How To Lead With Confidence

Moving into a leadership position often presents challenges. Leaders from Matillion and GigSmart share their strategies for gaining confidence in a new role.
August 30, 2022Updated: August 31, 2022

Only half of business leaders feel confident in their ability to guide their teams, according to research by Gartner, Inc. This begs the question: If leaders don’t have confidence in their own leadership abilities, how will their team members have confidence in them?  

Shifting into a position that requires providing feedback and holding employees accountable for meeting their objectives can be daunting, especially when those employees used to be people you grabbed drinks with after a long workday. 

“As a first-time leader, the biggest insecurity I had was managing people who were previously my peers,” said Madeline Hennessy, VP of commercial sales, North America, at Matillion. “It took about a year to realize that expecting top results and setting high standards as a leader is a more respectful way to manage my team than accepting average performance and being nice.” 

Remaining self-assured while empowering direct reports takes practice, but striking that balance pays dividends.  

“Throw any ego you have out the door,” said Tara Selch, director of product at GigSmart. “View your new role as a challenge to push any perceived ceilings around you, and set your team up for success.” 

At Matillion, which powers a cloud-native data integration platform, and GigSmart, which connects businesses with qualified workers in the gig economy, Hennessy and Selch are impacting their teams through their confident leadership, and Built In Colorado sat down with both to learn their strategies and advice for new leaders. 

 

Madeline Hennessy
VP Commercial Sales - North America • Matillion

 

What were your sources of insecurity when you first started out in a leadership position, and what was most helpful in dealing with them?

Transitioning from being a teammate — and sometimes a friend — to a leader who is liked,  respected and can implement discipline is difficult. One strategy I implemented was encouraging my team’s contributions to meeting agendas. Leaders will have a more collaborative team and diverse thinking if they create space for their direct reports to contribute to team meetings instead of showing up and talking at them.

 

What helped you build your confidence in your early days as a leader?

The difficult conversations are the most challenging ones to get right. When providing feedback on performance or communication to a direct report, it takes many conversations to practice how to present the information. Early in my career, I committed to having these conversations, no matter how bad I may have been at bringing them up. I got it wrong — a lot. But having the conversations early and often allowed me to find my rhythm, tone and approach, which has enabled me to provide feedback to my team frequently in order to help them grow. 

Something I learned recently is to allow for two-way feedback. When providing feedback to direct reports, it’s important for leaders to create space for them to give feedback as well. It’s also important to ensure that the direct report is in the right headspace to accept feedback during difficult conversations. I try to initiate challenging conversations by saying, “I have some feedback for you. Is today a good day to talk through it?” Based on their response, we can reschedule or continue.

 

How can new leaders build self-confidence?

Always have an agenda. Showing up as a manager without topics to discuss will make direct reports wonder if their time spent with you is valuable. Encourage direct reports to bring agenda items to meetings as well

Do not shy away from giving feedback. Accept that it might not go smoothly the first couple of times — you will start getting it right with practice. 

Do not shy away from giving feedback.”

 

Set high expectations and hold direct reports accountable. Challenge people in a productive way and ensure they know that you believe they can do it. You will not only help them reach their goal but also make them feel they are being invested in.

Practice your talking points and conversations. Messaging is important, and so is perception. Consider having someone with more experience listen to how you are going to deliver an important message and ask them for feedback

 

 

Tara Selch
Director of Product • GigSmart

 

What were your sources of insecurity when you first started out in a leadership position, and what was most helpful in dealing with them?

The many insecurities I experienced when starting in a leadership role were fueled by feeling unqualified and disconnected from my peers, who were the ones who enabled me and gave me the confidence to grow into the leadership role I am in today. I found the confidence and strength to overcome my insecurities as a leader by staying true to myself and always leading by example with a positive attitude, hard work, respect for others, an open mind and passion.

 

What helped you build your confidence in your early days as a leader?

The GigSmart team has continued to challenge me in a leadership role to better our processes, culture and product. I strive to be the first person to jump in to help in different areas of the company. These experiences across all teams have given me the confidence and perspective to provide value and insight.

View your new role as a challenge to push any perceived ceilings around you, and set your team up for success.”

 

How can new leaders build self-confidence?

Reflect on how you grew into your leadership position and remind yourself that you did not do it alone. Value and respect your peers who have supported your career growth, and know they will continue to do so. Finding success for your team will give you confidence and provide the most value you can to your company in your new leadership role.

 

 

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