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!

 

Leaders love feedback

SpeakerSpotlight

Cory von WallensteinIntelligent.ly Exchange’s fifth cohort kicked off with a bang when our partner, Cory von Wallenstein arrived as our first guest speaker last week. Cory was an instrumental leader at Dyn for six years, and recently launched a new startup, Adored, a customer loyalty app that’s revolutionizing the mobile rewards experience. Cory’s aptitude for embracing failure as a learning experience has helped him to become a model leader. The sixty minutes we had with him flew by, so here’s his advice in a nutshell:

Enjoy failing, enjoy learning: Cory’s humility in spite of his success stems from his failures. Instead of shying away from his mistakes, Cory has embraced them, leveraging what he’s learned to become a stronger and more impactful leader. You may be wondering why this guy is so gung-ho about failure. The answer’s simple—feedback. After every conversation with his team, Cory requests feedback so he can become the best version of himself, both personally and professionally. Rather than playing the blame game, he points the finger inward and asks himself how he can do better by his organization and his team.

CVW Fireside ChatI’m too busy” is the ultimate fallacy: According to this HBR article, the majority of managers “squander their time in all sorts of ineffective activities.” Leading is all about the people, Cory says, so it is a leader’s job to engage the team—no matter how busy they are. This means being crystal clear about what the priorities are, understanding what motivates each team member and how they define success, and not allowing procrastination or distraction to get in the way. Aligning their team with high-priority goals and helping each person understand how their role connects to the shared vision is the most important role effective managers share. Cory urges leaders to make time to discuss with each person their version of success and concrete steps they can take to achieve their goals.

And his actionable advice that everyone can do tomorrow to be a more effective leader?: “Have an impromptu 1:1 conversation with a team member about what drives them and how they define success. Open the door to more dialogue.”

From Sports Pro to CEO:
Sydney Atkins Mason Tells All

Sydney Atkins MasonAt this week’s Intelligent.ly Exchange, we were thrilled to bring in Sydney Atkins Mason, Investment Advisor at Goldman Sachs and founder of Synergy Inc. Sydney is truly a Renaissance woman; she has sailed professionally in Europe, won two Women’s Lacrosse NCAA Championships, taught high school biology, and became a CEO when she founded (and later, sold) Synergy Inc.– a sports-focused leadership development program for youths– all by the age of 21.

So how did she do it all? Her energy and zest for life’s curveballs definitely play a role, but she attributes her success to overcoming fear, building the right team, and having a Personal Board of Directors.

Deal with your fears

As a young CEO, Sydney admitted that she made a ton of mistakes, but she grew in spite of these challenges, because she kept her goal in mind. As Sydney said, you can’t sail right into the wind. Sometimes life doesn’t make it easy to progress toward your mark. You’ll need to take risks as a leader, and that can be terrifying, but as long as these risks are optimizing velocity toward your goal, they’re risks worth taking.

Know yourself, know your team

Fireside Chat w/ Sydney Atkins MasonFor Sydney, building the right team was the biggest challenge of being a new leader. She asked herself, “How do you know who you need when you don’t know who you are?” She had to become very self-aware about her own strengths (and growth opportunities) in order to determine who could supplement, not complement, her own style and skills to create the strongest, most diverse team. Success is not defined the same way for every person, and each team member has different values that motivate them to do their jobs.  Your team can’t meet their true potential unless you are able to fully understand and support them.

Personal Board of Directors

No one is successful in isolation. Sydney argues that a successful leader needs three specific valuable relationships:

Coach: A coach provides a working relationship where there are “no stupid questions.” Everything is valid, even questions about where to hang your coat and find pens.

Mentor: A mentor will never dole out the same piece of advice to two different people; mentorships are reciprocal relationships in which the mentee evolves over time.

Sponsor: Sponsor relationships are linear, and the sponsor helps the sponsee achieve career success. The most important part? Pay it forward and become someone else’s sponsor!

Stay tuned for more about the building your own Personal Board of Directors!

Her last piece of advice: Know what you want before you take your first step. People won’t follow you if you don’t know where you’re going.

Rachel WaldmannRachel Waldmann
Content & Community Specialist
@rachelwaldmann

Leadership Lessons: Ralph Folz

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folz__ralphLast week at Intelligent.ly Exchange, we had the good fortune to be joined by Ralph Folz, CEO of WordStream. Ralph got his bearings as a nerdy engineer, before getting bit by the entrepreneurship bug at age 26. As a leader, Ralph is genuine, honest, and deliberate about his strengths and limitations. He has a deep understanding of his communication style, and his sense of self-awareness and thoughtfulness make him an incredibly approachable executive. Wordstream was established just seven years ago, and has rapidly become one of the most respected high-growth search marketing software companies around. His secret? Embracing diversity, laser sharp focus, and goal simplification.

