The 8 essential entrepreneurial skills you need to run an all-remote business

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entrepreneurial skills

Throughout 2020, businesses scrambled to find ways to adapt their operations to accommodate all-remote workforces.

For the most part, their efforts paid off.

Studies have subsequently shown that the abrupt shift had a negligible effect on productivity.

That new reality has changed the dynamics in the business world surrounding remote work. As a result, it’s beginning to look like some of the pandemic-driven changes will become permanent.

That means workers will start to expect the ability to work from home, and businesses will have to offer that as an option to remain competitive for the most talented workers.

It also means that startups will have to embrace remote work if they want to compete in established markets. But unlike existing businesses, startups have the opportunity to create a work style and culture from the ground up that maximizes the benefits of all-remote teams and minimizes their shortcomings.

But none of that can happen without the right entrepreneurial skills needed to run an all-remote business.

To help the remote entrepreneurs of today and tomorrow do that, here’s a guide to the 8 essential skills they’ll need.

We’ll cover what the entrepreneurial skills are, how they help keep an all-remote business running smoothly, and some tips on ways to acquire them before and during the process of launching a new venture.

And on top of that, we’ll discuss when it’s advisable to bring in outside assistance in the form of consultants and new hires when specific skills are needed in a hurry.

But first, we’ll go over some of the challenges that all-remote teams encounter, to provide some context for the needed skills.

Let’s dive in.

The major challenges of all-remote teams

Believe it or not, it’s been possible for businesses to operate in an all-remote model for some time. Companies like Gitlab and Automattic have leveraged all-remote teams to create some of the most talented and nimble workforces in the world.

But the fact that other businesses didn’t follow this suit reflects that succeeding with an all-remote model is not easy.

The biggest challenge is finding reliable ways to keep everyone on the same page and working in sync.

In an office environment, managers do this by looking over everyone’s shoulders to ferret out small problems before they snowball into big ones.

In a remote setting, that style of management is impossible. And this becomes even more difficult if you have workers in different time zones. Problems that would be simple to correct under normal circumstances can lead to multiple wasted days of work.

It’s also hard to create the kind of camaraderie and teamwork that forms through close contact and shared challenges.

In a remote setting, individual team members may feel isolated and detached from their colleagues, leading to poor outcomes.

For an established business, this isn’t as much of a problem because pre-existing business culture and relationships will carry over to a remote setting. But for a startup that’s built around all-remote teams from day one, a different approach is required.

Essential entrepreneurial skills needed to run an all-remote team

When an entrepreneur sets out to build a startup that relies on remote teams, they need to bring several specific skills to the table to get off to a good start. Making sure to have them before making any other moves is essential.

Here’s what these entrepreneurial skills are, and how they help a startup function smoothly from its inception.

1. Remote engagement building

No matter the type of business, getting the greatest high-quality output from every employee is a key to success. And both experts and experienced business managers agree that doing so requires a high level of employee engagement.

To make that happen, entrepreneurs have to build a company culture that encourages engagement in every aspect of operations.

This begins with the entrepreneur first learning the skills to keep themselves engaged in their work. This is a bigger issue than most might realize, with a Gallup survey indicating that only 35% of management-level employees – including startup founders – are actively engaged in their own work.

The needed skills include:

1. Learning how to create and stick to boundaries

Since entrepreneurs tend to invest all of their time and energy into building their startups, they also suffer from high burnout rates.

Learning how to set boundaries and stick to them can combat that tendency by defining what’s on and off-limits. This includes the number of hours you work and how you use your downtime to unwind and recharge.

2. Learning how to celebrate success

The average startup will suffer countless setbacks, at least at first. And when they happen, it’s all too easy to get discouraged and check out mentally.

To avoid that, entrepreneurs must learn how to celebrate successes, no matter how slight. This can provide enough consistent morale boosts to help them to keep pushing forward.

3. Learning and understanding your strengths and weaknesses

Entrepreneurs wear many hats. But not all of them are a good fit.

That’s why entrepreneurs must have a good handle on their core skills and know where their own weaknesses are. That way, they can make sure to focus on what they’re good at and delegate the rest to others.

4. Other entrepreneurial skills needed

Once the entrepreneur knows how to stay engaged, they’ll have an easier time instilling the same techniques into the teams they lead. But leading by example isn’t so easy in a remote setting. They’ll also need to know how to get each remote employee engaged from the beginning and stay that way forever.

This should begin with the entrepreneur learning how to craft a high-quality onboarding procedure for each new remote hire.

Getting the small details right at the beginning and helping each employee get off to a comfortable and strong start in their work goes a long way toward keeping them engaged.

Then, the next step is for the entrepreneur to learn how to build a little bit of fun into the workweek to act as a pressure relief valve for the team. There are now countless virtual team-building exercises that accomplish this quite well. And adding them to the entrepreneur’s arsenal is a must for any all-remote startup.

Next, maintaining a high level of remote employee engagement comes down to the entrepreneur passing on the very skills they use to stay engaged to each employee.

