Tag Archives: management

Leadership is letting your team fail (safely)

“This is a bad post. Let’s delete it.”

My brain wasn’t wrong. It didn’t seem like a great post to me, based on my years of experience with content. But I kept my mouth shut. I let the post stay up. And, unsurprisingly, it failed.

Why did I do this? Because it’s way more convincing to learn from mistakes than from decrees.

Failure is Part of Learning

Think about your adolescence. Did you believe everything adults said, without question? No. You tried things on your own. You had crushing failures and exhilarating successes. You learned what did and didn’t work. You realized the world is relative and that you had to build your own system for navigating it. And hopefully your parents emphasized the right advice and rules: the ones that kept you alive while still allowing you to build your own personal spectrum of successes and failures. Too many rules leave you oppressed; too few leave you dead.

Failure is Part of Innovation

The professional world is no different. There are some hard lines, but not as many as you think; many of the major successes of the last few generations were due to bucking the status quo. It’s hard to argue with an employee that success is following the rules when Zuckerberg didn’t and is now worth 50 billion.

So how does one manage the business equivalent of a rebellious teenager? By letting them fail safely.

Too Much Freedom

I was managing a team of relative newbies, and our new project was content creation. They were fantastic at support, incredibly smart, and very empathetic – but they didn’t have a deep background in engaging content. I wanted to be the “cool boss” without too many rules, so I simply said: “Be creative.”

I told them to “think outside of the box.” I told them “there are no bad ideas.”

They came back with nothing.

Too Little Freedom

So I gave them more structure. I gave them brand guidelines and lots of examples. And they started to deliver! They had a direction to aim for, and so they moved.

Not all of it was good, of course. Some, to my trained eye, simply weren’t going to perform. At first, I said no to that content. But I immediately saw morale drop. They wanted to be creative – hell, that’s what I had asked of them – but I wasn’t letting them take risks. They trusted me, but they weren’t learning anything aside from my opinions. And it’s hard to get excited when you’re not learning.

Just Right

So I started saying yes. But I approved a lot of content I knew wasn’t going to perform. And? Most of the time, it didn’t perform. But the team was still excited and motivated.

Here’s the difference: They had been given the chance to experiment and see the actual result. They were much less likely to choose similar content again, because they knew firsthand what would happen. And they continued to be creative, because I gave them the freedom to.

By the end of my tenure, they were a content creation machine and could spot a high-quality piece of content from a mile away. Only occasionally did I have to weigh in, and often I was wrong!


As managers, it’s tempting to enforce rules and try to control people. We want a result, and the only way we know how to get it is by being in control. But this neither creates engaged employees nor scales.

Good managers give their team enough rules to avoid disaster and enough room to try, fail, and learn.

Support team retention? The MOST important thing.

ladder to the sky“So many support teams see members come and go. It’s the stepping stone for ‘more respectable’ jobs. This can be okay in certain organizations, but most of the time it simply results in lower quality of support for the customer. High turnover means training, re-training, and undocumented processes … your customers suffer, and usually the bottom line does as well. Keeping support members who are good at the job is vital.”

(From Chris Bowler‘s blog)

Couldn’t have said it better myself.

I’m encountering this a lot while hiring at ZOZI. This is the first company I’ve worked at that is very attractive to the general public (UserVoice was more “startup cool”) and lots of folks have literally told me “I’ve been waiting for a job, any job to open at your company” while I looked on at their marketing-heavy resumes. Some of them are promising (and hey, one of my existing, awesome team members came to us that way) but most of them are the types whose first question is about the career progression track is at the company. In short, they want to know how long until they can go work in Marketing.

I’ve always been focused on keeping my staff happy but this is a great reminder that it’s not just important, but essential.

(Via Andrew Spittle)


Photo courtesy of Prescott Pym.

Fall in love with the journey, not the destination

illustrationThis article rings so true. Falling in love with the journey is the right way to reach success.

“If you look at the people who are consistently achieving their goals, you start to realize that it’s not the events or the results that make them different. It’s their commitment to the process. They fall in love with the daily practice, not the individual event.”

I’m good at half of this. I like inventing things and making them work and figuring out how to optimize them.

Where I fall down is the follow-through. I’m stoked about inventing something but once it’s reasonably established I’m not as interested in following through with the minutia that makes it a long-term success.

I attribute this to two things:

1) Weakness of character. Honestly, I just need to get better at following through.

2) Delegation. Previously I had very few resources in terms of delegation, so any detail-oriented follow-through fell on me. I’m happy to do anything, but trying to balance company-wide strategy and editing HTML emails is hard.

I need to fall in love with making the minutia happen. I hope with a fresh attitude and a passionate team I can do this.