Resolving Management Issues in a Remote Team

Most employers assume that when their workers leave, it’s because they found a better paying job elsewhere – but nothing could be further from the truth. In fact, most employees leave their jobs because of their bosses, not in spite of them. This means that becoming a great manager, and investing in training your employees to be great managers, are vital for your business. This guide is intended to help entrepreneurs and managers identify key areas to improve upon and understand why these soft skills have a huge impact on their success in business.

The areas addressed in this guide are Communication, Understanding, Fairness, and Providing. These four pillars are essential to meeting deadlines while keeping your employees engaged. Your company will get more done and employees will stay longer, creating a highly valuable and experienced talent pool. For any organization, from remote companies to large multinational corporations, managers won’t be able to excel without these skills.


Communication comes first in the list because almost every other management issue stems from poor communication. Managers provide direction at every step of a project or business initiative, but they also have to be able to understand what’s going on with their team. Companies can no longer afford to think of communication as a one-way street if they want to retain top talent. Whether it’s written or oral, working on communication skills in these four areas is key to becoming a top manager.


Communication is only partly about making your own message heard. Another very important part of communication is listening so that you know what’s going on with your employees and what they need from you to stay productive and satisfied in their jobs. It sounds trite, but listening really is one of the most important characteristics for a top manager to have. While many managers do value what their employees have to say, it can be a struggle to make the time for listening to each reportee with a full agenda and looming project deadlines.

Instead, consider listening to your employees a fundamental part of your job – a long-term investment in your ability to get your job done. Maybe it won’t directly move you closer to meeting deadlines that day, but it will give you valuable information about where a project is going and what your employees need to get there. Moreover, listening to your employees also creates goodwill that makes them more engaged and willing to put in the extra effort at work.

To get your listening skills up to par, try working on improving these key areas of conversation:


Pay attention to the person in front of you (or the message or email) if you want to really listen and understand. Show genuine interest and maintain eye contact if it’s a face-to-face conversation, and if it’s online, temporarily close off other distractions while you’re reading. Nobody actually enjoys having to compete for the attention of someone who has power over them but who acts like they don’t care. Additionally, managers should take note that few people are able to actually understand something without focusing on it! So if you want to really understand information on the progress being made on work, roadblocks that have come up, or any other secondary issues, then listen.

Ask Questions

The person or people you’re communicating with will appreciate that you ask questions, and you’ll be able to fill in the blanks if you need more information before making a decision. Just one warning – if you weren’t focusing and showing genuine interest, and you start asking questions, they’ll know right away that it’s a sham and you’ll end up doing more harm than good. At the very best, you’ll only waste time by having the other person needlessly repeat information. In the worst case scenario, you’ll also have an employee who’s secretly demoralized, which can quickly spread to other members of your team.

Your questions have to be based on what the person was actually saying or left unsaid, which means you have to focus on their communication first. Ask yes or no questions that refer to what the other person has been telling you, and pay attention to their responses.

Check for Understanding

When you’ve actively focused on another person’s communication and asked questions to clarify as needed, rephrase what you think they’ve said and ask them if it’s true, whether it’s in person, on Skype, or via email. Often your perceptions may not match up with what they think they were communicating to you, and this isn’t always one person or the other’s fault – it could be due to intercultural differences, variations in communication styles, linguistic challenges, or a number of other causes. State your understanding in a matter-of-fact way without any judgement and if they correct what you’ve said, accept it at face value.

Be Silent

What’s the difference between having a conversation and watching TV? The TV streams content one way and never ever stops while it’s turned on, but in a conversation, one person talks while the other person stays silent and listens until it’s their turn to respond. Staying silent for effective listeners is anything but passive: they’re alert, fully tuned in to the other person, and suspending all their mental dialogue so they can hear what the other person has to say.

Setting Expectations

Once you’ve mastered the art of listening as a manager, the next most important area of communication is setting expectations for your employees. Listening comes first so that you understand where your employees are coming from – setting expectations helps them know where they stand with respect to their work and to your role as a manager. This allows employees to know what they’re expected to do and when they’re supposed to rely on the other, freeing up more time and energy for getting actual work done.

There are no hard and fast rules with regard to what expectations to set, because it depends on the company and the kind of work being done – a junior associate at a law firm has a very different set of expectations from management than a freelance copywiter on another continent. However, the way you set expectations follows several universal truths no matter where you work.

