What We’d Be Working On If I Were Your COO: Mid-Year Edition

Welcome to the 2021 Q2 Edition of, “What We’d Be Working on If I Were Your COO.” 

At the close of each quarter, I’ll guide you through the exact processes and reflections I work on with my COO clients throughout the year. You can expect actionable guidance, deep reflection, and ways to enhance your business systems to reach your goals. 

Curious about what we’ve covered so far? Check out the 2020 Q4, 2021 Q1 and 2021 Q3 blogs.

Believe it or not, we are smack in the middle of the year! It’s the end of Q2 and we’re looking ahead to all the possibilities Q3 has in store. 

Naturally, business tends to slow a bit in the summer months. It’s the perfect opportunity to assess what is and is not working in your business. You can take time to track your progress as you work towards those ambitious, but totally doable, goals you set way back in January

At this point in the year, I focus on three things with all of my COO clients. We work together to carve out time for the following objectives:

  1. Mid-year Check-ins
  2. Time Off
  3. Client Outreach

In this Quarter’s installment of, “What We’d Be Working on If I Were Your COO”, I’ll guide you through my step-by-step process. You’ll walk away from this post feeling ready to evaluate your business, set aside time off, and connect with your clients. 

Plus, if you stick around to the end of this post you’ll get a BONUS tip! This is one of the most important tasks I recommend all my clients do every single quarter! 

#1 Mid-year Check-in

It’s important to check up on your business regularly. But nothing is more important, in my opinion, than the mid-year check-in (except maybe the end of year recap and setup for the next year)! It may be hard to believe but we are halfway through the year! 

At this point, you’ll probably be happy to find that some of your goals have indeed been accomplished and some milestones are flourishing as you move closer to those long-term goals.

Unfortunately, you might also notice that a few of those things you prioritized back in January have been set on the back burner for quite some time now. 

You are human. 

Give yourself grace.

Let’s move forward!

The good news is, this check-in process will help you reflect on your goals while also giving you permission to reset and re-establish your priorities. 

Things change after all. 

A goal you set in January and forgot about by March might be an afterthought for a REASON. 9 out of 10 times it’s because that goal no longer aligns with your business and the direction you’re headed NOW. 

That is TOTALLY okay. 

On the other hand, sometimes those really challenging goals ARE important but may feel daunting. As a result, we tend to avoid these tasks. This mid-year reflection will help you get real with yourself so you can tackle the sticky stuff or consider outsourcing support. Either way, you’ll be able to push forward towards your business vision. 


Let’s dig into evaluating the goals you set in Q1. I coach my clients to do this with the following method: Review, Measure, and Refine. 


Most people fall into two goal-setting categories. If you’re in the first camp, you might have laser-vision focus on one specific goal. But, along the way you’ve forgotten about all the rest.  If you’re in the second group,  you’re a “set it and forget it” kind of goal-setter. Either way, it is completely normal to stray away from some of the goals you set in January. This is your opportunity to hit the pause button. 

I like to review by pulling up my goals one at a time and asking the following questions (you can even use these as journaling prompts):

  1. Would you set this goal today? If not, why? 
  1. Does this goal still align with your vision for the future?
  1. Have your motivations changed since setting this goal?
  1. Have you made progress towards this goal? Why or why not?
  1. Do you still feel strongly motivated to achieve this goal?

These five questions will help you identify what you have or have not focused on consistently in Q1 and Q2. With this insight, you can move on to the measure and refine phases of your Mid-Year Check-in to prepare for Q3.


Now that you have an idea of which goals are and are not serving the current state of your business, you will want to assess each of them. While the review process you completed was more qualitative, the measurement phase should be more quantitative. Set the feelings aside for a moment and let cold, hard data lead the way!

First: Pull your numbers and get friendly with your finances. Look at your income and spending patterns as well as your Key Performance Indicators (KPIs). This will give you an idea of how far you’ve come and how far you still have to go!

