10 Secrets to Great Leadership from Diane Hessan

Image: Diane Hessan, Startup InstituteAfter recently leaving her 13-year gig as Communispace CEO, Diane Hessan stepped into a new role as CEO of Startup Institute, a Boston-based company dedicated to helping people transform their careers and find jobs they love. There are few CEOs as charismatic and candid as Diane, so it’s no surprise that she is a stellar leader, committed to developing top talent in Boston’s startup community.

Last Tuesday night, Diane joined Intelligent.ly’s Abbie Waite for a fireside chat about leadership with 125+ members of our community. The audience was astounded by Diane’s openness—it was like chatting with an old friend about how she casually became CEO of an international organization. In spite of immense success, Diane maintains her humility, paying forward the wisdom she’s gathered over her remarkable career. Here are her top 10 secrets to great leadership:

1. Build your A-Team: From Diane’s experience, “A-players” transform teams and help take them to the next level. Diane supports her team by spending hours interviewing key players to ensure they’re a “fit,” build rapport, and learn what matters to them.

2. Being honest ≄ being mean: Leadership is about being direct and objective. Sometimes you need to have difficult conversations for the good of the company, but it doesn’t have to be mean. People value the truth, especially when it helps them in the long run.

3. There’s no such thing as, “I’m not a leader yet:” You can be a leader at any level. Leadership is more about empowering others to lead than getting them to follow.

4. Serendipity: Most of your life is the product of a few “aha” moments. Diane keeps these tucked away and remembered, and they shape how she leads her team.

Image: Abbie Waite, Diane Hessan5. Listen more than you speak: For her first month at Startup Institute, Diane did almost nothing but listen. She asked each team in the organization about their unique challenges, then began to formulate solutions.

6. You can’t do it all: You may be a leader, but that doesn’t mean you can do everything well. Instead, choose a few things you can do really well to impact your team, and focus on that!

7. Don’t keep secrets: Diane believes in being open and transparent with her team. Two weeks into her new CEO position, she laid out all the numbers for her team, a shocking and unprecedented move. This small action went a long way in helping her team understand how they contribute, building trust, and reducing anxiety.

8. Keep the conversation going: Leadership is all about having a continued conversation, and you never stop trying to raise the bar. Ask your team, “if you could wave a magic wand, what would this team be doing?” and get everyone involved in the vision.

9. You’re leading PEOPLE: Well, duh. But we truly can’t overstate this enough. Everyone’s different, and human beings want to know that they matter and that you’re thinking of them. They need to know what the team vision is and that it’s okay to screw up sometimes.

10. Embrace question marks: In rapidly growing organizations, scaling leadership is just as important as scaling the company itself. This oftentimes means not knowing all the answers, but rather having a diverse team who you can trust to have the answers you don’t have.

Want more great leadership pointers like these? Attend our next Leadership + Libations event OR learn more about Intelligent.ly Exchange!

 

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