B. Check your Team’s Progress

Check Progress Without Micromanaging


Now that you’ve delegated projects and tasks to your remote contractor – how do you help your team reach the desired outcomes? What’s the best way to support and ensure they are on track?  How to do all of this from a distance? 

Let’s begin by examining your perspective on productivity of people who aren’t working in the office. 

Even if you trust your team, do you ponder on the following?

  1. What are they doing?
  2. Are they accomplishing anything?
  3. Are they distracted working from home or wherever they are working?
  4. Are they working too much?

If these questions are at the top of your mind as you track your remote worker’s progress, you might be focusing on activity instead of accomplishment. Clarify what is more important for you: are people working hard, or is quality work getting done on time?

By focusing on the results and outcomes, you may find it easier to adopt the strategies presented below and gain a new perspective on the productivity of remote teams.


Use Simple Daily Stand-Ups

The work of progress-tracking begins from the moment you set your goals and identify key milestones. But after you have agreed on the goals, expectations, and success criteria, it’s time to execute the plan. There is no right way to go about this, and it mostly depends on your management style and your remote team’s needs. While it is tempting for new remote leaders to micromanage their way to productivity, it doesn’t have to be the case. 

But, how does one get consistent updates without micromanaging the team? First, share the responsibility of monitoring progress with your team. Be clear that they shouldn’t wait for you to ask before they give updates or report obstacles in the way. 

Make progress-check a daily activity by using Stand Ups. 


What are Daily Stand-Ups?

Daily Stand-Ups are very short meetings lasting around 10-15 minutes. It is an effective strategy for synchronizing teams working on shared goals. Pick the same time and day to meet for each stand-up meeting. For remote teams, it’s best to use video conferencing with the ability to share project boards or pages (where goals and tasks are listed). Try to make the most of it by connecting with your colleagues. 

Team members are given 1 to 3 minutes to share their wins, struggles and plans.  Some teams even literally stand up to make it quick and intense, even while they are on a video call. 

So, when does one conduct these? Most prefer it at the start of the day but you can also choose to have it at the end of the day. Take a look at the sample templates below. 

Template #1 – Start of the Day

Template #2 – End of the Day

Template #3 – Start of the Day

  1. What did you work on yesterday?
  2. What will you do today?
  3. Are there any impediments in your way?
  1. What’s your victory for today?  
  2. Is there anything that is slowing you down?
  3. What’s your plan for tomorrow?
Choose a backlog item or a delayed task.

  1. What did you accomplish for this?
  2. What will you do next
  3. What’s impeding your progress?

You can change the questions based on your goals but remember to keep your stand-ups short and sweet. For your stand-ups to be effective, understand its three main functions: 

  1. Share understanding of goals.
    One of the best ways to help people achieve goals is by regularly talking about it. Teams can better coordinate their efforts because stand-ups remind and confirm what they need to focus on.
  2. Share problems and improvements.
    Stand-ups provide remote workers the opportunity to help and ask for it. No one wants to be in a team where members are not comfortable sharing problems and do not help each other
    Cultural Note: Filipinos find it difficult to ask for help on their own because they don’t want to be perceived as weak, or dumb. But daily stand-ups normalizes help-seeking and makes it easy to open up about their struggles, and get help.
  3. Identify as a team.
    Remote work naturally creates a sense of isolation because people are mostly focused on independent work. But stand-ups create small moments of reconnection with your team that can make a difference.

So, what makes this deceptively simple practice beneficial for remote teams?



Firstly, your team will be accountable for their actions. After all, everyone knows what they will be working on. No one wants to be portrayed as someone slacking off on the job. It can heighten accountability to uphold what they announced to do in the daily stand up.


Active Listening and Collaboration

Next is it promotes active listening and collaboration. With this, the team will recognize challenges from everyone’s tasks. And by knowing each other’s difficulties, they can offer solutions or suggestions to ease their workload. They can work as one cohesive unit to reach your company’s goals.


Valuing Everyone’s Opinion

A lot of people are aloof at first. But to have a fully functioning team, you must have people who collaborate harmoniously. They should have a sense of belongingness that their work or project is more than just a job. 

