Mastering the Art of Delegation Part 2: How to Make it Happen

As a follow-up to mastering the art of delegation, with a specific focus on why it’s essential for leaders, this post is dedicated to the HOW.  How to overcome limiting beliefs and effectively create an environment that will set you up for success. Are you ready to reduce stress, enhance skills and increase growth potential? Let’s get started!

Congratulations! You’re ready to start delegating tasks to your team. It’s a big step.

Many people get stuck on the next part. To delegate effectively, you need a system in place to support the process. A delegation roadmap of sorts. 

That system should be built on a solid foundation. So before we begin, I want you to banish some pessimistic thoughts/beliefs that stem from common myths about delegation (many of these limiting beliefs I’ve had to overcome myself over the years).

Misconception #1: It’ll Make Me Look Weak

Some managers think that delegating tasks makes them appear weak. When done thoughtfully, delegation is actually a sign of strength and confidence in your team!

Truth: You don’t have to do everything yourself. Leveraging the talents and growth potential of your team is actually an signal of a strong leader.

Misconception #2: It’ll Make Me Look Lazy

Another misconception is that delegation is just a way to offload work. Effective delegation is actually about assigning tasks based on your team members’ strengths and providing them with the support they need to succeed. It’s anything but lazy.

Truth: Delegation requires you to invest time in training and support for your team. In order to achieve positive outcomes, it requires time upfront — inform your team your role in partnering with them. It will make it clear this isn’t something you are doing to avoid work. Your focus is in investing in their growth and long term, this will free up more of your time to focus on things like long term planning, coaching and strategic leadership motions.  

Misconception #3: It Will Be Too Hard

Some people choose not to delegate because they believe they can perform a task better or faster themselves. They know that the work to create delegating systems will take longer than the actual task, and never get around to setting them up. The reality is that wearing all the hats puts immense mental and emotional pressure on a person, which will eventually result in burnout. 

Truth: While requiring an initial time investment upfront, delegating pays off in dividends for both you and your team. By starting small and with lower risk projects, you can start developing your own playbook for how to make the process easier to “rinse and repeat.” 

Step 1: Set Up for Success  

The first step is to determine what tasks make sense to delegate and who the right person is to take on the work. Not everything makes sense to delegate so be thoughtful about the risk level before choosing work. Once you know what task or project makes sense, look for someone who not only has the necessary expertise but also shows enthusiasm and a track record of reliability in similar assignments.

Next, explain the work clearly. It’s generally best to have a discussion about the task rather than sending an explanation via email. This gives you an opportunity to check for understanding, answer any questions, agree on expectations/outcome and timing, and to discuss what support may be needed to successfully take on the work. 

Pro Tips:  

  • Ask how they like to learn – would it be helpful to record your conversation so they can replay it?   
  • Ask them to document the ask to verify understanding 
  • Schedule time to check in on progress 

In his short book, Effective Delegation of Authority, entrepreneur and author Hassan Osman suggests developing a template to frame up requests to ensure all critical info is covered. These could include:

  • Task Description
  • Main Goal
  • Timeline
  • Authority Level
  • Additional Materials

Step 2: Monitoring Mode

Once you have successfully delegated the work, you can shift into monitoring mode.  

Schedule check-ins but be mindful not to micromanage: discuss the best communication method and frequency to track progress. 

If there are things that need to be done a certain way, do share that but in theory, this is an opportunity to describe the outcome and give your employee a chance to figure out the how. They may just surprise you with a new and more efficient way to achieve the desired outcome! 

“Don’t tell people how to do things, tell them what to do and let them surprise you with their results.” -General George Smith Patton Jr. 

How to handle mistakes/roadblocks – if your employee hits a roadblock or begins to fall behind, it may be necessary to intervene. Use coaching, encouragement and additional resources as you see fit to get things back on track. 

  • Work on a plan of action and a timeline for addressing the issue – sync with your employee to align with the plan and ensure it’s realistic
  • Encourage the employee to come up with ideas for how to solve the issue

Remember – each delegation you make can be a learning experience – for you and the others in your organization. 

Step 3: Evaluation

This final step is the hardest but most important: Evaluate how it went! Schedule a debrief session to review lessons learned. This step offers an opportunity for documenting what when well and areas of process improvement! It is immensely helpful for both parties. 

Here are a few suggestions on how to assess: 

  • Ask for feedback on the experience – how did it work out? 
  • Provide positive reinforcement for the things that went well
  • Compare the results with the original expectations
  • Discuss possible improvements for future projects
  • Identify additional coaching/training that may help if appropriate 
  • Celebrate and recognize the employee for completing the work

At the end of the day, effective delegation is all about trust, communication and continuous learning. Trusting your team, trusting yourself, and trusting the process. Will there be mistakes? Probably. But once those initial wrinkles are ironed out, you AND your team will feel more empowered, connected and supported.

If you are interested in additional reading on this topic, I recommend another short book by Harvard Business Review:  20 Minute Manager Delegating Work.

Have any other proven tips for delegating? I’d love to hear them in the comments below.  If you are new to a manager role and want more support in this area, schedule Mentor Minutes time for 1:1 coaching to identify ways you can put this in motion for you and your team.

Happy delegating in the meantime!

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Danielle Cullivan

Career Insight Studio

Danielle Cullivan is a seasoned leader in tech with over 20 years of experience in Fortune 500 companies. She is also the creator of Career Insight Studio, a career and lifestyle blog dedicated to providing insights and new perspectives for working women. Danielle lives in the Pacific Northwest with her husband and high-school-aged son, and visits her college-age daughter as often as possible! 

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