Clarify Roles

It’s important to make it clear to employees what they’re expected to do in their jobs and how you’re allowed to help them. It’s also equally important to make sure that descriptions of job roles actually match the work that’s being done. Double check the roles you’ve set out in writing with the actual work your employee is doing, and if in doubt, ask them for feedback.

Invite Honesty

In setting expectations, each party has to be able to clearly and honestly state how they perceive the situation in order to calibrate their perceptions of how progress is going and what more should be done to complete projects.

However, when the conversation is between two employees of differing rank (like between a new hire and her manager), there’s a strong incentive on the employee’s part to please the manager. This can mean that unpleasant truths are not discussed – so make it clear that just as you’ll be giving feedback (see below), you also want them to be honest about letting you know what they’re doing and how much they can get done.

Keep the Conversation Alive

Finally, setting expectations isn’t a one-time conversation. Ideally, it’s a topic that keeps getting revisited as new assignments come up, as well as being part of regular conversations about work and satisfaction.


Employees need feedback often in order to correct problems early on and become satisfied, top performers in their role, and your business needs its managers to give frequent feedback in order to develop and grow its base of talent. Failing to provide the right kind of feedback at the right time is one of the most common management issues, and it’s also one of the hardest to correct because few people actually enjoy it.

Balance Critical and Positive Feedback

The kind of feedback you give should correlate to your experience of the employee’s work – stellar employees get mostly positive feedback and average employees should get at least a 50/50 mix. Going too far in one direction or the other isn’t good for your team or your business. Make sure your employees know when they’re doing a good job to encourage them to continue that behavior in the future. Balance this with critical feedback when you see a problem that needs correcting, but unless a person is a truly terrible employee, don’t make criticism a majority of what they hear from you.

Be Proactive

The best kind of feedback is timely – avoiding giving feedback until you’re frustrated, or until it’s time for the employee’s yearly review, is extremely ineffective. Giving feedback right at the moment that you see a problem helps to correct things before they get out of control. Employees might also appreciate a timely chance to get back on track, versus having to atone for all their past  mistakes in a performance review and wondering why you didn’t bring things up sooner.


The proper amount of friendliness is a tricky standard to set. Some employees prefer a more distant boss, while others feel as if their manager doesn’t care if they don’t show some interest in their personal lives. Most managers also want to be seen as friendly and approachable to the people on their team – but when it’s time to make tough decisions regarding your reportees, some people will be tempted to take advantage of a too-friendly relationship.

Getting friendliness right requires a delicate balance between a fixed standard – knowing where the limits of how friendly you can be while still preserving your authority as a boss – and a flexible adaptation of that standard to what each employee really needs from you.

Communication: Bringing It All Together

Effective communication isn’t just about motivating your employees or making them feel better – it’s about you being able to get the necessary information you need as a manager in order to do your job well. How you choose to implement this will depend on your style of working. In remote businesses, that means working on the principles of listening, focus, asking questions, checking for understanding, and silence via remote communication tools. For other teams working together in physical offices, there’s still the question of how to adapt these general principles to their company culture. In any case, this can be part of a larger ongoing conversation you have with your employees and management – don’t assume that once you’ve addressed the issue of communication in your organization, you’re finished. Continually check up to make sure you’ve got robust communication between different levels of hierarchy.


If you’ve mastered communication, you should now be able to attentively listen to your team, set clear expectations for them, give them regular feedback on their performance, and speak to them in a kind but professional demeanor. But do you really understand them?

Some skeptical managers might think this step is unnecessary – but when it comes time to really motivate your team for a big push towards deadline, or to assign them new work, lacking a deep understanding of who they are and what they care about will prove disastrous to their performance as employees – and to your performance as a manager. It’s time to think about your team’s motivation, engagement, learning styles, and skills both at an individual and at a group level.


As a manager, do you know what really motivates your team? Do you think it’s only money? If you look deeper, you might find you’re sorely mistaken. Chances are, the employees who act as if they’re only in it for the money are the least motivated of all.

Employees can be motivated by a variety of things. Some crave more recognition for their efforts, while others are deeply interested in having greater work-life balance. Other employees are motivated by positions that require them to constantly learn new things – mastering new skills is a huge thrill for lots of highly talented A-players.


Engagement is the million dollar question facing most businesses today. Working on this question requires applying nearly all the principles in this guide – what it doesn’t require is dismissing a lack of engagement as a symptom of a less valuable employee. Too often, managers learn to view their more engaged employees as more valuable, when instead they should be thinking of how to tap into the potential of their disengaged employees.

