Delegation leadership 101: How to save your sanity and strengthen your small business

Tuesday, December 06, 2022

Picture this. You’re just starting out the workday … and you’re already overwhelmed.

As you review the day’s to-do list wondering how you’ll get it all done, you hear a knock on your office door. An employee needs your help. One thing leads to another, and before you know it the clock strikes closing time. But you haven't even gotten through half your to-do’s thanks to the constant disruptions only you could handle. Oh, and now you feel a stress headache coming on too.

Sound relatable? All too often, “not enough time in the day” is the anthem of the small business owner. As an entrepreneur, it’s in your nature to want to do everything yourself.

We get it. Letting go and being vulnerable to trusting others with tasks you’ve historically only trusted yourself with is tough. Especially when it comes to something as personal as your business.

But here’s the hard truth: When you’re stretched too thin, chances are you’re not doing your best work anyways. So that self-sufficient, I’ve-got-it attitude could actually be hurting more than it’s helping.

Whether you’re in the process of building your small business or you’ve been established for a decade and want to refine how you’re operating, it’s a mistake to believe you have to do it all on your own. Building agility into the fabric of your business is essential to sustainable growth. And developing your delegation skills is the ticket to getting there.

Keep reading for our small business owners’ guide to delegation leadership, including:

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Delegation myths, debunked

Bad reputation, misinformation, interpretations gone wrong … whatever you chalk it up to, there’s a cloud of confusion surrounding what delegation is and what it isn’t. Let’s set the record straight.

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Myth 1: Delegation is just a fancy word for slacking off.

Actually, it’s just the opposite. The definition of delegation is entrusting a task or responsibility to another. While this does require stepping away from tasks in a direct capacity, it doesn’t equate to abdicating. When done right, delegation means investing in the empowerment of your people.

Whether it’s weekly check-ins or hands-on training, the work you delegate will need supervision — especially at the start. In other words, you’re still accomplishing important work, but you’re doing it by equipping others with the resources, knowledge and leadership they need to take on a new task.

Another reason delegating work is the opposite of slacking off? When you let go of non-essential parts of your to-do list, you’re actually increasing your own productivity by freeing up more time to focus on what you do best — the big picture work of growing your business.

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In fact, according to a Gallup study, CEOs who excel in delegating generate 33% higher revenue.

More than that, delegating allows you to protect your mental and physical health. So you can keep on leading your business without burning out. Now, that doesn’t sound like slacking to us.

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Myth 2: No one else will do as good of a job as you.

Raise your hand if you’ve ever caught yourself saying, “It’ll be faster/better/easier if I just do it.” Well, if you’ve been keeping the task in question all to yourself, that's likely true. But it’s also a self-fulfilling prophecy.

Here’s what we mean: If you never give someone else the chance to take on the task, they’ll never grow the skills they need to do it quickly or well, and you’ll never break the pattern of being the best person for the job. See how that initial assumption turns into a merry-go-round you can’t get off?

Spending a little time growing your team is a worthwhile investment — and an important part of effective leadership.

While they might make mistakes their first time (or first five), in the long run it’ll pay off. Who knows, they might even find a better/faster way to do it.

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Myth 3: Delegating will diminish your importance.

Here’s the deal. We’re all scared of feeling like we aren’t needed. But when you’re a leader, if a member of your staff shines, you shine. And so does your whole team for that matter. That’s why the most successful leaders delegate.

Here’s another way to look at it: Who would you rather work for? Someone who gives you the chance to take on important jobs? Or someone who guards all the good stuff for themselves? If you’re not trusting your team, they’ll notice.

But they’ll also notice if you do. Delegating tells your team you have confidence in them and that you care about helping them develop new skills. This also creates a domino effect of happier employees and a healthier culture. And as a leader, that’s your most important work. That’s what your team really needs from you.

But don’t take our word for it. Research shows that a positive company culture can increase revenue by 4x.

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two women discussing how the dos and do nots of work delegation with each other

The do’s and don’ts of effective delegation

Now that we’ve cleared up the confusion about what delegation leadership means, let’s talk about how it’s done. When it comes to how to delegate properly, it’s a bit of a balancing act. But that shouldn’t hold you back.

