Leading a startup team through storms and challenges

Leading a startup is comparable to sailing a boat. Before setting sail, it’s important to decide on a path to navigate, ready the ship and select the best possible captain. The captain must ensure the ship is well maintained and fit to sail, checking that weather conditions are safe and that you have the necessary provisions for your journey.

In a perfect world, you would easily reach your destination following a set path. In reality, there are forces outside of our control that could ruin any well thought-out plan, like encountering a deadly storm, hitting an iceberg, or sailing off-course and running out of supplies. The unforgiving sea can turn any capable captain into a lost sailor battling the elements in a relentless storm, with a broken boat and a demoralized crew.

That is precisely what entrepreneurs face everyday.

Leading a startup through a wave of disruptions and uncertainties, adapting strategies and motivating team members

Facing hardships as a team creates more resilience and perseverance. Startup teams can learn to work better together and deal with problems as they arise. As a leader, your role is to create enabling conditions that will allow your team to flourish.

“What matters most to collaboration is not the personalities, attitudes, or behavioral styles of team members. Instead, what teams need to thrive are certain ‘enabling conditions’.” – HBR’s Secret to Great Teamwork.

In this article, we look into four main factors surrounding great teamwork and a few helpful tips,as to how startup leaders can create the best environment for their teams.

On Team Culture

The collective values, beliefs and behaviors of a team define its culture. Culture often reflects the team’s vision , it enables its members to perform at their best to reach collective goals. Startup leaders should think of how the culture will be shaped early, when the team is still small. This will help hire individuals that fit the collective..Culture also sets boundaries on acceptable behaviour within the team, so that a certain level of professionalism and respect are maintained.

For example Chevron is a car company displaying an excellent example of strong team culture. They strive to enhance team betterment the ‘Chevron Way’. This is not mere posturing as the business back up employee care with fitness centers, massages, personal trainers and encouragement of wellbeing practices.

When discussing culture, we believe it’s more important to bring up a list of don’ts rather than do’s.

The Absence of Trust

In ‘The Five Dysfunctions of a Team’, Patrick Lencioni muses that the absence of trust is the core problematic value upon which a successful team cannot blossom.

“Absence of trust is the foundation of all dysfunctions. And the root of it is the inability and unwillingness of employees to be vulnerable and open to each other. Teams which share personal insights and experiences always show better results!”

Knowing you aren’t trusted is extremely damaging to self esteem, morale and motivation. If an employer needs to mollycoddle an individual through their tasks then perhaps they shouldn’t have hired that individual, or at least their assigned tasks should be revisited. Trust is the foundation of great teamwork. It is acknowledging that even though your team might make bad mistakes, trust gives your team hope and strengthens collaboration.

Compromising Core Values

As a leader, you should lead by example. Core values set a certain expectation on desired behaviors in the team, and they are the enabling factors that allow team members to respect each other and work better. Core values are made to live by; you cannot compromise and think people won’t notice. If you compromise on key values, your team loses trust in you and the organization. For example, if your team’s core value is putting customer’s needs first, but you create aggressive sales processes that force people to fall into the funnel without any empathy for their needs, you send a message that sales are more important than anything else.

Tracking by Hours

This model makes sense if you are in manufacturing. But if you are a startup team of knowledge workers, not only does this model not work, but it is draining. A person could be spending 9 hours a day in the office and achieve close to nothing compared to someone who gets to decide their own office hours. This is all about giving your team the autonomy to manage their own time. Productivity should be measured by progress and results, rather than by hours. Try giving your team flexible work hours, or allowing them to do remote work, and setting OKRs for them to achieve. Your team will thank you for making their lives easier.

On Communications

Great communication is the backbone of great teamwork. Teams that keep each other updated often work better, achieve more, and experience less confusion. There are multiple ways leaders can enhance team communications.

Allow Asynchronous Communications

We live in a busy world with an expectation for instant gratification. With the advancement of technology, patience has faded and we have come to expect instant responses, both to queries and with software solutions. Yet, this distracts us from doing deep work and focusing on our craft. Leaders can aid that by allowing asynchronous communication – i.e. communicating without expecting an immediate response. For example, we shouldn’t guilt team members for not being online and available 24/7; It’s healthy to turn off notifications while focusing on a task. Everyone should have access to physical spaces for deep work without distractions.

Adopting the Right Tools

How many tools are you using for teamwork at the moment? We’d guess five or six! That could be emails, messenger groups, spreadsheets and documents, file drives, and perhaps those cluttered sticky notes and to-do-lists. When there are too many tools to work with, communications often get messy. To avoid getting lost in chaotic file management, we recommend keeping everything streamlined to three or less platforms. Our suggestion is to use a single, powerful, project management tool to keep track of everything. These often include real-time messenger features and even the option to include external parties.

