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Asking the right questions can improve motivation, engagement and innovation within a team. Here’s what startup leaders should consider when managing their team.

The Chief Revenue Officer of a fintech startup and one of our coaching clients, let’s call her Jessica, was tasked with developing a go-to-market strategy and hitting aggressive revenue targets to meet financial commitments to investors.

Jessica was tasked to deliver in six months what had taken her 18 months to complete in her last role. The strategies that previously served her would no longer suffice. In her own words, she was “building the bus while it was moving”. Jessica needed to ensure her team was fully engaged and charging to meet the ambitious goals.

Leaders who start or lead a venture encounter numerous opportunities and obstacles. While there are several challenges for startups, team management and team engagement issues have a profound impact on the ability of new companies to execute their vision and scale the business.

One of the important aspects of managing a high-performing team is maintaining high engagement.

In fact, team issues are one of the reasons why the vast majority of startups – nine out of 10 – fail. Thus, one of the important aspects of managing a high-performing team is maintaining high engagement. Gallup defines engagement as the involvement and enthusiasm of employees in their work that leads to better business outcomes, regardless of the industry, company size or economic conditions.

Yet, only 23 percent of employees worldwide and 32 percent in the United States fall in the ‘engaged’ category, according to Gallup. Employee engagement is particularly critical for startup companies where business decisions need to be made and executed in a timely manner, and the speed of operation is critical to success.

As a startup leader, you play a critical role in driving your team’s engagement. And it starts with a conversation. By initiating a thoughtful conversation with an individual team member, you can deepen your relationships, inspire motivation and increase productivity.

Here are six questions you can ask to increase your team’s engagement:

1. What gets you excited about being part of this startup?

Your colleague will likely share why they chose to work at the organization. Their answers will help you to understand their motivation, passion and what contributes to their sense of purpose.

You can understand your colleague’s intrinsic and extrinsic motivations. This will empower you to find creative ways to recognize, reward and incentivize them without adding more cost to the bottom line.

Motivators may include:

• Autonomy: Being in control and having a choice promotes higher performance and job satisfaction. With their ‘20 percent work’ rule, Google founders Sergey Brin and Larry Page said: “We encourage our employees, in addition to their regular projects, to spend 20 percent of their time working on what they think will most benefit Google.”

• Mastery: Experience of competence and challenge drives higher performance and feelings of success. On-the-job development and learning opportunities that enhance skills and capability building increase employee’s satisfaction, and engagement and internal shadowing and rotations or externships are effective venues.

• Connection: ‘Connected culture’ drives a sense of purpose, enjoyment and sustained dedication. Thus, creating a climate that nurtures relationship-building is key. In fact, Gallup reports that having a best friend at work is critical to employee engagement success, and workplace connection is strongly linked to profitability, safety, inventory control and retention and to physical and mental health.

2. Who has been important to your career?

This question will invite your colleague to share a mentor, sponsor or advisor who has been influential in their work. Moreover, advisors can accelerate the growth trajectory of the startup.

By initiating a thoughtful conversation with an individual team member, you can deepen your relationships, inspire motivation and increase productivity.

Your colleague’s response will help you understand who has impacted them and why. We know that mentors are critical to professional development. Understanding the reasons behind your colleague’s choice will be just as important: what attributes does your colleague admire or has found to be helpful about this person?

The answer to this question may help you to understand the characteristics or values they consider to be important. If some of your direct reports do not yet have a mentor, you should encourage them to identify potential mentors in and out of the company.

3. What is one failure/risk you are most proud of?

Mistakes lead to innovation, fight complacency and teach valuable lessons and insight. Many entrepreneurs who eventually become successful experienced significant setbacks earlier in their work.

One coaching client, who is a tech founder, believes so strongly about the importance of learning from mistakes that he will not hire someone who cannot articulate a heroic failure.

However, even knowing the learning opportunities that come from a failure, it can be difficult to discuss them. This question invites your colleague to share more deeply about their professional journey, which inevitably includes setbacks or mistakes. You might want to share something you consider to be a professional failure first when posing the question.

To come up with your own failure share, reflect on these questions:

1. What is the failure that I have learned the most from?

2. What failed attempt later catapulted me to my bigger success?

3. How have past failures brought me and my teams closer together due to the experience?

4. What is something that you would like me to know about you?

This is an invitation for your colleague to share something that may be fun and light-hearted or more private and personally significant. When people are interested in deepening their relationship, it is important to match the level of openness and to create psychological safety.

If your colleague shares something personal and if you are inclined, share something about you that others do not know. Again, here’s an opportunity for you to start first and create the space for them to share their own. Some examples may include speaking about lucky rituals you do or mantras you tell yourself before any big investor meeting.

5. What advice do you have for me?

This question conveys that you value their insight. It also provides an opportunity for reverse coaching, which happens when a junior colleague advises a senior executive member. The data reveals that reverse coaching is astonishingly effective.

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For example, more than 96 percent of Millennials who participated in the reverse coaching program stayed in their job when nearly 50 percent of their counterparts contemplated leaving. Everyone desires to be valued and appreciated. When your team members share advice, show appreciation through active, attentive listening and verbal affirmation.

6. What can I do to help you be more successful in your role?

You express a personal interest in supporting them and their work by asking this. While your colleague may or may not know how to respond on the spot, they are likely to appreciate your offer and invitation. When your team member does make a request, be honest about what you may be able to do.

For instance, if your colleague asks you to review and give feedback on their upcoming presentation, let them know when and how much time you can allocate. Your colleague will likely appreciate your committing time to support them. Be sure to do this without expecting or requiring anything in return.

These questions will create authentic opportunities for the bonds needed to create and drive success.

Leadership author and inspirational speaker Simon Sinek said: “When people are financially invested, they want a return. When people are emotionally invested, they want to contribute.”

Strong engagement in a startup does not happen automatically and requires intentionality, effort and follow-through. As a leader, you can play a significant role in creating a culture of engagement by deepening your relationship with your colleagues.

Like any strong relationship, work relationships require understanding, shared interests and trust. These questions will create authentic opportunities for the bonds needed to create and drive success.

This article was co-authored with the following colleagues from New York University (NYU): Kathryn Landis is the Founder and CEO of team coaching firm Kathryn Landis Consulting. Kathryn is also an Adjunct Professor at NYU and a keynote speaker. Jenny Fernandez is an Executive and Team Coach, TEDx Speaker and Professor at Columbia and NYU. She consults with CEOs, executives and founders to enhance leadership effectiveness, team collaboration and innovative thinking.

Julie Lee

Contributor Collective Member

Julie Lee is a leadership coach, speaker and faculty at New York University. She helps CEOs, founders and executives to optimize their impact through their authentic leadership and purpose. She is a former Associate Dean of Brown University and has consulted with Fortune 500 companies and startups. Her work has been featured in ‘Harvard Business Review’ and ‘Fast Company’. Find out more at https://www.julieleephd.com/

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