Keep reading for best practices to follow and pitfalls to avoid on your way to developing your delegation leadership skills.

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Not sure what to knock off your list? A good place to start is doing an audit of your workweek.

While “audit” might sound intense, it doesn’t have to be formal or complicated. Simply go about your day as you normally would, but track everything you do by timing yourself completing each specific task and recording your findings. That way, you’ll get an accurate picture of how many minutes or hours you’re spending on different things each day.

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Once you’ve done that, analyze the results and start asking yourself some questions:

  • Do you have tasks that are major time sucks? (Identify areas where you’re spending a lot of time, but really shouldn’t be.)
  • Are there some tasks you’d just rather not do? (Think of those chores that induce instant dread.)
  • What about tasks you’re maybe not so good at? (Hey, we know you’re talented. But not everything can be in your wheelhouse.)

From there, ask yourself this: Which of these tasks are teachable and which can only be done by you?

To help with answering, classify your tasks by business impact. Here are the four main categories:

  • No income
  • Low income
  • High income
  • Legacy building

As you might’ve guessed, the tasks from your audit that fall into the no or low income categories are the areas that are safest to start delegating to others. As for your role as the business owner, the high income and legacy building categories are likely best sticking with you.

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Once you know what to delegate, the next step is deciding who to delegate those tasks to. There are a couple things you can do to ensure you’re connecting the right tasks to the right people.

First, play to your people’s strengths. Observe their natural talents, talk with them about what they enjoy doing and ask if there’s a certain area of the business they’re interested in learning about.

Once you know the strengths, weaknesses and preferences of the members of your team, you can create an employee roster to streamline the decision-making process of who to call on when it’s time to delegate.

Even after building your roster, tasks still might come up where you’re not sure who the best person for the job is. In that case, start small by assigning a simpler, lower-level, trial assignment to an employee to test the waters. If they do a good job with it, move forward with giving them bigger tasks. If it’s not a good fit, no big deal. See if it’s a better match for someone else.

Sometimes, no matter how hard you try, you won’t find the answer within your staff. That’s why as you hire and train new employees, it’s important to keep in mind which skill sets your roster is lacking.

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There’s a sweet spot between over-managing and being an absentee boss. And if you want to be an effective leader, that’s what you should shoot for. If you’re not sure how to find the right balance, use this guidepost: Your job is to set your employees up for success.

We know. Easier said than done, right? Let us elaborate.

Start by establishing clear expectations up front, defining the goal of the task and providing supporting resources and training. There's a time and place for passing down "lore" around the campfire, and your small business is not it. When you rely on verbal direction, things get lost in translation. Take some time to document your process before you assign a new task. As staff questions come up, you can always update your training doc along the way.

Beyond helping your employees get started, it’s important to remain available throughout their learning process. Give productive feedback, check in to answer questions and assign specific things to improve on. Then, step back and let them try again.

You shouldn’t disappear, leaving your employees high and dry. Nor should you stick to them like glue.

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A recent survey revealed that 85% of employees reported their morale was negatively impacted due to micromanagement.

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69% of employees considered changing jobs because of it.

On the other end of the spectrum, research has also shown absentee leadership to be a top complaint from employees.

Like we said, it’s a balance. But any way you slice it, great leaders will take the time to find it.

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When you hand off a job, it’s natural to want to see it done exactly the same way you’d do it. But we’d counsel you to be open to different ways of doing things. There’s no doubt about it, sometimes your way is the best way. But other times … maybe it’s not.

That’s the beauty of delegating. When you assign a task to someone else, you’re giving them the opportunity to put their signature on it, make it their own and bring new ideas to the table.

Just think: If you only ever do things the way you’ve always done them, how will you improve your business? The goal of delegation isn’t for someone to do a task exactly how you’d do it in perpetuity. More often than not, the desired outcome should be for them to use your example as a starting point, improve upon your process and make it even more successful. You might be surprised by the results.

