How Not To Lead, Part One: How Not to Delegate

Since high school, I’ve found myself taking on volunteer leadership positions in pretty much everything I’ve been involved in. I thought I’d share some of my thoughts on leadership from those experiences from time to time. While I’m calling this post “Part One”, I don’t have future parts planned yet, so it’s a bit of an ambitious title.

Volunteer leadership, like many things in life, tends to be a bit of a convex problem: There’s a sweet spot in the middle, and there are a lot of different failure modes around the edges. Organizations vary in terms of where exactly that sweet spot is, so I don’t want to focus on that side of the problem. Instead, in this series, I’ll focus on the failure modes, how not to lead. Being aware of what the edges are will help you stay near the sweet spot as a leader.

(By contrast, for instance, some organizations seem to find a lot of value in the edges, by approaching problems in an unusual fashion to generate something new. Some of them can even ride roughshod over the failure modes that I mention because it’s more compelling to live on that edge. If there’s a large amount of competition and/or novelty in your field, this might be the case.)

This lesson in particular has to do with the failure modes around delegation, allowing or assigning other people to do tasks.

Failure Mode #1: Not Delegating

The first failure mode, of course, is to completely fail to delegate. This can happen for a couple reasons.

Maybe you believe that no one else can do the job you’re doing. I’ve fallen into this trap a lot. In high school, I thought I was the only person who could run the math club, and basically wrested control of the club over from the teachers and parents in my sophomore year. I put a ton of effort into the club personally, but I wasn’t a particularly effective teacher and we shrank considerably.

The next year, I co-founded the Colorado Math Circle with a parent from Boulder who has continued to run the group to this day. This experience went much better for a lot of reasons, one of which was the multiple minds we had to plan things on top.

I should have asked myself: If you believe you’re the only one suited for the job, do you really know where your audience is at? How are you going to bring in perspectives and skills that you don’t have? Where are you going to turn if things don’t go according to plan?

Maybe instead you think it’s just too much work to find other people to help. This was my mindset when I took over leadership of the Veritas Forum at MIT in my second year of grad school. I centralized responsibility by effectively taking on 6 different leadership roles within the team that year. Naturally, the forum was basically all I did for the month before it happened.

Beyond my own time, there were also very few volunteers able to come back the next year, so we had to do a lot of recruiting, and that’ll be true next year as well, especially as I step down. It wasn’t a good long-term strategy.

Now, I’d ask: Do you feel frustrated with others not stepping up? How hard have you really tried to recruit? Are you trying to passive-aggressively make a statement by doing all of the work yourself?

Failure Mode #2: Suspicion Spirals

So you’ve realized that you need to delegate, and you’ve found some people to help you out. Great!

Unfortunately, there will be a lot of spillover of your emotions from the previous section. If it was hard to find people to help, you might be especially on edge if it seems like they’re flaking on you.

How you respond will dictate a lot of how the team functions. Machiavelli wrote that it is better to be feared than loved, but when it comes to volunteer leadership today, nothing could be farther from the truth. Introducing fear leads people too often to shut down and back away even more. If you make doing their job uncomfortable, it’ll naturally make it hard for them to get themselves to do it.

What’s most unfortunate is that this can sometimes introduce a positive feedback loop that can escalate the smallest tardiness into someone completely dropping the ball. Even the suspicion that they might fail can make you feel anxious if someone hasn’t responded to your e-mail a couple hours after you send it.

Talking to a friend recently, I gave this example as a reason that being optimistic is simply healthier. If you’re constantly suspicious that someone you’re working with will do something bad, whether they could fail to do their job or steal your work or glory, you’ll make life miserable for those you work with, and your suspicions could very well turn into self-fulfilling prophecies.

Failure Mode #3: Looking for Someone to Blame

Even without those compounding effects, something will inevitably go wrong, or at least not as you had planned. Those will provide another test to see how you respond.

My default is often to assume that the plan was good, but someone didn’t do their job, and we need to try to find that goat to blame. In other words, I become like Darth Vader:

Notice the reaction of the commander taking Admiral Ozzel’s place in the first clip, and feel the gravity of the admiral taking responsibility in the second. It’s no doubt why the Empire keeps making mistakes. (Where do these admirals come from, anyways? Why are they so willing to rise up the ranks, if they know what happens at the top?)

