In a thriving business, delegation isn’t a one-time act — it’s an ongoing process
“IF you want something done right, do it yourself.” You must have gotten that advice at some point in your work career. And you’ve probably also discovered how dangerous it is.
There’s truth in it — only you can do things exactly as you want them done — but unless you’re the sole worker in your business, there’s no way you could, or should, be doing every task. And even if you are working solo, you should probably be delegating some of your work.
The more you want to grow, the more crucial it is that you delegate. By delegating early and consistently, you create the space necessary for your own growth and the expansion of your business. In a thriving business, delegation isn’t a one-time act — it’s an ongoing process.
Beyond the importance of freeing up your time, there are other good reasons to delegate.
You’re probably very good at many things. At the same time, there are also things that aren’t your strong suit. You may be a whiz at marketing but terrible at numbers. Or you are innovative and excellent at coming up with out-of-the-box solutions — but when it comes to implementation, things fall apart.
This is where delegation comes in. Hire people who have the skills you lack, and then each one of you can do what you do best.
Delegation is also great for your team. If you keep your team confined to smaller roles without opportunities for advancement, you stifle them. Delegation gives them the chance to spread their wings.
Delegating Needs Empowerment
In a management course I attended years ago, the speaker stressed the importance of giving responsibility along with delegation. Responsibility doesn’t exist in a vacuum; you have to let go of it for someone else to take it on.
One year, a friend of mine told her kids, “I’m not in charge of the Chol Hamoed trip, you are. Here’s the budget and some basic parameters, go for it.” It worked out beautifully — they planned a great trip and went only slightly over budget, and that extra expense was worth it for her.
However, empowerment needs clear communication. Imagine if her children had planned a trip that started at 2 a.m., and she wasn’t willing to wake up then. She’d owe them an apology for not setting clear boundaries up front.
Isn’t it obvious that a trip is supposed to be during the daytime hours? You might be wondering. Well, it may be obvious to you, but it’s not obvious to teenagers. Bottom line: You can’t rely on telepathy for communication, and once you give others the responsibility, they can do it their way.
In one of my workplaces, middle management was responsible for end-of-year reviews but had no ability to determine raises. This put them in a tough position — saddled with a difficult task but without the responsibility that was intertwined with it. Clearly, they couldn’t be given a blank check and told to give any raises they wanted, but they could have been given a budget to divide among their direct reports, which would have been a fairer system.
Be a Coach
In their article “For Smarter Decisions, Empower Your Employees” on the McKinsey site, Aaron De Smet, Caitlin Hewes, and Leigh Weiss stress the importance of empowering employees in everyday decision-making.
Big decisions often get the attention they need, but smaller, routine decisions can fall through the cracks, leaving employees uncertain about their authority and managers unsure about how to support them.
The article plots decision delegators on a matrix:
Most managers begin as Micromanagers or Helicopter Bosses, heavily involved in every decision and often overriding their team’s choices. While this might provide quick control, it leaves employees feeling undervalued and dependent, ultimately slowing growth and accountability.
On the other hand, Cheerleaders take a hands-off approach, offering encouragement but little guidance. This can leave employees feeling unsupported and uncertain, particularly in challenging situations.
Additionally, when leaders only step in sporadically, it can undermine employees’ confidence and frames coaching as something you get when you’re in trouble rather than being something everyone needs.
There are several ways bosses can empower their employees and improve decision-making:
Clarify roles and responsibilities: Ensure everyone knows what decisions they are responsible for and where they have input. This prevents bottlenecks and keeps the process efficient.
Invest in training and development: Equip employees with the skills they need to make decisions and provide managers with coaching training to build confidence and competence.
Foster a culture of empowerment: Encourage a mindset where employees feel trusted to make decisions and where learning from mistakes is valued. A quote I often remind myself of is: “There are no mistakes or failures, only lessons.”
Decide when to get involved — and when to let go: Managers should carefully choose which decisions require their involvement and delegate the rest, focusing their efforts on the most critical areas.
Set it, Don’t Forget it
Know what you do best and what fuels your passion, and keep those tasks for yourself. The rest, delegate. However, delegation requires a system for monitoring progress. “Set it and forget it” works for a crockpot dinner, but not for delegation. You might think everything is clear, but everyone has their own definition of tasks, and monitoring helps catch any missteps before they escalate.
If you have a system in which your team updates you at frequent intervals, you won’t end up with a fully formed program or sales plan that you think is a disaster.
