Heroism Doesn’t Scale — Some Advice on Effective Delegation

“Heroism doesn’t scale, heroes become martyrs.” — Joshua Reeves, Gusto Co-Founder & CEO.

One of the biggest mistakes I see employees make is taking too much on themselves.

When you’re overwhelmed, so many things go wrong, both for you personally and for your whole company:

• Every project you’re working on is underserved. You end up doing lots of C jobs instead of a couple A jobs.
• You’re stressed out. You can’t enjoy time at work or time out of work.
• Eventually, you burn out. I’ve seen employees, co-workers, and bosses all hit a wall at 100 miles an hour. It’s always painful to watch, and it’s not always recoverable.

Bottom line: when you take on too much, your work suffers, and your life suffers. Don’t be a hero.

This post describes some ways to delegate things you’re working on — up, down, laterally, and out — to enable you to be both more successful and more happy at the same time.

Critical to note: what I mean by “delegation” isn’t just for managers; it applies to individual contributors just as much.

Background: How Did You Get Overloaded in the First Place?

Let’s start by admitting a key point: the things on your list are probably important, or you wouldn’t be stressing about them.

Moreover, they’re on your personal list because either they were assigned to you by someone else and you accepted the work, or because you volunteered to do them for a myriad of reasons (generosity, ambition, guilt, etc.).

The sources of the tasks are really important, and key to understanding the first key to delegating effectively: avoiding the tasks in the first place.

Delegate Out

The first key to delegation is to delegate out, which is to say, avoid doing the work yourself in the first place.

At Endeca, one of the most effective people I worked with was a product manager named Frank (fake name). He was respected from the CEO down, worked on the most strategic projects at the company, and produced amazing results consistently. And he did it all without even coming close to killing himself. Honestly, he really didn’t work very many hours. He made crushing it look easy.

The key? He avoided BS work like the plague. The other product managers used to joke that he was like Teflon because nothing would stick to him. He made avoiding BS work an art form. And both he personally and the company as a whole was better off for it.

Delegating out isn’t always easy. How, you might ask, do you push back on your boss (or whomever the delegator is)?

Start by asking some key questions:

• Does this actually have to get done? A lot of work looks important but won’t actually move the needle. Frank was very gifted at knowing the difference, and key to that is knowing to ask this question. If you ask any reasonable boss, “why?”so that you understand the reason(s) something must be completed, you’ll both better understand and appreciate the context if you end up doing the work. Or, understand enough to gently push back if you don’t understand it or disagree with the logic. I’ve personally experienced situations wherein I’ve given tasks to employees who then have dug into the “why” of a project and made me realize it shouldn’t be done in the first place!
• Is this the most important thing on my plate? If you already have important things on your plate, prioritize them in a list. If the new project is less important than your most important project, be clear that it’s not going to be your top priority or that taking it on will hurt your top priority. Often times managers and friends don’t have a good feel for what else you’re working on, and if you clarify the list for them, they may give the project to someone else, postpone it, or kill it.
• Am I the best person to do this? A lot of employees that suffer from being overwhelmed tend to take things on to look good or do their friends favors. If you’re not the right person to do a project, consider not doing it. Let’s say the new project has to get done AND is more important than your most important project; if you don’t think you can do a killer job on it, you should push back. Simply asking, “why me?” will sometimes lead a manager to realize maybe not you is better.

The benefit to pushing back? You keep your time, energy, and focus on the most important thing you should be working on at all times.

Delegate Up

“Delegating up” is asking for help from your manager or others up the chain of command at your company.

Many people have a really hard time asking for help, admitting that a project is harder than anticipated, and saying that they can’t do something alone. This is real a shame because failing to ask for help when you’re confused, overwhelmed, lost, or struggling with a project is the most surefire way to ensure the project’s (and, by extension your) failure.

Remember: a startup is a team sport; nobody expects you to do everything on your own. Employees that succeed and are promoted are those that collaborate with their superiors.

Why? People who ask for help are more likely to execute a successful project! Also, for me asking for help is a sign of humility and lack of ego; a sign that they want the project to succeed more than they want to look good doing it.

Another thing that asking for help does is help a manager understand when it’s time to hire more people. If a manager is getting honest feedback that her employees have too much going on consistently, then she is more likely to be able to push for a new hire earlier in the process, enabling the company to continue to grow without sacrificing employee sanity.

One really effective way to delegate up is through your 1-on-1s (if you’re not having them regularly you should demand that you do). Say, “I’m making progress on X, but not as fast as I’d like; can we talk through it?” Your manager might have 10 ideas that will help unjam things.

Delegate Laterally

“Delegating laterally” is asking for help from colleagues on your team.

All the same emotions of “delegating up” play into this and then some, because employees on the same team can be competitive (angling for the same promotion, etc.).

My wife just got out of her first trimester and has been very nauseous. She’s also in medical residency, which means 24-hour call shifts (in these shifts you’re working for 24-hours straight). She did a couple call shifts early in the first trimester, before she was telling anyone, in which she was throwing up every 90 minutes throughout the night while treating patients. They’re the hardest nights I can imagine, and she wasn’t awarded bravery points (other than by me!) for going through with it. Once she got far enough along in the first trimester, she shared what was happening with co-residents. They volunteered to pick up 12-hour overnight shifts in return for her picking up extra 12-hour day shifts.

Good teammates help you out. All you have to do is ask. Individuals on great teams know to lean on each other.

Remember, ask for help. Give help in return. We’re all human. You and your colleagues will be better off for the collaboration. If you’re having trouble sharing work with your co-workers, talk to your manager about it, since it should be an easy and natural thing.

By the way, this is true all the way up the chain: effective executive teams do this as well. I role play with other members of my executive team before having hard conversations all the time, and talk through problems I don’t have the answers to literally every day, and they do as well. Nobody has all the answers, and startups are hard enough without being able to rely on those around you.

Delegate Down

This is the classic form of delegation: a manager giving work to an employee.

The only interesting things I have to say about delegating down are:

• As a manager, you should see your role as making your employees successful. If you find yourself spending more time doing individual contributor work instead of mentoring your employees, you’re not doing it [management] right.
• You are responsible for managing the workload of your whole team/program. There are limits. A big part of managing up is making reasonable commitments and proactively asking for help from further up the chain at the very first sign that a project might slip for any reason.
• You can get your team to double down and work extra hard sometimes, but if you consistently rely on this, your whole team will hit a wall at 100MPH and you’ll lose the whole team.
• If you’re pushing your team hard a lot, hire more people, or focus more on “delegating out” on behalf of your team.
• Even as an individual contributor, you can often delegate down by outsourcing. Many tasks can be done for pennies on the dollar (easily expensed) using Mechanical Turk, Upwork, and the like. I’ve been outsourcing all kinds of personal and professional tasks and projects for years; it appears to most as if I’m doing the work when, in fact, I’ve outsourced it. You should probably talk to your manager about it first, though strong managers will give you the leash to experiment since they will understand that it may offer a relatively inexpensive way to boost her team’s effective capacity!

Onward

When you’re working at a startup, you need to use leverage to get things done. That leverage is delegation.

Once again, the point of all of this is to always be working on only the most important thing you can be working on. Anything that gets in the way of that is not productive or helpful. Delegation is key to hitting your personal home runs, as well as being an additive player on your team.

Summary of delegation methods:

• Delegate Out: avoid the work.
• Delegate Up: ask for help (from above).
• Delegate Laterally: ask for help (from across).
• Delegate Down: set the context for your team to be successful.