Bosses

Here's How Bosses From Hell Helped 6 Entrepreneurs Grow

From control freaks to being uncooperative, founders share what they learned from their worst boss.
Here's How Bosses From Hell Helped 6 Entrepreneurs Grow
Image credit: Michele Marconi
Magazine Contributor
4 min read

This story appears in the June 2018 issue of . Subscribe »

In business, sometimes the most valuable lessons come from the worst teachers. We asked six entrepreneurs: What's the greatest thing you learned from a bad boss

Related: The 6 Most Familiar 'Bad Boss' Types and What to Do About Them

1. Bring everyone in.

“A former boss was very hierarchical and discouraged collaboration. Everyone reported directly to her, and interdepartmental meetings were practically prohibited. It meant that only our boss had the full picture -- we missed a lot of opportunity for alignment and cooperation. Today at our company, it’s a priority to hold regular team meetings and foster a strong culture of collaboration. It’s crucial that our team members weave collective sharing into the fabric of their day-to-day interactions.” -- Melissa Biggs Bradley, founder and CEO, Indagare

2. Be vulnerable. 

“Don’t be afraid to show your emotions! I worked for a partner at McKinsey who was an incredible person but an awful manager because he kept his feelings bottled up. After a client presentation went awry, our team didn’t know where we stood with our manager. It was tense, awkward and demotivating. Showing vulnerability and letting others know when you’re genuinely upset can help everyone externalize their emotions, build trust and reassure employees that they aren’t alone. It sends a clearer message than stone-faced silence.” -- Leo Wang, founder and CEO, Buffy

Related: Do You Have a Bad Boss? Here's What to Look For. 

3. Lend a hand.

“I worked for someone who would never help out the junior staff with their work, even if he was finished with his own -- he’d simply pack up and leave early. I now make an extra effort to ask my staff if they can use a hand when my own workload is light. It’s created a culture that feels more like a tight-knit team and less like a hierarchy.” -- Adam Tichauer, founder and CEO, Camp No Counselors

4. Move as a group.

“When I was a nurse manager, I had a boss with no experience in healthcare. She wanted to change our process for keeping patients from getting blood clots. I knew it was a mistake, but she insisted. Ultimately, the change failed. It taught me the importance of empowering staff to speak up. At Extend Fertility, we collect feedback from customers via surveys. Results are shared with our staff, and together we develop action plans to address negative experiences. It’s the employees who interact with patients on a daily basis who have the best solutions.” -- Ilaina Edison, CEO, Extend Fertility

5. Trust your team.

“I once worked for a woman who joined our team after I had been working there for a while. Every time I stood up, she’d ask me where I was going, whether it was to the bathroom or to the printer. She had a fear of not having control over my time and work. As a young adult, this behavior really demoralized me, especially since I had excelled at the job for years prior. My leadership style is less neurotic. Once my team members have my trust, I’m pretty hands-off.” -- Denise Lee, founder and CEO, Alala

Related: Three Easy Tips For Handling a Bad Boss Professionally

6. Respect others’ time.

“Early in my career, I had a project manager who’d wait until the very last minute to review work, then convey lots of new information and requests. This happened at the end of the day or, worse, after hours, when I was home. It was demoralizing, inefficient and disrespectful. In my career, I’m conscious about reviewing work in a timely and complete way so my team can successfully incorporate my feedback without generating a last-minute crisis -- or lingering resentment.” -- Kirsten R. Murray, principal architect and owner, Olson Kundig 

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