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How a startup loses its spark

blog.johnqian.com

101–110 of 287 posts

Re: How a startup loses its spark

#101
post #54

I'll raise your spark for complete destruction. Here's an incomplete list that I keep around of the mechanisms that I've observed so far that have played a big part in the decline/destruction of an engineering team (and product thereof): 1. Too-technical leaders: As startup scales, there can sometimes be a mad dash to fill new leadership roles (e.g. VP of Eng, Arch, CTO, etc.). Super-star engineers present at startup…

Maybe by avoiding fast scaling, which implies avoiding VC money.

> Maybe by avoiding fast scaling, which implies avoiding VC money.

There are still things you can do, e.g. don't pick the offers in a round with the most $$$ - instead pick the 1 that will help you the most.

Set the right expectations. Most of the time it's not the VC money that's the problem but the founders being consumed by suddenly being "rich".

Re: How a startup loses its spark

#102
The failure modes I've encountered:

1. Toxic team members who can't be fired. These people will reduce morale down to zero and force your best people to leave. In one case it was the CEOs long-time friend, and in the other case it was one of the technical founders. If you find yourself as an employee in a similar situation, then go ahead and pack things up because it will never get better.

2. Selling to Fortune 500s without investing in a sales team. Basically, we built it and they never came because B2B at this level is much much different than B2C. So if this is your move then your sales team should be bigger than your engineering team by at least 2x.

3. Toxic team members in recruiting positions. I once worked with a business partner whose recruiting strategy boiled down to bullying people into joining the company. After a year's time we had a solid 12 person engineering team while the business team was exactly the exact same as when we started.

4. Focusing too much on writing code and not enough on building relationships in your domain. When it comes time to sell, you will need to reach out to someone, so start nurturing relationships early.

Re: How a startup loses its spark

#103
post #54

I'll raise your spark for complete destruction. Here's an incomplete list that I keep around of the mechanisms that I've observed so far that have played a big part in the decline/destruction of an engineering team (and product thereof): 1. Too-technical leaders: As startup scales, there can sometimes be a mad dash to fill new leadership roles (e.g. VP of Eng, Arch, CTO, etc.). Super-star engineers present at startup…

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Re: How a startup loses its spark

#104
post #54

I'll raise your spark for complete destruction. Here's an incomplete list that I keep around of the mechanisms that I've observed so far that have played a big part in the decline/destruction of an engineering team (and product thereof): 1. Too-technical leaders: As startup scales, there can sometimes be a mad dash to fill new leadership roles (e.g. VP of Eng, Arch, CTO, etc.). Super-star engineers present at startup…

Don’t forget: Hiring remote contractors to “speed up” things. Dev will slow to 50% and meetings will double as you attempt unsuccessfully to teach them how to code.

Re: How a startup loses its spark

#105
post #54

I'll raise your spark for complete destruction. Here's an incomplete list that I keep around of the mechanisms that I've observed so far that have played a big part in the decline/destruction of an engineering team (and product thereof): 1. Too-technical leaders: As startup scales, there can sometimes be a mad dash to fill new leadership roles (e.g. VP of Eng, Arch, CTO, etc.). Super-star engineers present at startup…

After 25 years in the full range of IC and management positions, I'm convinced there's no substitute for expertise, maturity and judgement. I could come up with some rules of thumb (eg. ICs need the maximum amount of agency they are capable of handling), but every rule has its exception. Distilled wisdom is easily misinterpreted, taken out of context, and cargo culted by those with insufficient experience to apply it.

I've seen how small dynamics resulting from individual personalities and nuances of org structure have led to massive dysfunction and productivity loss, even though everyone was well intentioned and doing their job to the best of their ability. I could list out hundreds of behavioral "flaws" that individuals exhibit, but there's no way to fix them all directly, good engineering can't be done by top-down edict and central planning. Instead, you need a critical mass of people, including engineers on the ground, with a good end-to-end understanding of the product and business so that micro-decisions can be suitably informed by the big picture, and the right concerns can be escalated for leadership attention. You need to be able to weigh the cost of product, design, legal, financial, support, security, and operations across both short and long-term to make the right decisions. This is only possible with a high degree of mutual trust and safety for experts to voice their opinion and find the right tradeoffs. It's very easy for egos and personality conflicts to come in the way, hence the need for maturity in leadership. Balancing a pencil on its nib is not a bad analogy.

