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The Ultimate Guide to Delegating Effectively (While Maintaining Control)

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The Ultimate Guide to Delegating

As kind-hearted, empathetic leaders, Sensitive Strivers tend to be reluctant to ask for help or delegate to others. Many feel it is their duty to protect their team’s time and energy, so they absorb responsibilities instead. 

And as people-pleasers, these Sensitive Strivers are worried about people not liking them or others getting upset and resentful over delegation requests. 

“I know I should ask for help, but I don’t want to be pushy.” 

“My team already has enough to do.”

“I hate asking people to do things.”

These are a few of the responses I hear from my Sensitive Striver coaching clients when asked why they’re resistant to delegating. 

Sound familiar? 

If so, then underneath these well-meaning reasons, may lurk several fears.

These fears may be unwittingly holding you and your team back from reaching your full potential and having a greater impact. 

The Most Common Fears About Delegation

Assuming you have the people, resources, and authority to delegate, then there are a few common fears that may be getting in your way. 

  • Loss of control. You may rail against the idea of letting go of control, operating under the notion, “if you want something done right, do it yourself.” 
  • Perfectionism. A close cousin to loss of control, perfectionism can also block you from delegating. You hold yourself to such high (read: unrealistic) standards that are impossible for you – or anyone else – to reach. 
  • Fear of failure. If you delegate and the project goes south, what will that mean about you and your capabilities? You worry mistakes will reveal your shortcomings as a manager – and a person. 
  • Imposter syndrome. Perhaps the biggest fear I hear is associated with imposter syndrome, the feeling of being a fake or a fraud. “I don’t want people to think I can’t do my job. Won’t delegating make it look like I’m not willing to roll up my sleeves and do the work?” 
  • Desire to be liked. You want to be the “nice” manager. You strive to keep the peace and make everyone happy, and therefore, you’re nervous about delegating tasks because you worry your team will be mad or conflict will arise. 
  • Excess time. You’re busy enough as it is. You’re concerned that having to train someone else would take even more of your already strapped bandwidth. 
  • Bad experiences. Maybe you worked for a manager who delegated poorly, either too much or too little. Or perhaps you tried delegating a little bit, and things went south fast. 

Each of these fears is convincing because they contain a modicum of truth. For example, while it may be true that delegation does take some upfront time investment, it ultimately disproportionately expands your bandwidth and saves you time in the long-run. 

Most importantly, there’s a big difference between simply offloading a task you don’t want to do and delegating work in an empowering way. 

Doing so requires redefining what it means to delegate from dumping work on someone to providing structure and a framework to help your team take on more responsibility so that everyone – including you – can be more productive. 

10 Signs You Need to Delegate More

Delegation takes work. Sometimes it requires difficult conversations or navigating politics – neither of which are a Sensitive Striver’s favorite. That’s why it’s easy to persuade yourself that delegation is a “nice to have” and not a necessary requirement.  

But here are a few signs delegation has become a non-negotiable skill to learn: 

  • You spend almost all of your time in “reactive mode”, putting out fires or responding to requests 
  • You have no time for reflection or big picture thinking
  • You find that important work falls to the wayside
  • You work excessive hours trying to keep up with your workload, including nights and weekends
  • You feel stressed because you’re never able to keep up 
  • You are the go-to person for everything, and thus, a bottleneck 
  • You can’t take a day off because work would screech to a halt without you
  • You feel a sense of outsized responsibility to be the glue who “holds the team together”
  • Your team is hungry to learn and often comes to you asking what more they can do
  • You’re a candidate for a promotion, but have been told you need to be more strategic

Nodding your head? Then it’s time to make a change and delegate more effectively. 

How to Delegate at Work

1. Shift your mindset

As with most things, becoming a better delegator at work begins on the inside – by shifting your beliefs first. 

When clients work with me to improve their delegation skills, the first realization is that delegation is not a punishment. Rather, it is a chance for your team and colleagues to learn, grow, and acquire new skills and competencies. 

Think about it. You can probably point to instances in your own career when a leader delegating led to greater visibility, authority, and advancement for you. Don’t deprive your team and colleagues of that same opportunity. 

You have to deeply believe delegation is about empowerment and frame it to others as such. If they think you’re merely dumping unpleasant work on them, they won’t be motivated. 

