18 Ways to Improve Your Project Management Skills as a Small Business Owner


When small business owners hear “project management,” it’s easy to also hear “more work.” As a small business owner, time is your greatest resource, and you’re accountable to your clients and employees for how you spend it.

But project management doesn’t always mean working more, it means working smarter. It can mean delivering projects on deadline, the first time. It can mean streamlining the proofing process, cutting down on the back and forth and actually getting the work done – on budget. Even if you don’t implement specific project management practices, applying project management skills in your own small business can lead to increased employee productivity and decreased costs.

1. If at first you don’t succeed, plan, plan, and plan again

Planning is the heart of project management. For small business owners, taking the time to plan out projects now will save your schedule, resources, and budget later. Think about what will really go into the work and what it will take to get there. Not just what you promised the client – but what it will truly require you and your team to accomplish.

Now is the time to sweat the details. The greatest enemy of good project management is deciding “we’ll cross that bridge when we come to it.” When you get there, are you going to be prepared for what you find? Do you know when a contractor can actually complete their portion of the project? Is a task really as simple as it seems, or will it take more employees to deliver? What about the timelines for supplies?

Practice asking and answering these questions realistically, and you’ll be on the path creating the right expectations for both employees and clients.

2. Focus on communication

A recent study found that two out of five projects don’t meet their original goals due to ineffective communications. You can plan as much as you’d like, but how are you going to share your plans with your employees and clients? Can clients expect status updates at specific times, instead of constantly emailing or calling about the job status? Instead of asking about their tasks for the day, can employees walk in knowing what’s expected of them and get right to work?

Experiment with the best ways to communicate with your clients and employees. It may require a weekly email or a morning in-person roundtable to discuss what’s on the list for the day. It may be handing off a paper checklist or keeping everything on the kitchen whiteboard. Once you find a communication strategy that works, integrate it into your project management process.

3. Find the right project management tools

Project management can look different for every team. A small coffee shop staff may need daily checklists written down and handed out while a design shop with remote contractors may require a cloud-based resource. However, more and more project management systems are trending digital, and your employees may want a way to check on morning supplies or schedules without calling in or coming in person to check the board.

Luckily, many project management solutions offer free trials so you can get a sense of what works for your team. Popular sites like Trello and Basecamp allow small teams to share updates and assign tasks on their phones. Instead of purchasing the latest app, take a few days to test out what your staff will actually use.

4. Establish firm goals or objectives

This may sound simple, but the keyword here is “firm.” From decreasing customer wait times to increasing the average order per customer, set hard numbers and stick to them. Make sure your employees know exactly what they’re aiming for, and what they’ll expect to walk away with when a project is labeled “done.”

5. Set yourself up for success with small wins

When setting these firm goals and objectives, don’t over-promise when there’s no chance to deliver. It can feel impossible to know where to start with a project that will eat up your entire next quarter, but it’s easier to manage a project when you know what has to be accomplished in the next two weeks compared to everything that has to be completed in the the next month. Set yourself and your team up for success with realistic deadlines and achievable wins along the way. Successfully planning out the entire project could be a small win in itself.

6. Understand (and embrace) the concept of MVP

In project management speak, MVP stands for minimum viable product, or the minimum amount of work necessary to get a product or service sellable and out the door. In the words of Eric Ries, founder of the lean startup movement, MVP “helps entrepreneurs start the process of learning as quickly as possible.”

Every small business owners knows that the hardest part is just getting started. By following the principles of MVP, instead of waiting and polishing your business to perfection, you should get your product on the market as soon as possible. That means sending your product out to consumers and requesting feedback even if it’s just a prototype.

For example, if you design websites for a living and spent an entire month tweaking a single website to perfection just to receive client feedback that forces you to start the project over entirely, you could’ve just sent the client an MVP version of the website. Your MVP would have fulfilled the client’s main requirements without any additional features, and you would have spent the rest of the month incorporating their feedback and refining the website until you delivered what they actually wanted. The goal here is getting the work done and learning through the process how to make your work better, instead of waiting on “perfect,” only to fall behind.   

7. Get things on paper

Ever had a conversation with an employee or a client, only to find out they meant something totally different than what they actually said? In project management, a paper trail is your greatest asset. Follow-up on verbal conversations with an email of clear takeaways and deliverables. If you decide to change the order of tasks or put a new employee on a different assignment, write it down. In fact, you might encourage all of your employees to write things down after meetings and share notes. What was communicated clearly? What was ambiguous? Who communicated with the client last, and what did they say?

By making sure everyone is keeping a trail of communication, decisions, expectations, and project requirements, you’ll build a culture of project management and ensure everyone is tracking their work. You won’t come to the end of a project and have to ask, “Well, when did this happen?” or confront an unhappy client claiming that the work wasn’t delivered as promised. You’ll be able to trace back in your notes and show if and why changes were made.

8. Examine your current productivity

If a project continues to be delayed, it’s time to find the weakest link in the chain. Is the person ordering supplies ordering them soon enough? Are you assigning the same tasks to people who may not be the best fit for the job? Are there manual processes that could be automated? Apps like If This Then That (IFTTT) can help with digital day-to-day tasks and increase productivity by updating and syncing new files, cataloging new email, and sending out reminders to your team automatically.

