Wisdom//

These Are the Best Things I’ve Learned From the Worst Bosses I’ve Had

Three decades of bosses later and I'm thankful for even the worst of them (11 lessons thankful).

Yanyav/ Shutterstock
Yanyav/ Shutterstock

I’ve had some great, role model bosses. Ones that were in-touch and led from the heart, ones that always delivered results, ones you’d follow into hell. And some that made you feel like you were already there.

But this is about what I’ve learned, not what I lament. From the first boss I had as a paperboy to my last as an executive, I’ve worked for all kinds across many different jobs. Looking back, I now extend thanks, not a middle finger, for these 11 lessons.

1. Nothing’s more transparent than when someone’s not being transparent.

We’re an intuitive species. So it never ceases to amaze me that some managers think they can get away with deception, grandstanding, and hidden agendas (which rarely remain as such). To these hucksters, I say everyone…sees…through…it. And it only takes one transgression from transparency to puncture trust.

2. Micromanagement crushes souls not goals.

I’ve never, ever, seen over-inspection lead to anything but misery. The offending manager believes they’re ensuring excellence but they’re really just showing their insecurity and lack of trust. It’s utterly disheartening to be on the receiving end of inspection. Quick test: raise your hand if you’re energized by being micromanaged? Yeah, I thought so.

3. Culture is a guiding thought–not an afterthought.

Ever had a boss who delivered intensity and results, but for all the busyness in the business, there was no soul? It was all head, no heart? These are the same people who think of culture as what you get to after strategy, failing to see that a great culture is strategy.

I’ve learned you can never care too much about/invest enough in a culture where people feel valued and valuable, worthy and worthwhile.

4. Keeping information close to the vest keeps others from being invested.

One boss I had believed the more information you withheld the greater your power. But she wasn’t exerting control, she was just keeping people from doing their jobs. Not being in the loop means you feel out of it, which is never good (unless you’re on vacation). You can’t expect employees to overinvest when you won’t invest the time it takes to share useful information.

5. Times of adversity call for a shield, not a shiv.

During crisis, upper management often shows up to “help” with constant questions and requests. It’s the boss’s job to shield his people from this chain-of-command barrage. Yes, leverage them for help, but establish what the team will do by when and create space for them to do it.

The boss should also not engage in finger-pointing during times of duress with barbs that feel like being stuck with a shiv. All shiv no shield is painful–been there.

6. If you’re quick to criticize and slow to praise, don’t be surprised if the work needs criticizing and isn’t worth praise.

You know the type. Nothing ever seems good enough. Getting a compliment is a rarity but receiving criticism happens with regularity. Supervisors guilty of this create a self-fulfilling prophecy.

7. Conduct inquiries versus inquisitions.

I’ve given many updates to bosses on things like new product launches, for example. The worst experiences were when he/she had a “you must get by me” or “prove yourself” mentality with their line and tone of questioning. It felt like an inquisition, not a helpful inquiry to better understand and find ways to help. I wished they would have questioned how they asked questions.

8. Take time for your employees, especially when you don’t have it.

Nothing says “My boss doesn’t care about me” more than when you can’t get their time. Employees don’t forget that–I haven’t. I also haven’t forgotten bosses who made time for me when I know they didn’t have it (like during the end of a sales quarter when everyone was time-starved). It’s exactly times like this that the boss is most needed.

9. Feedback isn’t a duty, it’s a differentiator.

Some give feedback well. The worst don’t, or don’t do it at all. When you work for a boss skilled at it, it differentiates them and helps you stand out from the pack, too. It’s a privilege to give feedback. I never forget that.

10. If you want employees to help advance your career, care about theirs.

Employees know if the boss doesn’t genuinely care about helping them grow personally and professionally. Simple.

11. Indecision is insidious.

It has an evil ripple effect. Indecision paralyzes organizations, creates doubt, uncertainty, lack of focus, even resentment. Multiple options (the dreaded “parallel path”) linger, sap energy, and kill a sense of completion. Timelines stretch while costs skyrocket. Perfectionism, insecurity, and fear of a wrong decision are at work making you not want to come to work.

Looking back makes me better moving forward. I hope my pain is your gain.

Originally published on Inc.

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