Category Archives: Systems Thinking

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.



All About Mind Maps

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Mind mapping is a powerful tool we can use as leaders to balance our logical thinking processes with expansive, innovative thinking about how to approach our work. We can also better understand and achieve our objectives with our teams. In this post, I will describe the benefits of mind mapping I have experienced, the key aspects of mind mapping that make it impactful for leaders and teams, a how-to guide for getting started, and explained examples.

Three Benefits of Mind Mapping for Leaders

  1. Enables Understanding and Clarity

When we mind map, we begin with a central topic or idea. By mapping a concept or your team’s vision, the leader gains clarity of how the team is structured and how all the pieces of the team’s objectives fit together. The same can be done for a project topic or to prepare for a meeting. Just like any map or visual representation, mind maps help us get complex, vague phenomena down on paper and we can then gain clarity and move forward.

  1. Promotes Expansive, Non-linear Thinking

Another important aspect of mind mapping is that it challenges us to think expansively or non-linearly. Many times, in structured working environments where we have processes, timelines, and to-do lists, we get caught up in continuing to do things the same way over and over or approaching a new project or team structure in the same way as in the past. This approach may seem efficient or acceptable but it can actually inhibit success and limit potential. You can use past processes and learning but mind mapping challenges us to continue to free associate and add newness with each new map. Mind mapping unlocks creativity, given its radiant nature, and is a perfect tool for brainstorming.

  1. Enhances Communications & Collaboration

Finally, mind mapping is a great collaboration tool because you can use it with your team to better understand a topic collectively or to brainstorm together in a meeting. The map can be a representation of the team’s thought process and mutual understanding of a topic, project, or team plan. Mapping out a new project together enables everyone to understand the thought process behind it and, as mentioned above, allows for contributions from everyone participating. As I talked about in Awake Leadership, alignment is so important in order for teams to move forward cohesively toward objectives. Mind mapping is a great communication, alignment, and collaboration tool.

A Quick How-To Mind Map Guide

Ready to try it out? Here’s a step-by-step approach for making your mind map. Among the steps below I have added completed applied examples to look at as you make your own.

  1. Begin with a topic. As with learning or trying anything new, start with a topic that interests you and you will find enjoyable to map. You can always start with a topic that is non-work-related for your first map, to get the hang of it.

A fun example: California

Leadership topics can range from your team or role at your organization, a project, a meeting topic, etc. Do you have a complex project in front of you? A complex objective to meet? Let’s map it out and see if we can gain some clarity on how to delegate, plan, understand, communicate, or think differently about how to approach it!

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Example from Awake Leadership exercises: Team Vision

  1. After you have chosen your topic, begin to branch the first layer. Create at least 4 sub-topics or branches off of your theme. What are natural sub-components or your central theme? Peek at my additional mind map Examples Explained if you need some inspiration.

Example: Brainstorming our Website Layout


3. Continue to branch. After making your first round of branches, create a second layer with sub-sub-topics.


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Example: Sales Brochure Brainstorm and Plan


  1. Pause to observe the two layers. How is the organization unfolding so far?


  1. Continue to branch or iterate. You can continue your map with a third layer or start over. If you feel you’d like to reorganize your map, begin with the same topic but create a new map, with the first layer organized differently.

Examples: Business Objectives Meeting

  1. Share it. Discuss the map with your team or your leader – whether it is finished or not! After making the map, you may have new insights about the topic or ways to communicating the topic to your team or leader. You may realize what parts are unclear or need further development. If it’s a project or meeting topic, maybe you can now begin to order the sub-topics in terms or chronology or relevance.


Remember: Mind mapping takes practice and iteration. There is no perfect mind map. Be patient as you practice and create your maps. Some may be just for “fun” and some may be for function… or, hopefully, for both. Like any tool, with time, you’ll see how it works best for you and your team. I found, as mentioned in my book, that it worked best as a tool at our weekly team meeting for aligning on our team’s current structure, mission, and objectives. Mind mapping is used in 3 of the 7 sections of my book! I also mind map regularly for fun and function in my everyday work and life. Mind maps are powerful tools and you’ll figure out how they fit best into your work and your team’s framework. Challenge yourself to use them to be a radiant, innovative thinker and collaborative leader in your work and your life.


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From The Mind Map Book, by Tony Buzan


Here are my example mind maps explained and the example mind map from one of the Awake Leadership exercises.

Follow-up Exercises

Try the following exercises this for deeper understanding, to practice expansive thinking, or to practice communication and collaboration for brainstorming and alignment in a team meeting.

  1. Mind map a project you’re currently working on
  2. Use mind mapping to plan or structure a meeting you are leading in the upcoming week
  3. Mind map your team’s vision (as detailed in Awake Leadership) 

Further Reading

Awake Leadership, by yours truly, Hilary Grosskopf 

The Mind Map Book, by mind mapping maven, Tony Buzan 

Suggested Tools

Colored pencils & paper, large post-its and colored markers (good for team meetings), white board and dry-erase markers (good for team meetings), Excel, PowerPoint, other design software tools


If you would like to discuss mind mapping for leadership, have questions, or want to work together on a mind map, please e-mail me.

