Humans are unpredictable. As a startup founder or leader, you’re not only tasked with building a successful business, but also being the best startup manager you can be to all of the people working to make your small business dream into a reality. In the past, there might have been a blueprint for how to build a successful business—but in the technology ecosystem, change is so rapid and disruption such a given that startup leaders simply have to get used to uncertainty and living in the grey.
This is where ideas from experts like Gillian Davis, leadership coach, author of First Time Leader and founder of Overtime Leader, a leadership and management advisory for tech leaders, come in. Gillian and her team have spent the past decade coaching and transforming founders and management teams of tech companies like Pinterest, Spotify, WeTransfer and TaskRabbit, and she wants the next generation of founders to avoid the mistakes they are often called in to fix.
So what can startup founders and others in leadership positions do to create a culture of cooperation and productivity from the outset? We’ve distilled some of the key points Gillian recently shared with a group of our early-stage startup founders, touching on themes from feedback to responsibility to hiring and firing.
1. Self-awareness is key
Bad leadership can happen to anyone. The leaders who create fear, toxicity and information bottlenecks (AKA, communication breakdown) in their organizations don’t wake up thinking, “I want to ruin my team’s day today.” Being a strong leader is constant work and it starts with self-awareness.
Gillian suggests that we use Ice Cube’s advice, who truth-bombed us so eloquently back in 1992, “Check yourself before you wreck yourself.” So, how can leaders become more self-aware and stop potential mistakes in their tracks? Breathing exercises, meditation and physical exercise are all a good start, but she also reminds startup founders and business managers that self-awareness isn’t a solo act, but a team sport.
“It’s a team sport and you need to create those checks and balances around you to make sure that you can check yourself. I work with a lot of people that think they’ve got it in check but when you ask the team around them, they’re like, ‘No. He’s lost it.”
2. Understand how to receive feedback
Creating those checks and balances extends to fostering a healthy working environment where feedback is openly communicated within your team. By modeling what it looks like to be open and responsive to feedback, others will feel safe to have tough conversations.
That might be easier said than done. Gillian’s top rule for receiving feedback? Listen to what the other person has to say without trying to defend, deny or criticize.
“Remember that if someone has taken this opportunity to give you feedback, they are in a very vulnerable state… If you then start to attack, you will shut them down. And you know what the first thing they’re going to do after that conversation is? [They’ll] walk out and tell everybody how horrible that conversation was with you. So then nobody is going to do it.”
If someone gives you feedback you’re unsure about, a good next step is to solicit more feedback from people whose opinions you respect — but be careful about confirmation bias. It’s important to find people who are both similar to you and very different so that you can get a balanced picture and be challenged in the right way on how you perceive yourself.
Finally, remember that feedback is perception. “If someone gives you feedback that you don’t agree with, go away and reflect. [Ask yourself] ‘How might I have behaved to create that perception?’” Gillian says. And if you still can’t come up with a reason? Go back to the person and tell them that you’d like to understand more… but never get into a dialogue around right or wrong.
“When you’re having these feedback moments, find that common ground, move your ego aside. Always go in asking “What can I learn from the situation about myself?”
3. Take responsibility
When a team member makes a mistake, it can be easy (and gratifying) to point fingers and play the blame game. But all that does is create toxic work environments, encourage bad habits, and shut people down. Individuals with strong leadership skills recognize that when there are problems in their startup or company, it’s a reflection of their own management and leadership.
“Point that finger at yourself first, because that’s who you’re really upset with,” Gillian says. “Think about how you can adjust your leadership style, your management style, to make sure that these conflicts or issues or communication problems don’t happen.”
By taking responsibility for outcomes, you will also show others that making mistakes is part of the trajectory toward success. Further, by acknowledging issues up front, nothing gets swept under the rug.
“Bad leaders [may] know a fire started and they just let it hopefully dwindle out… but we all know fires only get bigger.”
4. Get comfortable with the “leadership pendulum”
As a strong leader, you need to recognize when to take charge and when to let your team make decisions. Gillian calls this constant swing the leadership pendulum.
“This is an extremely challenging pendulum to swing between. It requires a heck of a lot of self-awareness to know: When do I need to wear which hat? Do I know how to let go? Do I know how to coach? Do I know how to take charge?”
Most people gravitate toward one style of leadership — they may feel more comfortable in a facilitative approach or conversely some people are instinctively more authoritarian. Gillian recommends looking at Goleman’s six styles of leadership to understand which feels the most like you.
“If being a coach is your natural place, then ask yourself: How do I practice taking charge where I feel comfortable and I can start to build that muscle?”
As above, recognizing what kind of a leader your team needs and when demands self-awareness. This also links back to creating feedback models so that you can better understand when you’re getting it wrong and when things are going right.
5. Don’t take the risk on a bad attitude
An incredibly tough part of growing a team is hiring and firing people. Gillian’s suggestion when it comes to new employees is to use probationary periods to really understand whether or not a person is a good fit with the culture of the team.
“Use that window of probation to do what it’s there for and create very strong OKRs or expectations or guiding principles on what you expect that person to deliver in the first three months,” she recommends. “If someone’s attitude is toxic, even if their skillset is good, at your stage of business, you can’t afford it.”
For recruits who have a good attitude but aren’t delivering on their work, Gillian suggests that there might be a need for more direction and hand-holding. If, after the extra help, they’re still not getting it, then it might be time to let them go.
“Good indicators of attitude are: Are they asking questions? Are they curious? Are they trying? Are they giving effort? Asking questions is usually very good key indicator of learning mindset and if you’ve got people with that mindset, you actually want to keep them — they just might be in the wrong job.”
It all comes back to self-awareness…
At the heart of Gillian’s commentary is the idea of self-awareness. This very much aligns with what we practice and preach at Real Ventures. Self-awareness is key to becoming an authentic, impactful version of yourself, but becoming self-aware challenges you to look at yourself in the mirror and be willing to be vulnerable. We encourage you to take that first step to becoming a superhuman leader!
**********
For more insights, fundraising advice, founder stories, ecosystem deep dives and industry trends, sign up for our newsletter and follow us on Twitter, LinkedIn and Facebook.
April 22, 2024 
Real Ventures 
