and blog about which ones were the best for getting emails done, relaxing, and having meetings. I was looking forward to walking 1:1’s. I used to have walking or coffee 1:1’s with my previous managers, which was just the best way to have open and candid conversations, rather than being trapped within the four walls of a conference room. I wanted to grab coffee with my co-founders, walk along the water, and talk about the things co-founders talk about. If I didn’t have the first two, I was looking forward to the impromptu whiteboard sessions. I'm a sucker when it comes to whiteboards. If someone on the team offered to do a whiteboard session, I would always be the first person to raise my hand. I love collaboration and thinking aloud… it’s when I do my best work. But, we all know that wasn't the reality.

What really happened

It’s no secret that COVID happened. I quit my job right at the beginning of the pandemic, so literally, all of my ‘dreams’ were crushed the week I started full-time. I didn’t even see my co-founders in-person until three months after the pandemic began.

In reality, I had my set-up in our guest bedroom while my wife was a few feet away in our family room. I spent most of my day staring at my screen on Zoom, talking to the team, investors, users, and advisors. I had coffee in hand, but it wasn’t the same. When I was stuck and felt like I needed that whiteboard, I just banged my head against the wall to try and think of what to do. OK, I didn’t hit my head against the wall (I didn’t feel like repairing drywall), but I lightly tapped my head against the wall waiting for inspiration to come.

Just like most professionals, it’s been tough to separate work and life. Several people hated their commute pre-COVID, but I loved mine. I used to walk to and from work, but ever since my wife and I moved, I started running or biking to and from work. My commute was my time to wind down, listen to a podcast, call my parents, or just clear my mind. Now, I walk 15 feet to my kitchen, cook dinner with my wife, and see my laptop staring back at me, asking when I'll come back. Since there aren’t many activities to do at night during the week with most venues, museums, and restaurants at limited capacity or closed altogether, both my wife and I just resorted to working after dinner. I'm running a startup; work is supposed to be everything. I agree. But, my wife is actually what's most important to me. When you can’t go out and explore and make new memories in the amazing city we live in, it’s taxing on your mental health.

Leading the team

Though we’re in a crazy time, and we all have to deal with staring at a screen, my co-founders and I need to lead a team and build. To help with this, we split apart our weekly meetings into smaller ones. We always have a weekly All-Hands. We reflect on last week, check in on our monthly goals, and prioritize for the week. Then, we have separate meetings per ‘focus’, one for product/engineering and one for marketing/sales. We do the All-Hands first, so we know what our goals and objectives are for the week as a larger team, and in the ‘breakout’ meetings, we can have more in-depth conversations around what needs to be done to accomplish our goals for the week. It’s not all done in one meeting because 1) Zoom fatigue is real, and 2) While engineering cares about marketing, time is better-spent building than worrying about the blog post topic of the week.

Everyone has standing 1:1s. We go into each meeting with 3-4 key topics we’d like to discuss. Typically, these are done on Fridays to reflect on the week and look forward to the following week. We use these 1:1s as a time to give feedback to one another and have open conversations. It’s a great way to ‘wind down the week’ and get excited for the following week. My favorite topic to discuss is ‘What are you most proud of this week?’ My advice –  have 1:1’s with your co-founders and everyone else on the team. It’s essential to create that space to have open and honest discussions and learn from one another.

Embrace the wins (big and small) and acknowledge the failures or shortcomings. We have two Slack channels, #ice-cream, and #no-ice-cream-for-you. We use the #ice-cream channel to give each other shoutouts when someone went above and beyond, thought of an exciting idea, or made positive impact on a project or to someone on the team. The #no-ice-cream-for-you channel is meant to be a place for self-reflection. What was something you tried that didn’t go so well? We use this channel as a way to call out our own personal ‘failures’ show what we’ve learned, and say what we’re going to change moving forward. Companies always say they embrace failure, but many don’t talk about it enough. Since our team doesn’t interact in-person, we don't want failure to feel magnified to a single person, but rather as something we can all learn from. This Slack channel is a way to acknowledge that and embrace the fact that failure is OK within the company.

My Advice

I always say to take my advice with a grain of salt. I’ve received great advice and some crappy advice over the years.

Get away from the desk. This one is obvious, but we don’t do it enough. I found myself staring at my screen or lightly banging my head against the wall for an hour, which was a waste of time. Now, when I get into that mental state, I’ll walk away from my desk and go outside for a 15-30 minute walk. I’ll listen to a podcast, call my parents, or do nothing. Then, I come back to my chair, completely recharged, and ready to go. Taking breaks are OK -- most times, that 30 minutes away from your computer is worth 5X the time you took to go on that walk.