Check out Tony Buzan’s amazing website and resources for more on how-to and general mind mapping ideas.

Zoom Out to Hone In on What is Important

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“An Awake leader can zoom in to understand detail and zoom out to see the big picture impacts.” – Awake Leadership

I have learned, largely through my experience at work as well as practicing and studying yoga, the importance of zooming out. So many times we get flustered and thrown off balance when something unexpected at work seems to be staring us in the face – a decision, a new obstacle, an urgent request, a conflict, or an issue. It seems unsolvable or frustrating in the moment. We often react by putting everything else aside and attempting to immediately solve it, fix it, or by trying to make it just go away. If we can’t solve it right away, we get anxious and it occupies some or all of our valuable focus. Through a lot of practice and experience with this type of scenario in my own life, I finally learned that I could much more skillfully, efficiently, and calmly respond to these types of stressful situations by zooming out instead of instantaneously reacting or getting obsessive about a complex new situation. My stress level, my contributions at work, and my relationships improve when I zoom out.

Zooming out involves pausing, stepping back, and looking at the larger picture of how this moment or scenario fits into the larger scheme of your life and contributions before taking action. If we think in terms of the larger timeline of our life, this moment is one small but meaningful chance to learn, take a positive action, and move forward toward our intentions. When we take the time to pause and zoom out to view each challenging, immediate situation from a broader perspective, we put it into a more real, spacious frame of reference. By creating this space, we don’t make hasty decisions in the moment that we later regret. We reconnect with our deeper intentions. We don’t go through the motions and make careless mistakes. We allow ourselves to let go of the stress and return to the fact that the current challenge we face is just that: a challenge.

When a new situation arises – an urgent e-mail, a desperate text message, or a conflict, pause. Step back and ask how urgent it really is. Can you take an extra few minutes, hours, or days to comprehend and think through it? Sometimes we even have to walk away or take a break for a while to allow our mind to let go of the urgency or gravity of the situation. Usually, when we do this, we realize that everything is really okay in the grand scheme of things. We can then think more clearly and take action from a calmer, more aligned mental space. Next, return to your larger intentions. Consider how your action – the words you use, the decision you make, or the tone you use – will impact the larger picture of who you are and what you are contributing. Also, remember that this is just one piece of your 1000 piece puzzle. You want every piece to be present and as shiny as possible but there are so many other important pieces too, to who you are as well as your contributions. When you zoom out, you can see more clearly where this piece, in what shape or form, will fit in and then more skillfully dive back into the detail to take action. Finally, and most importantly, ask how you could act out of maximum compassion for others and yourself.

It’s a big step toward freedom to step back and choose to not make an immediate situation your whole life in that moment but make it a part of your whole life. When we practice zooming out instead of freaking out, we become a proactive leader of our work and our life. Zoom out, offer your best, and receive the benefits.

Thanks for reading! If you’re ready to begin your Awake Leadership journey, order your guidebook here.

Three Ways to Use Interactive Visualizations for Collaborating with Your Team


Visualization : a representation of an object, mental image, situation, or set of information as a physical chart or other image.

Do you ever find it difficult to communicate the status of a project, educate your team members on the context of the organization, or describe how a specific system or process works? In our growing, global society, visualizations have the power to educate faster and more elegantly than spoken or written word. They also have the power to more deeply convey what you are trying to communicate.

Visualizations serve as decision-making tools, communication tools, and educational tools. At work, we often use visualizations in the form of charts in a presentation, linear to-do lists on a white board, or maps from a software tool for analyzing and communicating phenomena going on in our organization. Visualizations often represent physical phenomena too large to see with the human eye or trends over time. In the more creative realms, we also use visualizations to communicate mental images or intangible things, similar to metaphor. However, visualizations are also crucial for leaders and team members to use for collaborative efforts.

In Awake Leadership, visualizations aren’t just bar charts and heat maps used to display what is going on at department meetings. Though they are valuable for that purpose, different types of visualizations have the power to cultivate collective understanding of the objectives, context, and progress of your team. If a picture is worth 1000 words, a well-made visualization is worth 1000 insights for enhanced collaboration, decision-making, and progress toward objectives. A lot of the time, we keep using the same models and methods for working through things. We make very linear to-do lists or plans for the week or for a project. Making these visualizations with your team is a powerful, interactive new way to problem solve, develop creativity, and cultivate deeper engagement. Here are three visualization examples from Awake Leadership guidebook exercises.

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Mind Mapping: Make Connections

Mind Mapping is a powerful visualization tool for understanding a topic, project, or team vision as well as a method for coming up with fresh ideas and approaches. I love to use mind mapping as a tool for brainstorming and planning a project or understanding a topic. Mind Mapping elegantly mirrors how the brain works in making connections and as we mind map a project or a topic, we naturally rewire our brain to think big. In section 1 and 4 of Awake Leadership, we use mind mapping to make your Vision Plan and optimize your team’s tool belt.  

