Leadership Skills: Delegate with Confidence


As a new leader, one of the most challenging things for me to learn was how to delegate. I was used to receiving requests and adhering to specifications, but when I had a team and received a request, I hesitated to delegate it to someone on my team. It took time for me to develop the confidence and the knowledge about my team to delegate smoothly. As leaders, we must learn to hand off work in order to scale our teams and develop our team members. However, how do you learn who to delegate to and how do you do it in the right way? It can be scary, challenging, and it can have negative impacts if done with the wrong mindset and approach. In this post I’ll talk about delegation obstacles, how to decide if and who to delegate to, and mindful practices to reach objectives with ease and enthusiasm as a team.

Delegation Obstacles

I have seen a few types of leaders struggle with delegation. One type is what I’ll call the ‘hesitant delegator’. This leader is hesitant because they don’t want to burden their team with more work, they are used to doing the tasks themselves, or they are afraid of handing off to someone who might make a mistake. I have been this leader. Remember that you have a team to delegate to so that the work can get done with more efficiency. I learned early on that though I was hesitant to give my team more work, they actually wanted work and to learn new things. In the beginning, it felt like more time and work to teach them how to do the tasks I knew how to do but in the long run it pays off once they can do it efficiently too. You always want a backup for everything that knows how to do what you do and you want to open up time to tackle higher-level tasks. The time investment in training and refining is worth it. I had to get over the fear of potential mistakes and allow people to learn, which keeping a close pulse on how things were going without micromanaging. Also, your team members may have important skills and perspective that you don’t have and we only learn that by giving them the chance to show what they can do and contribute.

The second type is the ‘dictator delegator’; a leader that delegates unintentionally or feels that having a team means they have someone to do their work for them. This leader is not afraid to delegate but delegates by shooting e-mails at team members with short messages about “urgent timelines”, offers no support, and gets upset when things aren’t on time or done perfectly. This is obviously the wrong mindset to have about leadership in general and this approach won’t work for retaining team members who want to learn and want to participate in a culture of collaboration. Beware of ‘dictator delegators’.

I’ll detail Best Practices below for how to delegate with confidence and with grace but first, when do we delegate and how do we know who to delegate to?

Who to delegate to?

Once you have the confidence and right mindset to being delegating, the next question is when to delegate and when to do it yourself and, if you have more than one other person on your team, who to delegate to. For ongoing requests, you can zoom out and pass things off gradually to your team and spend time training. For ad-hoc requests, I have a quick thought process for delegation. When I receive a new project or task, I think: can I do this quickly and not have it re-prioritize my day? This would be fastest for the business and not throw off other tasks being done by the team. If no, who on the team would be best for it – skills and interest? Does it go well with their role on the team, something else they’re working on, or their knowledge base?

To delegate optimally, you have to know what skills and strengths you have as well as the skills, strengths, and interests of your team. One great tool for learning the inherent strengths of your team is StrengthFinder, which I detail in the Awake Leadership exercises in the Structure section, where we talk more about delegation. For skills and interests, learn through one-on-one’s with them and team activities over time.

Ready to delegate? Here is a mindful approach and some best practices I have found to be effective.

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Delegation Best Practices

Ask in person

It’s always best to talk in person or over the phone when asking a team member to take on new work. This shows that you, as a leader, value the new task at hand and also that the delivery of the ask is clear and understood. If it’s something small, you can e-mail or message them, but usually talking it through for a few minutes face-to-face goes a long way in showing you’re not throwing tasks at them and will also feel less like you’re a ‘dictator delegator’.

Tell them why

Secondly, give them the why behind the ask, the context, and the impact it will have. In some cases, giving one-off tasks to people may be okay and the reason may be obvious, however, in most cases, take a quick think about if they understand the reason or if it might take some explanation. Giving team members the context behind the ask will help them relate it to the larger mission of the team and the result will be more impactful and clear.

Be specific

Give them clear direction in terms of the timeline and expectations of what is to be accomplished. Talk about if the timeline is realistic and help prioritize with other tasks at hand if they need. 

Balance clear direction with freedom to learn and experiment

This is where the ‘hesitant delegator’ must overcome fear of the handoff. When you give the ask, be specific as to what the outcome should be, but leave the how open. If they seem confused or don’t know where to start, that is where it’s important to be a mentor and provide some guidance. However, don’t give the entire how-to. This promotes development, creative thinking and problem solving, and doesn’t feel as though they’re being micromanaged. Leave some space.

Leave the “door” open

Finally, offer ongoing support. As a leader, you’re also a mentor. Ask for feedback on if they understand the ask. Ask if they need further help in getting started, prioritizing, or obtaining the right resources or connections to get the job done.


There’s always a feedback loop; that’s how we learn as leaders. We are students of our team members. After you have delegated the work, make sure to check in regularly (but not too regularly) with your team to keep things on track and offer support. It’s your job to make sure things get completed efficiently and on time but be patient. Balance room for development, which involves making some mistakes and asking some questions, with structure and constructive feedback. It takes tact!

When you gain the knowledge about your team – their strengths, skills, and interests – and how the team works as a whole efficiently, delegation becomes fun and not something that anyone dreads. It flows. It cultivates community and a culture of teamwork and development.

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Thanks for reading! I hope this helps you feel confident in delegating.

If you’d like more exercises for learning ways to improve your delegation skills, learn about your team, and develop a team structure, check out my new book, Awake Leadership.



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