Delegation is a superpower, but 99% of people get it wrong.

Effective leadership is about striking a balance between the bigger picture vision and nailing the day-to-day operations. Delegation is one the most important tools that a leader has to do exactly that.

Empowering your team to take on work (that you would have otherwise done) is one of the highest leverage things a leader can do. And, if you have great people, the work output is usually BETTER than if you were to do it yourself! This allows the leader to spend more time ON the business instead of IN the business.

But if you get delegation wrong, it can cause more work for the leader than it alleviates. Making improper delegation a NEGATIVE leverage activity – you get less out than you put in.

This is why it’s critical to get delegation right.

In this article, we’ll cover why it’s important, the benefits when done right, and the 5 rules to mastering delegation…

Ready to get started? Let’s go!

Delegation is Necessary for Scale & Innovation

“Delegation is not a sign of weakness but of strength.” – Steve Jobs

But, most leaders are reluctant to delegate significant work to their team. The perception is that teaching them how to do something will take more time and effort than the work itself. 

But then things pile up, and the leader becomes the business bottleneck. Since time is the leader’s biggest constraint, there’s a natural ceiling on how much anyone can accomplish. So, to scale, you must get comfortable with delegation. Otherwise, you’ll always be the limiting factor of your business. 

Delegation can also be a fantastic source of innovation within an organization. Instead of telling a person WHAT to do, you give them the outcomes you’re trying to achieve and let them create a proposed solution. This approach also gives your team more purpose and pride in their work. Something that is sorely missing at most companies. 

But don’t take it from me.  A Gallup study of 143 CEOs on the Inc. 500 list found that CEOs better at delegating posted an average three-year business growth 112% greater than CEOs who don’t delegate well. Those businesses also saw 33% greater revenue. 

Founders who have and use high delegator talent can generate better business growth and venture success than leaders who get lost in the day-to-day minutiae of managing a business.

In other words, the best leaders understand that masterfully delegating ​​helps unlock a new level of growth in their business. 

Balancing Delegation & Trust 

Successful delegation is all about the right level of trust.

If you have low trust, you are unlikely to delegate anything. If you have high trust, you will likely empower your team with projects. You’re telling your team, “I have confidence in you.” You’re shifting from a ‘me’ mindset to a ‘we’ mindset.

But there is such a thing as over-trusting someone. I call it blind trust–a situation where you delegate something important to a person without the proper oversight. You ‘blindly’ trust it’ll get done exactly how you want it. This is rarely the case, especially when working with someone new. 

More often than not, if you delegate well, the person will surprise you with what they bring back (in a good way!). Multiply this across the organization, and you’ll be able to accomplish 100x more than you ever would have done solo. 

5 Rules to Master Delegation

Here are my 5 rules to always get delegation right. Here we go… 

1. Pick the Right Projects

Start by mapping out your week – think of it like a personal time audit. What do you spend the most time on? 

Categorize tasks (like marketing, sales, financial, etc.) and tally up the approximate hours you’re spending on each.

Now, here’s the crucial part: Identify the tasks that are ripe for delegation.

Take your list and give each one a score from 0 to 10 for these three factors:

The higher the score means it’s a project ripe for delegation: high dislike, high time, easily taught.

Usually, these are tasks that you KNOW are important but you aren’t skilled at or passionate about. A common example is accounting tasks, like closing the books each month, quarter, and year. For most CEOs, this is a task they don’t like doing – it takes them an incredible amount of time to do by themselves, and it’s relatively easy to teach someone how to do it (especially if they specialize in accounting). 

Now take the top 10 highest-scoring tasks, and let’s focus on those in the following steps… 

2. Delegate to the Right Person

Handing a task to the wrong person is like putting a square peg in a round hole — it’s a setup for frustration on both ends.

First, you’ve got to know your team like the back of your hand — that’s non-negotiable. Match the task with the team member whose skills and enthusiasm align the most. It’s a bit like casting for a movie; you want the perfect fit for each role.

Three things to consider when choosing:

  1. The person’s skillset (i.e., product design, finance, etc.)
  2. The experience level of the person 
  3. The time required to complete the project (likely varies based on #1 and #2). 

If your go-to person is already juggling too much, pass the baton to your next best choice. If you’re feeling short on bench strength, that might be a sign to bring in new talent. 

3. Provide Clear Guidance

It’s surprising how often this gets overlooked, but it’s probably the most important step. The payoff here is so huge for a little extra effort. 