Exercise. Regardless if you’re a co-founder, executive, manager, or an individual contributor, we all have stress. This stress can come from our work or personal life. I’ve always found a way to relieve my stress is to go out for a run. Most mornings, I'll go out for a run to prep myself for the day. It’s a great way to clear your mind and take in the beauty around you (and less screen time). Some days, I’ll go for a run at lunch to clear my blocked mental state and come back with a clear mind for the afternoon. It doesn’t have to be running, but you should always have something in your back pocket you can do that isn’t associated with a screen. Find a way to get the stress and doubt out of your mind.

Final Thoughts

If everything were what we expected it to be, life would be kind of boring. Like everyone else, I find myself learning new ways to cope with a world I’ve never worked in. In the beginning, I thought we’d be back in the office within 3-4 months (just like everyone else). As the months went on, it became apparent that it wasn’t going to be the case. So, I had to readjust. While it’s been crazy, challenging, and sometimes lonely, starting and leading a company in my spare bedroom has taught me more than I could have ever imagined.

This week marks month six since I left my full-time role as a Product Manager and went full-time on my start-up, Xoba. While I was expecting a rollercoaster, I didn’t expect it to be this wild of a ride.

After taking time to reflect this weekend, I wanted to share some of my thoughts, experiences, and learnings thus far.

My Wife is Amazing

Well, I already knew my wife is amazing… hence why I married her. I can write an entire blog post about how amazing my wife has been, especially over the last six months, but I’ll keep this one short. She’s been my rock throughout all of this. She has been so patient, helpful, and understanding, and I couldn't have made it the past six months without her. So a word of advice for everyone trying to start something, have a rock. That rock could be a significant other, a best friend, a sibling, or anyone. But you need someone to listen to you and bring you up when you’re down.

Leading Friends Is… Weird

One of the hardest challenges thus far has been working with my friends. The people I'm trying to build this company with just happen to be people I’ve known. Going from being friends and peers to then having me in the CEO role was a challenge for me. Since they’re friends, I wanted everyone to like me and I wanted it to feel like I wasn’t just pushing my own agenda. We were wandering in different directions for the first few months, and we struggled massively because of that.

It took time for me to realize that everyone was looking at me to set a company strategy and hold everyone accountable. Once I realized that, I set up more 1:1s and departmental meetings focused on learning and taking input from across the team. Then, I took the input, crafted a strategy, and presented it to the company. It was a game changer for us. When I first did that, it felt like a weight was lifted off my shoulders, and I felt much more comfortable as a leader moving forward. We had mutual respect for one another as friends and colleagues, but I needed to be the lead and hold everyone accountable.

Filter Advice

What I didn’t realize was that everyone wants to give you advice. I had countless people reach out to me expressing interest in what we were working on and offering to hop on calls and give advice. Our discussions would range from the logo to marketing strategy to product strategy to swag. It was a great feeling for the first couple of months until I realized it was actually causing more problems than what it was worth. I ended up second guessing myself countless times, gave conflicting direction to the team, and simply just wasted too much time.

I was always receiving conflicting advice. One day one person would tell me I should be doing X. It seemed logical and it wasn’t an area I knew a ton about, so I took their word for it. I’d sync with the team the following morning and suggest we take his or her approach. Then, later in the afternoon, I’d speak with another individual who would give conflicting advice and say that what we were doing before was smarter. I would go back to the team at the end of the day and tell them we should switch back to what we were doing before. It caused the team to be confused and frustrated, and frankly, me too.

It took me a little time, but I realized that I should be the one going out and seeking advice, not the other way around. When I would go to seek advice, I had specific topics that I needed help with and could find the right person (or the couple of people) to speak with regarding these topics. Then, I could compare my notes against everyone’s thoughts and make a more informed decision. Once I made that switch, I’ve been happier, and the team has been more satisfied and more productive.

Something is Better than Nothing

My motto has become something is better than nothing. I found the team stressing over every detail of a message or a feature, and we’d paralyze ourselves and take too long to ship something. We didn’t want to put junk into the world, but once we put something out there, we got people talking, received feedback, and were able to iterate quickly. So I told the team ‘let’s get something out there, and if it doesn’t work, or needs refinement, then we’ll take it from there’.

My favorite thing to do as a PM was to come up with a few variants of a feature that I thought would make for decent solutions after doing some initial research and hypothesis testing. Instead of listening to my customers ramble for 45 minutes about the 500 things they needed, I was able to extract concrete feedback within 5-10 minutes with just a basic mock-up. Something was and still is better than nothing...

