Why Messing Up Might Make you a Better Manager

I’ve been managing people for about 2 years at Distilled, and prior to that, I managed people in the various professions I dabbled in prior to finding myself in SEO.  All in all I think I have something approaching 10 years management experience.

As you might expect my approach to management has changed quite a bit over the years. Similarly my thinking on what makes a ‘good’ manager has also changed.

With this mind, I wanted to share something with you…

It was Steve and Tim‘s very first day at Distilled. They’d be reporting in to me. They’d been through the usual initial induction stuff and were busily trying to install and set up the various tools and apps we use, in addition to battling with Windows 8.


They started at Distilled on Monday 4th March. On the Thursday of that week  (7th) I was due to be flying out to speak at a conference in Italy and wouldn’t be returning to the office until Tuesday (12th). The following Friday (15th) I was down to speak at Distilled’s own conference, LinkLove.

I needed to prep 3 decks (I was speaking twice in Italy), practice said decks, and of course make sure both Steve and Tim were settling in ok, had work to do etc. I also needed to make sure Phil who also reports to me was ok with his client work, not to mention delivering work for my own clients too.

In an attempt to kill several birds with one stone I decided to do a run through of my LinkLove deck in front of our new recruits, plus colleagues Phil and Bridget who kindly offered to sit in and offer feedback.

I’d tried to manage everyone’s expectations ahead of time by highlighting that it was likely to be a pretty shaky run through; however that was kind of the point. In my experience the earlier you present your deck to others, the earlier you get the lowdown on what’s good, bad and just plain ugly – you can then make a bunch of changes and you end up with a much stronger deck as a result.

Sadly the run through which followed could only be described as an unmitigated disaster.

Seriously. It was horrible.

I’d prepared 150 slides for a 30 minute speaking slot which I somehow whizzed through at break-neck speed in less than 15 minutes. Part way through I kind of lost track of one of the points I was trying to make and said something like:

I’m definitely trying to make some sort of point here but I’ve no idea what it is. Screw it, I’m just going to move on.

Virtually nothing about the deck or my performance worked. My introduction was weak. There was no story arc – it was a weirdly ordered unrelenting list of tips. I made jokes which weren’t funny. I failed to engage with the audience. Or my material. There was no conclusion.

Did I mention it was horrible? Oh yes, I did… But it bears repeating – it was HORRIBLE.

So what’s the point? Where’s the punchline?

Sure, totally screwing up a presentation run through in front of new recruits on their first day isn’t perhaps the worst thing that’s ever happened. But I’ve yet to read the ’7 habits of highly effective managers’ post which touts:

Inspire your team by messing something up really badly. Bonus points for making them feel very awkward by asking them to try and constructively critique where you went wrong.

Now I still don’t feel great about what happened.

However rewind 5 years ago I would have beaten myself up about this for months. Back then I had very strong views on what constituted ‘good’ and ‘bad’ managers. ‘Good’ managers certainly didn’t show themselves up like I’d just done. They were inspiring, strong, and together. There’s just no way a ‘good’ manager would have let that happen. A ‘good’ manager would have been better prepared, would have practiced more, would have delivered a *killer* presentation even when they were only supposed to be doing a run through.

That’s all true, however, there are some good things which have come out of this.

Both Steve and Tim have seen first hand that it’s ok to mess things up.

They will also have seen that Distilled is a ‘safe’ environment where you can be vulnerable (and trust me – all the time I was busily messing up the delivery of that deck I felt very vulnerable) and rather than being ridiculed, you’ll get constructive feedback and encouragement to improve.

Finally, I hope that they’ll have seen that sometimes you need to totally mess something up in order to figure out how to make something better.

I think if I’d have been better prepped for that run through I might just have convinced myself and my peers that the deck I’d worked on was pretty much there. I think it would have been a worse deck as a result.

Perhaps messing up might actually make you a better manager.

If (like me) you don’t want your direct reports to fear failure, you can tell them so. But perhaps it’s better to show them. Show them that just because you messed something up (in a right royal fashion I might add) doesn’t mean it’s the end of the world or that there’s nothing salvageable.

It means you’re actively exhibiting the behaviours you’d like to engender in those who report into you. I think that’s pretty powerful.

Over to you dear reader – does messing up make you a better manager?

Or am I busily trying to justify myself post the event?

Image credit – Keep Calm & Carry On

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