Reduce Unnecessary Meetings

Scattered work and poor communication leads to a demand for more meetings, to sort the chaos out and leads to loss of productivity By improving organization and communication, you’ll not only reduce further unnecessary meetings. More often than not, it’s more effective to update progress or information through a central hub/collaboration tool. However, if there is really a need for physical meeting, you can make it more productive by defining an outcome, setting an agenda, and ensuring it starts and finishes on time.

On Leadership

We can’t talk about teamwork without putting an emphasis on the importance of effective leadership. If communication is the backbone of great teamwork, leadership is the heart. Leaders pump energy and vision to team members.

Make Decisions

As a leader, you make a lot of decisions everyday, and the worst thing you can do is to not make any.. In a startup environment where many things are fast-paced, it’s important that you make quick decisions and learn from them. It’s inevitable to make bad decisions, and it’s okay to be vulnerable and lean on your team for support.

Leader as a Coach

There are many different leadership styles out there that we can apply in different situations, but in startups, leaders should have the ability to mentor. Being a coach means being a grounding influence that empowers the team to solve problems. In a culture built on trust, leaders communicate goals clearly and put faith in their team to tackle the problems competently. Effective leaders ask key questions to develop critical thinking in their team and offer support when needed. Remember the key difference between a leader and a ‘boss’, is the ability to lead, empower and support rather than purely bark orders and oversee. The effective leader will develop team members to lofty heights whereby they’ll gain the skills to lead themselves.

Embrace Failing

Create an environment that allows for team members to take risks, and learn from any potential failures or mistakes. By using ‘black-box’ thinking, team members can improve processes and continue to grow and develop. An effective leader will have to risk such potential failings when making decisions, and team members should be granted that opportunity too. Learning from your mistakes is an integral part of growing that is difficult to replicate.

Don’t Avoid Conflicts

Conflicts and confrontation can be useful. A leader may feel the need to keep the peace, but that doesn’t mean stifling creative conversation. Team members should be given the platform to debate opposing ideas and viewpoints, and fight for what they believe to be best. The leader’s role should be to ensure that the forum to do this is both healthy and respectful, so that conflicts are productive and constructive.

On Goals

Teamwork is about a group of people working together to achieve a common goal. Teams work better together when they know what they are working towards. Leaders can amplify that by:

Setting Priority and Objectives and Key Results (OKRS)

Setting a clear priority is crucial for teamwork. For a startup, the first and foremost priority should be getting the basics right. If you’re selling a product, you should make sure it delivers its promise before you advertise it. We often consider the minimum viable product, i.e. what is the least we could do to effectively meet our goal.

It’s better to have one clear priority than having five or six met halfway. Once you set your priority with a realistically achievable timeline, your team can start defining OKRs – Objectives and Key Results. Objectives are the goals to be achieved, while Key Results are the measurement values of those objectives that you’d deem a success.

For example, if you’re launching an App, perhaps you’d consider 5000 downloads in the first month to be a success. Or, 300 subscriptions to your newsletter.

This helps organize the work your team does around a common goal – in this case, achieving the set priority. Defining objectives for tasks helps align everyone with the same priority; it positions the startup as one that focuses on outcomes.

Drive, Mission and Purpose

Our generation is driven by the need to contribute to a greater cause. Not only do we strive to find jobs that challenge us but we seek jobs that contain meaning and connect us to a bigger purpose. In order to attract and maintain talent, a leader’s role is to convey their vision with enriching purpose. That way, your team feels fulfilled knowing that their work is making a significant difference. Leaders must ask themselves how they are impactful beyond profits and how does their organisation contribute to greater good and frequently remind their people. They must use the reason as an anchor for all strategies and decision-making, model desired behaviors for teams, and empower them to act.


Leadership is not about being in charge. It is about caring for those you are in charge of.” – Simon Sinek, author of “Start With Why”.

It’s clearly apparent that effective leadership requires a great deal of consideration for many aspects of team management. Through strong communication structures, trusting teams and defined vision, it’s possible to navigate through the toughest situations. Much like the sailing boat in the storm, a solid team can face the greatest challenges as a unit to combat failings with contingency plans and revised learning.

This article is a partnership with Bloo, a project management software that helps teams stay organised and work better together. Teams that use Bloo improve their collaboration and work process; They report having more clarity over their work progress as everything is in one place. Bloo has a 14-day free trial and a supportive team behind to help you get started – Visit them: www.bloo.io.