How to Address Timeless Start-up People Challenges?

Recently, I was asked by someone ‘What are the top challenges start-ups face?’; a question I get asked quite often. Since then, I’ve boiled down the challenges into 3 key areas that are not mutually exclusive and drive each other, particularly when we’re talking about people. 

The three questions top of mind for a start-up are: 

  • How do I hire the right talent?
  • How can I scale effectively?
  • How can I build a high-performing culture?

While we can’t ignore the fact that the size and stage of a start-up may provide different answers over time, some of the principles in the zero to a hundred headcount stage (which I’ll focus on) will still stand the test of time regardless of stage. 

How do I hire the right talent? 

I personally believe this area always poses the biggest long-term risk to a company. This is because the people build the strategies, the culture, the product, and the operating systems. While it’s easy to say that different hires will bring different skill sets over time, the operating and people architecture and cultural DNA will still be difficult to refactor if misaligned or not sufficiently scalable (and therefore a cost) and thus my advice is to strive to build the best foundation from the start. 



 Answering these questions will tell you the level of experience you are likely to need, where they may need to come from, and whether this work requires full-time, contract, or part-time hires. The cost will likely increase with higher levels of complexity, speed, dependency, and knowledge. You can then start drawing out the skills required, and whether this needs to be brought internally or outsourced. This will support you in covering the basic alignment of skills and level match to the work and speed required. 



Answering these questions along with a good assessment will tell you whether new hires will align with the things you care about the most as a founder and company to achieve your mission and whether new hires have the character to cope, /adapt / and behave with the day-to-day challenges and needs of your company. Thirdly, you can then determine your future direction, and whether the new hires can take you on that journey and inspire others along the way. 

How can I scale effectively? 

It doesn’t hurt to hire senior team members across functions early on that are ‘operationally minded’. In my experience, this is the biggest compliment to the ‘visionary founder’ whose natural gravitation is towards product, customers, and culture. This relieves this type of founder from having to make every decision autocratically as they are confident in delegating more of the day-to-day running cross-functionally. This is needed as you’re in a ‘from scratch’ position, genuinely building the company. Ensuring you have people who lean into design frameworks around light principles, policy, processes, and systems and are passionate about the mechanics of your company early on can really accelerate you. Your dashboard wizards and pure strategists can come a bit later. 



How do I build a high-performing culture? 

This is my favorite question of all, but it is too multi-faceted for one blog. There is no truly objective definition of a ‘good’ or a ‘bad’ culture. As such, I prefer to talk about ‘strong’ and ‘weak’ cultures, which can be easily identified. It’s also important to understand that the outcome of a strong culture aligned with a solid strategy is high performance and in turn, is evident in your position in the market. 

However, in my experience, a signal of a weak culture is company politics and politics creep in due to one thing: lack of alignment. People moving in different directions, wanting and seeking different goals or agendas will kill your culture. And so, regardless of the size of a company, absolutely ensure people are on the same page, or at least create and ensure buy-in from everyone on the below: 

  • The purpose (Why does the company exist? What problem(s) is it solving?)
  • The mission and vision
  • The company values
  • The goals and in turn priorities

Truly shared goals become important for leaders to align on as this dynamic and relationship at the top around goals and priorities is how the team’s underneath will work together (or in the case of misalignment, teams work against each other). 

Leaders who are aligned on the strategy, goals, and priorities are less likely to quibble over total resources, spend, and time distribution across the company. Objectives and key results can support alignment, but sufficient time together as a leadership team sense checking that the shared goals are truly felt is time well spent. A founder needs to pay careful attention to this and call out if they recognize someone pulling in a different direction early. Seeds always grow into trees. 


Sign Up for Our Newsletter