The Art of Startup Firefighting

Arturo Dos
Philosophy of Entrepreneurship
8 min readJun 9, 2022

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tl;dr — the art of fighting fires in a startup with growing pains, is one that requires rapid response and patience.

The general approach is to sustain, to insulate, to stimulate and then to stabilize.

Since I started working on my first company in 2009, I have always been a “Version 1” founder or manager. In the sense that I either co-founded the companies, or I joined early to help launch the initial breakthrough product.

You could say that I’ve seen more 0–to-1 entrepreneurial action that happen mostly at or before Series B, spanning from the ideation phase to the MVP phase, and finally extending into the growth phase of a startup. The journeys obviously encompass a few pivots along the way.

Three years ago, I took a job here in Asia for the challenge posed by a decade-old tech company going from 1 to 5, or even 1 to 10.

The challenge what I would now label as the “Version 2” challenge.

source: unsplash

Defibrillators on Standby

At this stage…

The startups had gone through a spiked growth phase and are often facing mounting growing pains, often in the form of managerial difficulties.

and…

The startups are close to breaking even or could break even, but are underperforming growth expectations.

What initially seemed like good product-market fits, turned out to be a games in more-crowded-than-expected or smaller-than-expected markets.

Then of course what happens next is a familiar playbook:

Founders and execs are tapped out. Ran out of tricks, and now they argue.

And then of course…

Pressure continues to exact its toll on the team. People crack. People leave.

The company struggles to launch something new, not to mention the already-plateaued core business is now slowing declining.

Sounds familiar?

What happened to the Ideal Scenario?

It’s easy to talk smack about what the ideal scenario is. Especially for people who execute but never manage.

When engineering manager goes on and on about how the nature of a problem is not writing tests, not conforming to a paradigm, or not agreeing to certain design patterns — you know this person has never fought real fire before.

By that, I meant a person who is working within a comfortable amply-funded or ultra-profitable company at which time and talent are cheaply affordable staple.

By “real fire” — I’m talking about a real fire that is burning down a building.

As a startup metaphor, I’m talking about product and engineering catastrophes that are actively corroding the company’s profitability, operational efficiency, amicable work culture, etc — and you only have a few months to turn the ship around.

That’s fighting a real fire.

Now, let’s talk about concrete steps.

First of all, To Sustain — Prevent Disruption of Service

For early-stage startups, the mantra is usually to ship something that is innovative and disruptive, or nothing at all.

But when you have a running business, it doesn’t matter if it’s SaaS, e-Commerce or IoT, the moment your business stops shipping and maintenance, that’s the point of downward inflection.

In the past when I encountered product-engineering catastrophes in a SaaS or in an e-Commerce startup — usually in the form of a dysfunctional team with trouble makers,

the first things to do in order to prevent disruption of service is to identify a series of stable releases and minimally viable resources to keep the service operating.

Come up with a three-month plan for running the service on life-support.

Yes, this is far from ideal, but your job right now is to prevent a death-spiral, not to shoot for the moon.

Let’s be pragmatic.

Then, Identify All Knowledge and Skill Gaps

Now that you have bought your team at least three months of time, it’s time to get down to understanding the nature of the problem on the team.

Usually a dysfunctional team has two facets to its problems: a cultural one, and an expertise one.

First let’s focus on the expertise problem, because this one is the one that could be predictably solved.

Go and map out the entire workflow within the team and within the organization, and then find out what each team members knows and does not know.

From there, you can identify single points of failures (SPF)— usually knowledge and skills that only a single person possesses and the person is refusing to cooperate.

If no existing redundancy could be employed, now would be the time to come up with a recruiting and a transition plan for the SPFs.

To Insulate —Building Architectural and Organizational Safeguards

Now that you have identified points of failures both in terms of operating and shipping the product, and in terms of people management, it is time to take action.

This means to Componentize, Modularize, and Comparmentalize the system so you can isolate risks.

I personally call this “Building Fire Alleys” — quite literally, to stop problems in one system blowing across the aisle and setting another system on fire.

To put it bluntly, carve out system components and people that you believe are causing problems, and make sure they interact with the rest of the system and the rest of the company through strictly defined interfaces.