Second: Think about your milestones. What milestones have you hit on your path to reaching these goals? How many more milestones do you need to reach? How far are you from reaching them?

Third: Check your momentum. Are you hitting milestones faster or slower than expected? Are your numbers stronger or weaker than you hoped? Are you creating momentum to propel yourself towards your goal, or are you getting in your own way somehow?

Fourth: You now have a clear picture of your progress. Be sure to take a minute to celebrate and acknowledge how far you’ve come! 

COO Tip: Celebrating the little wins along the way will motivate you to keep going!


Once you’ve reviewed and measured your goals, you can easily see which ones stuck and which ones were put to the side. You can think of the last step, refine, like dejunking your house. 

We’ve all encountered that moment. The moment when the storage closet is overflowing and those pretty bins you bought at the Container Store can no longer contain the chaos of STUFF spilling off the shelves. The mess has been hidden behind that closet door for too long. You know it’s time to purge.

So you start to sort your items into a “keep” pile and a “toss” pile. 

Some things are easy to categorize, but others are harder to define. The keep pile tends to include obvious, nostalgic items like my daughter’s first baby shoes or practical items like scissors.

The toss pile is trickier. That shiny red handbag I LOVED 10 years ago but never use anymore is hard to part with. I reason with myself:

 “It was expensive, I can’t just get rid of it…” 

“Maybe the style will come back in 5 more years…”

“One day I’ll finally find the right shoes to wear with it…”

But when I get honest with myself, I know that those explanations are lies. 

The truth is: the handbag’s just not my style anymore. 

So it’s been sitting there collecting dust and taking up space! When I can finally let it go, I’ll create more space for something that DOES serve me.

We can think of our goals in a similar way. As you sort through your goals, think about what you’d like to “keep” and what would feel better to “toss”.

Keep Pile

Take a look at the goals that still feel aligned to your current business needs on an emotional and practical level. See if you can make these goals more actionable or clear. I love using S.M.A.R.T. goals. Ask yourself if your goals are:

  • Specific – Be as clear as possible. Instead of saying, “my goal is to have more retainer clients” you can specify, “my goal is to have 3 new 6-month retainer clients by the end of September.”
  • Measurable – How will you know when your goal is achieved? This should be data that can be assessed quantitatively with numbers.
  • Attainable – Work towards something challenging, but don’t expect to take over the world in a day! 
  • Realistic – Be honest with yourself about what you and your team are capable of.  Be sure to set yourself up for success. Be honest with yourself about the challenges you will likely encounter on the way to this goal. 
  • Time-bound – Give yourself a deadline. Try not to be wishy-washy about your timeline. Consider the steps and how long you anticipate each piece will take.

Toss Pile

Next, look at the goals that fell to the wayside. They may have felt right 6 months ago, but today they don’t feel quite the same. You will want to look at each one and decide to either discard the goal or refine it. 

I like to think of refining goals as “repurposing” to better align with your new vision or reality. We tend to think of repurposing physical items more than we do ideas. 

That rusty bike in your garage could be repurposed into a neat flower planter! 

Likewise, those goals may just need to be re-worked with a creative perspective to fit your current state.

Systems & Processes

Now that you have spent time realigning with your big picture goals, it’s time to hone in on the building block of any successful business: the systems and processes that make it all possible!

Take some time to make sure the systems and processes you have in place are still working well for you and your team. 

Systems and processes go hand-in-hand. A system is an overall course of action you take regularly as you work towards a specific goal in your business.  It is made up of processes, or steps, that support the system so it can work more effectively. When it comes to workflows in your business you will want to improve your systems and processes by automating, systematizing wherever you can, and documenting.


When it comes to systems and processes, I like to automate as much as possible so that everything flows well. This prevents human error or forgetfulness! Plus, it takes things off your plate so you can stay in your zone of genius. Systems encompass anything from workflows, automation, software, or technology.