Start with your Goals and Objectives

In the beginning, my co-founders and I put together a six-month plan that outlined the focus for each month and the milestones we wanted to hit. We knew it was going to change, but at least we had something down on paper we could strive towards and check ourselves against. The problem was that we were getting conflicting advice and I struggled in the beginning leading my friends and holding them accountable. So, for the first two or three months, we ignored the plan and just ‘went with it’.

For that time period, we went in circles. We seemed to be changing strategy weekly and the team didn’t have a sense of direction. The team was confused and didn’t know exactly what we were working towards and how we know when we’ve actually accomplished anything.

I remember going to the park with a notebook in hand and just spent the morning writing down all my thoughts. During that time, I knew that we needed to implement some kind of framework to set goals across the organization and a way to hold ourselves accountable to those goals. So, the following week, I drafted a new strategy. I made it clear what we were working on, what we weren’t working on, what our core objectives were, what we were going to do in order to work towards the objectives, and how we were going to measure ourselves. The goals and the strategy you set out might be the wrong ones, but going back to my motto of ‘Something is better than nothing’... it gave our team a way to align on something and have a sense of where we need to go.

Now, on the first of every month at our all-hands, we reflect back on the previous month. What went well? What didn’t go so well? Where should we be doubling down on? Then, we review the current month’s strategy and goals. At the end of the all-hands, everyone is clear on the plan, who owns which parts, and the expectations. At every all-hands throughout the month, we spend the first 20 minutes reviewing the plan, tracking our progress, and course-correct if needed.

We also now take it a step further and craft daily and weekly goals. Every morning our team gets together in a brief standup for 15 minutes and we go over what we accomplished yesterday, what we didn’t, and what we want to accomplish today. It’s a great way to keep everyone aligned across the team and aligned to our larger goals and objectives. It’s the best 15 minutes of my day.

Over the past three months, this approach has been one of the most beneficial things we’ve done as a company.

Data Data Data

One area I was most excited about when starting a company was my ability to build out a data pipeline and to play around with data. Data was an area of frustration for me at my last organization, so I wanted to change that with Xoba. My advice -- From the get-go, build a plan to collect and analyze data across your organization, from marketing to user data. Even if you don’t think you’ll use it for a while, it’s better to start collecting it from the beginning.

Having some level of data is a way to start a conversation, test hypothesis, and track goals. Going back to our monthly plan, we always have a baseline, and that comes from the underlying data we collect and present.  Whenever we release a new feature, we have a section in our PRD called ‘Analytics’. So our engineering team knows when building a feature what we’re aiming to measure and can implement it from the beginning.

I recall one of our advisors asking, ‘Hey, how many of your users are doing X then Y?’. That pattern never occurred to me, but since we had been collecting data from the beginning, I could extract that data pretty quickly, and I learned something fascinating about our usage patterns. Then, our minds started to race and we sliced and diced the data in different ways, uncovering more about our users, the marketing approach, and more.

My advice is to have three core KPIs that you believe are important to your business, track them, and report on them frequently. These KPIs will change as your business develops. For example, one of your core KPIs the first six months of your business might be the number of newsletter sign-ups, but then at six months, it might be newsletter to user sign-up rate. Align your KPIs to your goals and objectives, measure them, report on them, and talk about them. If the numbers are bad, bring them up to the team and focus on how you can improve them.

Conclusion

Six months. I’ve never second-guessed myself more, had more lows, doubts, and struggles in the last six months than probably in my entire life. But, I’ve also learned so much, have had the opportunity to meet so many amazing people, become a better leader, and have higher highs than ever before. This whole startup can crash and burn tomorrow, but I wouldn’t trade this experience for anything else. It’s genuinely something that you need to do yourself to truly understand what is going through a founder’s head, the challenges they face, and the mental stamina they have or have developed.

I’ll continue to dive into specific topics around being a leader at an early-stage startup. Subscribe below to keep up to date!

I believe that what you do on your birthday will reflect what the next year looks like. I've always tried to do something positive to get me amped up for the year ahead.

For the last five or so years, I've ran a 5K on my birthday. I call it the 'Birthday 5K'. Has a nice ring to it, right? It isn't an 'all-out' 5K, rather a fast 5K to measure my performance over the last year. It's like a yearly measuring stick. It's fun, and it doesn't take too long.

This year was my 29th birthday. It marked the beginning of the last year of my twenties. It's been a defining decade from graduating college, to getting my first job, moving to San Francisco, getting married, buying our first home, and quitting my job to start a company. Years 10-20 were solid too, but I can't recall that much from when I was 10 years old. This year, COVID robbed me of many of my big running milestones, goals, and aspirations, so I wanted to do something a little different...

So, what did I end up doing this year for the last birthday of my twenties?

