Delegating Complex Tasks

I need halp.

Many leaders struggle with complex delegation.

Failure to delegate often makes you a bottleneck. There are few things more demoralizing for a team than spending days trying to get a leader to do something that takes them minutes,

Failure to delegate also creates key person risk, leaving you as the only person with critical knowledge, and, as a result, the only person to call when that knowledge is needed. Getting repeatedly paged at 3am because you didn’t delegate is a literal wakeup call.

Most leaders can delegate simple things - e.g. teams, metrics - pretty well. Most leaders struggle with delegating complex skills or responsibilities.

Herein we’ll discuss two proven methods for delegating complex tasks that you can use right away.

Exponential training

The types of problems that are especially prone to growing key person risk tend to have the following traits:

• The problem requires deep knowledge

• That deep knowledge can only be gained through lots of at-bats

• There aren’t a lot of at-bats available

A great example here is the plight of The Database Guy. The Database Guy at your company is often someone who was there early and had to wrangle all the database issues. Then they realize that to scale they need to get other people to understand the databases too. Often this realization comes when the failure to delegate means they’re getting paged constantly.

So The Database Guy does a training on indexes and sharding and networking and query optimization and throttling operations and restarting tiers of hardware and how to get ahold of someone at your third party provider who can fix your problem. They then nod contentedly and figure they’ll get some much earned sleep. That night the Database Guy gets paged again.

The problem is that you don’t learn deep skills by watching a PowerPoint. You learn them by doing. But complex, high-risk problems (like database failures) don’t happen often enough for passive learning to work.

The way to solve this is via Exponential Training. Exponential Training works like this:

• Train one person deeply. Instead of running a big seminar, work one-on-one with a single person for a quarter.

• Give them real at-bats. Have them handle database issues for all teams, not just their own. Make them the primary responder.

• Use historical incidents as practice. E.g. set up real-world drills in a dev environment.

• Repeat. Each trained person teaches someone new the next quarter. After a year, you have a whole bench of experts.

When done right, it only takes 12-24 months to get a sizable set of people really knowledgeable on a deep skill.

Most people do not do this because:

• It’s perceived as slow. This is a classic rabbit and hare issue.

• Leaders don’t know how to get people the at-bats. Often a leader has access to much more data or opportunities than other people and this encumbers other’s ability to get experience. The answer is to give people more access.

Especially if you have deep key person risk at your company, consider exponential training as a slow-to-start, fast-to-finish process for actually solving your problem.

Suboptimal Standardization

Suboptimal Standardization is the idea that you should be quick to delegate complex problems as long as they have checkpoints for quality control.

The problems that require Suboptimal Standardization have similar conditions as ones that require Exponential Training - low opportunities for hands-on training and deep knowledge required. The difference is that Suboptimal Standardization problems can have quality control checkpoints.

Two good examples here are making offers to candidates and budgeting processes. Leaders often own these processes beyond the point at which they have become a bottleneck. Leaders delay delegating them because:

• They think it’s too complex to delegate. One of the biggest hurdles to delegating a responsibility is that some leaders don’t know or want to admit that their decisions actually aren’t that complicated. Decisions are almost never that complicated and failure to articulate how decisions are made should speak more to the weakness of a leader than further the mystique of their ability.

• They claim it’s important to be able to optimize. In reality, the benefits of delegating almost always far outweigh any optimization you’ll ever do. This is especially true once you’ve become a bottleneck - when you don’t have the time to do any real optimization anymore.

Let’s explore the example of making offers to candidates.

When you decide how to make an offer to a candidate, you have to consider interview performance, market changes, equity, bonuses, competing offers and more. There are many things to consider, but there aren’t that many things. The complexity is enough though that many leaders decide to treat it more like an art than a process.

When I was at a company at the size where department heads created all offers, I personally held onto making offers for a long time because it seemed impossible to get others to consider all of the factors involved. I needed to get it right, so I held onto it.

Eventually I became a bottleneck and it caused problems. Once that pressure forced me to reconsider, I realized two things:

• What I was doing was actually not that complicated.

• I was prioritizing little micro-optimizations vs speed of execution and federated ownership

So I challenged myself to really write out what it was I was doing, and I made a system that looked like:

• Step 1: If interview performance is X for role Y, the offer is Z.

• Step 2: If they negotiate, here are the standard counter-offers.

• Step 3: If there’s an exception, escalate to me.

Everything got better once I delegated making offers. This is because:

• Giving my team the ability to run this process gave them the ability to think about the rules and optimize them.

• Candidates got fairer, more predictable outcomes.

• Recruiters could avoid mis-representing compensation ranges due to clearer expectations.

When you find yourself as a bottleneck on a complex decision, create a Suboptimal Standardization. To do this:

• Force yourself to write down a decision tree of how you actually make decisions

• If the factors you consider include information your team doesn’t have access to, give them that information. Similar to Exponential Training, this is often a major blocker to delegation and you need to rip the bandaid.

• Set up an approval process. When you make approvals, tweak the process as you notice things you hadn’t coached people on.

If you do it right, Suboptimal Standardization quickly becomes more optimal standardization.

An Afterthought

It was only through writing this post that I realized how often access to information is a throughline in delegation failure. Per the examples above and more, this often happens because:

• Giving people access to messy information can be stressful or risky. For example, giving people access to all recruiting offers being made across all teams (beyond their own), creates risk. In many cases it’s a form of showing your work that leaders prefer not to be judged by, or exposing harsh realities you’re afraid of making people aware of (like some teams getting paid more than others).

• Leaders can have egos around information access.

If you’re bottleneck at anything as a leader, challenge yourself to consider if information asymmetry is a problem you’re creating. Amongst the other benefits, I’ve found that trusting my team with sensitive information has often deepened trust (in both directions), grown leader maturity, and increased fairness faster than almost any other thing I’ve done.

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