It turns out that if you’re okay at being responsible for people and things, you eventually get made responsible for more people and things.

The real ramifications of that morequalifier are that are that you might very well end up with less time to engage in the activities that contributed towards your success in the first place.

I know its trite, but there might actually be a grain of truth in the old Peter Principle. If you keep getting promoted until you are in a position where you can no longer reliably engage in the activities that led to your success in the first place, its probably going to manifest as incompetence.

I’m sure you can guess why I’m mentioning this…

Alone I Break

Historically, I’m used to being able to absorb a information from multiple sources and retain it. I have something of a reputation for remembering a wide variety of things in a work context, and even outside work my head is filled with far more useless information than I really care to think about (there’s a lot of Warhammer lore in there for example, praise Sigmar).

The problem is, as I get involved in more things, I’m finding it more and more difficult to keep up with everything all at once.

Perhaps I’m getting old, and my brain is not as good as it used to be (very possible), but I think I’m just running up against the real limitations of my memory for the first time. Prior to this, I could always just focus down on one or two things at most, even though there was a lot of technical complexity in play.

The degradation was gradual.

The first thing to go was my ability to understand all the technical details about what was going on in all of the teams I was working with. That was a hard one to let go of, but at the end of the day I could still provide useful guidance and direction (where necessary) by lifting my focus and thinking about concepts at a higher level, ignoring the intricacies of implementation. Realistically, without the constantly tested and tuned technical skills acquired from actually implementing things, I wasn’t really in a position to help anyway, so its for the best.

The second thing that started to go though was the one-on-one interactions, and I can’t let that fly. I’ve been in situations before where I wasn’t getting clear and regular feedback from the people who were responsible for me, and I did not want to do the same thing to those I was responsible for. Being unable to stay on top of that really reinforced that I had to start doing something that I am utterly terrible at.


All In The Family

Its not that I’m not okay with delegating, I’m just bad at it.

There are elements of ego there (i.e. the classic “If I don’t do it, it won’t be done right!”), but I also just plain don’t like having to dump work on people. It doesn’t feel right.

But the reality is that I won’t always be around, and I can’t always pay the amount of attention to everything that I would like to, so I might as well start getting people to do things and make sure that I can provide the necessary guidance to help them along the path that I believe leads to good results.

The positive side of this is that it gives plenty of new opportunities for people to step up into leadership roles, and I get to be in the perfect position to mentor those people in the way that I believe that things should be done. Obviously this represents a significant risk to the business, if they don’t want things to continue to be done in the way that I do them, but they gave up the ability to prevent that when they put me into a leadership position.

With additional leaders in place, each being responsible for their own small groups of people, my role mutates into one of providing direction and guidance (and maybe some oversight), which is a bit of a change for someone that is used to being involved in things at a relatively low level.

And letting go is hard.

Got The Life

I’ve written before about how I’m pretty consistently terrified about micromanaging the people I’m responsible for and destroying their will to live, but I think now that being aware of that and being appropriately terrified probably prevents me from falling too far into that hole. That doesn’t mean I don’t step into the hole from time to time, but I seem to have avoided falling face first so far.

Being cognitively aware of things is often a good way to counter those things after all. Its hard to be insane when you realise that you’re insane.

So letting go is actually in my best interest, even if the end result of a situation is not necessarily what I originally envisioned. At the end of the day, if the objectives were accomplished in a sustainable fashion, it probably doesn’t really matter anyway. I’m still free to provide guidance, and if the teams involved take it as that (guidance), rather than as unbreakable commands, then I’m probably okay.

A healthy lack of involvement can also break negative patterns of reliance as well, making teams more autonomous. Within reason of course, as a lack of direction (and measurable outcomes) can be incredibly and rightly frustrating.

Its a delicate balancing act.

Be involved just enough to foster independent though and problem-solving, but no more than that so as to avoid creating stifling presence.


This is another one of those wishy-washy touchy-feely posts where I rant about things that I don’t really understand.

I’m trying though, and the more I think (and write) about the situation the better I can reason about it all.

The real kicker here is the realization that I can’t do everything all at once, especially as my area of responsibility widens.

The situation does offer new and interesting opportunities though, and helping people to grow is definitely one of the better ones.


You might think that a quote from the cult classic Scarface is a poor way to start a blog post about leadership. I mean, Tony Montana isn’t exactly a beacon of good management. You probably shouldn’t look up to him in any way, shape or form.

But its a good quote all the same, because really, if you’re in a leadership position, one of the things that you should value the most is your word.

If you can’t keep it, than you should have kept your mouth shut in the first place.

