The Resilient Entrepreneur, Edition #111
Hi there
I hope you had a great week!
Here are the topics in today's edition:
- Good Cop, Bad Cop: A Must‑Know Tactic for New Professionals
- Entrepreneurship in Troubled Times: Don’t Deny, Don’t Delay
Please reach out with comments, questions, or suggestions for articles!
Talk soon,
Tom
TACTICS FOR RESILIENT ENTREPRENEURS
Good Cop, Bad Cop: A Must‑Know Tactic for New Professionals
The good-cop-bad-cop tactic is not obvious to juniors. Teach them the roles, and take on the bad-cop role for them to succeed.
When I was young, I often heard from older colleagues: “You need to have more experience to understand this.”
I hated it. What a stupid way to say “shut up.” What a stupid way to teach the next generation.
Now in my mid-forties, with a substantial amount of professional experience, I often work with junior colleagues. I pay close attention to never saying the E-word to my junior colleagues. I do this in my role as Founder & CEO of Yonder, a B2B SaaS company, but also in my role as an active reserve officer in the Swiss Armed Forces, where I command a battalion.
But that doesn’t mean I’m not trying to teach the following generation of professionals.
In this article, let’s look at a very specific example: good-cop-bad-cop tactics. This is one of the most powerful tactics in leadership, yet young people need a good coach to learn it.
Why Bother?
Why did I choose the good-cop-bad-cop tactic as an example? It’s for two reasons: First, it’s not self-evident to junior colleagues. As most junior colleagues have never worked with senior people before, their solution space only includes their own capabilities. You can’t blame them; it’s not their fault that they are young. But you can show them what solutions exist beyond their experience.
Second, it always works. No matter if you need to secure a proposal from a second supplier for a new firewall or if you try to sell your company, the tactic always works.
Teach It
A baby would never start eating with a spoon without being taught. Naturally, babies eat with their hands.
Similarly, why would a young professional naturally employ the good-cop-bad-cop tactic? Here are two examples of why you must teach the tactic.
In the first example, a young colleague approaches you, visibly agitated. No matter if he or she had a dispute with a customer, was blocked by a supplier’s inactivity, or fundamentally disagreed with a colleague from a different department, he or she is locked in the bad-cop role. That’s because of the emotions and the agitation. And when young colleagues are locked in emotion and agitation, they miss an important point: Usually, it’s the young colleagues who interact daily with customers, suppliers, and colleagues from different departments. You can’t be the bad cop if you need to interact regularly with other people. The bad cop should be the senior colleague.
The second example is about inactivity. How many times have you witnessed a young colleague saying, “I’ve sent a reminder email to them, but I’m not getting any replies.” Unfortunately, that’s a common problem. Junior colleagues are often ignored by customers and suppliers — their email signatures give away their position in the organization. In such a scenario, the tactic works like this: Tell your junior colleague to write to the customer or supplier again, saying that they need a reply for their senior leadership, and put senior leadership (i.e., yourself) in cc. This even works in small organizations where hierarchies are flat — people always want to talk to the top dog. Too bad when they don’t realize that the top dog plays the bad-cop part.
Brief It
So far, we’ve been talking about situations of daily life. However, good-cop-bad-cop is a tactic originally intended for negotiations. When two representatives of your organization go into a negotiation, you can play the roles in real-time.
As in everyday situations, the junior colleague mostly takes on the good-cop role, while the senior person plays the bad cop. Depending on how badly the senior colleague needs to behave to achieve the desired negotiation result, you need to brief your junior colleague on what’s going to happen. If they don’t know how you will behave in your bad-guy role, they might feel intimidated or surprised — remember junior colleagues’ limited working experience with senior leadership.
Conclusion
Isn’t the good-cop-bad-cop tactic a nice example of why it pays off for junior colleagues to go to the office and interact with more senior colleagues? You don’t learn from senior colleagues in your home office and in video calls.
And what’s in it for senior leadership? If you stop employing and teaching junior colleagues, there won’t be anybody around to play the bad-guy role when you retire.
STRATEGIES FOR RESILIENT ENTREPRENEURS
Entrepreneurship in Troubled Times: Don’t Deny, Don’t Delay
What connects an airline pilot in April 2020, a Serbian taxi driver in January 2020, and today’s Iran war? Two survival rules for leaders.
When COVID-19 struck 6 years ago, Yonder, the B2B SaaS company I co-founded, was just closing its seed round. Given our heavy focus on aviation, COVID-19 severely damaged our pipeline and significantly deteriorated our business outlook.
At that time, as a very young company, we had manageable fixed costs, could shift down a gear, and weather the storm. Not so a friend of mine who was an airline pilot at the time. Airlines have huge fixed costs, and pilots are used to high salaries and living standards.
I remember the day in April 2020 when he called me to say that he had decided to leave his airline job. He told me he wouldn’t count on a rebound in aviation after COVID-19.
Remember, April 2020 was just one month after the pandemic started, and long before we had an mRNA vaccine and COVID certificate apps. No doubt my friend did a bit of scenario planning before deciding to leave his well-paid, much-loved job as an airline pilot.
Fast-forward to 2026 again. Here are two lessons entrepreneurs can draw from my pilot friend’s 2020 decision.
1. It Pays Off To Act Early
My pilot friend acted earlier than most other people working in aviation. He was already settled into his new job when the first airline layoffs materialized. And when aviation rebounded after the lockdowns, and all airlines were short of pilots, he even secured a part-time comeback as a pilot.
Acting early pays off, as long as you act consciously and without hyperventilating.
My pilot friend is not the only person who acted early in the COVID-19 pandemic. I remember a taxi ride in Vienna, Austria, in January 2020. I chatted to the taxi driver, who happened to be Serbian. We were chatting about this novel virus in China, when, out of nowhere, the taxi driver told me that he had sold two of his three cars and fired all his employees. With a puzzled look on my face, I asked him why he did this. He said, “Look, I’m from the Balkans. For my entire life, I’ve seen crises come and go. This China virus thing can wreck the whole travel industry, so I want to be ready. I can always rehire people and buy cars again once the crisis is over.”
What a contrast to the lazy, cozy, and risk-averse mentality in the spoiled West. We should learn from the Balkans.
2. Talk About Bad News And Crises
Another thing the spoiled West should learn is to talk about bad news and crises. When two entrepreneurs meet in the West, the first thing they do is to ask each other how business is going. The second thing is that they tell each other that business is going great.
Really? Maybe this answer was right in the boom years between 2009 and 2020. But today? I would suggest you follow my pilot friend’s or the Serbian taxi driver’s approach: Talk about bad news and what you intend to do about it. Everything else is denial.
Why should you talk about your entrepreneurial difficulties? The first reason is your own mental sanity. If you continuously fool yourself into thinking that everything is fine, you will be shattered when you suddenly hit a wall. The second reason is that as a leader and entrepreneur, you have a responsibility you cannot delegate. You cannot walk away from adversity just because it’s difficult. But you can talk about your difficulties to other people. And the more people you talk to about your difficulties, the higher the likelihood that somebody will point you towards a good solution you wouldn’t have found yourself.
About Me
I’m a tech entrepreneur, active reserve officer, and father of three — writing about entrepreneurship, leadership, and crisis management from hard-won experience. No AI, no fluff, no promos. Just plain-text insights for people building and leading under pressure.
When I’m not solving problems, I find clarity in the mountains around Zermatt.
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