Startup CEOs face intense highs and lows — but rarely show it. However, revealing emotions in CEO leadership can be a strength, not a weakness.
It’s lonely at the top. What’s true for a Fortune 500 CEO, is also true for a startup CEO. The CEO is the last line of defense, the last level of escalation, and always makes the final decision. Not an easy job.
For startup CEOs, add a dose of rollercoaster riding on top of the regular CEO burden: Building a company is a rollercoaster. And in contrast to Disney Land, this rollercoaster will last for years, not minutes.
This sounds like a pretty emotional job. Well, it is. However, CEOs are not expected to show too much emotion.
Speaking for myself, I’m a rather rational person. But being a rational person doesn’t mean I don’t have emotions.
Let’s look behind the facade.
Positive Entrepreneurial Emotions
All entrepreneurs have positive emotions when they win deals — even more so when you’re in an industry with long sales cycles. Whenever we win a deal, we celebrate it with a glass of whisky, but we also remember the times of hardship that led to that deal.
As a B2B SaaS entrepreneur, new features also trigger positive emotions in me. Especially when those new features relieve some long-time pains for our customers or our customer success team, or when they open the door to a new market segment. Personally, the most positive emotions I get out of a new feature is when I see that our team did a great job of meeting customer requirements, user experience, and feature completeness — without taking too much time to build the feature.
Last but not least, as a founder, trust from investors is key to mastering difficult situations. Trust is built by not just sharing good news, but also bad news with investors. At Yonder, we have done so since the very early days. Sharing bad news isn’t necessarily connected with positive emotions, but receiving support from investors in very difficult situations certainly is. We’ve received great support from our investors on several occasions, and their feedback was that their pledge of support is based on our honest communication in our regular investor reporting, no matter if good or bad news. In difficult situations — of which there are plenty in entrepreneurship — such feedback feels better than any won deal.
Negative Entrepreneurial Emotions
Change of scene.
The rollercoaster ride is approaching its low at full speed.
The most negative of all entrepreneurial emotions is uncertainty. When I know I screwed up, it’s easy to take corrective actions — say sorry, improve the offering, fix the bug. But most of the time, as an entrepreneur, you don’t know why something went wrong.
A large deal just got delayed by one year by the means of a simple email. Is it because the prospect is no longer interested in our solution? Is it because the prospect will undergo a merger with another company? Or is the prospect even in financial trouble and doesn’t want to tell you?
Delaying deals is bad, but losing deals is worse. Why did we lose a deal? Was it an issue of price, or was it a missing functionality? Or was it some shady behavior of a competitor behind the scenes? We’ve experienced all three, but we haven’t received honest feedback from all lost deals even if we asked for it.
Most of our customers are large organizations with plenty of internal politics. Often, we’re the playball for something outside of our influence, and it doesn’t necessarily have anything to do with our product or our services. That’s a frustrating situation, but we have to live with it and turn it for the better.
Last but not least, one of the most negative emotions in entrepreneurial life is when you get the feeling that an employee is underperforming. Hiring is arguably the most difficult task an entrepreneur faces, and the transition between “doing a good job” and “not meeting expectations anymore” is often vague, giving you plenty of uncertainty about whether you have to part ways or not.
How to Keep Up With The Emotions
One of my early investors once said: “Whining is not an entrepreneurial discipline.” So let’s discuss what a startup CEO can do to keep up with the emotions.
First and foremost, you need confidantes. In my case, those are my co-founders. I share with them my emotions no matter if they are positive or negative. Without my co-founders with whom I can share anything, my life would be a lot more miserable.
Second, always remember entrepreneurship is a rollercoaster ride. When you’re at a low point, remember there are also high points, and life will soon be good again. No reason to despair.
Third, whenever a situation looks hopeless, I always remember that so far, I always found a good solution just in time — no matter how big the challenges are. This insight has helped me over many dark moments in my life as an entrepreneur.
Last but not least, busy entrepreneurs need occasional timeouts, too. For me, it’s the mountains. Every time I step off that train in Zermatt, I have a smile on my face — irrespective of the darkness of the entrepreneurial clouds.