The start of Q3 is a great time to look at your tasks and see what can be automated in your business. Optimize your time by automating as many systems as possible such as email, scheduling, and capturing client inquiries.

Identify Patterns

You can (and should!) systematize anything and everything in your business that happens on a recurring basis, whether it’s annually, quarterly, monthly, or even daily. Take time to notice these rhythms of your business. This will help you to identify the systems you need so you can create processes that support it and keep it running!

Some systems and processes to consider…

  • How you are measuring and managing your business finances
  • Your marketing plan and any content creation you are doing
  • How you are managing your clients, projects, and partnerships

If you don’t have the right systems in place, you are working way harder than necessary! Stick to the tried and true motto, “work smarter, not harder!” 

If you’re not sure where to begin when it comes to setting up your systems, I created this freebie to get you started! It outlines the 3 systems you NEED to have in place to run your business efficiently and make it happen!


I notice many entrepreneurs skip over this part and overlook establishing their business processes. A lot of times you may have everything in your head, but it’s important to document as you grow and expand so that small pieces don’t fall between the cracks

This documentation is called a Standard Operating Procedure or SOP. Creating an SOP will make it easier to hand off tasks to team members without skipping a beat!

In addition, taking the time to establish your processes can keep you from having to duct tape things together on the fly. 

Don’t reinvent the wheel!

There is most likely a process and procedure for most parts of your business out there already. You can simply utilize what other people do in their businesses and customize it to fit your particular needs. 


Midway through the year is a great time for reviews and check-ins with any team members. I coach my COO clients to focus on the following pieces as they conduct reviews with their team members:

  1. Assess their work. Take time to look at the quality of their work so that you can intentionally build a growth plan with each member of your team. This will ensure that you are helping them grow in an appropriate direction. Without taking the time to genuinely reflect on their skills and room for improvement, you may be blindly building their skill sets on shaky ground. This part of the review will help you create a strong, intentional foundation.

  1. Review their workload. This is a great time to look at the kinds of tasks and responsibilities your team members are responsible for. Do they have the capacity to take on more? Are they feeling overwhelmed with their current workload? 

  1. Plan areas of growth. Take this opportunity to figure out where each of your team members is looking to grow. Consider how you can both support one another and the business in the months ahead.  This is an opportunity for you to be transparent about the vision you have for this role and how this person can support your business goals. At the same time, it will make sure that what you have in mind aligns with your team member’s professional goals. 

Don’t have a team yet? You can give yourself a review too! Consider your strengths and where you have room for growth. This is great practice for the future as well in case you DO decide to bring on team members.

#2 Prep for some mid-year time away

Vacation time

I’ve said it before and I’ll say it again, “rest is productive!”

I encourage all entrepreneurs to prioritize time off. This is a non-negotiable for me and my own business. Summer is the perfect time to step away. You may even have a vacation planned already! The problem is, so many of us struggle to truly be away from our business for a set amount of time. 

It can feel scary if you’ve never done it before. However, with the right systems and planning in place, you really can enjoy a vacation without ever checking an email or taking a client call at the beach. You can do all this while still serving your clients well and maintaining momentum in your business.

If you’d like to learn more about the systems I use to vacation without the stress or guilt, check out my blog post, “The 5 Essentials Every Entrepreneur Needs For an Unplugged Vacation.”

CEO time 

In addition to vacation time, I believe it is so essential to take some intentional time away from your day-to-day business tasks. This is called “CEO Time”.

Put away the other hats you wear on a regular basis: the social media manager hat, the copywriter hat, the customer service rep hat. Hang them up for a bit. The only hat you need is your CEO hat.

“CEO Time” is a block of time that you carve out to focus on the big picture of your business. You put aside the regular daily tasks and embody the role of Chief Executive Officer.  Let’s break down when, why, and how to take CEO time.


You can take CEO time whenever you’d like, but I’ve noticed it can be especially impactful after a restful vacation. You’ve relaxed, recharged, and you now have the energy to jump back into your business. You have also given yourself a bit of distance from your work. With that comes a new perspective that you simply can’t find when you’re living in your business 24/7/365. 

