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Common Startup Blindspots
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Common Startup Blindspots

Michael DeHaan
May 13
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What are the things that people in new startups don’t know? Or maybe what are some anti-patterns that we tend to replicate as a result of our exposure to past companies?

This is kind of a mix, but here’s a list:

  • Communication blindspots - it’s hardest to explain a product when you know what it is and how to use it. You will leave out examples, steps, and won’t know what people don’t know or what their concerns are. You will assume others know what you are talking about. You fix this by having lots of outside reviewers and always working to have tons of conversations - and this should never stop. This also makes better products, but it also makes the whole effort so much more rewarding when you are working to make people happy and get exposed to the users you are helping. Communication is fundamental, and it’s not easy. Spend at least 4x as much time editing as writing. Constantly ask yourself what would someone else think and who is looking at everything and why.

  • Defensive Mental Models - Have you ever tried to talk about something and people rush to resolve the conversation instantly? People rush to categorize something as true/false or good/bad based on one past experience or other advice, ignoring timing factors or the idea that one strategy does not fit all environments and situational context. Instead, incorporate mental models as fields of probability and having more choices for battle plans when new situations arise. If you hear something you disagree with, a knee-jerk disagreement isn’t what you want. You should ask a question and learn from it. Think of yourself as a neural net where each piece of new information is something you can adjust from, and as you see it more, adapt more.

  • Tunnel vision - It’s easy to be focusing on a goal and not realizing continuous change is always possible, that there is no need to commit to a set path. We must destroy ego in our to enable this change. Often in corporate structures “failure” damages political capital, and folks feel like they cannot express doubt or change course. I’m not saying “pivot often” but I am saying if something is starting to go off track, it’s easier to steer than turn a car into a boat.

  • Isolating the engineering team - how often does your engineering team get to experience customers directly? How do you expect them to build better products when they only hear about customers 3rd hand? When product teams complain about engineers working too much on internals, this is why it happens. This is not a complaint about the engineering team, this is a complaint about organizations that don’t work to include them. People say they want to allow them to work free of distractions, but the engineering team doesn’t want that. At least, you should not be wanting to hire engineers that want that. These are some of your best problem solvers because they are there finding faults and programming defensively all day long, and they love designing complex systems. Your business is a design challenge. Don’t put departments in boxes. Build the whole company around user land.

  • Process blindspots - people create engineering cultures that are like engineering cultures they experienced in the past, such as adopting counterproductive practices like Scrum when they don’t need them, possibly increasing their labor costs by 40-50%. If you are starting a new startup, don’t repeat this mistake because it is all you have ever known, having twice as much development time would make a gigantic difference!

  • Corporate structure blindspots - kind of the same thing as the above. people create businesses that are structured like businesses they worked for, including modelling all the duties and firewalls between business units and dysfunctions. As a result all companies feel oddly familiar, but it seems they shouldn’t have to, and that’s got to be suboptimal. People who work for more businesses should try to create the ones they do want to work for.

  • Departmental blindspots - also somewhat similar. Often something one department can do has ripple effects and isn’t incentivized to care about other departments. Product management doesn’t consider engineering maintaince cost of a random idea they have, or think they need to do validation that it needs to sell. A CEO isn’t worried about hiring business development, but what about the chaos it is going wreck on his organization to suddenly demand an unrelated product line and tons of integrations that are not bringing in more money? Does engineering care that this feature they are only treating casually will generate lots of support tickets? Does marketing care that their bland and generic web page content is leaving sales money on the table, or do they think it’s fine because it looks like everyone else and it is shiny? Folks are measured in specific ways but things are better when everybody works to help everyone, yet almost no companies work that way.

  • Quality blindspots - how many developers have you hired? Have you hired a dedicated QA engineer yet? A customer will remember your bugs far more than they will remember what parts of your application work. Everyone tends to think about QA last. Put them first. They have a better opinion of your product than almost anyone in your organization.

  • Growth blindspots - I’m not sure this fits in this post, but a lot of people have very unique approaches to doing whatever. If you throw a lot of them in a group the approach gets averaged out with other ideas. Whatever style was there originally gets washed out, and everything can become mediocre and average. I’m not just talking about design of content here, I’m talking about technique, business strategy, everything. There is something that makes you YOU, and you maybe don’t know what it is, but you should embrace something and not lose it in the midst of growth. People want growth because it makes them money, but growth dilutes who you are more than it dilutes stock.

  • Hiring blindspots - no matter how much you try in an interview (I’d suggest not trying super hard and making it an excruciatingly long process since it just turns candidates away), you never know an employee until you’ve worked for them for about six months. You may be able to tell some people you really don’t want to hire - don’t hire them - but it’s really hard to tell that someone is going to be good or not. The same goes for employees knowing what a company is really like. I think a lot of this comes down to interviews being about persuasion and filtering, and both sides never really drop their guard.

  • CEO blindspots - I’ve seen this one a lot, but it’s easy for a CEO to get caught up in the fundraising process and defer his company to his executive team. Maybe this should be their job, but it leaves companies with no one in charge. This is a good reason to bootstrap. A friend once shared the advice “ if you really love doing something, the best way to not do it is to form a company around it”. And that’s somewhat true.

  • Company Vs Customer Focus - it’s easy to focus on what you are doing every day too much. Like if you’re walking down the street and see a little kid with a bike, he’s likely going to hit you because he’s looking right at you. You are in your company every day, and there is a real danger that you see the company as being more important than the customer. Too many companies look at the customer as someone to sell to, a source of money, someone to persuade, to trick, to make sign up for something, to launch a drip campaign at. The customer is why you exist, and who you are there to help. Customers and how you can make their life better should come up in discussion constantly. Companies who look at themselves as being on top and the customer as being on the bottom are going to design worse products over time. Some will still be successful, but many won’t.

  • Market blindspots - you can build anything, but you’ll only think of things to build that you know are problems. What is the best thing you could possibly build? Tech people try to launch tech products for tech companies because that is what they know, but they may have an easier and more rewarding opportunity creating products to solve simple everyday problems that appeal to wider audiences or specific industry verticals outside of tech. This requires just knowing a few people and learning how to approach selling into the market, but it feels like we build way too much for ourselves and not enough for others. As a result, everything we build gets more and more complicated, and we begin to enjoy complexity, which seems to be the opposite of what we should be doing.

Ow, that’s a lot.

Companies are weird beasts. It’s all about people working together to help other people, or should be, and there are so many externalities to root out. Because we work in them for so long, we think the way they do things are normal or even optimal, but really nothing is. And then we perpetuate the patterns.

“I learned it from watching you!”

Kind of weird. If you’ve got a new company though, you have an opportunity to try to bend the pattern just a little bit. Good luck!

Not sure what topics would be good next.

If there’s anything you’d like to hear about that you think I know, drop me a line and let me know, and I’ll see if I can share something about it.

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