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The Resilient Entrepreneur, Edition #53

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Hi there

I hope you had a great week!

Here are the topics in today's edition:

• I Missed the Target a Thousand Times - And That's Why I Hit It
• How to Master Risk Management in JIRA in 7 Easy Steps
• Why I Write: Sharing the Realities of Entrepreneurship, One Post at a Time

Please reach out if you have comments, questions, or suggestions for articles!

Talk soon 👋
Tom

KickKerK

LEADERSHIP FOR RESILIENT ENTREPRENEURS

I Missed the Target a Thousand Times - And That's Why I Hit It

Europe would do its entrepreneurs a favor if it would stop stigmatizing failure, and adopt more of an American approach to success and failure.

One shot, one kill.

Well, it’s not quite that simple for entrepreneurs. Whilst most people might aim, but never shoot that arrow, some people at least shoot a lonely arrow at the target:

What do entrepreneurs do? They shoot one arrow after the other in what they think is the general direction of the target:

Sooner or later, they will hit the target, if they keep shooting:

I love this analogy. In my 10-year stint as an entrepreneur, I have seen so many people talking about entrepreneurship, but not ever giving it a try. I have seen so many wannabe entrepreneurs, trying one single time and giving up once the journey became a little rockier.

As the Founder & CEO of Yonder, I had to try and fail many times before we arrived at where we are now: Wrong tech decisions, wrong hiring decisions, wrong market assumptions. Let’s look into these in more detail.

Tech Decisions

Shooting many arrows in the general direction of the target is one thing, but as an entrepreneur, you have to shoot those arrows fast. In the early days of a product, speed is more important than stability. For a software product, this means limited scalability and edge cases that are not properly handled.

In the first days, that doesn’t matter. But later, when you have found product-market fit and your business starts to scale, those early tech decisions will need to be revisited. And because you taped together your initial product at lightning speed, you probably didn’t spend too much time on proper tech documentation, so you’ll likely need to shoot another few arrows to get it right. Straightening your initial tech stack won’t be a single shot, either.

Furthermore, don’t forget one thing: Building a stable product takes time. This means that you will lose the speed at which you can ship new features when you start focusing on stability. Your new customers will expect stability, while some of your long-time customers will question why you can’t ship new features as fast as in the past.

Hiring Decisions

Hiring is arguably the most challenging task for founders. When you set off to build a business out of nothing, there isn’t an HR department that can help you find the right people. So you will likely hire people who prove to be the wrong choice for a dynamic workplace like a young company. Other people you hire will be good fits for the initial jungle phase of your company, but once you enter the dirt track or even highway phase of your company, they will no longer be good fits and you will have to replace them. And finally, you might even choose a co-founder that proves to be unfit for the entrepreneurial journey.

Every flawed hiring decision reflects an arrow that misses the target. And just because you know that you will likely hire some misfits, you can’t stop hiring people.

Market Assumptions

This one is my favorite. When you start a company, you make a ton of assumptions about the target markets: Pricing, required features, non-functional requirements, segments. The longer you are in the business, the higher the likelihood that the market needs something slightly different than you originally thought.

We’re back at the arrows analogy. Keep shooting more arrows, adapt your product and your company to what the market needs, or you will disappear sooner or later.

Conclusion

Shooting many arrows and missing the target all the time can take a high mental price on an entrepreneur. There is no way around getting used to it, and accepting that you look like a failure every now and then. That’s hard, but it’s necessary to achieve success eventually.

Europe would do its entrepreneurs a favor if it would stop stigmatizing failure, and adopt more of an American approach to success and failure.

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LIFE HACKS FOR RESILIENT ENTREPRENEURS

How to Master Risk Management in JIRA in 7 Easy Steps

Are you looking for the easiest way to set up risk management in JIRA for your ISO 9001 certification? Follow the steps in this cheat sheet, and you will be done in very little time and with very little cost.

Here is a step-by-step setup guide for your risk management in JIRA.