Honesty Is Actually The Best Policy

I’m a firm believer in being honest and straightforward when communicating with anyone. It doesn’t matter if they are a general colleague, someone who you are directly responsible for or even your own boss, you should tell it like it is. Of course, nothing puts an honesty policy to the test like making a huge mistake, so when I look back, it seems to me like I’m pretty consistent about that sort of thing.

There are a bunch of benefits to being consistently straightforward and honest, but one of the most valuable is that its a natural trust builder. Of course, that doesn’t mean that people will necessarily like what you have to say, but that’s another thing entirely.

Regardless, if people know that you are transparent, regardless of the situation, then they know what to expect and don’t have to worry about spending cognitive resources deciphering what you really meant. That means more mental power dedicated to actually getting things done, which can only be a good thing.

Expecto Patronum

Interestingly enough, setting the correct expectations can actually be quite difficult, even if you’re being straightforward and honest.

The best possible situation is when you are able to supply full, unadulterated information, clear in purpose and unambiguous. In this case, there is little to no room for assumptions, and if the other party misinterpreted the information given, it is much easier to clear things up, as the misinterpretation is usually pretty obvious. That doesn’t mean its easy to clear up misconceptions, just easier. People are complicated animals after all.

Other situations are more challenging.

For example, if there is a situation and you are unable to provide all of the information to the appropriate parties (maybe you don’t know, maybe its sensitive), then its entirely possible and likely that the people involved will fill in the blanks with their own assumptions. In this case there is little you can do other than be as clear as possible that this part of the picture is fuzzy and unclear, and to ensure that as soon as you know more, they know more. The quicker you learn and disseminate information, the better. It leaves less time for assumptions to fester.

The last case is quite possibly the most painful.

Sometimes you set expectations, that through no fault of your own, end up being wrong.

Expect The Unexpected

To be clear, if you can do anything at all to prevent incorrect expectations being set, you should do it. Expectations that are incorrectly set and then not met are easily one of the most damaging things to the professional happiness of a person, and can result in all sorts of other negative side effects like loss of trust (which is horrible), loss of motivation and a growing desire to be somewhere else.

A growing desire to be somewhere else is a dangerous thing. In comparison, it is normal and healthy for your people to keep themselves well informed about the job market and opportunities available to them, and you should do what you can to encourage that behaviour. Remember, you serve the overlapping interests of your people and your organization, but if push comes to shove, your people come first. This doesn’t mean that you are encouraging people to leave; quite the contrary, you want them to stay because they want to stay, not because they can’t go anywhere else.

If the worst happens and the wrong expectations have been set for some reason, then you should do everything in your power to ensure that those expectations are met.

I mean, obviously if the expectations are ridiculous then you’ve clearly screwed up, and you need to have a much longer, harder look at your own behaviour as a leader. There will be damage in this case, and you will have to do your best to mitigate it.

If the expectations are reasonable though, and your actions lead to them being set (miscommunication, poorly worded statements, communicating information that you believed to be true but wasn’t), then you should move heaven and earth to follow through and hold true to your word.

Even if it costs you personally.

Consider it the price paid for a valuable lesson learned.


At the end of the day, as a leader, you need to be acutely aware of the impact that you can have as a result of words that come out of your mouth.

Do not underestimate the damage that you can cause as a result of incorrectly set expectations not being met.

Its trite, but with great power comes great responsibility.

“Great power” is probably overselling it though, but the phrase “with mediocre power comes great responsibility” just doesn’t have the same ring to it.


Its been about two months since I first posted about Dungeons and Dragons, which seems like a sane amount of time to wait before writing a followup. A lot can change in two months after all.

And change it has! As is unfortunately sometimes the case, we had to do some pretty classic organizational restructuring and as a result, our old DM has gone the way of Gary Gygax.

To be clear, he’s not dead, but he's definitely no longer with us. His absence is keenly felt, both from a D&D point of view and from an organizational point of view. Also it makes me sad.

Its not all doom and gloom though.

His departure provided a natural opportunity to refresh and revisit our D&D group and paved the way for a second “season” of D&D campaigns.

Where once there was a mere eight players in a single group, now we are legion. Surely it is only a matter of time before the entire company pivots and we flip to some sort of D&D related business.

And I for one welcome our new draconic overlords.

The Phoenix Returns To Life In 1d6 Days

While the dissolution of the first group was a sad day indeed, our attempts to reform were immediately met with a fresh wave of interest from a wide variety of people.

I like to think that its all because of the masterfully crafted email that I sent out looking for fresh blood, but its probably more likely that the buzz generated from the ridiculousness of the first groups campaign provided for solid word of mouth advertising.