Before we move on, we have one more thing to note: Don’t forget to say thank you. If an employee does step up and puts a new-and-improved spin on the task you assigned them, make sure you acknowledge that. Rewarding a job well done can go a long way in cultivating employee satisfaction and deterring resentment. They’ll feel more invested in their role and more motivated to keep doing good work for you.

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3 ways to start delegating at your small business

So, we’ve covered what delegation is and how to do it right. Now it’s time to talk about the next part of the delegation process: understanding your resources and how to use them.

Up to this point, we’ve mainly discussed delegation in the sense of transferring a task to an employee. But that’s not your only option. Below, we’re breaking down three different groups — consisting of human and non-human resources — that you can and should delegate to at your small business.

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1. Employees

The first group is your employees. While we’ve already talked about this type of delegation at length, it’s worth reiterating.

After creating your employee delegation roster, documenting your processes and training your employees on how to take over the tasks you’ve decided to delegate, you can take it a step further.

Consider cross-training your team members on tasks you want to consistently delegate. That way, you’ll have multiple people on staff who are capable of handling different duties when peak season, vacation time or emergencies arise.

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Studies have shown that businesses with highly engaged team members are 21% more profitable.

So, when you take the time to delegate to and engage your staff members, you’re also increasing the collective strength of your entire business.

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2. Gig workers

Say you have a certain task you want to take off your plate, but you don’t think anyone on your current staff fits the bill — or you don’t have the budget to add another W2 employee to your payroll.

This is where the gig economy comes in handy. Consider hiring independent contractors that have the competencies and skill sets you’re looking for to fill in the gaps on your internal staff list.

This option is especially useful for limited-time needs, projects that fall outside the usual duties of your business, specialized skill sets or talent levels you can’t afford to bring on in-house and busy periods like the holidays when you need extra hands on deck.

Whether it’s project management, market research, graphic design or most anything else, the gig economy could be your answer to how to delegate some of those trickier tasks.

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3. Technology

When you think “delegate,” you probably think of tasks being transferred between people. But technology is one of the most valuable delegation resources you have at your disposal — especially when it comes to time-consuming and tedious tasks.

Been spending long hours laboring over administrative work and scrambling to fix the fallout of human error? Well, suffer no longer. You don’t have to wait to ditch the humdrum of manual labor. Fintech is one of the best ways to break free and let the right tools take the reins for you.

Here are just a few examples:

  • Inventory

    Been doing inventory by hand? A point of sale system with inventory management software can track your inventory for you with custom fields and grids, and build reports to help you stay stocked.

  • Payroll

    Spending hour after hour hunched in your back office crunching numbers for paychecks and trying to decipher complicated tax requirements? Payroll tech can automate your payroll processing, simplify payroll tax management and so much more.

  • Scheduling

    Is your sticky note scheduling system turning into the stuff of nightmares? Time tracking software can help you build smarter schedules with drag-and-drop technology, move shifts, manage employee requests and forecast overtime expenses, at your desk or on the go.

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Get ready to reap the benefits of delegation

If you’ve made it this far, you’re ready to put what you’ve learned into action. It’s time to give those shoulders a rest and share the load.

While it’s no easy feat, the long-term benefits of delegation far outweigh that initial awkward transition period. Developing an agile business, increasing employee morale, evolving your style of leadership into one people want to stick around for ... The list goes on.

Building delegation into the structure of your business and everyday processes is key to success.

As it happens, it’s also the key to finally going on that vacation you’ve been dreaming about but couldn’t possibly take because your business couldn’t survive a day without you. You can go ahead and book that trip now. Your team will take care of business while you’re gone — because you taught them how.

If you’re looking for more entrepreneurial content, head over to The Entrepreneur’s Studio to get your daily dose of inspiration and leadership development from fellow small business owners who’ve been in your shoes. Be sure to follow and subscribe so you don’t miss any future podcasts or courses!

Heartland is the point of sale, payments and payroll solution of choice for entrepreneurs that need human-centered technology to sell more, keep customers coming back and spend less time in the back office. Nearly 1,000,000 businesses trust us to guide them through market changes and technology challenges, so they can stay competitive and focus on building remarkable businesses instead of managing the daily grind. Learn more at