Landscape: Put Your Work Into Context

Making a landscape of our organization’s physical network enables us to understand and connect with our larger purpose within the organization. We zoom out to appreciate how we fit into the big picture. The visual serves as a discussion point and we can begin to talk about what we want to change or what will change, why, and how to move forward. In the Context section of Awake Leadership, I guide you through making a map of your organization’s company network.

Block Diagrams: Show the Flow

Another favorite visualization of mine is a block diagram, which represents a process flow or how a system works. Block diagrams include the multiple components of a process connected sequentially. The connections represent a flow of information. There is also often a feedback loop. This visual can be used to describe to your team or leader how an ongoing process works for education or discussion about incremental improvement. In Awake Leadership, the diagram below describes how the Awake spiral staircase works, as you iterate the method and progress toward your objectives as a team.

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As famously noted many times: when we teach something to others, we often learn more ourselves. Many times, we have an idea stored in our head or we want to think through something but it’s stuck in our mental space. Getting it out on paper, on a white board, or out through art can help us to really think through what is going on, communicate it to others, and make a platform for brainstorming as a team. While working through the creation of a visualization, you often uncover important realizations and remove blind spots for yourself as well as your team members. As we work through making a visualization with the team, everyone will learn something new or uncover blind spots about their work. With collective understanding of the team’s vision, context, and processes, you can better work toward making informed decisions about how to improve or respond to change. If you can visualize it, you can understand it and you can make impactful, positive change. Do you use visualizations as a tool for setting objectives for your team, enabling collective understanding the organization, and communicating processes?

Thanks for reading! To learn more about how to lead your team through these visualization techniques step-by-step and to discover many more, order your Awake Leadership guidebook here and learn more about how to work through the guidebook here.

Simplifying to Scale: 5 Attributes of Scalable Systems


One definition of a system is…

A set of components organized and connected in an intentional way to achieve an objective.

Using this definition, systems can be products, services, or methods we use in our lives to serve a purpose. When you think about systems that have scaled to serve millions of people, what products or services do you think of?

What makes a system scalable? Why do some products and services scale successfully? Here are five attributes of scalable systems. I’ll use two modern examples to illustrate.

1 – Clear Purpose

A scalable system has a simple, clear purpose. It achieves an objective that is needed or adds value for the user. The purpose doesn’t have to be complex; it actually should be simple and still deeply meaningful.

In Amazon’s case, they focus in on getting any and all products to customers in the fastest time possible. In the case of a car, the objective is to travel to a new destination quickly and easily.

2 – Dependable

For a product or service to gain traction with many people, it also has to be functional at a low error rate in achieving the objective. It has to achieve that objective and fulfill its purpose without fail. If a system has a clear purpose but it can’t consistently achieve that purpose for people, people will not use it.

Amazon relentlessly works to deliver in 2 days or less. Though everyone has their fair share of car problems, no product or service is perfect, they meet the objective at a high success rate.

3 – Responsive & Adaptable

Scalable systems still achieve their objective despite the wide range of circumstances that can happen. When new policies, natural phenomena, new technology, or user changes occur, the leadership adapts the product quickly and effectively so the objective can still be met with equal or improved quality.

Amazon delivers to remote areas and difficult delivery circumstances. Car companies constantly add user-friendly features as the technology becomes available. By adding functionality that allows the system to work in a variety of circumstances, the system can function for many types of users seeking to achieve the same core objective.

4 – Easy to Use

A scalable system also has easy-to-use features and processes. The more complex a system is to use, the more likely people will not be able to use it or they won’t adopt it. Ease of use also involves clear communication about how to use the system. For products and services, clear communication is important in both marketing as well as user materials like directions for use and troubleshooting.

Amazon’s service is extremely easy to use. They have one-click ordering. Amazon makes it easy to get in touch with customer service. Cars have a manual and many local resources for education and policy. Cars have easy to use functions as well like breaks and shifts.

5 – Scalable Platform

Scalable systems also have a means of communication for reaching more users and a means for offering the system to more users – means for scaling! Users need to be able to find and use the product or service easily. The Internet makes it easier and more efficient to spread the message about a new system. However, you also have to have the ability to replicate the product or have a means for providing the service on a large scale.

In Amazon’s case, they have an Internet presence but their physical distribution network and labor force model has shown to be very successful in scaling. Car companies have developed manufacturing processes that make delivering products to customers efficient and scalable.

With all five attributes, you may notice that simplicity is key. It’s always tricky to find the balance between simplifying enough but not diluting the message or impact of the product or service. However, products that have successfully scaled have managed to figure it out. When we take the excess material out of our objectives, processes, and communications, we have space for responding to specific circumstances and for improving the product as new audiences emerge and global change unfolds.

What are your favorite scalable systems? Do they have these attributes?

Whether you’re seeking to a system – a business, a message, or whatever it may be – try thinking about your approach in terms of each of these attributes and identify where you’re approach could be stronger. I hope this helps.

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Thanks for reading!

For scalable solutions for your team operations and leadership development, read my new book, Awake Leadership.