1. Set up a new JIRA project

Set up a new JIRA project for your risk management — in our company, we call it “risk inventory”, and we use the standard JIRA software project template.

I assume you have administrator privileges in your JIRA tenant and am therefore not covering the required steps to get administrator privileges.

2. Set up the Risk Register plugin

If you want an easy graphical risk matrix, set up the Risk Register plugin, available directly from the JIRA marketplace:

As for all plugins, there are alternatives available, but Risk Register has served me well so far.

3. Define JIRA statuses for your risks

All your risks will be JIRA tickets. Since every JIRA ticket must have a status, you must define the statuses you want to use to track your risks. In our company, we have chosen the following statuses:

• Backlog: Mitigating the risk has not started yet
• In Progress: Mitigating the risk is in progress
• Eliminated (External): The risk was mitigated externally
• Resolved (Internal): The risk was mitigated internally
• Accepted by Informed Decision: Some risks cannot be mitigated, but need to be accepted

These statuses are configured in the Kanban Board Settings as displayed below:

4. Create a JIRA ticket for each risk

Now it’s time to create a JIRA ticket for each risk in your company. We have created a new issue type “risks” and defined a few custom fields for each risk:

• Description: What’s the risk?
• Scenario: What could happen?
• Mitigation Measures: What can we do?
• Risk Reporter: Who reported the risk?
• Risk Owner: Who is responsible for the risk mitigation?
• Risk Assignee: Who is working on the risk mitigation?
• Impact: Categorized as “insignificant”, “minor”, “major”, “severe”
• Probability: Categorized as “remote”, “unlikely”, “likely”, “almost certain”

You can add more custom fields to your risk issue type if you need more to fit your organizational needs. However, I suggest you use as few custom fields as possible — it’s always easier to add data fields later than to eliminate them later!

We took a few iterations to define risk impact and probability so that they cover both financial and non-financial aspects of our business.

Here are our risk impact definitions:

• Insignificant: No relevant impact on company financials and reputation
• Minor: Small impact, up and until loss of smaller customer(s)
• Major: Large impact, including loss of enterprise customer(s) and/or fines by authorities
• Severe: Potentially existential impact on company financials and reputation

And here are our risk probability definitions:

• Remote: Black-swan considerations, <1% chance of risk materialization
• Unlikely: Chance for risk materialization is <50%, but still possible
• Likely: Chance for risk materialization is 50/50
• Almost Certain: Risk materialization is imminent, >90% probability

While this might sound like too much information, collecting all that information helps you get an accurate picture of risks and generate meaningful dashboards.

5. Create a JIRA epic for each risk type

JIRA tickets belonging to the same topic can be grouped into epics. We have defined an epic for each risk type in the company, where we used and extended the PESTEL analysis framework as a basis:

• Political and Reputation
• Economic — Customers
• Economic — Competitors
• Social
• Technological — IT Security
• Technological — IT Infrastructure
• Technological — Tools & Frameworks
• Technological — Suspected Incidents
• Environmental
• Legal
• Organizational

Again, I wouldn’t recommend copying the above epics without customizing them for your organization.

6. Link risks and epics

Now link each risk to an epic, and you will get your first overview of all the (reported) risks in your company by using JIRA’s roadmap feature.

Here is an excerpt of our risk roadmap:

The green bar indicates mitigated risks, the blue bar indicates risk mitigations in progress, and the grey bar indicates risks that haven’t been addressed yet.

7. Create a dashboard

Our risk matrix looks like the textbook standard, but it is generated directly and allows us to drill down and see the risks contained in each field:

Clicking on one of the risk counts in the above risk matrix opens a list of all risks with the corresponding probability/impact values, and from there you can access the details of each risk.

