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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15 Responses to “Why Messing Up Might Make you a Better Manager”

  1. Iain Bartholomew says:

    In my inexpert opinion I wonder whether it perhaps isn’t so much the messing up that makes you a better manager as having the self-awareness that comes from knowing you have messed up, will mess up again and don’t have a monopoly on wisdom or talent?

  2. Luella Ben Aziza says:

    Clearly it’s not the messing up that makes you a good boss – it’s your approach to dealing with it. Shit happens, but if you know how to turn it around, you can repair any perception damage easy.

    Empathy and transparency are also, IMHO really important things to have in an effective team. They make you free to fail at some things, which is important, because usually the biggest successes happen AFTER you’ve learnt from trying & failing at something related.

    “If you’re not embarrassed at who you were or something you did last year, you’re not learning fast enough”

  3. Hannah Smith says:

    @Iain – excellent point; if you have no self-awareness ( kinda like David Brent) you’ll likely mess up continually and yet remain a pretty poor manager.

    @Luella – Agreed. Also, I love that quote :)

  4. Nah. Only weak people screw up. I’ve never screwed up.


    We all know that’s not true. I vividly remember the look on Lynsey and Hannah (L)’s faces when I did the first run through of my ignite-style deck with auto-advancing slides.

    I also totally know that cringe-worthy feeling you get in your stomach as you’re halfway through a screw-up like this. “Do I stop now? Carry on? Aaaaaaaaaaaagh”.

  5. Alan Bleiweiss says:

    Great post. And absolutely true!

    The whole “don’t let them see you sweat” notion, and the “never show weakness” philosophy may work for some people. I just don’t live in the “killer mentality” arena. So yes, allowing others to see us when we are vulnerable, and observe how we handle it is critical for our own growth and it allows them the opportunity to then learn valuable lessons from that observation.

    At the end of the day we can’t dictate how they process it, so it won’t ALWAYS result in that outcome. Yet that’s okay as well because it’s not for us to live their lives, only to be true to our lives.

    And of course, it helps us remember that those WE observe are okay, and not “terrible”, and that they’re “only human” as well.

  6. I like this. A lot. Your transparency helps us learn from your experience… and your humility (and willingness not to beat herself up) helps your team learn from you.

    This is a great, approachable piece about an aspect of management worth remembering: you don’t have to be perfect. But you do have to be vulnerable and real. And when you are, your team will learn to not fear failure.

    Nice work, Hannah.

  7. fifty6 is only 3 people, and it’s been my only management experience. As such, I kind of didn’t have much of a choice than to mess up pretty regularly in front of them. Just by not wanting a nervous breakdown, I’ve also had no choice but to be OK with messing up in front of them. It seems to work, and I’m glad you’ve put into words why that might be the case :)


  8. Hannah Smith says:

    @Will – Completely! I *really* wanted to just stop. And possibly go home and hide under the duvet :)

    @Alan – I’m likewise clearly totally ill-suited to the ‘killer mentality’ arena; I’m very thankful to be in a workplace where that’s not something that’s celebrated.

    @Jonathon – Thanks so much for your comment! Funnily enough this post was very nearly titled ‘Why allowing yourself to be vulnerable might make you a better manager’ :)

    @Jason – Being OK with messing up is the toughest part – or was for me at least! Thanks for your comment :)

  9. Rick Noel says:

    Great post Will. I think messing reminds others that we are human which helps great managers connect on a personal level.

    Another message you sent is that preparation is important and necessary to shine as a presenter.

    Your dry run in front of new recruits fosters a culture where input is valued at all levels.

  10. Hannah Smith says:

    Thanks Rick!

    My name is Hannah though :)
    Or was that a response to Will’s comment? Colour me confused.

  11. Alessio says:

    thanks for sharing this.
    I’m managing people since 2 years, and I did screw up few times, and maybe I will even tomorrow. But what I think my team appreciate is that I’m totally transparent and honest and I’m able to say: you know what? I did a big mess, and I’m sorry. Help me out!

    A good leader is able to inspire people even with something NOT strictly work – related. And show them you are human at the end is helping a lot.

    I remember first time I saw you in Italy at BeWizard. You had a problem with the mic, and you were a bit angry and sad. That for me was a good lesson: you’re not perfect, you care, and things sometimes are complicated even for people who I admire a lot.

    So you see, you were a great leader for me in that moment.

    There are TONS of way you can inspire someone else, but the first step is always being yourself and being humble.

    thanks again for sharing!

  12. Hannah Smith says:

    Thanks for commenting Alessio – totally agree with you re being yourself and being humble.

    Had forgotten about that mic issue at Be Wizard… Very funny after the event, entirely cringe-worthy at the time :)

  13. [...] an SEO experience, but I think it can be applied to basically any field. Hannah Smith shares Why Messing Up Might Make you a Better Manager and is very open about a managerial screw-up in her own recent past. This post is vulnerable, [...]

  14. Greg says:

    Messing up definitely humanises you and makes you seem more approachable. If you’re a heartless totalitarian monster pouncing on every little mistake, your staff won’t last long.
    But if your staff understand even you make mistakes, they’re much more likely to come to you with problems or mistakes of their own as they know everyone succumbs to them.
    Great Post

  15. [...] Why messing up might make you a better manager [...]

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