And one way to have that is by valuing everyone’s opinion. What are their ideas for campaigns or projects? During these daily stand-up sessions, they can express their views. And when they feel that their ideas are valued, they might be more productive in the long run.


Asynchronous vs. Synchronous

The challenge is how do you do daily stand-ups when you’re not really huddling in person.

You can do synchronous and asynchronous stand-ups. For different time zones, find a common time that overlaps with other teammates, and schedule the 15-20 min session at that moment. This synchronous stand up will let you reap the benefits above.

But what about the difference in time zones? How do you convene together? It is where technology comes in. You still have project management tools like Trello or a simple work tracker created through Google sheets. 

In this way, you can be updated with the team’s accomplishment even without gathering every time in a single time zone.


Maximize Check-ins for Tracking Progress and Assessing Performance

Check-ins are one of the most useful productivity tools available to a leader. It is a one-on-one meeting done typically face to face, with your direct reports. If done right, you can check progress and assess performance at the same time. And, check-ins are also great for connecting with your remote workers on a personal level. 

Effective one-on-ones establish rapport and demonstrate that you care and value them. Your Filipino workers will genuinely appreciate you taking the time to get to know them individually. 

So, how to  ensure time is well spent on these meetings? 

Let’s start with the basics:

  1. Block regular time in your schedules.
    Schedule check-ins as an on-going, repeating event. Decide the frequency depending on your remote team’s size or needs. (e.g., should it be bi-weekly or monthly?) During onboarding, it’s good to make it frequent to help you establish trust and rapport early. As your working relationship improves over time, you can adjust and make it monthly. Don’t cancel your appointments, but try to reschedule it as soon as possible if it’s inevitable. Regularly showing up on time also speaks volumes to your remote staff.Cultural Note: Filipino workers usually appreciate regular check-ins initiated by you because it’s more difficult for them to ask for your availability and schedule a meeting. They don’t want to risk being perceived as needing help.
  2. Make it a conversation.
    Prepare a simple list of topics or questions you want to discuss and share it with your direct report. Ask them to do the same. Collaborating with your remote worker on discussion points gives them a chance to raise concerns and share their thoughts.Their questions may reveal more information than their answers. Filipino workers especially find it difficult to speak up about problems or concerns. So they benefit from a structured process that requires them to open up. Even with a prior agenda, be flexible and listen well to what your staff has to say. Also, don’t just stick with questioning: try to share relevant information about what you are up to, especially if it affects them.Making your one-on-ones a conversation instead of a formal meeting is a simple way to make every team member feel valued.
  3. Be intentional with your meeting.
    To get the most of every check-in, be thoughtful with your questions. How’s it going?’ is such a generic question that depends on the person’s mood and skill to open up. Choose more thoughtful questions such as “What don’t you like about our product? What part of your work do you enjoy the most?You can also choose strategic questions, and problem solve. You can encourage your direct report to list down current challenges they’re facing along with potential solutions in advance of your meeting. Then, you can offer constructive feedback.If you intend to discuss professional development, inform them in advance as they need to reflect and give it some thought before your meeting. Having focused and meaningful check-ins means you can deliver immediate, relevant feedback and sometimes, real-time course correction.There is a fine line between checking-up and checking-in. If during your meeting you are simply asking whether they finished their tasks or you are only interested in how they are achieving their goals, then it’s probably just checking-up. This can be seen as micromanaging and it makes people feel anxious when they feel their boss is checking up on them. Unless this is explicitly preferred by your direct reports,  you run the risk of negatively affecting their motivation and performance.Once you have established check-ins as a regular occurrence, you are now ready to utilize it to assess performance. Here are some strategies you can use to make your check-ins more effective when assessing performance.

Observe and Gather Data

First of all, you need to know the strengths and weaknesses of your team. By observing and gathering data, you can pinpoint what you can capitalize on and supplement the one that is lacking.

With their updates, you can plan a course of action based on your previous OKRs. Where are they with their goals? Based on their current progress, will they reach it?

During these check-ins are the time you observe and gather data.


Provide Timely and Specific Feedback

With the weekly check-ins, you can provide timely and specific feedback to your team. There’s a great chance that you can spot problems before they turn into something irreparable. Or maybe, you can bridge the gap between what they can do now and what needs to be done.

