Business Education

You’ve Missed the Tax Filing Deadline (Again) But That May be the Least of Your Problems

April 15th has come and gone. Now, you find yourself in a regrettable but familiar predicament. On one hand, it’s not like you’ve missed filing your taxes before the deadline, but on the other hand, you certainly don’t look forward to the pain and cost that come with missing the final filing date. Yet, this may be the least of your worries and long-term problems. If you are constantly missing deadlines while running your business, you’re inevitably disappointing clients, and it may not be too long before you don’t have any real business left.

How Small Business Owners Can Break the Bad Habit of Missing Deadlines

For small business owners, missing deadlines can erode trust, frustrate clients, and derail growth. The habit often stems from overcommitment, poor planning, distractions inherent in wearing multiple hats, or a combination. Breaking this bad habit requires intentional strategies that balance discipline with flexibility. Here’s how to get on track and deliver on promises consistently.

Understand the Why

First, identify why deadlines slip. Are you taking on too much? Underestimating task complexity? Getting sidetracked by urgent but unimportant tasks? Self-awareness is the foundation. Track your time for a week using a simple tool like a notebook or an app like Toggl. Note what derails you—client calls, social media, or perfectionism.

Recognizing patterns helps you target the root causes rather than just the symptoms. For example, a freelance graphic designer may notice missing deadlines due to hours spent tweaking designs beyond client requirements. Once the designer pinpointed perfectionism as the culprit, that entrepreneur could address it directly.

Set Realistic Commitments

Overpromising is a trap. When clients push for tight turnarounds, saying “Yes” to secure the job is tempting. But unrealistic timelines breed stress and subpar work. Practice saying, “Let me review my schedule and confirm what’s feasible.” This buys time to assess your capacity.

Use a calendar to map out existing commitments. Block off buffers—say, 20% more time than you think a task requires. If a project seems doable in five days, promise seven. This cushion absorbs unexpected delays, like a sick day or a client’s last-minute feedback. Clients appreciate reliability over speed.

Break Big Tasks into Small Chunks

Big projects can feel overwhelming, leading to procrastination. Split them into smaller, actionable steps. For instance, instead of “complete website redesign by Friday,” list tasks like “finalize homepage layout Monday” or “source images Tuesday.” Smaller goals feel achievable and keep the momentum going.

Tools like Trello or Asana can help. Create a board with columns for “To Do,” “In Progress,” and “Done.” Move tasks across as you complete them. The visual progress motivates and keeps you focused on what’s next rather than the whole mountain.

Prioritize Ruthlessly

Not all tasks are equal. The Eisenhower Matrix—sorting tasks by urgency and importance—can clarify what deserves your attention. Focus on what’s both urgent and important, like a client deliverable due tomorrow. Delegate or delay what’s less critical, like updating your portfolio.

Learn to say no. If a new request clashes with a deadline, politely decline or negotiate a later start. For example, “I’d love to help, but I’m booked until next week. Can we start then?” This preserves your bandwidth for existing commitments.

Use Time-Blocking

Time-blocking allocates specific hours to specific tasks. Each morning, plan your day. Assign, say, 9–11 a.m. for drafting a proposal and 1–2 p.m. for emails. Stick to these slots as if they’re meetings. Silence notifications and close irrelevant tabs to stay focused.

If distractions persist, try the Pomodoro Technique: work for 25 minutes, then take a 5-minute break. After four cycles, take a longer break. This structure harnesses short bursts of focus, making tasks less daunting. Apps like Focus@Will or Forest can reinforce this habit.

Communicate Proactively

If a deadline is at risk, don’t ghost. Reach out early with a clear update: “I’m finalizing your report but need an extra day to ensure quality. Is that okay?” Most clients appreciate transparency over silence. Regular check-ins—such as a quick email on project milestones—build trust and align expectations.

For instance; let’s again use the example of a designer, who started sending clients rough drafts midway through projects. The client’s feedback helped the designer stay on track, and the customer felt involved, reducing the designer’s stress about delivering the final product.

Build Accountability

Share your goals with someone—a mentor, peer, or even a client. External accountability adds pressure to follow through. Alternatively, join a mastermind group or online community of entrepreneurs. Regular check-ins with others facing similar challenges can inspire discipline.