But they have to back those skills up with the right kind of support.

For example, if you help your employees to set boundaries only to make excessive demands on their time, all of the hard work to build engagement will have been for nothing.

2. Remote time management

In a remote setting, employees have far more freedom to shape their workday than they might have in an office. This can result in one of the biggest problems that remote teams face.

To keep things on track, an entrepreneur leading remote teams must master the art of remote time management. Building this skill begins with mastering one’s own day.

For busy entrepreneurs, a great place to start is to learn and adopt the 80/20 rule to stay productive at all times. Not only will this keep them from getting overwhelmed with the minutiae of running their business, but it will help them to free up enough time to be available to support each member of their remote team.

Then, it’s advisable to implement and learn a time management platform to manage the whole team’s scheduling in one place. This should provide the kind of visibility into the remote team’s activities that the entrepreneur would have had in an office setting.

But since knowing what’s going on is only a part of the equation, they’ll also need to learn what to do with the information they uncover.

For that, entrepreneurs must learn how to analyze their team’s workflows to look for ways to improve performance. With a remote team, it’s easy to encounter process bottlenecks due to things like time zone differences and scheduling deficiencies. Getting those ironed out is the best way for entrepreneurs to get the most out of their remote teams. The data coming from their time management platform is the key to getting it done.

3. Intentional learning skills

In any startup, the entrepreneur is most often the driving force that shapes the direction of the venture. But that can also mean that the development of a startup is limited by the entrepreneur’s ability to learn new skills and remain curious about what they don’t already know. In a remote setting, this is complicated by the fact that there’s no direct interplay between team members. This can rob the entrepreneur of the experiential cues that spur curiosity and learning.

For that reason, entrepreneurs have to develop what’s known as intentional learning skills. This refers to the skills that help the entrepreneur to embrace a path of lifelong learning without needing external stimuli. And the core of those skills includes mastering:

  • Setting clear learning goals to stay on track
  • Making time to practice new skills as you develop them
  • Practicing productive self-assessment
  • Seeking new experiences outside the context of work

The good news for entrepreneurs is that they can apply their intentional learning skills to improve their startup’s performance in a variety of areas. And with the wide availability of online learning platforms, they can do it from anywhere at any pace that suits their schedule.

For example, they might choose to take online digital marketing courses to help with the promotion of their new startup. Or, they can choose to learn about the intricacies of accounting so they can run a tighter financial ship from day one.

Whatever they choose to learn, the very act of purposefully setting out to build new useful skills will get the entrepreneur into a mindset that keeps them curious and always developing their greatest asset – their own mind.

4. Information technology skills

Running a business these days requires an entrepreneur to be well versed in a variety of new and emerging technologies. And for a remote-first startup, having a decent handle on some basic information technology skills is a must.

After all, in an all-remote business, technology is at the heart of everything you do. Whether it’s keeping communications systems up and running or managing cloud-based collaboration tools to keep teams on the same page, failing to understand how the startup’s digital infrastructure works leaves the business at the mercy of its service providers.

At a minimum, entrepreneurs should seek to build up their knowledge about computer networking. This should enable them to provide basic desktop support to their early employees (as well as themselves). This is important because there won’t be an IT department to rely on in an early stage. Plus, every minute of tech-fueled downtime is equivalent to being out of business.

But beyond those basic skills, entrepreneurs have to be ready to become the master instructor for their employees. They should be able to teach them the ins and outs of the remote technology that makes the business work.

That means having a working understanding of things like how VoIP systems work, how file and document-sharing platforms function, and how videoconferencing and collaboration tools operate.

It’s not essential to become an expert in every area. But they should be able to answer basic questions. It will save the headaches of waiting for tech support from the plethora of vendors they are working with.

5. Strategic communication

Knowing how to communicate effectively is a necessary skill for entrepreneurs. They need it to secure financial backing for their businesses, to sell customers on their vision, and to generate interest in their ideas among industry peers. The trouble is, the kind of one-on-one, persuasion-driven communications skills that entrepreneurs tend to rely on don’t always translate well in a remote setting.

Remote teams only thrive when they can communicate in effective, direct, and reliable ways. There’s no room for ambiguity or guesswork. And making that a reality requires a purpose-driven communication strategy. But because no two teams are the same, there’s no one-size-fits-all approach to effective remote team communication.

But there are some communications skills entrepreneurs can leverage to be effective at strategic communication. These include:

1. Proactive communications

Learning to reach out to team members early and often. Not to take for granted that they’ll come to you when they have a question.

2. Communications scheduling

Understanding how to set a schedule for one-on-one and group meetings that provide structure to the team’s communications.

3. Communicating clear expectations

In a remote setting, it’s essential to know how to give instructions and set expectations in ways that leave no room for confusion.

4. Respecting team communication preferences

Figure out the communication methods and styles that work best for each team member. Then integrate them to provide what each individual needs to thrive.