I ran 29.29 miles…

It was Saturday and I turned to my wife and said, I think I am going to run 24 miles on Monday for my birthday. She was like, why? I said, 'I don't know, it would be cool to run the distance of my birthday date.'  Then, I thought if I do 24, I should go for the full 26.2 (marathon distance). The next thought in my head was like 29 miles for my 29th birthday! I was kind of joking… but once it was in my head, I felt like I couldn’t back down.

On Sunday night, I mapped out a route and decided to go for it. The amount of preparation I did was next to none. I worked out the day before, I didn't meal prep, didn't stretch, nothing. My original plan was to go out and try to run a Boston qualifying marathon time (3:00 hours, 6:53 per mile) and then chill the last 3 miles. Talking with my friend the night before… he said, 'just go easy… enjoy the run. It's your birthday. The last thing you want is to feel like crap running up all the hills to get home'. I thought he was right… so I dropped the idea of running a Boston qualifying time.

Monday morning, I had a couple of meetings to attend to, but then it was off to the races. I woke up to a funny text from one of my good friends.

Just Getting Started...

After the meetings were done, I drank some water, ate an apple, put on my running clothes, and laced up the shoes. I planned my route to go over the Golden Gate Bridge (though it was so foggy you couldn't see anything), past my old office, and the places I've lived at in San Francisco. A little trip down memory lane if you will. The first 20 miles were easy. By mile 20, I was around 7:25ish. I felt good, and it was still almost a minute slower than my actual marathon pace, so I just kept going. The miles were just passing one by one… easy.

I had eaten 2 GUs, and my stomach wasn't feeling 100%...but my legs were just fine. I stopped at a local store to grab a Vitamin Water around mile 23. I knew I needed sugar, but couldn't eat another GU (They're terrible). I haven't had Vitamin Water in like 8 years, but it looked like the best option. That's when it all went downhill (funny enough, I had 2.5 miles of climbing uphill after that). My legs were doing OK all things considered, but my stomach just collapsed.

Downhill...

I made it to mile 26.2… then, I literally had to stop, and I started throwing up in the middle of the street. My co-founder literally texted me as I was throwing up…

The next 3 miles were miserable. Every half mile, I stopped, threw up, took a breath, and kept going. I had consumed one apple, two GU packets, one bottle of water, and ¼ of Vitamin Water… and by mile 28, it was all out of my system.

Mentally, I wanted to give up. I thought to myself, I've already finished 26.2...I can just walk home and be done. But my head went back to… your behaviors today will set you up for the next year. I've always told everyone that running is 90% mental, and I genuinely believe that. It was at mile 28 I said to myself that, and that's what kept me going. I literally went step by step and chose a marker 100 feet in front of me to keep the motivation high.

The Finish...

Finally, I hit 29.29 miles (that was intentional) and then dropped onto the grass and laid there. I called my wife and said, bring me water. Luckily… I fell right in front of our home :) I felt amazing right at that moment. My stomach pain went away, and I felt like a million bucks. I had just completed my longest run ever, first 20+ mile day in 6 months, and first marathon distance in over a year. Honestly, it wasn't meant to be this painful. If I would have prepared correctly, put more into my stomach beforehand, and didn't 'test' new GU packets, and drinks, it would have went better.

Was it really about running 29 miles? No. It wasn't the distance, it was more about whether i could push myself through this challenging journey to achieve my goal. Currently, I’m the co-founder of a small start-up. Every day is a challenge. Some of those challenges are small, some large. I've always seen parallels between being an endurance athlete and being a start-up founder. It's not easy, you make so many mistakes along the way, you want to give up (especially when things are rough), but if you keep pushing, the outcome is totally worth it. Ultimately, I’m proud I could prove to myself that I could still push through, even when it sucked. Honestly, I'll take staying up late to finish a presentation or emails than run a marathon everyday...

Every year, I do something to push myself physically and mentally to prove that I still have it. This year was no exception, and I'm beyond excited to see what the last year of my twenties has in store for me.

So you may ask… will I do 30 miles on my 30th? The answer is no.

It's Sunday afternoon, and I just finished writing and sending a weekly update for my startup. Especially in the early days, your head is so down in the weeds all day that you often forget to look up and realize all the things that you've accomplished for the week and things that you may have forgotten to do or didn't do so well.

In the first few weeks after going full-time in my startup gig, I realized just that. We were doing a bunch of things, but we never reflected on what those things were. So, we'd go into the following week, not really realizing what we did well or didn't do so well the prior week. By no means is it a new idea, but the revelation came to me when I was feeling down on a Sunday evening. I told my wife I felt like I didn't do anything well the past week. I looked back at our #daily-updates channel in Slack (everyone posts their updates in a Slack channel daily) and I was taken aback. We had accomplished so much as a team that week. From engineering pushing out new features to successful cold outreaches, to an updated website, I forgot how much such a small team was able to accomplish in a given week.