Try asking yourself and your employees why they’re not engaged. Is their work boring for them? If so, can you find something more interesting for them to do that creates value for the project and for your company? If not, maybe there’s another way they can consider their work that you can help them to see.

Learning Styles

It’s rare for everyone on the same team to learn identically, at the same rate. Some people learn best by listening; others are more visual; some need to test out their new skills in the field in order to really learn them while others prefer to learn alone, in silence, until they feel they’ve mastered their new material. Making space for your employees’ learning styles is the key to ensuring that they understand new information, which is part of ensuring your team can adapt to a changing business environment. 

Skills and Capabilities

Finally, managers need to understand their employees’ unique skills in order to delegate work to them that they’ll excel in doing. Not only will this give the employee a sense of satisfaction with their work, it also helps the company produce better results. Observe how your employees do with different assignments and also listen to their own self-assessments; speaking at a client presentation is perfect for the person who loves being on stage, while making financial projections might be better for the person with great attention to detail. When you understand your employees’ strengths, your whole team will be able to perform better by doing the work at which they excel.


It’s important to treat your employees fairly for many reasons – unfair treatment can have major legal and PR repercussions for your business, as well as seriously damaging morale on your team. From any angle you consider it, showing biases is a big mistake for management. Sometimes, bias can be very subtle and unconscious, so continually evaluate your behavior on the following grounds to make sure you’re treating your teammates fairly.


Blatant cases of discrimination are obviously wrong, but sometimes bias can be subtly unconscious – a manager may feel as though they have a better time relating to someone from a similar background and treat them differently just because of the ease – or lack thereof – of understanding them.

If you catch yourself naturally relating better to someone of your same gender, background, or beliefs, make a conscious effort to reach out to the reportees and employees you’re having a harder time relating to. They’ll notice and appreciate the effort (as long as it’s genuine), and you’ll be investing in their long-term satisfaction in working with you. This means your pool of employees will also be more diverse, giving you a greater breadth of perspectives to draw upon when creating your work product.


It’s natural to have an affinity for someone – everyone has particular personality types that they prefer, and other personality types that just don’t jibe. Especially with managers, the high performers on your team are natural subjects for your praise and admiration because they move you closer to your goals and help you meet deadlines. For other managers, the team member who always displays a cheerful attitude might be their favorite on the team.

But beware of giving your favorite too much praise – your other employees aren’t stupid, and they’ll know when you start treating your favorite better than others. This leads to resentment and an overall decrease of productivity for your team; the high performer or cheerful worker won’t become more productive as a result of being treated favorably, but everyone else on the team will lower their output in response to perceived unfairness. Keep your preferences to yourself and make sure that praise is given equally to the people on your team in response to their achievements.


Once you’ve laid the foundations of healthy communications as a manager, made sure you understand your employees as individuals, and ensured that you treat them all fairly, it’s time to ensure that you’re providing them with everything they need to get their jobs done.

Why is providing an important area for managers to improve? Imagine if you were placed in a room and told that your job is to knit wool hats. Your manager asks you if you understand the project and if you need help learning how to knit; learns what interests you most in doing the job; and makes it clear that they’re available if you have questions. But in your room there’s no yarn, only one broken knitting needle, and no clear way to order more supplies. At the end of the week, your manager asks what happened to the 15 pink crocheted scarves you were supposed to make, which are supposed to be delivered to the client tomorrow – never mind that you didn’t have the needles you needed, or that you were originally supposed to be knitting hats made out of wool. A rational person’s reaction might very well be to quit the job because they weren’t provided with clear goals and the resources they need to achieve them.

Defined Goals

The more clearly you define goals for your employees, the easier you make it for them to get their jobs done. They’ll have a standard against which to measure their performance and it’ll be clear where they stand with you. If you don’t define goals, people on your team muddle through their day and don’t get anything done. They don’t know what their work means, what they’re working towards, and they have no way to prioritize without this greater context.

Using the SMART goals framework is a great place to start when setting goals. For example, with Hubstaff, you might want to use time budgeting and activity percentages to tell your employees that their weekly goal is to work 15 productive hours at an average activity percentage of 70%, which is definitely achievable for most people when they’re focusing. That way, they’ll be able to freely choose among their assigned tasks in order of priority and personal preference, and you’ll know that no matter what they’re working on, they’ll be moving forward toward completion if they meet their minimum activity percentages.

