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11 Questions To Cover During a Midyear Check-In
by Brett Farmiloe
January 26, 2023
Two people sitting at an office desk laughing

As a business owner, what is one question you should ask yourself during a midyear check-in to best prepare for the next half of the year? 

To help you ask yourself the right questions for proper midyear check-ins of your business, we asked entrepreneurs and CEOs this question for their best insights. From “How am I doing with my short and long-term goals?" to "Who are my top-performing  employees to reward?" - there are several critical questions for the midyear evaluation of your business plans may help you steer things in the right direction for growth. 

How Am I Doing With My Short and Long Term Goals?

At the start of each year, I always recommend creating both 12-month goals to aim to achieve by the end of the year, as well as shorter-term  ones. Whether you choose to make objectives to be done at the three- or six-month mark, they offer an excellent opportunity to tick off smaller steps in pursuit of your overall annual goals. This means that the year's halfway point  is an excellent time to ask yourself how you've progressed towards reaching these. In particular, if you haven't achieved your shorter-term goals, take the time to consider why so you can make adjustments accordingly. You should also see if your shorter-term achievements are still putting you on track to reach those annual goals to ensure that your objectives for the second half of the year are setting you up for success.

Anna Barker, LogicalDollar

Am I Taking My Best Customers for Granted?

Midyear is the perfect time to make sure you check in with your best customers. It's critical to reinforce that you're not taking them for granted. Share plans for new products or new initiatives scheduled for the second half of the year. Listen to their concerns and recommendations. Make your most valuable customers feel like part of your team. Drill down on their business to see if they’re meeting their numbers. What can you do to help? Let them tell you what adjustments you can make to help them succeed. A midyear check-in is a valuable tool for feedback and improved retention. Don’t squander the opportunity.

Joshua Chin, Chronos

Does My Performance Meet Expectations?

Take a realistic look at your beginning projections and ask yourself honestly if your expectations meet the reality of your business’s performance. Think of your business plan for the year less like a “to-do list” where you can check off accomplishments as they come and more like a game of chess. As the dynamics of your business change from external factors you have no control over, so should your goals and strategy to control how you respond to them. Remember, no battle plan survives first contact with the enemy; get a realistic view of where you are and adjust.

Jason Reposa, Good Feels

How Effectively Are We Reaching and Gaining Customers?

One thing business owners should prioritize during mid-year check-ins is to focus on critical KPIs, namely new customer acquisition. This indicator provides you with essential insight to ramp up marketing efforts and ultimately result in more optimized strategies. Additionally, it’s helpful to reach prospects with the same potential value as existing customers by engaging in social media campaigns. Genuine and effective efforts to build comprehensive relationships with customers is key to a business owner’s success. An effective look at new customer acquisition puts in perspective the scope at which you may have to adjust strategies to better set your business up for success for the next half of the year.

Michelle Arnau, Rowan

Who Are My Top Performing Employees To Reward?

"Among the team members, who contributed the most and worked the hardest?"  

While thanking you and your team for a job well done in the first six months is good on its own, you can take an extra step by acknowledging and rewarding the top performers. This question is an excellent introspection for business owners to determine the most hardworking employees and rightfully reward them. It sets them up to do better in the second half of the year while motivating the rest of the team to do the same thing, creating a healthy workplace competition to your business's benefit.

Georgia McBroom, Camper FAQS

What New Relationships Have I Developed?

New relationships are a sign of new business opportunities. So ask yourself, "What new relationships have I created?" allows you to evaluate the success of your outreach efforts for the year. You can round up your marketing and sales teams and strategize ways to nurture those new associations into beneficial partnerships. Your connections could blossom into promotions or collaborations that help scale your business within the next six months. On the other hand, if you struggle to answer that question, you may want to invest more resources into professional networking throughout the next couple of quarters.

Stephan Baldwin, Assisted Living Center

Can My Business Survive an Immediate Financial Emergency?

Because of the work, I do with small businesses looking to obtain capital, I can say that a midyear check-in can help you avoid financial or logistical emergencies. If you can only ask yourself one question, it's this: could my business survive an immediate financial emergency? This is essentially contingency planning, and after the pandemic, we have seen that you can never be too careful. If you don't have access to capital immediately for emergencies, your business will flounder. You don't want a broken coffee machine or lack of employees to be why you can't afford to stay open. 

Many of the businesses I work with could have had less urgency to their financial worries if they had done a mid-year review of their access to usable capital.

Gates Little, altLINE Sobanco

Are My Employees On Track With Their Own Goals?

Are you doing enough to assist your employees in reaching their year-long objectives? As a business owner or a CEO, it's easy to forget that your employees often have just as many personal work goals as you do. Creating a healthy, productive work environment that provides a gratifying experience of employment involves assisting employees to achieve their growth. That can’t happen if you don’t have a strong understanding of what their goals are. Around the midyear, consider reaching out to your employees to check their progress on their own goals and ask whether they’re receiving everything from you and the company that’s needed to achieve them.

Alex Wang, Ember Fund

What Mistakes Am I Making So Far?

Asking yourself what mistakes you made in your midyear check-in is one of the best ways to have a positive next half of the year. What did you learn from customer experience, and how do we implement those changes? How is the team’s time management? Did we lose any opportunities because we weren’t efficient enough? How are we growing and evolving as a company? Were there any setbacks due to life under coronavirus restrictions, and should we implement an education service or program to get everyone on the same page? Mistakes happen. We’re all human. But being upfront with yourself about those mistakes and learning from them is a great way to adjust midyear and set your company up for a successful second half.

Tony Staehelin, Benable

What Learning Opportunities Did I Take Advantage of?

Reflecting on the last six months of work, it is valuable to ask yourself a question that relates to learning. Think about  “What learning opportunities did I take advantage of? Were there any that I missed?.” This question allows you to keep track of your personal and work development. By identifying the learning opportunities that you have taken advantage of, you are ensuring that you are constantly moving forward. Pointing out the opportunities you missed and justifying them, in turn, allows you to adjust your development goals for the next six months. As a result, your progress is conscious, and you are sure that you are not standing still (which is the worst thing you can do for yourself and your business).

Nina Paczka, MyPerfectResume

How Can I Improve My Social Media Strategy?

An effective social media strategy is a year-round endeavor. A midyear check-in is an excellent time to evaluate your business’s strategy and key metrics to make adjustments if needed. Social media must be part of your marketing strategy, so it's critical to take the time to develop an effective plan to optimize your reach. A lot can happen in half a year to warrant changes in your strategy  - industry trends change, priorities shift, business fluctuation, and previous tactics may have simply proven ineffective. Take advantage of a midyear check-in to reassess, retool, and refine your social media strategy in preparation for a successful run in the next half of the year.

Ray Leon, Pet Insurance Review

About the author
Brett Farmiloe
Brett Farmiloe
Brett Farmiloe is the Founder & CEO of Featured, an expert insights network that connects subject matter experts with publishers to create Q&A content.
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