So, I decided every week to send a weekly recap to the team. I haven't looked back since. I've been sending out weekly updates for the better part of three months now and wanted to share how I format and send ours out.

My Format

My format is pretty straight forward. I want the team to actually to read the notes, so I section them off and stick to bullet points. I have an intro that recaps the entire week and what I'm looking forward to the next week and then dive into the sections.

Every initiative/team (Engineering, Product, Design, Marketing, etc.) is vital to success, especially in the early days. I don't call out just one team/initiative, but instead, I focus on each one and make sure they're represented. Also, I find a way to tie them together. If your team launches a new feature and there was a blog post written about it… that's great!

Here is an example of my intro:

Another week in the books. Overall, a good week in terms of execution. As I mentioned on Friday, I felt great because we had another week where the entire team focused on the same thing — the beta. Engineering focused on getting new features and integrations out. Marketing focused on getting content out there and driving traffic to our site, Business Development focused on building out new outreach lists and solutions guides, etc. It was great to see all the Slack messages and Zoom calls focused on our goals. We fell short of our DAU goal, but we have some great stuff to promote next week to get more users and excite our existing users. Kurt, one of our users, says he is more inclined to use Xoba now because of the Slack integration. Brittany said she was holding out for GitHub and now Xoba has more perceived value to her. I'm excited to see how their behavior in using our product changes over the coming weeks.

We've been executing on the groundwork over the past couple of weeks, and that's great. Now, we need to continue to build the groundwork, but we have some ammo to go out there and start driving more leads, having more conversations, and getting beta users. Rahul and I have a good story along with some content to begin going outbound with Xoba. We have great content (and getting more soon) to help drive traffic inbound. Now we can have some fun and experiment since we have real traffic coming to the website. A new week, same focus, new goals. Let's go!

Highlights

I like to open up with great news. Highlights are an opportunity to recap on the tactical things completed over the week (e.g., we released a blog post) and the 'feel good' items (e.g., user X said they're going to use the product more now because we released this feature!).

• Search Xoba within Slack capability! Can't wait to promote this and use it as a lever to generate leads
• Two solution guides (Compliance & Sales Onboarding) drafts complete. These will be ready first thing next week to start distributing for our outbound lead gen
• First full week of daily check-ins with Marketing/BD. Overall, they were great and helped us stay aligned and focus on our goals for the week.

What we could have improved on

This section is not meant to call out a single person or a team. Instead, it brings to light some of the goals that we may have missed and things that were brought up during the week. Typically, I follow up with a suggestion on how we can improve or add it to the Monday All-Hands meeting to discuss as a team.

• We're struggling to get responses from our new users for feedback. Moving forward, we'll ask them to provide feedback via email (give them an out). We're looking into offering gift cards for feedback calls.
• We need to continue to test out ways to convert visitors to beta users. Lots of traffic, but conversions are still low. Let's revisit our hypothesis tomorrow and see what action we want to take this upcoming week.
• While we set ourselves up well for next week, we didn't have good engagement from our current users. We need to continue to find ways to improve this. Let's discuss in our all-hands tomorrow. Please come with two ideas.

A tip: Every week, go back to the previous week's 'What we could have improved on' and follow-up. If you didn't improve on it, then call it out in this section. Whatever you do, don't just sweep it under the rug, because your team members will remember.

Looking forward to next week

You want everyone to be excited about the upcoming week, so make sure to highlight key areas or items that the team will be working towards. The first sections were all about what we did last week and how we set ourselves up for the following week.

• Testing out new content and messaging on the website to get more beta users
• Starting to leverage our solutions guides (and the story around them) to do outbound lead gen
• Getting more content out in the wild (Blog posts and solution guides)

FYIs

This is a quick section with some notes for the upcoming week. I typically repeat these in our All-Hands on Monday, but it's always good to keep records. Typically, I focus on upcoming events or let everyone know who will be out of the office for the week. For example, if someone is taking Friday off, we'll put it in this section.

• Shawn is taking a half-day on Friday (It's his 1-year wedding anniversary weekend)

After it's written up, I will post it in our company intranet (we use Notion). Then, I take the beginning section and post it in our company Slack channel with a link to the details.

If you have advisers or a mentor, it's great to share the recap with them as well. They have a good perspective and can offer thoughts on the 'where we can do better' section.

It was roughly three years ago when I stepped into product management from an engineering role. If you want to read about my journey, you can reference the ‘blog series’ I wrote here. When I became a PM, I knew it would be the only job I’d ever want, aside from starting a company. Today, I started the job that I’ve genuinely always wanted… co-founder and CEO of a startup.