For example, the OKR of one of your sales teams is a 10% increase in sales for this quarter. If they only have 2% this month, you might need to talk to them to remedy the situation. It allows you to provide timely feedback to change strategies.

Another is employee behavior and attitude. If you see nuances that can affect your team in the long run, you can address it earlier.


Spot Those Who Needs Help

We all have strengths and weaknesses. There is no such thing as a perfect employee. That’s why during these check-ins, you have to spot those who need help. They might not say it directly. But you can assess while you are in the meeting. 

You can check the friction between team members and the roadblocks they have when working with each other. Maybe there are miscommunications that hamper effective collaboration efforts. Or the resources available aren’t enough. 

In this way, you can provide solutions with their call for help.


Document Your Observations

After every check-in, always record your observations. But be very objective. As much as possible, include measurable metrics with every observation. Include both good and bad remarks in your personal reference.

For ease of tracking, make sure to record the date and specific findings on that check-in. 


Identify Possible Causes of Poor Performance

So how do you process all the information? What if you found out that there is poor performance in your team? How do you go about it? First is to find out what causes poor performance. What are the roadblocks for your team? Here are some common reasons.

  • Inefficient Processes

A successful business relies heavily on processes. How do you handle transactions? What are your protocols for specific concerns? Sometimes, your employees can’t function well because you have inefficient processes in place. 

Maybe, it takes too long to get approval because of bureaucracy. Or there are too many “project managers” in a team. Or maybe the current IT systems are outdated for modern operations or for the new normal.

Review your processes. Some might not be effective today as they were before. And if possible, eliminate these problems along the way.

  • Workplace Tensions

In a team, there will be times that people are irate with each other. It’s totally normal. There will be friction when ideas are clashing. But sometimes, prolonged workplace tension can be detrimental to the team’s productivity.

How can you work together when you don’t like each other? When you spot this friction, you can find ways to lessen the tension. It can be through a mediated dialogue between the parties. Or maybe a work arrangement that can accommodate both. 

  • Work Overload

Energy is a finite resource. We can only finish enough tasks for the day. Yes, we can always push through the pain and do more. But oftentimes, it comes with a hefty cost. 

Work overload will let you do more, but it might cost you the accuracy and quality of work. When people are always pressed with deadlines and mountains of work, they can be ironically unproductive in the long run.

So check the numbers  of tasks you are giving. Are you pushing them to the point of exhaustion? Reevaluate because this might be the reason for their low performance.

  • Personal Problems

Your employees have a life outside their work. And it will directly affect their performance in your company. After all, we are emotional beings. If they are happy, that can translate to more productivity. If they have personal problems bothering them, it can also result in lower output. 

Filipino workers place a lot of importance on their families. Any emergencies or problems at home can inadvertently affect their work. Build a relationship with them more than just work. In this way, when they are faced with personal problems, they can open up. And you can suggest ways to lighten their spirits up.  


How to Confront Your Employee With the Findings

After all the observation and information gathering, how do you act upon the findings? It actually depends.

Discern first what’s the root cause of the poor performance. Is it due to the inefficient processes or the person? Is it a temporary problem? Does the employee have direct control over the situation?

In general, it’s not worth addressing the problem if it’s something temporary or the employee doesn’t have any control over it. For example, delays in performance because of taking too long for approvals is not really in their control.

But for apparent performance issues, this is where one-on-one assessments come into play. It’s not healthy to pinpoint a person’s mistake with all their colleagues tuning in. That’s why you need to schedule one-on-one assessments, especially if poor performance needs to be addressed.

Discuss with them the situation and what needs to change. But affirm to them that even if this is the case, they have your support and the capability to improve and grow.


Increase Visibility with Visual Systems

Some projects involving knowledge work are complex, and your team operates with a degree of uncertainty and ambiguity. Monitoring the process and systems in place and ensuring they are working as they should is vital for such projects. But stand-ups and check-ins may not be enough to get real-time visibility and feedback. 

Most leaders find themselves relying on status updates from meetings or written reports, which take time to prepare. But delays in information can happen and you miss the chance to make improvements before the results are in. Remember that remote work can magnify such delays if communication practices are ineffective or information is not organized and managed.