It wasn’t long before I had a list of about twenty people who wanted to see what all the fuss was about. The best part was that the people were from all across the business, and ranged from other members of our development team, to our support department, all the way through to marketing.

Having discovered in the first season that seven players and one DM is somewhat challenging to run (similar to how large teams get less effective), the goal was to try and limit each group to five players. Using the power of maths, that meant we would have four groups.

Of course, with the departure of our sole DM, we’d need to find a new one. Actually, we’d need to find four new ones, as running even a single group can be time consuming at the best of times, let alone four completely different groups.

Taking into account everyone’s availability, the desire for each group to have a mixture of newbies and experienced people and the fact that the volunteer DM’s would also like to be able to play was somewhat….challenging. My logistical skills are pretty good these days though, so once I’d exited the fugue state brought on by all of the constraints, we were left with four groups organized over Monday, Tuesday, Wednesday and Thursday evenings and everybody reasonably happy.

Also, I was a DM, because I’m a sucker like that.

Behind The Curtain

Having only played D&D once before, peeking behind the curtain was both enlightening and not really all that surprising.

To make things easy, the fresh DM’s all picked solely from the pre-built adventures supplied by Wizards of the Coast. Its a lot simpler to get a handle on the responsibilities of being a DM when you are provided with some guidelines and ideas that are easy to extend (or not) as you wish, without requiring you to think of absolutely everything.

I picked Hoard of the Dragon Queen, which is a pretty big campaign that is actually the first half of a massive two-part adventure (the other half being Rise of Tiamat). Using our very first group as a high water mark, I’m not sure we’ll ever finish it, but that probably doesn’t matter as long as we have fun while we try.

For me, already being in a leadership role, the transition to being a DM is probably only about half as hard as it is for someone who has never had the experience of organising and guiding a group of people. Of course, that leaves the other half of the difficulty fully intact, so its not all easy riding.

To compare:

  • As a player, you really only have to know the details about your own character and the basic gameplay tenets, and even those are not super important if you have a solid DM to guide you.
  • As the DM, you need to know everything. Literally everything, top to bottom, all the rules and constraints, how the game flows in the abstract and how your campaign needs to progress. You also need to be good at improvising, as you can plan for a huge variety of things, but once it gets into the hands of your players, all of that might go out the window.

Finally, the last (and possible most critical part) is knowing when to step in and when to let things go. You have to be careful to not spoil anyone’s fun (within reason) and to enable those cool D&D moments to happen as organically as possible, but you also need to maximise the amount of fun happening across the entire group.

Like I said in my first post, its a fine line to walk.

Epic With A Capital E

Interestingly enough, with multiple groups running at the same time, we might eventually be able to do some sort of epic crossover. Imagine a campaign where one or more different groups are working together to accomplish a greater goal, or even better, maybe the groups are working against each other, possibly without even realising it.

You could probably retrofit multiple groups acting together into one of the pre-built campaigns, but to be honest, you’d be better off putting a custom one together that was built with the concept in mind from the start.

Its a neat dream, but as we have people who are both players and DM’s, we would have to be pretty careful as anyone filling both roles would know too much.

I think I’d be more than willing to give up the ability to play to put something like that together though, as it would be an amazing experience for everyone involved.

Cure Wounds, Gain 1d8 Hit Points

Last but not least, one of the completely unintended side effects of running D&D groups at work is employee retention.

This comes in two flavours.

The first is the simple presence of social activities that help to bind people together around more than just work. For us, D&D is just another addition to an already healthy space, but being focused on much smaller groups it results in slightly different benefits (tighter bonds, closer friendships, etc).

The second is the continuity of the campaign itself. D&D groups are essentially engaged in collaborative storytelling, weaving an epic, personalised tale together over time. Its hard to pull away from that on a whim, so it tends to increase the barrier to leaving for non-critical reasons.

I say non-critical, because if your workplace is bad enough, no amount of social activities will keep the good people around.

Having said all of that, I would never prevent a former employee from continuing to participate in D&D. As long as they can regularly make the sessions, they are always welcome in any campaign that they were already a member of. Obviously current employees get preference when it comes to putting together new groups, but there is no reason to be a jerk about it just because someone has moved on.


We started this whole thing because there were a few of us that just wanted to play D&D, and having a bunch of people who were already together on a day to day basis made it a lot easier to organise. Its pretty hard to get a group of adults with various adult responsibilities together on a regular basis after all.

The result of that initial, relatively selfish desire has been a wealth of social activity that is effectively linking a bunch of different business units together, and is helping to smooth out some of the natural stress inherent in working in a challenging environment.

All in all, I think its been a worthwhile usage of my (and other peoples) time and I highly recommend it.