It is also beneficial to take CEO time once you have already completed your mid-year check-in. You are aware of the state of your business and can dream about the future with eyes wide open.


CEO time will allow you to:

  • be creative without distraction
  • dream big 
  • realign your vision for the year & beyond
  • check-in with yourself

This is a time to reflect on your business to ensure your business is still serving you, aligning with your values, and serving your clients in the way you want!


Many entrepreneurs feel overwhelmed when I suggest they take MORE time away from their daily business routines. 

“But I just took off for vacation! How can I be away from the day-to-day of my business AGAIN?!”

Think of CEO time as an investment. You are working on your business, not in your business. It is a time investment now that will pay off in the long run. 

Plus, CEO time can look however you want it to look! It could be as quick as a day or even as long as a week. But, no matter what you choose, boundaries on your CEO time are essential!

No client calls. 

No day-to-day stuff.

Only big picture planning. 

This is your time to reflect on the business you’re building, clients you’re serving, and services you’re promoting so that you can step back into your work feeling confident that all the moving pieces are aligned and feeling good. 

You can step away for some CEO time by:

  • Automating Systems
  • Delegating tasks to team members
  • Communicating your availability early and often 

When you come back to your regular tasks, you’ll feel inspired, ambitious, and focused on the next chapter in your entrepreneurial journey.

#3 Mid-Year Client Outreach

I am a huge advocate of client experience and mid-year is a perfect time to tend to these partnerships. I encourage all business owners to make time for client outreach during this slower season. 

Strategic Partner > Transactional Relationship

I love buying fresh flowers. 

They brighten up my home and make me smile when I see them set on the kitchen counter each morning. A friend of mine was recently telling me about her favorite place to buy flowers. It’s a flower truck that camps out at local coffee shops in her neighborhood! 

They have a wide variety of unique flowers. Plus, you can build your own floral arrangement with the help of a seasoned floral designer. They ask you questions and consider your preferences to help you pull your favorite hues together into a stunning piece of art you can take home or gift to someone special. 

This friend has also bought flowers from the grocery store, as we all have at one point or another. 

Here, she might stumble upon a nice, pre-made arrangement. She may not have chosen the individual flowers herself, but it’s fine. She scans the plastic wrap at the register and the transaction is done. 

But now that she knows flower buying can be an experience, she goes out of her way and is willing to spend a little bit more, to find out where the flower truck is parked that day. She looks forward to the custom experience and care. 

As business owners, it is our goal to be like the flower truck and less like the generic grocery store floral department.

How to Get Client Feedback

To show your clients that you are invested in being a strategic partner for their business needs, you’ll want to initiate a dialogue. This is a great time to chat with current and past clients about their experiences working with you. 

This could be something as simple as a digital survey, or as personal as taking them out for lunch! No matter the format, this is your opportunity to collect data, listen deeply, and ask the right questions. 

You’ll gather information about their hopes, goals, challenges, and dreams so you can create new offerings, extend contracts, and expand the scope of your work together.

In order to build a sustainable business you need to retain your clients. It is better to keep and nurture the clients you already have than exert additional time, energy, and resources to constantly recruit new clients. I wholeheartedly believe that Retention and Referrals = Revenue! You can learn more about the 3 Rs of growing your business here.

Always think about how you can serve your clients in the future and what you can do for them next. As you build your products and services, be thinking about what the next phase of their journey will be so you can anticipate the kind of support you can offer. 

What Questions to Ask

In order to become a strategic partner for your clients you need to be a good listener, but most importantly, you need to ask the right questions! You’ll want to dig deep to find out what their goals and dreams are so that you might support them through new offerings, extending a contract, or expanding the scope of your work together. 

I always recommend entrepreneurs ask their clients these questions:

  1. What are your current pain points and challenges?
  1. Where are you seeing the most growth?
  1.  What are your 3-month and 6-month goals?
  1. What new projects or services do you have on the horizon?