When you’re handing off a task or project, make sure you’re crystal clear on three things:

  1. The Why: You’re not giving them this project just to tick a box off your list. Explain to them why this task matters. How does it fit into the bigger picture? Don’t just delegate tasks; delegate purpose.
  2. The What: Spell out what needs to be done, and don’t skimp on the specifics. If it’s complex, write it down and provide the necessary tools – prep them as if you were prepping yourself. And remember, if they have high skill and experience, focus on the outcomes you’re trying to achieve, not the exact solution to get there. Let them figure that out themselves. If the person has a lower level of experience, then pair the outcomes with more specific instructions.
  3. The When: Deadlines are mutual commitments. Both parties should agree that the deadline makes sense and the work (or a phase) can be completed in that period. For bigger projects, give them the reins to scope out the timeline.

Shake on it, and continue. 🤝

4. Inspect, Trust, Inspect

The goal here is to provide oversight without micromanaging. 

First, you should schedule regular check-in meetings with the person leading the project. If it’s a short project (takes a week or less). But for anything longer, you’ll want at least one check-in meeting halfway through.

For people with high experience leading a relatively simple project, you don’t need a long check-in meeting. It can be as simple as 5-10 minutes during your normally scheduled 1×1 meeting. If they are leading a complex project, I’d recommend carving out at least 20 minutes to go through things with them. 

You should spend more time with people with less experience during your check-in meetings.

Let the person leading the project take the lead on these check-ins. Ask how things are going, have them walk you through where they are at, and if they need any help or guidance.

Your job is to help coach them through the blockers and ensure they aren’t drifting off course. Your job is NOT to nitpick every project detail during these check-ins. But you should look for more significant red flags, like: 

  • Red flag #1: Stalled Progress: If things haven’t been moving since the last check-in, you need to figure out why. Then, tweak the game plan together.
  • Red flag #2: Off-track Progress: If things are moving but veering off course, it’s about recalibrating the direction, not redoing their work.

If you see a red flag, you should opt for another check-in meeting in a week’s time (or shorter, depending on the project). This is when you need the person to show that things are getting back on track. 

And don’t forget to praise progress! Part of the magic of delegation is seeing your team grow and thrive. Celebrate those victories – they’re as important as the finish line.

5. Constrain the Final Review

Reviewing someone’s work is a balancing act between quality and time/cost. “Good enough” vs. “Perfect”. You optimize this tradeoff by constraining review cycles and setting an acceptable quality bar. 

In most cases, trying to get a product to “perfection” is a fool’s errand.

It’s typical for leaders to get stuck in endless review cycles on the last 5-10% trying to make someone else’s work look like their own. In reality, they aren’t improving anything in the eyes of the end-recipient. They are just wasting time and adding cost. 

You have to be willing to approve a project somewhere between “good enough” and “perfection” based on who the customer is. If it’s something that’s internal and will only be seen by a small group of people, then maybe “good enough” is fine. You want to optimize for speed. 

On the other hand, if the project is a client-facing project that you know will be scrutinized by many important stakeholders, then you want to spend more time ensuring quality. 

Step 1: Provide clear, specific feedback. 

When reviewing the final product, provide feedback in written notes (so it’s easier to remember and track). Aim for one review cycle (if possible) and give feedback that correlates to the appropriate quality level of the task (i.e., don’t give 7 pages of super detailed feedback if you’re willing to accept a “good enough” quality level). 

Balance constructive criticism with well-deserved kudos. The way you serve it up can make all the difference.

Be clear, be honest, and most importantly, be the kind of leader who turns feedback into fuel for improvement.

Check out how to stop giving sh*tty feedback here.  

Step 2: Make sure the feedback is fully incorporated.

While you want to minimize review cycles, you also want to make sure that the feedback is fully incorporated. I don’t bend on this one unless the person convinces me that it was a poor suggestion (i.e., they tried it, and it didn’t work). This happens, so be open to it. 

Then, get it out the door and move the business forward. 

Each project is a stepping stone, upping our game bit by bit. After approving something, if there was an area that could have been improved (but wasn’t worth the extra time), I let them know how to improve it on the next project they do. 💪

Delegation is not just about distributing tasks. It’s about developing leaders. Done right, it’s one of the most important things you can do to move your business forward. 

How I can help you… 

Are you a founder, executive, or manager? I’d love to support your professional growth. 

Here are three ways: 

  1. Connect on LinkedIn and Instagram – where I post practical tips about leadership and startups every day.
  1. Subscribe to my free newsletter – where I go deep on a variety of management and operations topics that will make you a better leader & operator. 
  2. Join Highland – my executive coaching program for founders, where we help you become a top-tier CEO who can scale into the tens of millions & beyond.

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