It all started when I was probably eight or so years old. My brother and I would go around the neighborhood and ask people if we could cut their grass. Then came the fall, and we would offer to clean up their leaves. When the snow hit, we would shovel their driveways. We were running a nice little business, and it was awesome getting paid by someone else for your hard work. All while your friends were sitting inside playing video games.

My first business lesson

When my brother went off to college, I ‘took over.’ I’ll never forget, my first new customer was the corner house in the neighborhood. There were tens of trees and leaves everywhere. I knew I had hit the jackpot. I ‘hired’ a couple of friends, and we cleaned up the yard. It took three full days and nights to get this yard cleaned up. Then, when we were all finished, the homeowner asked how much? I was about to say $75. My friend said how about $20? The homeowner jumped at it and handed us a $20 bill. I was livid. I just worked so hard for three days, and after splitting it, I made $8 ($6 to the other two that helped me). I had to pay my dad $3 for gas (thanks, dad), so I ended up with $5. My friend felt bad asking for more money. It should go without saying, but that friend never helped me again.

As the years went on, I had other side hustles (computer building/repair business, consulting, to-do list app, etc.). The goal of those was to ‘have something on the side,’ never to take it on full-time. But I’ve always wanted to go off and try to build something full-time. The goal out of college was to get a job, save some money, learn, and then leave to start a company within two years. Well, it took me four additional years, but I’m finally here.

The start of a new journey

Today, I fully made the transition from PM and part-time CEO, to full-time startup CEO. Well, I am ‘CEO’ of nothing, really. We have a team of three (including me), a beta, and our first investment. My role will change drastically over the weeks, months, and years (hopefully we get there). I am nervous, scared, and beyond excited all at the same time.

So what do you do one ‘Day 1’ as a full-time startup CEO? Well today, my to-do list consists of:

• Weekly planning with the team
• Make company profiles on LinkedIn, Crunchbase, and Angel’s List
• Send out a monthly update to investors and followers
• Prep for a call with XXX around pricing strategy
• Finish application for business credit card
• Test new features before we roll them out to the beta users
• Find channels to promote public beta of our product
• Deploy a new company blog platform

I’ll continue to write about my thoughts and experiences as a CEO through this journey, how I maintain a healthy relationship with my wife, how I stay healthy, how I make sure there is ‘me time,’ and whatever else related.

If you’re reading this during the current coronavirus pandemic, I wrote a blog post in March around quitting my job right before the pandemic hit.

It was February 28th, 2020. After weeks of discussions with my wife and my founding team, I decided it was time. It was time to quit my day job and to take on this startup full-time. The coronavirus was a global topic, but I wasn’t very concerned at the time. Nervously, I told my boss that I was leaving. He was shocked, but for someone who has also started his own company before, he understood and was excited for me. I agreed to stay on for the next month until the end of March to make sure it would be a smooth transition. After all, I’m leaving to start a company, not because I hate where I work today (it’s actually a great place to work). But, since then, each day has become more unpredictable as the coronavirus has developed into a worldwide pandemic…

Every day since giving my notice has been a whirlwind. In the morning, I wake up, go for a run, and am pumped for my last day in my current full-time job so I can spend 100% of my energy on my startup. Then, a new ‘breaking news’ notification every hour makes me question my decision. Standing in the grocery store line, I get a notification that Tom Hanks has coronavirus, the NBA is canceled, and the US is enforcing a travel ban. The next day, the Dow has its biggest drop in 10 years in a single day. My thought is, ‘OK, maybe this is a bad idea. Maybe I should rescind my resignation and see how this virus plays out’. After talking everything through with my wife and a night’s rest, I wake up feeling excited again. I work on our messaging, talk to our team about the roadmap, test new features, and feel so alive. On the inside, I’m worried, anxious, concerned, pumped, and optimistic. It’s a vicious cycle...

Then, I read Twitter, and that becomes a black hole. Everyone all of a sudden thinks they’re an expert on the virus. Some VCs are saying ‘no investments for awhile. If you’re a startup, brace yourself for the worst’. Other VCs are saying ‘Our doors are open! Let’s chat over Zoom. I just signed two term sheets last week!’.

I don’t know what to think.

No one knows what’s going to happen within the next hour, the next day, or the next month. If we did, we’d be in a much different situation right now. If someone told you ‘Quit your job and in 5 years, you’ll have $10M’, a lot of people would probably do that! In reality, it’s ‘Quit your job! Your chances of failing are much higher than succeeding. Maybe you’ll make it, but who knows’. Because of the uncertainty, only a small percentage of people take the chance. And with the current pandemic, uncertainty is growing.

