5 Leadership Lessons from a First-time Startup Founder

As we look forward to the new year, I have been pondering what are some of the biggest leadership lessons I’ve learned this year. WOBB has gone through significant growth, starting from just me (one person sitting at home in my pyjamas), to a 25 person team, with some of the most talented employees in the business.

I’ve definitely made many mistakes and learned a lot from them, but here are my personal top 5 leadership lessons.

1) The team doesn’t live inside your head

I’ve met founders who said that they were frustrated when the team doesn’t seem to be able to deliver exactly what they’d would hope for. “Sometimes if you want to get something done right, you have to do it yourself.” Admittedly I’ve had this thought myself too.

But what I’ve learned over time is that poor communication from the leader can cause a lot of these problems. When leaders don’t communicate with clear instructions and specific expectations, it causes the team to try to figure out what they think you are looking for, based on that they know, and of course, they are not going to get it right. Because they are not mind readers, they don’t live inside your head.

I always try to remind myself that as the founder of the company, I have access to information from other founders, investors, clients and competitors etc. I’ve been in the company since the beginning, and have clear context of everything that is going on in the company, because every team reports to me.

I can see the full picture. The full picture that individuals in the company do not have access to.

It is therefore our responsibility as leaders who have all the information, to see that your team can’t see everything you see, unless you make that effort to show them clearly what you need, or give them access to the information that will help them. Be clear and specific about your expectations.

Because if you don’t make that effort and just expect them “to know”, it’s your fault that they are not delivering good work, not theirs.

2) Be quick to weed out the “show horse”

(To be kind, I have changed some details of the following story to keep the person anonymous, but the essence of the story is here.)

Jim joined our company full of enthusiasm. Every time I spoke to him, he was incredibility helpful, looks so engaged and was always willing to do everything that I asked. He was also a very bright kid, someone I could ask a question to, and he’ll somehow find an answer.

I really liked Jim, and was thinking of promoting him.

Then one day, someone came to me and started sharing his concern that he caught Jim spending his time watching Youtube during working hours, and sometimes even during meetings, when I’m speaking at the front, he would be watching a video on his laptop instead of paying attention to the meeting.

I was surprised to hear that. There’s no way Jim would do that. Not the enthusiastic Jim that I know.

Then over time, I started hearing other concerns from other people in the company. Uncollaborated, totally independent stories.

“Jim doesn’t go for any client meetings, his calendar is always empty. He spends more time trying to talk to you than get any meaningful work done.”

“Jim is rude to me and doesn’t take feedback well when the team asked him to work harder.”

I started to wonder… wait, is Jim behaving differently in front me because I’m the boss? I paid more attention to his actual work and how he spends his time in the office.

And it turned out to be true. Jim spent most of his energy trying to appear to be doing a great job rather than actually doing it. He had the lowest activities, and delivered the least results. Everything that he touched either stagnated or became worse.

Jim spent most of his energy trying to appear to be doing a great job rather than actually doing it.

It was so easy to be blinded by this “showhorse” had I not made the decision to be unemotional about this and looked at it objectively without any biases.

Suffice to say, Jim didn’t stay long in the company after I started paying more attention to his actual performance rather than appearances.

Remember to watch out for the showhorse.

3) Embrace your “followers” as equals because they make you a leader

As single founder, people always ask me whether it feels lonely not having a co-founder I can share my worries with, or to bounce off ideas. And when I tell them that I can do all these with my core team, it always surprises them that our team is so engaged.

In fact, the team is so passionate about the performance of our business, that I often find them seeking out to do more for the company, seeing problems that worry them and proactively figuring out how to fix these problems, and sharing a lot of the stress that I share as a founder.

But what’s the secret? There no big secret. Just pull them into your world as an equal. As someone that you genuinely value, with opinions that you value, with actions that you trust.

Of course, some of you are now thinking “but not everyone in my team is at the level where I can trust and empower them in such a way”. In which case I would ask you to either:

  • Try anyway, because are you sure you can’t empower them? Or is it because you don’t have the courage to let go?
  • Start thinking about your talent attraction / employer branding strategy so you hire better people

Either way, this video from Derek Sivers reminds me all the time how your followers make you a leader.

4) You dictate the culture of your company

Leaders play a critical role in influencing the culture of their teams. After all, you decide that is acceptable behaviour and what is not. You decide what behaviours get rewarded, and what gets punished.

So if you’re ever in a situation where you’re frustrated that your team is “lazy”, or always late, or don’t openly share their ideas, very often you’ll find that it’s you (the leader) that made the culture what it is.

Whether it’s because of your decisions to hire the wrong people (that ultimately influenced your team’s culture), your inability to publicly reward the right behaviours or punish the wrong ones, or because you do not lead by example, it really all comes down to you to dictate the culture of the company.

Your inability to publicly reward the right behaviours or punish the wrong ones… it all comes down to you to dictate culture

If you don’t want others to be late, then you shouldn’t walk in late just because you’re the boss. If you want your team to share ideas and act proactively, then don’t get annoyed whenever you hear an idea you don’t like (how are they supposed to know what ideas you don’t like, over time they will just learn to speak less).

At WOBB, we even went as far of building our own 9 core values that are specific and actionable to give the team clear guidelines on what is expected behaviour. We obsess about these values, and it’s what drives a lot of our business decisions.

WOBB’s Wall of Values is situated in the middle of the office and takes up an entire wall, as a clear visible reminder to the team about expected behaviour in the company.

5) You should pay more attention to your star players, not less

A common mistake I find many leaders make is that they tend to leave their best people alone, get out of their way. In their mind, if they have a star player that has earned their trust, they should leave their star alone. That’s called “empowerment”.

These leaders then tend to focus their time and energy on their weakest players in their team, which they believe needs “fixing”.

I believe that’s not a great strategy. Because not only will you find that spending time with your weak players doesn’t guarantee they will perform better, you will also soon discover that your star players will also start to get demotivated.

Your star players will soon feel that they are no longer growing in their role, or no longer getting a lot of recognition for their achievements. After all, they are star players, they are always expected to perform and deliver, and over time, it just becomes “normal” and no longer celebrated.

They are no longer coached, because how do you coach someone that is already at the top of their game? And this adds on to your star players feeling stagnated.

I’ve always believed that a better strategy would be to focus your time and energy on your star players instead. These are your best people. They are the most engaged. They have high will. They want to keep growing and they care deeply about their performance and your business.

Give them recognition for their achievements, no matter how many times they keep hitting their goals (that’s a good thing right? Celebrate!). Spend time strategising with them, supporting them, working on making them better.

Paying attention to them is not about you not empowering or trusting them. In fact, very often, high achievers want attention, because that’s what drives them, and it’s a mistake to stop doing that.

And how about coaching? How do you coach someone that is already a star? The real question is – why are you making it so easy for them? They are your star players! Give them bigger tasks, challenge them to do more. Make them uncomfortable.

That is your opportunity to coach them so they keep growing and pushing boundaries. Celebrate whenever they raise their standards. And support them when they need help.

And other people in the company will look to them as examples of how to excel in the company.

In short, investing your time building your best people is a much better long term strategy that will produce a high performance team.