Furthermore, we set up some JIRA dashboard elements to increase the overview of the risks:

• The risk count shows how many open risks there are, and how many are being worked on. If I see that the backlog is growing and progress is dying, we take action as an executive team.
• The unassigned risks report shows if any reported risks are unassigned. We aim to always assign all JIRA tickets to a person — because nobody will take ownership of an unassigned ticket. So therefore, to make things happen, assign all JIRA tickets to somebody in your organization. When the unassigned risks report is empty, I’m happy. If it isn’t, we take action by assigning all unassigned tickets to the right person.
• We use a report showing new risks reported in the last 30 days to make sure that new risks are being addressed.

And that’s it. There is no more to do to produce an effective, dynamic, and actionable risk management system tailored to your organization!

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INSPIRATION FOR RESILIENT ENTREPRENEURS

Why I Write: Sharing the Realities of Entrepreneurship, One Post at a Time

No matter how busy you are, share your experience with fellow entrepreneurs. And don’t forget to leave your bubble now and then.

“Tom, when do you find time to write all the articles I see on Medium and LinkedIn?”

Yes, as the Founder & CEO of Yonder, there is always some kind of urgency you need to attend to.

Yes, as a father of three, there is never a dull (or quiet) moment.

So why on earth do I invest my scarce time into writing about resilience and entrepreneurship?

It’s because many people have a distorted view of what it takes to build and run a company in uncertain times. It’s because many fellow entrepreneurs can use practical tips now and then. And it’s because it helps to reflect on all the stuff that entrepreneurs experience along their ride.

Let’s look into some of my arguments.

Entrepreneurship is a Lot Less Glorious Than Suggested on Social Media

​Maybe you think I’m living a glorious and successful life, but most of the time, it’s anything but: Success as an entrepreneur comes from what I call The Grind — year-long, daily hard work to advance the thousands of different tasks required for a company to succeed. More often than not, things take longer and take more effort than anticipated. Most of the time, you will have to put aside your personal gain for a long time to make sure that your company can thrive.

If you don’t have enough challenges with running the business, just add a healthy dose of administration on top. Lengthy hassles with procurement, preparing for ISO 9001 or ISO 27001 certification, or dealing with lawyers.

If admin didn’t make you cripple, the apparently glorious entrepreneur life is often ambushed by all the mistakes you make along The Grind. Looking back, my journey is full of mistakes — I have hired the wrong people, I have made the wrong technical decisions, and I have dealt with the media in a less-than-ideal way.

Entrepreneurs Should Help Each Other

My motivation to write is to share my experience from The Grind and talk about my mistakes as an entrepreneur, intended to make life just a little bit easier for fellow entrepreneurs.

No matter if I write about hiring, frustration, or urgent bugs, I call things what they are, and I write practical posts — as an entrepreneur, I have benefited most from practical tips & tricks from other entrepreneurs rather than from theory.

It’s a Connected World

In a connected world, it pays off handsomely to leave your bubble now and then to get new inputs and ideas. For me, I do this by serving as an active reserve officer in Switzerland’s Armed Forces.

Besides serving my country, the active reserve system let me meet people I wouldn’t have met without the military, and develop my leadership and crisis management skills. I even had the privilege of teaching crisis management as an active reserve officer to civilian companies and MBA students.​

Entrepreneurship includes a healthy dose of leadership and crisis management, which is why some of my articles are about the parallels between leadership in the military and entrepreneurship.

Spread The Word!

Entrepreneurs often organize in communities to share experiences and learn together. Therefore, I am welcoming all comments, inputs, and questions to my posts. I will answer them directly in the comments section or take them up in future posts. If you have any inputs for topics to be covered in future posts, please use the comments section in this article!

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About Me

Growing a company 📈 in uncertain times 🔥🧨 is like running a marathon—it demands grit, strategy, and resilience.

As a tech entrepreneur 💻, active reserve officer 🪖, and father of three 👩👦👦, I share practical insights and experience on entrepreneurship and resilience in The Resilient Entrepreneur, my weekly newsletter.

When I'm not solving problems, I recharge and find inspiration in the breathtaking mountains 🏔️ around Zermatt 🇨🇭.

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