Four Challenges for Virtual Teams in Startups

One of the biggest changes in project management in the last few years has been the rise of virtual teams. First, it was multinational corporations that had to grasp the challenge of coordinating people in different locations. Then, increasingly, it was smaller businesses that grew by harnessing virtual teams of professionals in different organizations.

But now, even the smallest micro-organizations and entrepreneurial startups are having to learn how to make virtual teams and collaboration tools work effectively because the talent they need is not always located where the founders set-up shop.

We’ll set aside the debate that swings like a pendulum about whether working from home or at the office is best. Instead, we’ll accept that it you may have to collaborate with remote workers for many reasons, and ask, “What are the challenges, and how can we rise to them?”

how to manage virtual teams in your startup

1. Trust

For me, the single biggest challenge is building a culture of mutual trust between your remote team and your in-house team. Because our social skills have evolved to assess trustworthiness of people in close proximity, and we have also evolved to feel the greatest social obligation to the people around us, trusting off-site employees can be difficult.

Related: How to Build a Team of Freelancers Like a Pro

On top of that, we have seen the impact that the distance that social media gives us on our inhibitions. Many people now say things via these tools that they would never have said out loud in a public place.

So, building the trust of people who aren’t here, and learning to trust them, is a huge challenge.

Act “As If”

The first step to building trust is to act ‘as if’ that trust is there already. Treat people as trustworthy, and they will feel a greater compulsion to meet your expectations. This is the “if you build it” principle applied to social trust.

Small Wins

Look for ways to create small proofs that people can trust you and that you can trust them. Once we form an opinion based on events, it’s harder to shake that perception. So, make a special effort to keep promises, and early on, set tasks that will be easy for your virtual team to fulfill.

Respect Their Norms

Everyone has their own ways of working and behaving. And the further they are from you, geographically, then typically, the greater the differences in social norms. We won’t discuss the differences between cultures (cultural norms) that amplify the challenges of virtual teams to a new level.

Here, I’m referring to work habit differences between one employee, who always takes a full lunch-break to walk her dog, and another who is happy to work through lunchtime when he needs to. Keep those differences in mind when assigning workload and time-relevant tasks.

Courtesy, Openness, Fairness, Reliability

There are so many standards of behavior that can signal trust, and none of them are too hard to adopt. It simply takes presence of mind to exercise them all continuously.

And of them all, courtesy is the one I’d single out as the easiest to do, but also the easiest to let slip. So, make a deliberate practice of being polite to everyone. It’s a short hand that says, “I respect you, and you can respect me.” When you build a culture of courtesy, and supplement it with scrupulous fairness, appropriate openness, and constant reliability, trust will come easily.

Related: How to Manage with Servant Leadership

2. Challenging One Another

Creating a space where team members can comfortably challenge one-another’s thinking can be a big obstacle with virtual teams. This is not least because it can seem rude and disrespectful in the cold realm of virtual communications.

Yet, done well, it is anything but. And, ideas and decisions that go unchallenged can easily lead to disaster. So, it is vital that you can build a culture where everyone feels comfortable both giving and receiving challenges to the ideas that are on the table.

Formal Roles

I’d always start with formal processes when discussing ideas that will lead to important decisions. Asking a virtual team to find drawbacks and anticipate problems invites challenge in a structured way.

You can take it further, by appointing one or more people (two makes it easier to avoid social isolation for the one) to act as a devil’s advocate. And my favorite approach to use Edward de Bono’s Six Thinking Hats method.


One approach I particularly like leans heavily on Honda’s Waigaya process. While they use it for on-site meetings that are distinctly not virtual, a vital principle is that once anyone puts an idea into the discussion, they no longer own the idea. It belongs to the group. It is for the group to evaluate it and stress test its rigor.

Avoid Decision-Maker Stating Position Early

Have you noticed that when the boss—or an expert—states their position, people become reticent to share their own ideas? It’s a well-understood effect that combines two cognitive biases: anchoring and authority. The most effective facilitators of discussions know this. They create respectful challenge among peers by looking to experts and decision-makers only after everyone else has debated the topic.

Related: Top 10 Brainstorming Ideas for Your Team

Inscrutable leaders will give away nothing about which arguments weigh heavily with them, until they have heard enough to make their decision.

Regular Cycle

The best way to get everyone feeling comfortable with challenge is to make it a habit. Build it into every staff meeting, or discuss ideas and decisions on a regular cycle.

3. Responsibility

My third challenge for virtual teams is how to create accountability, responsibility, and appropriate levels of control among people who aren’t there. I have three suggestions, and the first two work well with co-located teams too.

Visible Progress

The more you can make progress and responsibility visible, the greater the incentive to contribute. This is the basis of team boards and progress charts, posted in factories. Modern technology allows you to easily create counters, dashboards and kanban boards for people to share remotely.

Jiminy Cricket Effect

If you want someone to do what they will say they will do, there’s little that beats looking them in the eye and asking them the yes/no question, “Will you do it?” and then waiting for an answer. Treat any answer that is not an unambiguous yes, as a no.

You can do this on a video call (just use proper phone etiquette), and you can amplify the effect by asking for the response in writing by using email. Best of all, ask your question in front of other people.

Geographical Exchange

It’s easier to let people down when they are just an anonymous “someone else.” But when we meet them in person, all that changes. And if we spend some time walking in their shoes, we get a sense of what it’s like being them.

So, arrange for people to spend some time with remote colleagues, and bring remote colleagues into the main offices. It doesn’t need to be often, but each time you do it, you top up levels of trust and co-responsibility.

Related: How to Stay on Task When You Work From Home

4. Connection

The final challenge of a virtual team is to make sure we are all accessible to one-another and make the effort to communicate well. Chatting and sharing stories come as naturally to human beings as any other bodily functions. It’s just that remoteness feels unnatural and blocks our natural instinct.

Chat Time

A simple fix is to allow informal time to chat and gossip at the start and end of conference calls. Imposing overly rigid structures on these calls takes away the naturalness of the conversation and inhibits free-flowing sharing of ideas, challenge, and therefore, trust.

Related: 20 Icebreakers to Make Your Next Meeting Fun

Disclosing Something About Yourself

Nothing builds connection like shared experiences or concerns. And, to help people identify the things you have in common, you need to be prepared to share your own interests and backstory.

Now, I’m British. So, I’m not talking about letting it all hang out. And you absolutely must respect social norms. But a small amount of self-disclosure about family, friends, interests and past can go a long way to building connection.

Sharing Cultural Norms and Expectations

Of course, you may not be British. In fact, looking at the populations of Britain and the world, there’s a little less than a one percent chance that you are.

So, you’ll have different cultural norms and social expectations to me. And that’s fine. So, how can we know what to expect of one another? And how can I tailor my approach to help you feel comfortable?

Yup, you got it. We need to talk about these things.

Regular Cycles

And last, but not least, if long distance communication is hard, one thing will make it easier. The more you do something, the easier it gets, and the better you become at doing it. Set up regular communication, so you and your virtual team become more and more familiar with each other.

Commit to Your Virtual Teams

Every one of these suggestions is simple. But simple is not the same as easy. It’s not easy to do all of this. But if you discipline yourself to do more and more of it… Guess what? It will work.

Virtual teams are more common with startups, but they’re being used in traditional businesses, too. If you’re managing a remote team, then you need Our cloud-based project management software allows everyone to work collaboratively, no matter where they are or when they work, while updating tasks in real-time to avoid blocking other team members. See for yourself by taking this free 30-day trial.

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