Delegation also involves giving people the space to work independently while retaining ultimate responsibility. I once delegated a programming task to my team. On a short winter Friday, they told me the job was done and tested. I trusted them and allowed it to go through — and then the client found several bugs.
When my manager confronted me, I told her I’d been informed that it was ready to roll. She told me that as the leader, it was my responsibility to check it myself before allowing it to be sent to a client. That was a valuable lesson.
To avoid such pitfalls, always delegate in small, manageable steps. Monitor progress without hovering — establish a clear monitoring process from the start so it doesn’t feel like a lack of trust. You decide whether to give an employee full autonomy, offer occasional input, or retain veto power. The clearer you are, the smoother the process will be.
If you told someone from the get-go that you’re retaining veto power, it won’t feel hurtful if and when you choose to use it. And if you’ve been monitoring throughout, it’s unlikely that you’ll need to veto anything significant.
Clarity is crucial. A manager I know had given a weekly task to someone on her team. Early on, she reviewed one of the final products and said, “I think it will work better if you’d switch xyz to abc.” The employee kept the original version.
It wasn’t critical, so the manager let it go. But this scene repeated itself every few weeks over several years, and the manager’s resentment slowly built up.
One day, she finally snapped and said, “Why can’t you just do what I ask you to do?”
The employee was shocked. “You never asked me to do anything. You made suggestions. And I thought my original version was better, so I kept it. If you wanted me to make the changes, why didn’t you just say so?”
This manager thought she was being nice by phrasing her requests as suggestions, but her black-and-white team member took her suggestions at face value and didn’t realize they were thinly veiled commands. Nothing is as nice as clarity.
We’re all Works in Progress
When delegating, remember that the work will hopefully be done well, but it won’t look exactly as it would have if you had done it. And that’s okay; perfection is not the goal.
I recently read a devar Torah from the former CEO of Timberland, Jeff Swartz, who quoted Rabbi Jonathan Sacks z”l discussing the concept of leadership in parshas Devarim. Moshe, recognizing that no single leader can govern alone, called for wise, understanding, and well-known leaders. However, when the Torah describes the chosen leaders, it omits “understanding.”
The Midrash picks up on this — and takes it a step further by comparing Moshe’s criteria with Yisro’s earlier list in Shemos. The list there included seven qualities, adding that they should be men of means, yirei Shamayim, truthful, and resistant to corruption.
The differences between these lists reveal the reality that leaders who contain all the ideal virtues may be impossible to find. If leaders with all the desired traits aren’t available, communities should seek those with as many qualities as possible — even if it means settling for just one. Because perfection doesn’t exist in this world. We should aim for it — and then work for our reality.
Don’t Mix Blame into Responsibility
Sometimes when we say someone is “responsible for” something, it’s a way of blaming them. But the two are not interchangeable. Blame looks backward, pointing fingers at what went wrong, while responsibility looks forward, focusing on how to move ahead.
Covid and the current war in Israel were not in any way my fault, but navigating Temech and providing women with tools to deal with the resulting economic turbulence through these crises was my responsibility.
When delegating effectively, it’s crucial to frame the question: “We are at point A and need to reach point B. Who’s best positioned to take us there?”
Now, it may be that the person who was originally responsible for that can no longer do so due to past performance and the subsequent lack of trust. However, it should be about identifying who can best achieve the desired outcome based on current needs and past performance, not about punishing mistakes. Thinking things through carefully ensures the best path forward.
Don’t Make These Delegation Mistakes
Here are some of the ways people slip up when they’re delegating:
Delegating the wrong job to the wrong person. Before delegating, ask yourself, what are this person’s abilities, then ask what does this job need? Make sure the person has the skills to do the job.
If a person tells you they don’t think they can do the job, take them seriously. You don’t need to back down immediately, but do find out more. Ask: Why do you think that? What could I do to make it possible for you?
If the stakes are exceptionally high and you are ultimately accountable, you may decide to ask for help instead of delegating.
Don’t hover. I’m clumsy, and so are some of my children. One of my kids was carrying a fragile dish that had sentimental value. I kept telling him, “Be very careful.” The kid finally said, “The more you tell me to be careful, the more likely it is that I’ll drop it, because I’m getting so tense.” Warnings can create anxiety and hinder performance. Provide guidance, but trust your team to perform.
Perfection doesn’t exist in this world. We should aim for it — and then work for our reality