You can also self-enforce accountability. Set reminders on your phone or use apps like Habitica, which gamifies task completion. Reward yourself for hitting deadlines—a coffee treat or an evening off. Positive reinforcement strengthens the habit.

Reflect and Adjust

Review what worked and didn’t at the end of each week. Did you overestimate your capacity? Did a tool help or hinder? Tweak your approach. You may need stricter time blocks or fewer meetings. Habits form through repetition, so small, consistent adjustments compound over time.

Breaking the cycle of missed deadlines isn’t about perfection—it’s about progress. By understanding your pitfalls, planning realistically, and staying disciplined, you’ll build a reputation for reliability. Clients will notice, stress will shrink, and your business will thrive.

Want to Accomplish More?

Do you want your company to grow faster and earn more while spending more time with your family doing everything you started your business to do?

We can make that dream a reality. Give us 30 minutes and we will show you how to get your life back. Skeptical? Good! Put us to the test.

You can call us for your free appointment at 480-636-1720, or, if you prefer, Waters Business Consulting Group to learn more about us and the services we offer.

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Help! My Dad Retired from the Family Business Years Ago but Still Tries to Run It and It’s Causing a Lot of Problems

March 31, 2022 No Comments

It can be difficult when a parent retires from their job within the family business but continues to act as if they are still in charge. They may make unnecessary demands or try to micro-manage things that are no longer their responsibility. This can cause tension and conflict among other family members who are trying to run the business smoothly. If you find yourself in this situation, it is important to set boundaries and communicate effectively with your parent. So, let’s discuss some tips for how to do that. The “Unable to Let Go” Syndrome Some people, be it a father, mother, or even another family member, who’s worked for long periods of time in a family business regard the company as part of their identity. It’s simply part of who they are and therefore, it’s not easy to walk away. It becomes even more difficult when handing the operation over to children, who don’t have all their years of experience. One of the most agonizing experiences that any business faces is moving from one generation of top management to the next. The problem is often most acute in family businesses, where the original entrepreneur hangs on as he watches others try to help manage or take over his business, while at the same time, his heirs feel overshadowed and frustrated. Paralleling the stages of family power are stages of company growth or of stagnation, and the smoothness with which one kind of transition is made often has a direct effect on the success of the other. —Harvard Business Review Unsurprisingly, this can easily lead to a father, mother, aunt, uncle, or even a cousin to hang around. Perhaps to the extent that he or she still continues to “run” the business, without the permission of their successors. He or she may make promises, enter into deals, or offer discounts that undermine the new authority of their successive family member(s). Of course, this can cause resentment, anger, frustration, and might also be the cause of unnecessary fighting and/or financial trouble. How to Deal with a Parent Who Keeps Interloping in a Family Business After Retiring Fortunately, if you’re in a situation where one or more of your family members has retired but still continues to interlope in the family business, there are steps you can take. First, you need to have a discussion with your parent about their role in the business now that they are retired. It is important to be respectful yet firm in this conversation. Explain to them that while you value their opinion, they need to respect the fact that you are now running the business. This means that they should not try to make decisions or give orders without consulting with you first. You may also want to set some ground rules about how often they can come into the office or participate in business meetings. It is also important to stay calm and avoid getting into arguments with your parent. If they continue to try and take control, it will only escalate the situation and make it more difficult to resolve. Instead, try to have a rational and calm discussion about the situation. If necessary, you may need to involve other family members or even a mediator to help resolve the situation. Additionally, it may be necessary to speak privately with any customers who aren’t completely clear about who is actually running the company and who makes the decisions. This could help in the future with communication and in other important areas. If you find yourself in this situation, it is important to set boundaries and communicate effectively with your parent. By doing so, you can hopefully avoid conflict and maintain a healthy relationship with your parent. Have you ever dealt with this type of situation? What would you do to resolve it? Please take a moment to share your experiences and thoughts so others can benefit from your input. Interested in learning more about business? Then just visit Waters Business Consulting Group.