Despite the increased uncertainty, I’m still taking the chance. There is never a good time to leave a job to start your own company. You’re giving up a predictable salary, working with good people at a good company (hopefully), and the comfort knowing that you’ll be OK even if things get tough (e.g., you get sick, family members get sick, etc.). But, there is so much potential upside to being able to own something and build something from scratch. I’m excited to learn more than I ever have, build and lead a team, meet new people, and ultimately build a company that enables others to provide for their families. It wasn’t a now or never situation for me, but I felt like the timing is right given the founding team, the stage we’re at, and my overwhelming desire to now dedicate my time to this startup full-time.

At the end of the day when I take a step back (particularly a step back away from those news alerts), even with everything going on, I’m still excited. My founding team is exceptional and I genuinely believe in the problem we’re solving. We had been playing around with this problem/idea since October of 2019. One of my co-founders decided to put his notice in a little over a month later, and we wrote the first line of code in late December of 2019. We released our private-beta at the end of January, and we have a small user base providing useful feedback, and we continue to improve the product offering. I feel confident in our teams’ ability to execute and to build a product people want. But, I can’t do that unless I am thinking about it 100% of the time. 7-10 PM on weekdays and a few hours on the weekends just doesn’t cut it anymore.

Fortunately, we’re joining an accelerator. So, we have some initial cash and will be surrounded (for now, virtually) by founders, ex-founders, advisers, investors, etc., all of which will help accelerate our product and business. We were given notice that the first month of the accelerator (when you typically have the opportunity to meet all these folks in-person), will be remote. This is the right call given everything going on right now, but I have to be honest and admit that I’m bummed. I take pride in the relationships I’ve built in-person over the years, not over Zoom or some other video platform, but it’s no one’s fault and everyone is in the same boat. We simply don’t know what tomorrow or next week will bring, but having this community, regardless of in-person or virtual to lean on, is a big plus in our minds.

Ultimately, I won’t know whether or not this decision to go build a company during this time is going to be the right decision for quite some time. Successful companies were founded after the dotcom crash and in 2008. However, many that were started during this time failed too. I hope my team and I land on the ‘success’ side of the coin, but regardless, what l do truly believe is that I’ll look back at some point in my life and say ‘Hey, that was a hard decision, it sucked at that time, but I learned a lot, and I became a better person/husband/CEO/… than I would have become otherwise‘’.

You miss 100% of the shots you don't take

This company is a shot I want to take. Some hours and days, I want to keep the ball in my hand because it feels the most comfortable there, other times, I want to shoot it 100 times a minute.

If you’re also going through a similar situation, I wrote this to let you know that you’re not the only one. Feel free to comment or reach out. I’d love to share thoughts, experiences, and help others get through this. I’m excited to continue writing about my journey as I start a company. Arguably, it’s more interesting at this point than it would have been nine months ago.

Lastly, shout out to my wife, Helana. She has been the most supportive person throughout all of this. She is my rock, my inspiration, and my motivation. I wouldn’t be able to do any of this without her!

Think about the last concert you went to. There is a high chance that at one point during the show, the lead singer stopped singing, the band continued to play their instruments, but relied on the crowd to actually sing the lyrics.

One of my favorite examples of this is when The National (one of my favorite bands), gets the entire group together front and center and just plays their instruments. The whole crowd sings the song from start to finish with little to no involvement from the lead singer. You can hear the entire crowd singing the song in unison, without microphones, all from memory. I encourage you to watch it because it is my favorite part of the whole concert.

Think about it for a minute, a successful artist is a lot like a successful Product Manager. In the example above, artists have a large group of people, all with different backgrounds or motives, singing in unison without the leader singing or reiterating the message. Your North Star as a Product Manager is to walk around to Sales, Support, Engineering, Marketing, etc. and all have them repeating the same message back to you without having to ask them or remind them. If Marketing is talking to Sales about your new feature launch, they can accurately represent the value prop, the launch date, the positioning, etc. without you even being in the room. Or, if you are, you can step back and listen to them talk about it, just as if you were the lead singer of a band.

Ok, that is great. But how does an artist achieve the ability to not sing at their own concert? How does a Product Manager accomplish the ability to not have to be in the room for every discussion? The key for both parties is repetition, simplicity, and excitement.

Repetition

How many times have you heard a song only once and been able to sing along the second time around? I bet it’s pretty rare. Typically, you’d have to listen to that song over and over. Eventually, you’ll start humming it. Then, when you go to the concert, you’re singing along with the band as they’re playing that song. At some point, they'll stop singing, and you’ll keep going because the song is ingrained in your head. Sometimes, you won’t even notice that the artist stopped singing.

