Lead by Delegating

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🔗 Jake’s Picks

Must-Read Resources for Founders

🚀 Scaling Startups

• Four rules for scaling a business (Forbes)

🧠 Founder Self-Development & Mental Health

• Why every leader should invest in their own professional development

  (The CEO Magazine)

📈 Productivity Hacks

• The productivity hack that really does boost careers (Financial Times)

🛠 Tools for Scaling

• Cleft is an AI-powered voice notes app for your iPhone and Mac (LifeHacker)

💡 Hiring Insights

• Struggling with retention? Improve how recruiters and hiring managers work together (HRExecutive)

👀 ICYMI

• Scale yours and your team’s productivity with these systems (Scale Smarter Newsletter)

🔐 The Delegation Unlock

One of the most common “good problems to have” as a founder is the now what moment you experience once you’ve raised a round and can actually hire resources so you can take off some of the numerous hats you’ve worn since day 1.

Founders typically have a hard time giving up the work that got them to this new milestone.  After all, you’ve now watched your baby grow from an idea into something tangible that the world has taken serious interest in.

But now what?

It’s often said hiring the right employees is the true unlock to success, but effectively delegating the right tasks is what will solidify this newly formed foundation, and enable you keep that hockey stick growth going.

From encouraging and empowering your employees to offloading your own tasks, here’s where you can start:

Build a Competent Team

Take the time to find your day 1’s that you know you can rely on and who will continue to build out the foundation you’ve set in place. These hires should be the extensions of all the things you don’t have the time to do or are simply better than you at doing it.

Identify Delegation Opportunities

Categorize the tasks you can pass off based on complexity and strategic importance.  Knowing how tasks and projects rank based on their complexity and importance will make it easy to figure out what you pass off and what you keep.

Remember: Something that’s boring for you could be an amazing learning opportunity for someone on your team!

Empower Team Members

Your team will want to feel like they can own the work when it gets passed off.  Creating a layer of trust, accountability, and autonomy will go a long way when the work gets passed off. Don’t be afraid to let them bring their own personality to the task to feel even more ownership over it.

Set Clear Goals and Objectives

Being extremely clear in your objectives, expectations, and essentially what success looks like will further enable your employees to not only take on the work, but also eliminate the amount of back and forth you’ll need to do when it’s passed on.

Provide Continuous Support

Instead of building the ship, you’ll want to be around to answer questions about how and why the ship gets built.  When the work is passed off, you’ll take on a new supportive role with your team.  Open communication is key here.

Monitor and Adjust

Regularly reviewing processes and outcomes, alongside checking in with your team will give you the feedback you need to adjust your delegation strategy as needed.

Pro Tip: On new tasks, I like to do an early check-in within a day or a couple of hours to make sure they are on the right track, and again at the mid-way point in case they need any redirecting.

🚩 The Delegation Trap

Effective delegation isn’t just about passing off work to other people and wiping your hands clean.

Even with the best of intentions, you can still get caught in slippery slopes that just end up creating even more work for you.

Assuming the ship will keep sailing once the work has been assigned is one way to fall into common delegation traps like the ones below.

Knowing how to navigate these inevitable situations will level you up as a founder and more importantly, as a leader for your employees.

Choosing the Wrong Person

Does one bad apple ruin the bunch?  It might if you’re not careful.  In the early days of scaling, your people will have impacts on the company that everyone can see, including your customers.  Choose wisely.

Micromanagement

You’ve been doing so much of the work for so long, your first instinct will be to want to know everything that’s going on with everything.  Remember, nobody likes a micromanager.

Pro Tip: Avoid this by setting up the right systems. For example, instead of constant meetings or slack messages, have your team send a weekly update email or set up a dashboard to track progress.

Lack of Clarity

I’ve seen founders delegate work but provide very little direction and then wonder why their team isn’t producing the way they hoped they would. Your people need to know exactly what they’re doing and why they’re doing it.

Poor Communication

It’s amazing what happens when you talk to your team.  It’s not so amazing when you don’t talk to them.  When the work has been passed off, your people need to know that they’re going down the right paths for you.  But even more importantly, you need to know that they’re doing what you had asked them to do in the first place.

💡Try SMART Goals

The more specific and clear you can be when delegating tasks to employees, the more likely you are to receive the desired outputs.

You’re also more likely to reduce the back and forth with your team, further freeing up your time.

People just want to know what they should be doing and why they should be doing it.

A great framework to try out when delegating tasks is the “SMART” method:

Specific

Define the goal clearly, the more precise the goal, the easier it is to understand and achieve.

It should answer the questions: Who, What, Where, When, and Why

Example: Instead of saying “Increase sales”, say, “Increase online product sales by 20% in the next quarter through targeted social media campaigns.”

Measurable

Quantify the goal and establish criteria for measuring progress and success.  This helps you and your team stay focused while tracking progress.

Example: “Increase online product sales by 20%”, where 20% is the measurable metric and something that be tracked and reported against.

Attainable

Set realistic goals based on the resources available or constraints that exist.

Take into account the time it will take, financial resources, and skillsets available.

Example: If current sales are increasing by 5% per quarter, aiming for a 50% increase probably isn’t going to realistic.

Relevant

Align the goal with broader objects and strategies that matter to the business.

The goal should be described in how it relates to the overall business and why it matters.

Example: If the business’s overall strategy is to expand its online presence, increasing sales through targeted social media campaigns is aligned and relevant to this objective.

Time-bound

Setting a clear timeline for achieving the goal will help employees prioritize their work.

Deadlines are key in setting expectations when the work has been distributed amongst the team.

Example: Increase online product sales by 20% by the end of the quarter where end of the quarter sets a firm deadline for employees to work towards.

Delegating tasks to your employees with a framework attached to them may feel like a lot of work up front, but in the long run, it will create a positive domino affect across the company.

Your employees will get used to not only how to ingest new tasks assigned to them, but how to distribute them as well.  After all, being the leader means showing how to delegate as well.

🎬 TLDR — Your Actions For The Week:

• Scaling Your Startup: Start delegating thoughtfully, avoiding common traps

• Scaling Yourself: Reduce the back and forth with your team using the SMART framework

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