The Resilient Entrepreneur, Edition #76
Hi there
I hope you had a great week!
Here are the topics in today's edition:
- Gouverner c’est prévoir: Why Long-Term Planning Beats Firefighting
- Topic 2
- Topic 3
Please reach out if you have comments, questions, or suggestions for articles!
Talk soon 👋
Tom
KickKerK
LEADERSHIP FOR RESILIENT ENTREPRENEURS
Gouverner c’est prévoir: Why Long-Term Planning Beats Firefighting
In government, they say “gouverner c’est prévoir.” As an entrepreneur, I live by this mantra for financial planning and the product roadmap.
“I’m completely under water.”
“I’m trying to work through my backlog.”
“Give me some time to catch up first before I review your request.”
Sounds familiar? I would be lying if I said that I had never fallen behind in my work, even though I have a reputation for being organized. For my personal work organization, I always plan 2–4 weeks ahead. That works well to stay on top of day-to-day activities and tasks.
Still, sometimes I am drowning in urgent work that turns my beautiful plan upside down. Why is that?
It’s because for strategic topics, planning ahead for 2–4 weeks is not enough. You will not compensate strategic urgencies with better personal organization. Rather, you will have to work hard to achieve what I call a strategic advantage.
Sounds confusing? Let’s look into two real-life examples from Yonder, the company I co-founded.
Cash Flow Plan and Business Plan
Cash is king for both businesses and households. That’s why maintaining an elaborate and accurate cash flow plan is a key activity for any entrepreneur.
How far ahead should you plan? The general recommendation is to forecast cash flow for 2–3 years, and to use a business plan for anything beyond 3 years.
Now, how can you achieve a strategic advantage with your cash flow plan and your business plan?
I recently merged the cash flow plan and the business plan into one huge Excel spreadsheet. Every revenue and expense item is modeled and aggregated for monthly and yearly figures. For the next ten years.
A static cash flow and business plan doesn’t earn you a strategic advantage. The strategic advantage is achieved when you incorporate scenario planning into your plan. What happens if customer X doesn’t renew the contract in September 2026? What happens to our revenues if the U.S. Dollar nosedives? And as a consequence, when do I have to lower which cost items to still cut a profit?
All these questions can be answered in my merged cash flow and business plan, and the results are shown instantly in updated liquidity and P&L charts.
Now, how does this turn into a strategic advantage? I can plan for the worst case long before the worst case occurs. As a consequence, I’m neither surprised, nor do I suddenly have super-urgent financial problems on my desk that draw me down.
Product Roadmap
The other strategic planning tool I use is the product roadmap for our SaaS product.
In the early days of the company, we often had to make feature promises to win the first few deals. Also, the early features still had lots of room for improvement, so customers made many feature improvement requests. We couldn’t always keep our promises, as bugs took more time to resolve than planned, and new requests from new customers who screamed louder came in at inconvenient times.
Fast-forward a few years. The product has matured, and so has the product roadmap. We still receive feature improvement requests and new feature requests from our customer base, but we consolidate them much better than in the early days. We discuss roadmap items both internally and with our customers to make sure that the priorities serve the majority of our customer base.
And that’s the key word to achieve strategic advantage: Priorities. It means you accept that you cannot do it all at the same time. That’s a struggle to communicate internally and externally, but there is no way around it.
But before you can communicate the priorities, you need to have an overview of all the roadmap items and feature requests at hand. Achieving and maintaining that overview is your true strategic advantage.
Conclusion
Planning years ahead in terms of cash flow and quarters ahead in terms of the roadmap might sound like a waste of time: Surely, things will change, and as a consequence, you will have to replan.
Yes, you will have to replan and replan again, but that’s less strenuous than reacting to unfolding major events without a plan.
It’s an old saying in government: Gouverner, c’est prévoir. To govern is to plan ahead. And what’s true for a government is true for any business and any household.
Don’t get me wrong, I’m not a pessimist, but you will have to plan for the worst and hope for the best. That’s the way to avoid strategic urgencies that make you fall back in your day-to-day work.
LIFE HACKS FOR RESILIENT ENTREPRENEURS
A Step-by-Step Guide to Cleaning Up Years of Digital Garbage
It’s incredible how much digital garbage amasses over time, even if you run an orderly organization. Here is how to clean it up.
Summertime laziness is an ideal time to get things done that you have wanted to do for a long time, but never found the time for. Each summer, I hide in the mountains and work undisturbed for days, getting much more done than on regular office days.
This summer’s focus was a digital cleanup of our JIRA tickets and Confluence pages. At Yonder, the B2B SaaS company I co-founded, we used JIRA not just for the development team, but for the entire company.
As time has shown, this decision was only partially successful. Imagine what JIRA looks like after 7 years, with all the twists and turns our company has taken since incorporation.
How It All Started
We recently had a change in the leadership team. Our new Chief Customer Officer told me he wanted to get rid of JIRA in his team. JIRA would not help him maintain the overview, so I agreed.
We also agreed to do the JIRA cleanup together, and that we would not delete a single JIRA ticket before having taken a look at it.
This proved to be a good strategy. Out of more than 3,500 tickets, we saved 40 tickets from deletion. 39 of those tickets needed a quick chat with the customer team and could then be resolved. And the last ticket proved to be a bug reported by a customer that was somehow getting lost in the wrong JIRA project. We transferred that ticket to the bug queue so that the issue could be resolved.
When we went through the 3,500 tickets before deleting them, we noticed that there was a huge mess with epics and labels. These two elements are designed to bring order and structure to a JIRA project, but over the years, they have created more chaos than order in our JIRA projects.
One JIRA Project at a Time
After cleaning up the customer team’s JIRA project, I dared to look into the product and development team’s JIRA projects. It came as no surprise that it was a mess in those projects, too.
Even worse, the development team’s JIRA project still contained the very early tickets from the time we started developing our software. From today’s perspective, those tickets don’t describe our software anymore. Too much has changed in the requirements, and much of the code has been refactored in the meantime.
So we decided to delete all the JIRA tickets relating to the development of the initial version of our software. Also, we deleted all the JIRA tickets relating to retired features. Again, no ticket was deleted before we took a look at it.
The cleanup of the development team’s JIRA project slashed another 5,000 tickets. And it was the same mess with epics and labels that we’ve found in the customer team’s JIRA project.
Once the development team’s JIRA project was cleaned up, I attacked the last one, the product team’s JIRA project. That’s where we store all the customer feedback and feature requests for future improvement of our software. In this project, we only deleted the duplicate requests and grouped the tickets intelligently into relevant epics.
What Survived In The End
Only four JIRA projects survived the cleanup session: The product team’s JIRA project, two development JIRA projects for the Mobile and the DevOps team, and our company risk register.
On the labels side, we deleted all the labels that were somehow duplicates of epics, and just the labels for the different customers survived. In this way, we have a good overview of the open issues with each customer, and we visualize them in an orderly JIRA dashboard that fits onto a laptop screen.
Conclusion
Even if you think you’re running an orderly organization, digital garbage will amass over time. JIRA is no exception; we encountered the same mess when we migrated from Google Business to Microsoft 365 some time ago.
If we were still living in the paper world, we would have cleaned up the information mess a long time ago — our office would be so full of paper that we couldn’t even open the door.
In the digital world, garbage is invisible. That’s why you need a cleanup session now and then. Why don’t you schedule this for your next summertime laziness period?
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 write about my experience in entrepreneurship, leadership, and crisis management.
When I’m not solving problems, I recharge and find inspiration in the breathtaking mountains 🏔️ around Zermatt 🇨🇭.
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