The Five Most Important Startup Leadership Attributes

My nearly fifteen year professional career has been in the world of tech sales in various go-to-market roles. In most cases, the companies I have been a part of have been very early stage, and I’ve had the opportunity to be a first go-to-market hire or even a first hire multiple times. I spent half my career in one company called Next Caller, following its journey from inception all the way to its exit (by acquisition) a few years ago. All this to say, I have what I think is a unique perspective on what makes for effective leadership in tech startups.

One of the reasons I’ve enjoyed startup life is because I feel like my role simply matters more. It stands to reason that the fewer people there are, the more each individual’s impact can be felt. But with great power comes great responsibility. Every role is magnified that much more in a smaller organization with fewer resources. This means that it is absolutely critical that the leaders of a startup are well-positioned to perform their functions effectively. Most startups fail, statistically speaking. The cards are stacked that much more against you if you have incompetent leadership.

I think there are a lot of attributes specific to startup leadership that are must-haves. The list I am going to present is certainly not exhaustive, but it should at least be a good start for aspiring founders and startup executives. Let’s dive into it.

5. Delegation

Something I’ve observed in my work advising and consulting for startup founders is that they often have a hard time “letting go” of various things. The founder of a company is often the best salesperson until they inevitably need to hire real salespeople. Founders typically love having control. After all, the company is their baby, and they have taken tremendous professional and financial risk by putting themselves out there and gambling that they can beat the odds and build a successful startup. 

What this means is that delegation becomes a critical skill. You need to be able to delegate responsibility to other capable people. Of course this invariably means that you also must do good hiring, and that you also need to find trustworthy individuals while also being trusting yourself. Those are peripheral attributes that also contribute to delegation. 

Sometimes delegation even includes humbling yourself and consulting with experts to help you. I’ve worked in startups where we brought in consultants to help with product or go-to-market planning. Even hiring a banker to help with an M&A deal at the end of the road is one form of delegation. You simply can’t assume that you can do everything yourself, whether its as the founder or even as the entire leadership team. It’s OK to ask for help. In fact, it’s better to do it at the earliest possible moment you recognize that you need it. Stubborn refusal to have the best people do the job simply means that you are not optimizing your chances of success.

4. Flexibility

Good startup leaders have to be flexible. The reality with startups is that things are changing constantly. In one startup I worked at, we spent years building a product and a team, only to pivot to an entirely new product. We downsized our team and fired all of our customers overnight. Our new vision ended up working out, but we needed to be flexible (and realistic) about the fork in the road we were facing, and fortunately, our flexibility led to our success.

Part of being flexible means you question everything. Not to sound hyperbolic, but you need to have some paranoia about your current path at all times and be proactive about asking yourself if alternative directions are superior to the one you are taking. 

The reality in startups is that oftentimes expectations are not reality. You might hire a first salesperson and believe that that individual will make a lot of money. But the reality might be that you have not yet achieved product market fit, you hired the individual too soon, and you may need to be flexible about how you compensate that individual in light of new information that you receive. “New information” is the key term. As long as you are principled in being data-driven, you will remain flexible in the best of ways.

3. Empathy

Startups are fast-paced and processes are often not defined very well, if they even are defined at all. What naturally ends up happening is conflict. With few well-defined roles and processes, people just run into one another and they need to find a way forward. This is especially complicated since people will wear many hats in startups, so sometimes people inadvertently end up swimming in someone else’s proverbial “lane.”

With people moving at breakneck speed and often bumping into one another, it is important to set a culture of empathy. In one startup I worked at, one of the mantras our leadership team developed was “be solutions-oriented.” This means that when you have conflict, you dwell on the solution rather than the problem. You are not invested in finger-pointing; you are invested in finding a path forward. It requires empathy to have such a mindset as you need to be willing to understand that everyone is doing their best and working towards a common goal.

2. Accountability

There is little room for error in startup world. That means there must be a culture of accountability. When people mess up, they need to own it, adopt the growth mindset, use it as a learning experience, and try to do better next time.

Post-mortems are wonderful for startups. In my last startup, we did a post-mortem on every deal we lost. Running these post-mortems helped us to understand some major issues with our qualification and account grading system. Once changes were implemented, our conversion rates skyrocketed.

Accountability also means that you must have well-defined KPIs and OKRs. These metrics should be discussed often as a leadership team with very clearly and well-defined “inputs” for how each functional leader intends to achieve their desired “output.” Additionally, these metrics should be shared at the board level so that the founder can be held accountable to his or her bosses, too. Accountability leaves us open to feedback that we can leverage to enhance performance. We should never shy away from it. Stubbornness – about a failed go-to-market plan or, say, lack of product market fit – will easily be the death of a startup if it goes unchecked.

1. Transparency

If there is one attribute of startup leadership that far surpasses the others in terms of importance, it is transparency. I have been a part of teams where it felt like the leaders were being shady and not trusting of the employees. What quickly festers is a toxic work environment where the employees gossip with one another and question everything they are told to do. As they say, people don’t leave jobs, they leave their manager. The moment everyone feels like they are being lied to by their managers is the day they have one foot out the door, either actively looking for a new job or simply passively performing their current one (or both!).

Founders sometimes don’t trust that their employees or even their leadership team can handle bad news. Realistically, everyone is an adult and should be treated as such. Whether it’s about runway, fundraising, the cap table, or something else, founders almost always have some sort of bad news to give to at least someone in the company at all times. When you get out ahead of the bad news, you give employees the confidence that there is nothing bad lurking around the corner. When people feel like they have all of the information, they feel that it is within their own locus of control to be successful. In the absence of that, employees are left feeling that no matter what they do, there may be something obscenely bad that derails their efforts in any circumstance.