Re: How a startup loses its spark

#106
post #54

I'll raise your spark for complete destruction. Here's an incomplete list that I keep around of the mechanisms that I've observed so far that have played a big part in the decline/destruction of an engineering team (and product thereof): 1. Too-technical leaders: As startup scales, there can sometimes be a mad dash to fill new leadership roles (e.g. VP of Eng, Arch, CTO, etc.). Super-star engineers present at startup…

As a corollary of these people problems, I would add: 1. Not correcting problem hires fast enough. First time founders are often too hesitant to give negative feedback, demote a too-technical manager who should have stayed an IC, or remove a problem employee who isn’t working out. The anecdote that comes to mind is a local startup that hired a C-level executive’s UI designer friend into their VP of Product role. He w…

Ray Dalio talks about this in his book "Principles."

The specific advice he offers is "hire slowly, fire quickly."

Re: How a startup loses its spark

#107

Earlier quoted context omitted.

> The arguments articulated are entirely false: ex. N^2 communications. This is reductionist and absurd I think you’re being unnecessarily harsh and reductionist of the article’s arguments. I’ve experienced exactly this failure mode in startups. The counter-example you described is an example of properly managing the N^2 complexity, not an example of it not existing.

But it doesn’t exist. For any task the number of contact points is almost always fairly small. Just because the possible N might be large most are occluded by lack of relevance to any specific task. I would note that the author categorically says it’s not possible for a startup like environment to exist in a large company. That’s what I disagree with.

How have you developed a sense for organizational friction? What observations of culture can I use to make an educated guess about how easy it is to do my work?

I agree with your point that a large org does not guarantee what the author claims. The author claims that the organizational friction can be measured by productivity, but you recognize culture as the better diagnostic criterion. The big O metaphor does not extend well to the argument, as you point out.

I'm looking for hard hitting interview questions so I don't waste my time on "soul sucking" positions.

Re: How a startup loses its spark

#108
post #54

I'll raise your spark for complete destruction. Here's an incomplete list that I keep around of the mechanisms that I've observed so far that have played a big part in the decline/destruction of an engineering team (and product thereof): 1. Too-technical leaders: As startup scales, there can sometimes be a mad dash to fill new leadership roles (e.g. VP of Eng, Arch, CTO, etc.). Super-star engineers present at startup…

As a corollary of these people problems, I would add: 1. Not correcting problem hires fast enough. First time founders are often too hesitant to give negative feedback, demote a too-technical manager who should have stayed an IC, or remove a problem employee who isn’t working out. The anecdote that comes to mind is a local startup that hired a C-level executive’s UI designer friend into their VP of Product role. He w…

Yep, this very much resonates with my experiences.

At the end of the day, startups are run by people, who generally prefer to work with their friends, avoid conflict, etc. There's no great mystery. The mystery is when things work well.

Re: How a startup loses its spark

#109
post #54

I'll raise your spark for complete destruction. Here's an incomplete list that I keep around of the mechanisms that I've observed so far that have played a big part in the decline/destruction of an engineering team (and product thereof): 1. Too-technical leaders: As startup scales, there can sometimes be a mad dash to fill new leadership roles (e.g. VP of Eng, Arch, CTO, etc.). Super-star engineers present at startup…

Don’t forget: Hiring remote contractors to “speed up” things. Dev will slow to 50% and meetings will double as you attempt unsuccessfully to teach them how to code.

More general hazard: Treating engineers as fungible resources

Re: How a startup loses its spark

#110
post #9

It almost feels like the "efficiencies of scale" you get from large organisations (e.g. specialised people for recruitment, people matters, quality assurance, user research etc.) are not really efficiencies. Perhaps it's better to grow the organisation by repeatedly cloning the smallest effective team you ever had, rather than creating a more "efficient" organisational structure. How those "mini-companies" communicat…

I agree and this is a practical method that I've seen work well in several companies I've worked for. However I think there's a bigger problem that contributes to the loss of "spark" that the author strangely didn't address at all. The fruits of labor grow ever higher. By which I mean: In the early days of a startup the problem space is ripe and plentiful, the impact you can have is outsized, and the pool of people w…

There is also a dynamic aspect to that: the original team who started the startup has battle scars, they used to take risk, but now they have a natural incentive to be more conservative, preserve the way things were done.

Rands has a great article on that topic well worth reading: https://randsinrepose.com/archives/stables-and-volatiles/

It matches my experience with startups experiencing challenges as they grow.

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