Sorry, not sorry: Lessons learnt from building startups

From my experience working with startup founders, I have identified 7️ mistakes that are commonly made and can be avoided. In this article, I will focus on hiring, as it is particularly challenging in the early stages of a startup. Having made many mistakes myself, I believe these errors can be corrected quickly with the right approach.

❌ 1. Not having a plan

Imagine that you have received an investment, there is pressure to fill all the roles at once, and yesterday was already too late. Roles such as VP Sales, AE, Engineering, Recruiter, Designer, Product Manager, Marketing, and Finance Director need to be filled.

Before you start, I suggest making a well-thought-out plan. Spend time thinking about what roles you need, what you expect from them, and how these roles are linked to your business goals. You can illustrate this by having each team member sketch out their idea of an org chart — a structure at the end of the year or some other timeframe — and determine what roles you have now and which ones you need to fill. Prioritize the roles so that you don’t fill all of them at once.

Asking questions such as the following can help you come up with a goal for each role.

• What work actually needs to be done?
• What happens if we fail to hire this specific role?
• Is our plan realistic? Do we have enough resources to fill this plan?
• Do we need to work with an agency or hire a recruiting team?

You can also think about their 30–60–90 plan. This can help you avoid hiring someone who would be unnecessary.

❌ 2. Hiring too quickly

It can be a mistake, especially when you’re under pressure from investors after raising money. Waiting six months to fill a critical role can be tough, but hiring someone who is just OK is not the solution. If you hire an average person, you’ll create a vicious cycle where the best people won’t be attracted to your company, while the average ones will attract other average ones. In the long run, it’s better to wait for the right candidate who will raise the bar in their category, even if it means growing more slowly. Patience is key when it comes to hiring.

What if you’ve already made that mistake? Let’s discuss a few practices for saying goodbye. Here are some tips we’ve gathered from our journey:

• Act quickly and don’t wait. If you made a quick hire that turned out to be toxic or a low performer, identify what went wrong and how you measure goals.
• Put the person on a performance improvement plan (PIP).
• Ask the person to write a self-reflection and retrospective, and collect 360 feedback on them.
• Communicate transparently with the rest of the company.

By following these practices, you can handle the situation effectively and minimize any negative impact on the team and organization.

❌ 3. Not knowing who should be your first hire

You are in a situation where you need to hire people for the GTM team, and you have to choose the first person. Will you look for an individual contributor or an experienced leader?

Well, you should always be looking to hire a player-coach; someone who can roll up their sleeves, has experience building infrastructure, and has the potential to lead a team in the future.

❌ 4. Outdated hiring model based on volume

The hiring model that focuses solely on inbound candidates, which involves optimizing ATS, job boards, and job descriptions, is outdated. While these methods may help attract some candidates, they do not solve the most pressing issue of how to attract top talent, especially in the early stages. ATS such as Greenhouse motivate recruiters to reach inbox zero, which is a success for them, but not necessarily for hiring top talent. If 5 mediocre candidates apply, then that’s considered a win. This approach does not target top talent.

Today’s top candidates are likely being well taken care of by their current employers because they understand their value. These individuals are not actively seeking new job opportunities. Therefore, you must make an extra effort to build real and deep relationships with them as the foundation of your hiring process. A candidate who is considering a career change is likely motivated by purpose and meaning. By the way, I am sharing a really powerful tactic here. 😉

❌ 5. Lack of knowledge of the new function

Starting a new business is tough! As a founder, you’ll need to be a jack of all trades in the beginning, handling everything from sales to customer communication to HR. But there comes a point where you’ll need to hire experts to help you grow your business. The only problem is that you may not fully understand the roles you need to fill, which could make it tough to find the right candidates.

For example, let’s say you’re hiring your first marketing expert. You might not know what marketing really involves, but you know you need someone to help you get the word out about your product or service. So, how do you know if you’re hiring the right person for the job?

Well, first, you need to determine what level of seniority you require and have a chat about it. And since you might not know all the ins and outs of the role you’re hiring for, it’s a good idea to have an advisor with experience in that specific field to help you interview candidates. For instance, if you’re hiring a Head of Marketing, you could have an experienced marketing advisor, like someone from Deepnote, to assist with the hiring process. Remember, founders can’t do everything on their own forever. Eventually, they'll need to rely on advisors and experts to help you build the right team for your startup. So they shouldn't be afraid to ask for help.

❌ 6. Not investing time in sharing

The engineering team has informed you that a serious problem occurred in production. They also mentioned that the issue was interesting from a technological standpoint, and even experienced developers had never encountered it before.

Now, let’s discuss why people don’t share certain content on social media and how to encourage sharing:

1. Communicate the importance of sharing. If your founders are encouraging sharing content and writing articles, speaking about its importance at conferences, and emphasizing it in all-hands meetings, that can make a difference.
2. Make it easy for people to share. Provide links that are easy to share and schedule time for writing in their calendar.
3. Help people overcome imposter syndrome by connecting them with a content writer.
4. Show people the results of sharing.

❌ 7. Copy paste solution

Copying big tech processes is not always a solution because every company has its own unique infrastructure and context. To succeed, you must become adept at scrappy startup building. Most of the work is invisible but necessary for scaling. When transitioning from Productboard to Around, I expected to use everything I learned and did at Productboard as a template for building teams and people ops infrastructure at Around. But then I hit a wall. I had to adapt because the two companies were built on completely different foundations. Around was built as a remote-first company while Productboard was built around an onsite culture that required real-time presence. When Covid hit, our Productboard team had to find ways to spend time together online, such as through virtual concerts, firecamp, lunch, and other activities. Meanwhile, the Around team focused on building an application for remote teams that helps with asynchronous communication. Values and benefits differ between companies, so it’s important to find what makes your company unique. Everyone has a sense for something different, and that’s what inspires others. I realized that organizing daily happy hours or spending too much time on video calls was not aligned with Around company’s values and goals, and was therefore a waste of time.

Building a successful startup requires making smart hiring decisions, which can be particularly challenging in the early stages. However, by avoiding common mistakes such as not having a plan, hiring too quickly, not knowing who should be your first hire, relying on outdated hiring models, and lacking knowledge of the new function, you can increase your chances of finding the right candidates for your team. Remember, hiring is a critical process that requires time, patience, and careful consideration. By investing in your hiring process and focusing on finding top talent, you can set your startup up for long-term success.