Defined Scope

Stream of Consciousness by Steve Jurvetson / CC BY 2.0 Generic

Ideally, your projects will have a defined scope and stick to them. Otherwise, what’s known as scope creep can occur. The lack of clear boundaries for projects can sneak up and destroy them – causing budgets to be overrun, deadlines to be missed, and employees to stop taking their bosses seriously. In terms of motivation, scope creep basically causes your employees to feel as though their work lacks direction. It’s hard to believe you’ll be held accountable to reaching your goals when everything becomes much more fluid later.

As a manager, it’s vital to make sure every employee has enough information to produce their tasks on time and within budget for the project. Time tracking tools can help, especially if you’re working with independent contractors or billing a client, but you need to have a clearly written project scope that’s agreed upon by all major stakeholders. This can then serve as the basis for delegating out tasks and budgeting your employees’ time.


A manager can listen, treat all her reportees fairly, and understand their working style, but if the team itself doesn’t have the human talent, budget, or time to reach their goals, they’ll be setting themselves up for disappointment at every level.

When you’ve established a healthy pattern of communication with your team, you understand their abilities and their motivation, and your project scope and goals are defined, giving your people the resources they need to do their jobs should be easy. You’ll be able to have open, honest conversations about what each of you needs in order to bring the project to completion. It’s important to note that this isn’t a one-time conversation – unforeseen circumstances often arise that require a new or different set of resources to be resolved. Be proactive about checking in (but not too much – see below) and make sure that your team has the material resources that their jobs require. If they don’t – then do your absolute best to give it to them.


Just like with friendliness, the issue of attention involves walking a very fine line between too much and not enough. On one side of the spectrum are the motivation-killing micromanagers, whose constant hovering and interruptions stifle independent thinking and isolate self-motivated workers. On the other side of the spectrum are managers that are so completely hands-off that their employees do their work in good faith – only it turns out to be completely different than what the project required, all because their manager didn’t check in during the process of completion.

If you’ve done the work of establishing healthy communication habits and understanding your employees, you’ll know by now how they work and you’ll be able to get honest answers from them about what they need. Make sure you’re checking in enough that they don’t feel completely alone, but not so much that you’re damaging your company’s long-term ability to grow self-motivated learners and leaders. Balance that against your need to get projects done and use attention sparingly to prod them when things are going too slowly.

Risk Management

Now that you’ve learned how to communicate with your employees, understand their motivation, and treat them fairly, you should have a team that’s engaged in what they do and updates you regularly on their progress. Your job as a manager should now focus on managing risk. Your employees will do their work – it’s your job to focus on the big picture.


The first step as a manager is to set aside time to analyze the risks of a given project. It’s tempting to ignore risk management altogether when your schedule is full, but just like with communication, consider it an investment in your ability to get work done as a project manager and block off time for it.

Talk to experts outside your project area who can identify common pitfalls you might not have considered; brainstorm with your team; and scour over your project’s paper trail (or online document trail) to identify risks to completing your project.


Analyzing the nature of risk will help you understand how to prioritize it, plan an appropriate response to it, and communicate that to your team. There are a variety of risk analysis techniques you can use – simple cause and effect, orders of magnitude, or having a standard set of questions that you use to assess a project.


Treating all risks equally might make your life simple, but it won’t necessarily yield the best results. Some risks have higher impacts than others, as you’ll discover in your risk analysis. If your time is limited, which it usually is, you need to spend the most time working on the biggest risks. First, address any showstoppers that could completely derail your project, and then deal with the other risks in order of importance.


Once you’ve identified risks you can take three kinds steps to deal with the negative risks – risk avoidance, risk minimization, and risk acceptance.

Risk avoidance is one of the most drastic strategies for managing risk – you basically reorganize your project so that there is no more risk involved. You might choose to no longer depend on the flaky supplier, or to move all your documents to the cloud, or you might even terminate a project to avoid spending more money on something that’s doomed. Risk minimization involves working to either change the causes of a risk or decreasing the negative effects that could result. And finally, risk acceptance involves learning to live with the presence of a given risk if its consequences are minimal, or if the costs of fixing it are such a burden that they don’t justify the effort.

Planning for risk opportunities, also known as positive risk, is different – you’ll want to institute policies and procedures that help your team to seek out these risks, maximize the valuable ones and ignore the small ones.


This is a general plan for identifying management issues and taking steps to resolve them in your organization – the specific steps you need to take will depend on what sort of company you’re running or working within and what kind of work you do. For any questions or comments, please feel free to reach out to Hubstaff on Twitter, Facebook, or via