As a Product Manager, sometimes you think because you told your colleague a piece of information (e.g., a date) once, they are going to remember it. Well, that date is near and dear to your heart because you own the launch. Your colleague may have 10 other things going on at the same time and forget about that detail. You can never repeat your message, your launch date, or your value props enough. The more you repeat them, the more valuable they seem to the other parties, and the higher the likelihood it will stick in their heads. There will be a point where they will repeat the information back to you or say, ‘Yes, I know the launch date is X; you don’t have to tell me again!’. That is a great state to be in.

You can never repeat your message, your launch date, or your value props enough.

It’s valuable even in a single presentation or discussion to start and end with the message you want to drive home. For example, when I give updates to Sales Engineers on features, they care most about the launch date (most of the time). So, I start off my presentation with the roadmap and make the dates simple and clear. Then, we get into the bulk of the presentation. At the end, I wrap up with the same roadmap and repeat my message.

When that person or group of people all understand what you are trying to get across (e.g., a date, to value props, etc.), the chances of them being able to repeat it accurately to others increase. This will help support building alignment across teams without you having to sing your message to every person in the organization.

Simplicity & Conciseness

Why do songs become so catchy that even your grandparents know it and can repeat some of the words? Well, because some of our most popular songs consist of 7-10 words on repeat. Even if it isn’t one of those songs, artists tend not to use complex words. When is the last time you listened to a song where they used a word like Extirpate? They aim to create art and creativity from ‘everyday’ words. This makes it easier for people to comprehend the song, memorize it, and sing along at live concerts (or in their cars).

As a Product Manager, if your message, value prop, roadmap, or whatever it may be is not simple to consume, the chances of people remembering it and being able to repeat it to you are very slim. For example, If you say a feature is going to launch on X date, but we’re going into Alpha on Y date, then Beta on Z date, etc. people are going to have the wrong date in their head. People easily forget, and they attach to what is easiest for them. So a single date that you drill into their heads is most appropriate. Think about what your audience cares most about in that moment in time, and make sure your clear.

If your message isn't simple, the chances of people remembering it is slim

Think about the game Telephone. If the first person starts with a long sentence, the chances of the message being correct after 10 people are much slimmer than if the original message was three words. Like Telephone, you have a better chance in a smaller organization (fewer people playing the game) if your message happens to be more complicated. But, as your organization scales (or you add more people to the game), this quickly falls apart. Regardless of the size of your team or organization, maintain a simple, concise message.

Once an artist puts out a song, it rarely changes. Sure, there are mixes and renditions of it at concerts, but the lyrics, the meaning, and message behind that song remain the same. One of the hardest parts of being a Product Manager is that things are often a moving target. One day, the launch date is in 1 month, and the next week it slips to 3 months out because of an unforeseen hurdle. All of a sudden, you need to find a way to tell all the people you told earlier that the date has changed. Luckily, if the message is concise and straightforward, it is easier to go back to those individuals and change your message. Just like a live version of a song, one or two words may change (like a date), but the underlying message (e.g., value props) is still there. Now, if you have to change your messaging, the launch date, and value props all at once, you will have to go back to square one.

Encouragement & Excitement

When you’re at a concert and the artist asks you to start clapping your hands in a certain rhythm, they don’t use a monotone voice. They aim to pump up the crowd and get them excited, so they’ll follow along. The same goes for when they want you to sing along with them or sing the part of the song where they’re not involved. No one goes to a concert to be bored, and it’s the artist’s job to make sure that you’re not.

A Product Manager has a very similar job. When you go up in front of Sales, your job is to get them pumped about the new feature or product you’re releasing. If a Product Manager used a boring presentation, mumbled, and had a monotone voice, the Sales team 1) Isn’t going to remember what you’re saying and 2) They’re not going to be motivated to go and sell your new feature or product. The same goes for other functions in the organization. No one follows or remembers the boring, monotone message. People remember the upbeat, exciting, encouraging message and want to be a part of that. People want to be a part of something bigger than themselves and make an impact. As a Product Manager, this is your chance to be a leader and bring people along for the ride.

Going to a concert and singing along with all your favorite songs is fun. That’s why people pay 10-50X the cost of the song to go and see the artists they like. Put yourself in the artist’s shoes and see how they must feel when they have the crowd singing and dancing in unison. They feel excited, accomplished, and motivated to keep going. After the concert, when you go back to your day job as a Product Manager, think about the feeling they must have and how you can achieve that for yourself in that role.

As a Product Manager, you are the artist of your product. Your goal is to get the crowd (your organization) singing along with you so you can bring a great product to market, or in an artist’s case, have an awesome concert and keep people wanting to come back for more.

Repeat your message, make sure it’s concise and straightforward, and get people excited about it! See what I did there... :)