Yes, in code, that would be data interfaces or APIs; and in terms of people, that would be a set of clear protocols to produce paper trail and documentation.

The point here is to set things up so you can prevent risky actors in the company from reaching into other people’s scope of work; and if they still attempt at it, there will be paper trail for you to review and to act on.

Now, the Cultural Problem

This one is perhaps one of the toughest ones to tackle.

Because we are all social-cognitive creatures, in the sense that our social environment interact bidirectionally with our knowledge and skills, often forming a virtuous or a vicious cycle.

Truthfully, identifying core values of a healthy work culture is not that difficult, nor is spending to recruit a new team that adheres to these values.

Statistically speaking, it is extremely difficult to navigate out of a toxic team culture.

Thus, the true challenge here in this “Launching Version 2” situation, is to recruit and to transition into a new team culture, without letting soon-to-be ex-teammates with old grudges poison the well for new hires.

It is easier said than done.

It sounds cunning, but isolation of the would-be Version 2 Team from those who are to be managed out, usually works.

Setting Clear Management-wide and Company-Wide Expectations

What has been said thus far should be no secret to the company’s management team.

It will hurt, both emotionally and financially, and all the managers need to know that.

There is no point sugarcoating what is happening and what is about to happen.

The communication with the rest of the company, however, is a bit trickier.

You obviously can’t go out on a limb and tell the whole company that you are looking at months of organizational turmoil and culturally detox — no sane human being would realistically want to stick around for that — it is bad for personal wellbeing, and it is bad for career growth.

Therefore, to effect a strong and assuring communication the whole company, it is better to focus on the new cultural norms in focus, especially the ones that exemplify positive progress.

On a one-to-one basis, communicate potentials of career and personal growth opportunities.

Try to steer away from conversations that highlight mishaps and wrongdoings.

You can be transparent about how certain things that have not worked in the past will be changed or swapped out, but that should not be the focus of your communication to the company.

Now, To Stimulate — Rebuilding Communication with Project Management

Referring to Conway’s Law, the contrapositive tells us that a team that is no longer producing, likely has a faulty communication structure — hence a faulty collaboration model.

The beauty of fixing project management, is not just to manage work per se, better — the fixing of process, in fact, reveals those on the team is willing to play ball and are upbeat about the company’s direction— and those who do not and are not.

Transparency always helps.

Here I am not going to go into details of what project management methodology to adopt, you can read more about my approach to this specific problem here:

The end goal here is to create a process that mimics your ideal organizational structure — one that holds stakeholders accountable and one that establishes transparency around resource allocation.

Reestablishing Knowledge Management Transparency

At this point, your new hires should be coming in, and some people may have been managed out.

Now it is time to look into the future and figure out a robust training the growth plan for your new team.

At this stage, you want to identify where knowledge and skills are lacking and make sure each individual has a training plan in place to grow the person into his or her new role.

Also, establish clear growth and performance expectations are important.

Sure, you can use OKRs (Objective Key Results), KPIs or whatever instrument of measure you and the team see fit.

The point here is to be transparent and pragmatic about growth of the new team, under a healthy work culture.

Finally, To Stabilize — Rebuilding Product Roadmap

Ok, so you kept the engine running, you got rid of bad blood, and you brought an upbeat new team into the company.

What’s next?

Let’s build out a new product roadmap!

This in itself is a whole discipline, so I am not going to get down to the nitty-gritty.

But I will say that there are two main approaches that should be taken to form a good product roadmap.

The first is to conduct good research into product-market fit, and the second is to keep pulse on existing products and find opportunities to enhance them.

The first requires a lot of reading and analysis. It is good to align on company mission, product strategy and product goals first:

And then, there are probably a few good frameworks you can try to help you organize your research and decision-making:

The second will require good product analytics tools, which can be broken up into event analytics tools:

And business intelligence tools:

In short, researching into product-market fit helps you find new product ideas and opportunities; Keeping a pulse on your existing products helps you identify low hanging fruits to milk more out performance of your existing resources.

When you get to this stage, it means your team and your company have already rebuilt capacity to grind and to deliver, and should be on the right track to growing your Version 2.

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Serial Entrepreneur in Education and B2B SaaS. Product and Engineering Management. AI, Education and UX. Philosophy, Dance, Music and Culinary Hobbyist.