Hone Your Strengths

In Ralph’s words, “There are different flavors of people.” Leaders can maximize team success by targeting each team member’s specific “flavor” or strength. You can’t make employees into something they’re not; all you can do is hone in on what each person can bring to the table, celebrating the diversity of skill sets among your team. For all you Red Sox fans, Ralph described it like this: if you had nine Manny Ramirez’s in the field, you’d hit a million home runs, but you probably wouldn’t win.Ralph Folz Key Takeaways

Focus

No matter how large your company is or how quickly you’re scaling, maintaining a focus on your core values is critical. Ralph noted that clarity about your core values not only creates direction, but can also help frame difficult conversations. He humbly admitted that in fact, he isn’t perfect; owning that helps him create the right team. For so many startups, growth is hectic and not easily planned. Strongly aligned values keep teams rowing in the same direction, as the environment around them rapidly changes. Transparency and conviction in upholding the culture that makes your team unique are key to developing a thriving business.

It’s all about 1’s and 0’s

In a successful team like Ralph’s, all members have the same core values, so when problems arise, everyone is able to keep their eye on the common goals. At Wordstream, the executive team shares four core goals, which allows the team to approach conflict more objectively. Alignment of goals helps the team to embrace healthy conflict with rich debate before choosing the best course of action. Ralph is an engineer at heart, which means everything can be measured. He quantifies goals as simple 1’s and 0’s. I know what you’re thinking–really? We’re bringing math into this? Fret not! Ralph assured us that success can be determined objectively, with each person focusing on three simple, measurable goals. At the end of each quarter, goals can be defined as a 1 or 0–either they were achieved or they weren’t. If there are 0’s present, the goal needs to be defined more clearly. Clear goals and values drive decisions toward success and keep the team hungry for that sense of achievement.

His last snippet of advice: Have a mentor and a network. Overcommunicate.

Thank you, Ralph!

Rachel WaldmannRachel Waldmann
Content & Community Specialist
@rachelwaldmann

Be like Mike!

Mike Troiano“All the pain in your life will be caused by distance from the truth,” said Mike Troiano, CMO and self-proclaimed “Communicator-in-Chief” at Actifio. Think that’s profound? Now think about how a company that’s only 5 years old is already worth $1.4 billion dollars. With Troiano and a group of seriously intentional leaders at the helm, it’s no surprise that the copy data management company is rapidly growing into one of Boston’s biggest success stories.

On Monday night, Mike joined Intelligent.ly’s Abbie Waite for a fireside chat about leadership with 200 members of startup community. Perhaps most impressive about Mike is how he commands a room, like that funny uncle who you deeply respect and are also a little afraid of disappointing. In spite of huge success, he maintains his humility and charisma- admirable characteristics of a seasoned leader.

During the evening, Mike relayed sound words of advice. As a new professional getting my career off the ground, I’m making them words to live by. The resounding theme was that people are perhaps the greatest (and sometimes most difficult) part of being in business, and as a leader you have to establish enduring trust and open lines of communication right from the start.

Mike broke effective leadership into three actionable buckets:

Be Human
“Understand people, what matters to them, who they love, and what they’re afraid of,” Mike advised. Starting with the human side of management helps leaders motivate their teams, foster healthy conflict, and drive results.

Mike entertained the crowd with an anecdote about the epic difference between Italian sauce and gravy; sauce takes 20 minutes to whip up, while gravy is an all day affair, that requires slaving over a stove, and putting blood, sweat, and tears into the final product, but is worth every ounce of effort. The effort Mike puts into his gravy is paralleled only by the thought he puts into building relationships with his team. Ultimately, good business is good people, and exceptional leaders understand what motivates and challenges each individual member of a team.

Prioritize, Prioritize, Prioritize
Mike Troiano
Mike asserted that managers need to ask themselves, “What are the three most important things right I can do to grow our business right now?” Focus solely on doing those (and only those) three things. Take for instance, when Mike joined the executive team at Actifio. His first move was to identify key stakeholders, focus on understanding their needs and challenges, and create lists of each team member’s goals. Within the first week, he realized where the communication gaps were, and set a clear vision for moving forward. He asked himself, “What am I good at?” and set an actionable strategy for using his skills to fill in the gaps and add value to the team.

As a leader, you’ll have boundless opportunities, but Mike urged us to proceed with caution to avoid falling victim to the overwhelming choices that come with growing a company and a team. Choose a few areas where you can add value to your team, and give them all you’ve got. Prioritize.

Keep it Simple
Mike drove this home over and over: it’s a manager’s responsibility to set clear expectations for each team member right from the start. Communication should be clear, direct, and honest. This is the best (and if we’re being honest, only) way to retain employees for the long haul.

When a team member lacks success, leaders need to take a good hard look at the mirror and think about why this person’s results are not measuring up to the expectation. And then you have to think about what you can do to support each individual on your team. Do you need to clarify your expectations? Provide your team member with a tool or resource to improve their performance? Is there tension within the team? Whatever it is, it’s up to the leader to provide clarity. It’s as simple as that.

Preach, Mike. Preach.

Rachel WaldmannRachel Waldmann
Content & Community Specialist
@rachelwaldmann