6. Code switching between cultures

Even in the most diverse conventional startup, teams will have a shared geographic experience tying them together. That means that they’ll all have something of a shared understanding of what to expect from other members of their team. In an all-remote startup, that’s not always the case.

The entrepreneur may engage the talents of people all over the world to build the right team to power the business. When they do, they’re going to have to learn how to approach each team member on their own terms in a manner consistent with their local culture. This requires a skill that the Harvard Business Review dubbed code-switching between cultures.

This means not only learning about the cultural norms in different places but also adopting those norms when necessary. For example, an employee in the US might expect criticism of their work to be softened by praise for what they’ve done right. But a team member from India might expect a blunt, straightforward assessment that doesn’t spare their feelings. And an Australian might be comfortable with you using colorful language that would make an employee from the UK blush.

The point is, to get the most out of a remote team, entrepreneurs have to get comfortable learning about multiple cultures and behaving in ways that are appropriate for each team member.

This might be a bit taxing and awkward at first, but the reward will come in the form of peak performance from everyone involved.

And If the startup is going to have an especially dispersed workforce, it’s probably worthwhile to engage with an experienced outsourcing firm that knows the potential pitfalls involved in cross-cultural team building that can act as a guide for the startup.

7. Emotional intelligence

One of the biggest challenges involved in running a remote team is finding ways to prevent team members from feeling isolated and detached from the group.

The daily interpersonal contact that occurs in an office setting plays an outsize role in knitting a group of individuals into high-functioning teams.

With no such contact occurring in an all-remote setting, entrepreneurs need to come armed with the right skills to support their employees and mold them into a team.

Broadly speaking, the skills needed fall under the category of emotional intelligence. This includes knowing how and when to show empathy, how to use humor to keep spirits high, and having a sense of when to simply quiet down and let others command attention.

In other words, the entrepreneur needs to learn how to be a support system, mentor, and friend to their remote employees.

This is a skill set that’s far more important than many realize. According to a recent survey, a full 82% of employees indicated that they’d leave a job to work for a more empathetic organization, and 78% would work longer hours for such an employer. Emotional intelligence is a must-have skill for an entrepreneur to attract skilled workers and get the most out of everyone.

8. Conflict management

There are plenty of advantages that come from building an all-remote startup. But there are also significant downsides that entrepreneurs have to be prepared to deal with.

One of them is that remote teams are prone to developing internal conflicts that traditional teams don’t.

Some experts put this tendency down to team members becoming accustomed to working alone, which reduces their willingness to compromise with others.

And in some cases, it can be due to a curious facet of remote communications known as the online disinhibition effect. This refers to the fact that people often act out online in ways that they wouldn’t consider in person. This can result in pushback from other team members who don’t appreciate their behavior.

No matter the reason, entrepreneurs have to build some conflict management skills. They must know how to spot trouble and act to resolve it before their teams break down. This includes learning how and when to deploy one of the five main conflict resolution types, which are:

1. Avoidance – knowing when a dispute isn’t worthy of intervention and escalation

2. Accommodation – knowing when it’s best to take action to satisfy the demands of one team member or another

3. Compromise – finding solutions that satisfy some of the needs of both parties that are agreeable to all involved

4. Competing – knowing when to place the business’s needs above those of the individuals involved

5. Collaboration – finding solutions that solve the problem without leaving anyone dissatisfied

When to seek outside assistance

It’s rare for any entrepreneur to have the time or bandwidth to master every skill required to make an all-remote startup work well.

And although it’s worth building their skills in every area listed here, some tasks are better left to others. And that’s why every entrepreneur should try to be mindful of their strengths and weaknesses. This can guide them determine when to look for outside help.

For example, it’s good for an entrepreneur to play an active role in developing their onboarding procedures to get each employee engaged from the start. But, there’s no reason they shouldn’t consult with an expert in digital onboarding that knows how to create a suitable user experience for their team. That’s the kind of skill that the entrepreneur won’t have to use more than a handful of times. That’s why it’s better left to someone else.

The same thing holds true for tackling later-stage issues like human resources and accounting. There are already all-remote services that can take care of those needs at competitive costs. Therefore, it’s not worth spending too much time developing in-depth skills in those areas.

The general rule of thumb is, if you’re reasonably adept at something, take the time to home that skill. If you’re not, find someone who is.

Off to a great (remote) start

In today’s business environment, it’s becoming clear that entrepreneurs are going to have to get comfortable building and running remote teams if they want to succeed.

And even if doing so involves building some entrepreneurial skills that don’t come naturally, it’s worth the time and effort. That’s what it’s going to take to build success in the new normal.

So now’s the time to get started and build these most essential entrepreneurial skills you’ll need to run an all-remote business.

About the Author

Andrej Kovacevic

Andrej Kovacevic is a digital marketing specialist, founder at TechLoot, and a contributing writer for a variety of other technology-focused online publications. He has covered the intersection of marketing and technology for several years and is pursuing an ongoing mission to share his expertise with business leaders and marketing professionals everywhere.

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