Visual systems complement stand-ups and check-ins for tracking progress. When working in the office, visual systems can be designed with simple whiteboards or corkboards. It simply requires a visual way of tracking workload and getting meaningful information on the team’s overall progress and performance. 

But for remote teams, digital tools are the way to go. It can be a simple spreadsheet or document that is available to members or it can be as complex as using a project management software.

Before we list down some of the popular tools for this, let’s discuss the key elements of a visual system. 


Elements of Effective Visual System

You can use an existing template or create a new one for your visual system. You must understand your goals for tracking and identifying what information is meaningful for your decision-making. Define progress and performance in the context of the work of your remote team.

  1. Process
    Break down your process into its repetitive and predictable tasks. Don’t just capture the final outputs. You can get valuable information from process information. Get real-time feedback on how the overall process is functioning. Making the process visible also allows the team to recognize how each member contributes to the results.
  2. Progress
    Do not limit yourself to the information in the existing templates. Try to be thoughtful in deciding what information to include. Progress tracking, if done well, sustains your team’s motivation. But if done poorly, it leads to anxiety and stress. Only you and your team can determine what information is worthwhile in terms of monitoring progress. Do try to differentiate between individual and group progress to help with your one-on-ones and performance assessment.
  3. Priorities
    Requirements and plans change all the time. But an excellent visual system helps your team respond and stay on track by clarifying priorities. Add information that helps your team prioritize what needs to be done. It can be as simple as using a 3 level priority ranking: low, medium, and high. When all tasks are important, then nothing is and your team can quickly get distressed. When priorities are clear, your team can strategize on how they will approach the tasks.
  4. Resource
    Most projects have three core resources, regardless of their type: human resources, time, and budget. Workload information can come from tracking these. Workload affects performance; making it easy to see everyone’s workload helps you manage and makes it easier for your team to help out one another.
  5. Insights
    A visual system should make it easier for you to get insights. Insights may be information invisible to your team or problems/concerns they are hesitant to talk about. Examples of insights are why this task got delayed or which jobs are best for an individual. It is valuable information that helps you plan things ahead or do course-corrections before it’s too late.


Digital Tools for Visualizing Progress

Progress tracking tools are software or visual tools that help you see a project’s completion with one glance.  One can opt for simple spreadsheets or documents. Another can use project management tools with more advanced features. What is right for your team will depend on the nature of your project and processes. But it’s good to start simple and as soon as it stops working for you, explore more advanced tools. 

Useful Features of Project Management Tools

Screenshot from Monday

  1. Task Lists/ Kanban System
    Tasks are created and assigned to users. Set deadlines, priorities, status, and get notifications for critical updates. Most modern tools feature a Kanban board where progress is tracked by moving tasks into different boards (e.g., not yet started, on-going, completed). It’s one of the easiest ways to visualize what is going on with a project at a glance.
  2. Schedules and Gantt Charts
    Gantt Charts capture a project’s timeline and milestones. It is useful for tracking if the entire project is on track or risks getting delayed.
  3. Time Tracking
    It allows you to keep track of the hours spent on individual tasks and the project as a whole. Use the information for reporting or billing clients and other stakeholders. It also helps you assess the accuracy of work estimates and check the productivity of your team members.
  4. Collaboration and Communication
    Team members need to share information and files. Most tools offer features to allow teams to gather feedback and even report issues on tasks. It also includes asynchronous communication features from within the app.

    Screenshot from Trello

  5. Document Management
    Because file sharing is important for collaboration, most tools will have a way to link or even store files. With the proper context, task lists are easier to manage because you can easily find relevant documents or project artifacts.
  6. Reporting
    Status reporting is usually automated in these tools.  It is a useful feature for clients and leaders because it makes the project progress transparent to everyone.
  7. Resource Management and Allocation
    Details about each resource are available such as cost or current stock of inventory. This informs project managers how to plan and distribute resources for projects.  


Key Benefits

Organization and Centralized Information

Progress tracking tools capture a lot of information that is useful for the team. Keeping all of it in one place instead of scattered across emails and multiple channels makes it easier to maintain transparency. People don’t lose valuable time preparing for status updates.

Visual Feedback

The best part about these tools is the visual feedback. It’s far easier to find important information because it uses boards, Gantt charts, and the like. Modern software is intuitive and can arrange information in multiple views depending on your needs. 

