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Traps & Challenges of Building Your Startup Team

Your biggest challenge may not be building your product but assembling an effective startup team. In the early stages, founders will typically take on multiple roles. For this reason, many founders tend to hire “generalists,” employees that can hold a multitude of functions. But what may work fine at the beginning may prove ineffective later down the road, where a more formal process could be called for.

Filling the business gap

Although there may be many functions that are important, you will likely need to prioritize the “must haves” versus “nice to haves” for your first hires. Taking an honest look at the skills you possess versus those you do not, is essential. It will help you identify your business gaps. Does your startup need to fill positions in sales & operations, technology, design & UX, or possibly marketing strategy or finance? These are all key roles most technology startups should consider filling. Some good questions to discuss and write down are what the expectations are from each role, who might be the best fit for it, and how frequent should personal evaluations be.


If you are interviewing candidates, it’s advisable to provide an honest description of the difficulties the startup is facing and its future goals over a sugar coated narrative highlighting job perks. Committed and determined candidates, who are open to taking on challenges, are the ones you want on-board. A shortcut to this process is hiring someone you have already worked with on a project prior to starting your business, so that you already have a sense of their work ethic. But do not rely on that entirely. The pressures of a startup are different. Think about setting up an assignment or two to test out the ground.

You may also consider a group interview in order to gauge how well a potential employee works as well as relates to the actual members of the team. If hired, the employee should be greeted by the team members who were involved in the interviewing on his or her first day to ease the on-boarding process.

What project managers bring to the table

Many technology founders prefer a non-hierarchical organization. However, to a certain extent, your startup might benefit from structure as well as reporting chains, and you should not be fearful of them. Managers can contribute to freedom within the framework and stand to have the greatest influence on whether a new-hire’s orientation is effective or not.[1] You can leverage their experience in assessing candidates who can effectively collaborate with difficult people and in challenging situations. If your managers are involved in recruiting, ask them what their interview process looks like both to learn from it and to assure that it is not improvised.[2]

A word on culture

Intentionally building a positive culture in your organization could significantly impact the future of your startup in more ways than you can imagine. Investors not only evaluate your product but also assess the values and character of your team. Starting the conversation early among founders both sets the tone and helps smooth expectations.

Some team building activities such as leadership games may come out as a forced way to create positive work relationships, but not all team building activities are created equal. Volunteer work, walks for a common cause and shared meals are just a few examples of activities that can be highly effective in strengthening your team.

Last Tip

With time the company grows and the dynamic between the team members evolves. Taking on a coach to periodically evaluate your team is a great way to add objectivity and promote the health of your company.

[1] Onboarding Essentials: What Really Matters to New Employees (Infographic)/Entrepreneur

[2] How to Hire/Harvard Business Review