9. Choose the right people for the right jobs

When it comes to project management on a small team, it’s important to remember that everyone is a project manager. Everyone has to communicate and deliver work on time. Everyone has to work towards their small wins and the greater deadline.

Look for unexpected strengths in the people around you, and find the right people for the right tasks. Don’t put the person who always procrastinates in charge of enforcing deadlines. Maybe put the server who always arrives early in charge of updating the project board. If one of your baristas is a natural communicator and establishes an easy rapport with customers, assign them the responsibility of checking in with other team members and making sure everyone is communicating effectively. While you may be in charge of overall project management, make sure you’re assigning the right tasks to the right people for better productivity.

10. Keep clear and accessible schedules

Make it obvious when deadlines are due, when employees are assigned to work, and keep the schedule somewhere everyone can access it. That could be a white board in the office, a Google calendar, a Trello board, or a scheduling app like When I Work. Everyone should know exactly when their tasks should be completed, when they can expect next steps from others working on the project, and when they’re working next.

11. Ask for feedback

Did you know that the best leaders are the ones who ask for more feedback, more often? Asking for feedback isn’t a sign of weakness, it’s a strategic way to find out what’s working for your customers and employees. How are you going to know if you’re doing well if no one tells you otherwise? Ask for feedback at regular intervals – after implementing a new policy, training employees in a new software, or starting a new project management system. Formal project management may not be the best way your employees work. They may perform better when there’s more time spent on planning and not need the daily check-ins you believe are valuable. There’s no way to know for sure unless you ask.

12. Boost morale

As we said in the beginning, good project management doesn’t equal more work, it equals better work. However, not everyone may agree. People may be resistant to change and want to work the way they always have. Show your employees that project management can actually make their lives easier and celebrate each stage of the project management process. It can be as simple as thanking everyone for showing up to the meeting on time to planning rewards like free lunch around your small wins.

13. Set realistic expectations

Good planning, great communication, staying on budget, clear objectives, increased employee productivity – all of these are powered by realistic expectations. A good project manager knows that you can’t set your team up for success without first setting realistic expectations. You can’t provide great customer service if customers don’t know what to expect from you.

If customers reach out for updates, make sure they know when to expect communication back. If it’s going to take weeks to order new materials for a flooring project, build that into your planning process and don’t demand the impossible. Under promise, over deliver, every time.

14. Emphasize accountability

Project management thrives on everyone performing their roles and delivering their portion of work on time. As you divide up the work among your employees, it quickly becomes clear: everyone must be accountable for their share. Accountability doesn’t mean reporting on other employees for lack of progress. It also means identifying where they may be struggling and how and when to step in, which leads to…

15. Address problems early

No one likes conflict, and no one likes to be the bearer of bad news. Still, it’s always better to address issues now instead of later. If your deadlines are too aggressive, adjust your schedule. If you find out that you’re going to need to replace a sewer line on a job site, bring it up with the client and update the budget now.

It’s important to create a culture of problem-solving, not avoidance. Consider an open-door policy where employees feel comfortable reporting issues you may have missed or offering suggestions. Open the floor to potential problems at the beginning of every meeting.

Once problems are identified, decide who will be responsible for informing the client, who will be in charge of re-arranging schedules, and how everyone else will be notified of project updates.  

16. Organize your resources in one place

If your team needs to access client files, where do they go? You shouldn’t have to spend time emailing back and forth to chase down the latest version of a document or hunting down receipts in your glovebox. If you are, you could be wasting the equivalent of a full work day every week searching for information. Instead, save time by creating a clear filing system, whether digital or physical.

Google Drive and Dropbox offer free and paid file storage and sharing, and free apps like Shoeboxed can help track receipts and mileage on your phone. Most project management software also allows users to attach documents and edits to individual tasks. Like project planning, organizing resources may take more time on the front end, but will save you valuable time in the future.

17. Host project debriefs

After your latest project is completed, sit down by yourself or with your team and find out what worked and what didn’t. What could’ve been done better? Was the planning helpful, or should more have been done in a different stage? Did everyone have clear tasks? Did deadlines actually work, or require more time? What was done well that should be continued in the future? How did customers respond?

Set aside some time to work through these questions and find out how to incorporate them into the project management process next time. And if you’re already writing things down, you’ll have an ongoing record to check in and see how your project management skills have improved in the future.

18. Identify and embrace your strengths and weaknesses

To be a good project manager, it’s important to be honest with yourself about what you can and cannot do. Can you really hold morning staff meetings, or are you usually onsite with clients? Do you thrive at planning out projects, or is it better to leave the small details to someone else? Are you better on the phone vs. email? Would you rather spend more time doing the work instead of managing?

The more you know about yourself going into the project management process, the better manager you can be for your employees and the better service you can provide to your customers. If there are skills you need to learn, consider taking free classes or joining an online community of other small business owners. Find out if your employees have outside passions or experience they can contribute. In small business, everyone wears multiple hats, but some fit better than others.

18 Ways to Improve Your Project Management Skills as a Small Business Owner