How to Deal with a Client Who Keeps Breaking their Promises

September 3, 2020 No Comments

What do you do with a client who keeps breaking their promises? It’s certainly not an easy problem to solve. And, even more difficult when you come to the realization you’re a bigger part of the issue than you originally thought. As is the case with so many complicated circumstances, you probably share a good amount of fault. That isn’t to excuse the promise-breaker. But, it does serve as a reminder that it takes two people to take responsibility. About Promise-Breaking Clients It’s a more common phenomenon that you might believe. Not that it’s justified or even reasonably expected. However, clients have many reasons why — yes, some are excuses — for not following through with their word. It could be something beyond their control. Or, just a change of heart (and perhaps, circumstances). It’s an old rule of life that we teach people how to treat us. Yet often we can struggle when it comes to managing accountability and calling people on broken promises. It just feels like less stress to say nothing; even to just do it ourselves. But here’s the deal: when you decide not to call someone on their broken promise and ill-managed commitment, you’re, albeit inadvertently, being part of the problem. —Forbes.com Regardless of how often it happens, it does happen. So, that’s something you should be prepared for, because eventually, you’ll run into it. Usually, it’s not out of malice or selfishness, but rather, unrealistic expectations. When it does happen, you should know how to respond. How to Deal with a Client Who Keeps Breaking their Promises There’s an old saying in the real estate sales industry, “Buyers are liars.” It comes from a modicum of truth, but is obviously more of an exaggeration. Although, it does point out how people tend to embellish or overstate their resources and intentions. If you have a client who doesn’t always follow through on his or her promises, try these suggestions: Remind them. The first time won’t be the last. So, let him or her know what you expected and that you’ll expect them to deliver in the future. You don’t have to be rude, just stern but kind. If you show you’re willing to call them out, he or she will be less likely to do the same again. Don’t make up for them. It’s tempting to pick up the slack yourself but that rewards their behavior by avoiding consequences. After all, you value your reputation and take pride in your work. So, you make up for the short fall. But, this will only backfire. You’re only teaching him or her you’re always there to make things right. So, they don’t have to worry about it. That will only lead to more trouble. Don’t stay vulnerable. This is the most difficult, though it’s sometimes unavoidable. If it happens more than once and you don’t say anything, expect it to keep happening. Conversely, if you let them know you’re not going to tolerate his or her behavior, you can help break the cycle. What other suggestions do you have for dealing with a client who breaks their promises? Please share your thoughts and experiences by commenting! Interested in learning more about business? Then just visit Waters Business Consulting Group.

3 Biggest Signs of Early Startup Success

June 28, 2018 No Comments

It’s not always easy to know where you stand. Sure, you’ve made it this far and there doesn’t appear to be any big trouble on the horizon. In fact, things are going quite well. Yet, you wonder if it’s just a matter of perception. Or, is your startup really going to make it? Well, there is no guarantee. But, that certainly doesn’t mean you can’t size the situation up at all. There are a few ways to tell if your startup is on its way to success. Why Most Startups Fail Of course, you should first know what causes most startups to fail. Perhaps the largest reason is they run out of cash. Investors only give so much, both in money and time. If you’re burning through cash and there’s little or no profit, you’re obviously running a really big risk of going out of business. Another reason startups fail is due to a lack of clear strategy. Put another way, they don’t know the way and don’t have a concrete idea of how to go from one goal to another. Most startups fail. But there is a common thread among some of the most successful startups: Consumers, not investors or tech blogs, find them first. A few examples: Facebook, Instagram, Pinterest, Most recently: Snapchat. —Business Insider.com Then, there’s tons of bad advice. It’s out there and if you take the wrong advice, you’ll probably see the consequences quickly. That’s your chance to act and change course to make it a lesson learned. Another reason why startups fail is the market moves in an unexpected way. They just aren’t prepared for contingencies. Or, fail to make necessary adjustments when needed. 3 Biggest Signs of Early Startup Success But, how do you know when you’re on the right track? What tells you that things are not only going well, but likely to continue in a good direction? Here are the three biggest signs of early startup success to lookout for: Positive cash flow. It’s no mistake the first factor in failure is due to lack of cash. If your company is bringing in cash and making a profit (that is, your intake minus your expenses), then you’re definitely off to a good start. Customers find you. Take a quick look at the quote above and let that thought sink in for a moment. If customers are finding you without you having to identify and chase them down, you’re fulfilling a crucial need and that’s a really good thing. Rhythmic, rock solid team. Another sign a startup is on the right path is when it’s crew recognizes they work well together and work toward goals as a team for the good of all. It means the right people are in the right positions and that’s a huge factor in success. What other signs signal a startup will succeed? Or, what might happen which means there’s trouble ahead? Please share you thoughts and experiences by commenting! Interested in learning more about business? Then just visit Waters Business Consulting Group.