Automated Workflows

Many mundane tasks can take a lot of time when it comes to project management and task monitoring. So these tools usually come with the options to automate the repetitive stuff. For example, by synchronizing email and calendar apps, your team can automatically update status updates and other important notifications. 

The degree of automation will vary per tool, so it’s best to know in advance what part of your processes and monitoring you would like to be automated. 


Highly-Rated Software for Everyday Project Management

A lot of the following tools have been popular among remote teams. They make it easy for leaders to track important information without requiring additional work from their team members. 

Our list of softwares is not exhaustive. We selected the following tools to give you a good idea of the range of features you may want to consider.

Key Features

Pricing Options

Best For 

Google Workspace Communication : Real- time chat and asynchronous comments

Collaboration : Simultaneous file editing and easy file-sharing

Document management : Cloud storage with simple version control 

Drawbacks: Not designed for project management – Requires additional work for task management

Business Starter :$8.40 AUD /user/month 

Business Standard :$16.80 AUD /user/month 

Business Plus :$25.20 AUD /user/month 

Good for small teams, simple projects and predictable workflows

Highly intuitive for Microsoft Office users


Kanban Boards : Organize tasks into cards and track their status across boards.

Advanced Check Lists: Integrated scheduling and assignment

Automation :Cut down repetitive work without coding.

Drawbacks: The free version is not suitable for bigger teams and complex projects and has limited storage.

Free Version

Business Class – $9.99/user/month (with 14-day free trials) Enterprise – $17.50/user/month (for teams of 20 users) up to $7.38/user/month (for teams of 5,000 users.) 
Remote teams that want a lightweight, free tool that is just as powerful as others.

People using sticky notes for monitoring tasks will find it easy to use.


Task Management : With progress tracking, status and priority notifications, and time tracking

Collaboration : File-sharing, comments, and feedback systemsReporting and Smart Timelines :Interactive Gantt Charts and Calendar ViewsDrawbacks: No Kanban board views yet, although they are working on this. Timesheets don’t have a timer.
Free Version – individuals and freelancers

Premium – $2.99/user/month for SMEs, Start Ups (with 14-day free trials) 

Business – $2.99/user/month for Larger Corporates (with 14-day free trials)

Budget-conscious teams that need comprehensive features for project management.

It offers in-app walkthrough so everyone can learn to use it without any issues.


Highly customizable : Comes with pre-made templates that can be tailored to your workflows

Automation and Integrations : Set tasks with IFTTT (If this, then that) and integrate behaviors with other apps

Task Management : Includes scheduling, prioritization, time-tracking, and resource management

Visual and Appealing – like a digital whiteboard with  multiple views

Drawbacks: It is costly for large teams and  laggy with big projects. No dependencies and recurring tasks 

Free 14-day trial 

For 1 to 40 users only: Basic: 8$ /user / month

Standard: 10$ /user / month 

Pro: 16$/ user/ month

50 users and beyond will need a custom quote

For small to big projects that need custom workflows and want to improve cross-team collaboration.


Remote Work Tools  : It features message boards, to-dos, schedule, document management, file-sharing, and  group chat

Automatic Check-in Questions : Keep everyone in the loop and make it easy for people to report  

Notifications : Centralize important updates and choose how you receive notifications to minimize interruptions 

Drawbacks: Lacks native time tracking, Gantt chart view without a third-party add on

Free Version (up to 20 members with limited features)

99$ per month. Flat rate.
All-in-one project management solution that wants everything in one place.

Large and growing teams that prefer a flat fee instead of per user pricing scheme

Final Thoughts

After setting clear goals and giving a real sense of ownership, the next task at hand for leaders is to nurture daily progress and help their remote workers solve problems and overcome obstacles. It matters that they celebrate small wins, stay flexible and responsive to changes in plans, and coach remote workers in their failures and mistakes.

The progress principle is powerful and making progress in meaningful work boosts morale, improves perception, and keeps your people motivated. How you track your remote contractor’s progress will make an impact on your team’s performance. Besides fair and equitable pay, most remote professionals value the opportunity to succeed and do well. 



In a Nutshell

Quick Guide on Tracking Tools

List of Popular Tracking Tools

Daily Stand-Up Template