2. Take ownership to change your bad habits

As a Sensitive Striver, you can be relied on to follow through, keep your word, and meet deadlines. These are extremely admirable qualities that make you a powerful, empathic leader. 

But you may also fall into the habit of over-functioning. This means taking on responsibility that isn’t yours and really belongs to someone else. As an over-functioner, you operate with the worry that if you don’t do something, no one else will. 

Beyond exhaustion, one of the biggest problems with over-functioning is that it creates an unhealthy dynamic that allows your team and colleagues to under function. When you assume responsibility for “fixing” situations, rescuing other people, or otherwise absorbing work, they don’t have to do their part, which can be frustrating at best and damaging at worst. 

3. Figure out what needs to go

For one week, track your time. Document the tasks you perform as well as what gives you energy versus what drains your energy. Ask yourself at the moment if this is how your time is best spent and what you would do if you were unavailable to complete this task – how would you get it done? This can help give you an initial idea of tasks that would be beneficial to delegate. 

Tasks that are great candidates for delegation include those that are:

  • Administrative, tedious and require a lot of your time 
  • Repeatable processes that are straightforward and teachable 
  • Tasks someone else has a special skill set for 

4. Invite people into the process

The fear of people-pleasing convinces you that delegation is a negative thing because your team and colleagues will be resentful of it. This couldn’t be further from the truth if you approach delegation correctly. You do this by approaching delegation assertively, that is, as a partnership and collaboration balanced with clear direction, rather than aggressively, as one-way, top-down commandments. 

Invite people into the process by first understanding what work they enjoy doing and how they’re motivated to grow. This helps you match tasks to a person’s strengths. Also, consider asking your team to propose ideas of what they can take off your plate. Many of my clients are very surprised by what their employees come up with, either because they didn’t realize someone would want to do that task or because their team member proposes something they didn’t think of. 

5. Start small 

Delegation is not abdication. It’s a recipe for failure to think you can completely hand over a project in one fell swoop. Instead, focus on up-skilling and transitioning tasks over in parts. This builds trust because you see your team members can do their job, and it builds confidence in them because they build competency that they can master (and make you happy as a result).

6. Train efficiently

Delegation takes time at first. That’s okay because you can make training more efficient by training people in real-time while you work on the task. 

For example:

  • Have the person shadow you while you complete the task and create a standard operating procedure based on the steps you follow
  • Record a short video of you completing the task and save it to a library for future reference
  • Hold office hours where you make yourself available for 30-60 minutes to provide on-the-spot instruction

7. Build-in check-points 

As you’re ramping up, set up checkpoints every week or two weeks to check-in on the person’s progress and to provide support for questions and feedback. 

Coach them. Prompt the person to answer open-ended questions about their reasoning and approach to completing the work, such as: 

  • How did you arrive at that decision?
  • What influenced your choice to X? 
  • When you’ve hit setbacks, how have you navigated them? 

8. Know your role

Your job is to define the “what” and “why” of the project. The outcome or deliverable (the what) and purpose, intent, or context as to why it matters and is important (the why). You must be crystal clear about your expectations, criteria for success, and boundaries upfront. 

While you still share final accountability for the tasks you delegate, give the person full authority to define the “how.” It may be similar to how you achieve the end goal or different. Let go of micromanaging because it doesn’t matter how something gets done as long as the final work product meets expectations. It’s far more important your team or colleague feel ownership and autonomy. They need to discover the best way to follow through for themselves. 

9.Get comfortable with feedback

Giving and receiving feedback is tough for Sensitive Strivers because you sometimes tend to take criticism to heart. However, your sensitivity also gives you the gift of being kind, thoughtful, compassionate, empathetic, and appreciating what others miss – all of which make you especially skilled at motivating others and communicating transparently. 

Harness those strengths to provide regular constructive feedback about improvements and new areas for growth. One of my favorite techniques is to frame feedback in terms of (1) what is going well and (2) what could be even better. 

And don’t forget to be generous with praise. Everyone wants to know they are doing a good job, the people you are delegating to included.

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Hi, I'm Melody

I help smart, sensitive high-achievers overcome insecurity and overwhelm so they can thrive in the workplace.

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