Once you’ve taken inventory of their business growing pains and goals, you can offer solutions. 

This is where you jump in and say, “Here’s how I can help you achieve your goals and dreams. This is how my team and I can support you along the way.”

Not only will your client be in awe of your ability to anticipate their needs and solve problems before they even become an issue, but your own business will benefit as well! As a business owner, client outreach can provide you with the security and stability you need to run a business with predictable revenue. 

Instead of constantly searching for new leads and clients, nurture the people you already have a relationship with. Continue to pour into them and find creative solutions to the things that are holding them back from the success they are striving to achieve.

# 4 Bonus Tip: Audit Your Evergreen Content

Audit your evergreen content each quarter. By definition, evergreen content is fresh, relevant information across your digital spaces. 

What happens all too often, however, is we create evergreen content that becomes outdated. If we don’t come back to our content to refresh it on a regular basis, we are essentially asking for trouble. Our messaging becomes confusing, pricing may not be accurate, and our services may change. 

Here are the most important evergreen content pieces to update each quarter:

  1. Website and Landing Pages. Be sure to pay special attention to your services and products pages to make sure you still offer everything listed. In addition, all new services and products should be included. If any prices are listed, they should match across platforms and reflect your current rates. You’ll also want to check that you don’t have any broken links on your page.

  1. Social Profiles and Bios. As your business grows, your title or niche may change, even if just slightly. Your bios should be clear and should represent your business in its current state so that your ideal audience can find you!

  1. Blog Posts. As you learn new information or adjust your beliefs, you may want to go back and update your blogs. In addition, as your blog grows, you can backlink to previous articles. This is great for SEO and will help your readers find additional resources that you’ve already created.

  1. Courses. If you offer courses as part of your product suite they must reflect best practices and cutting-edge information. New features or modules will entice new customers and will also be a wonderful surprise for people who bought your course in the past and have lifetime access. It may even remind them to reach out to you or check out other products in your suite so they can continue through the customer journey you’ve laid out.

  1. Emails. Take time to update your email sequences and automated messages so that they are accurate and speak to the current state of your business. 

  1. Schedulers. Your availability will likely change over the course of 6 months or a year. Check on your scheduler like Calendly is synced with your Google calendar. You’ll also want to update your hours of availability so that you don’t have to worry about being double-booked. 

  1. Team Members. Double-check that all employee lists and titles are up to date on all platforms. Any time there are changes in your team it’s important to update who is and is not a part of your business.

  1. Messaging. Across any and all platforms pay attention to how you talk about your business. Brand messaging should be consistent. If you have a team, take care to provide them with this information so that everyone is representing your company with intention and transparency.

Reviewing all of your evergreen content can feel overwhelming all at once. That’s why doing this once a quarter makes it so much easier to flag! And since you know I love systems, I also suggest setting up systems and processes to support this evaluation.

Let’s Sum It Up

You now have all of the tools you need to reset and feel confident stepping into the second half of the year. The beginning of Q3 is the perfect time to conduct a mid-year check-in, take time off for a vacation AND CEO time, reconnect with your clients to stay on the pulse of their needs, and refresh your evergreen content. 

These are all the things I do at this point of the year with my COO clients. If you have questions as you move through the process, please reach out. 

I offer free strategy sessions and would love to support you as you make Q3 your most impactful quarter yet!

  1. […] COO Tip: I am a huge fan of taking CEO Time for this type of strategic brainstorming. This is time you carve out to wear your CEO hat.  I love to leverage this time for vision planning or to assess big picture systems and operations outside of the day-to-day of my business. If you want to learn more about how taking CEO time can give you the space and clarity you need to set healthy rhythms in your business, check out this blog post.  […]

  2. […] about what we’ve covered so far? Check out the 2020 Q4, 2021 Q2 and 2021 Q3 […]

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