Anyways, I think I picked up some of this tendency to blame from watching sports. Take the fateful interception at the end of the last Super Bowl, by Malcolm Butler in the endzone. The conversation afterwards was dominated by whose fault that play was. Was it Seahawks coach Pete Carroll’s decision-making to go for a pass play rather than a running play with running back Marshawn Lynch? Quarterback Russell Wilson for the throw? Receiver Ricardo Lockette for letting Butler beat him to the spot?

Professional athletes are mostly already numb to the constant criticism — they’re celebrities, and they need to learn how to deal with it at some point in their careers. But when we take the blame-first approach to personal relationships, it can backfire badly.

One unexpected area where this often arises: playing cooperative games. In particular, I’ve seen this time and time again in the card game Hanabi.

Hanabi is a clever game that has become quite popular among many of my friends in the last couple years. Each player holds a hand of cards facing away from themselves, so everyone else can see it but themselves. The players take turns playing, discarding cards, or giving each other hints about their cards within specific parameters. The goal is to collectively play cards in a specific order before the deck runs out; everyone scores together as a team.

With these limits on communication, it becomes a game all about reading subtle signals that we give each other, and thinking ahead to what’s going to happen in the turns following yours. Most experienced players establish conventions to handle these things so everyone knows what to expect, which introduces more ways to know you’ve messed up. (Hence why I don’t like to establish those conventions for most players’ first game.)

When something almost inevitably goes wrong, it often leads to a blame game afterwards. “You should have warned me about that 5 before I discarded it!” or “Why didn’t you play that card that I had told you about?” dominate the debriefing. We get in the mindset of comparing each other with an ideal level of play and keeping track of the mistakes each person makes. We might say we’re trying to improve, but in the end, we often just get angrier at each other than if we had been playing a backstabbing competitive game, ironically.

I’ve come to realize that it’s rarely healthy to try to assign blame to individuals like that, even more so when blame is not nearly as clear cut as it is in Hanabi.

First, it’s almost never just one person’s fault. This obviously applies to communication problems: If they didn’t do what you wanted, you probably could have communicated better. If you didn’t do what they wanted, you probably could have asked for clarification. Whatever the mistake, step outside of your own rage and think about what you could have done differently to reduce the likelihood of failure, even if it seems to you like their fault.

Second, it leads us to ignore environmental factors at play. In Hanabi, sometimes bad shuffle luck can make the game go poorly without any one person being at fault, and we can forget that in processing what went wrong after the game. The Fundamental Attribution Error is the mistake of assigning personal reasons for others’ behavior when we assign environmental blame for our own. Find and acknowledge the environmental reasons as factors at play whenever mistakes are made.

Third, it’s quite problematic to be wrong about who to blame. If someone is unjustly accused, they can take it personally, and possibly see it as a part of some larger bias that you have. Moreover, they might be right; bias easily plays a role if you’re firing out blame at will. Even if you take the blame yourself more than called for, that can also seem and be a bit passive aggressive. (“No one else steps up and takes responsibility around here, so I guess I have to do it,” you implicitly say, hoping people notice.)

Finally, it’s very hard to know what to do with individual blame. Should they just feel ashamed for what they did? It can feel satisfying to say that this mistake was entirely someone else’s fault, but the problem solving doesn’t end there. Even if they truly are responsible, there’s probably something they need to change to prevent it from happening again, and in social leadership, you can potentially help them find that, but only if you don’t tear them down for the mistake in the first place.

I hope this post is helpful as you learn to lead by delegating and avoid some of the pitfalls around it! Remember, delegation is important, negative suspicions can escalate, and you really don’t want to turn into Darth Vader.

2 responses to “How Not To Lead, Part One: How Not to Delegate

  1. Likai Liu June 18, 2015 at 4:45 am

    Thanks for sharing your thoughts about leadership. It inspired me to write an essay about leadership, but from a different perspective.


  2. Pingback: If You Want to Speak Last, Speak Best | The Christian Rationalist

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