The success of a startup depends on more than just ideas; it hinges on the collective strength of its people working towards a shared vision. One-on-one meetings between executive leaders and team members are crucial for effective communication, relationship building, company core values, and staying aligned on goals.

In this article, we’ll explore practical strategies to make these meetings powerful tools for collaboration and growth. CEOs and executives can achieve this by building trust, setting clear agendas, actively listening, providing constructive feedback, aligning goals, and adapting to individual styles.

Let’s dive into actionable insights to enhance the efficiency of your one-on-one meetings and foster a culture of empowerment and innovation within your tech startup. 

1. The Meeting is Not About You

I’m going to cheat and offer two. First, the 1:1 is about the report, not about you. This meeting is sacred space for your direct report to openly discuss their questions, successes, and concerns. Leave the most space for this agenda item, and practice active listening. Second, use this space to provide an ongoing stream of feedback related to performance and behavior. Don’t wait for formal reviews, do it in real time. Listening and providing real-time feedback maximize trust and performance.

Joseph Loria, Founder at RetentionCX

2. Ask Open Ended Questions

Prioritize the employee’s perspective in one-on-one meetings. Ask open-ended questions about their projects, challenges, and career goals. This approach fosters a supportive atmosphere and strengthens the employee-manager relationship.

Emily Finkelstein, Founder and CEO at VentureXpert Advisors 

3. Reflect Before the Meeting 

Give yourself prep time to reflect on what needs to be discussed. Have they been exceeding expectations on recent projects? Take time to recognize that! Have they been struggling? Help find the root of the problem and offer your assistance. This also gives you the time to set expectations for that 1 on 1.

Abbey Szentes, HR Generalist at Trava

4. Cherish One-on-Ones as Trust-Building Conversations

Beyond meetings, one-on-ones are vital conversations. Every word shapes trust, understanding, and shared success. It’s where bonds deepen, ideas flourish, and paths to achievement unfold. These moments are not just talks; they’re the heartbeat of our shared journey, paving the way for collaborative growth.

Trilok Dandu, Manager – Business Operations, Narwal

5. Begin with Curiosity and Listening

Start with listening and curiosity. All of us want to feel seen and valued, and our direct reports are no different. This is a meeting, not an email, so rather than starting with a status update, check in with how your report is doing. When we approach these meetings as a time to come together and connect, we can all leave feeling motivated and engaged.

Anne Welsh, Clinical Psychologist and Executive Coach, Dr. Anne Welsh

6. Foster Open Dialogue and Active Engagement

Building a strong rapport with your direct reports begins with active engagement during 1-on-1 meetings. One vital tip is to encourage a two-way conversation. Give them space to share their thoughts, concerns, and ideas. Actively listen, ask probing questions, and offer constructive feedback. Creating this open dialogue fosters trust, enhances collaboration, and empowers your team members to perform at their best. Remember, a successful 1-on-1 is not just about discussing tasks but also about understanding and supporting your employees on their professional journey.

Christopher Salem, Business Executive Coach, CRS Group Holdings LLC

7. Invest in Relationship Before the Meeting

One-on-one meetings are ten times easier when you invest in the relationship with that person in advance. When that person trusts your motives and knows how much you care, they will be more likely to listen to your counsel and direction. Moreover, they will be less likely to reject hard news or constructive criticism from you. So, invest in getting to know the person, not just the worker. Find opportunities to serve them, listen to them, laugh with them, and be real with them before important one-on-one meetings become necessary.

Brent Hafele, M.A., ACC, Executive Coach and President, Vibrancy Unlocked

8. Create Space for Employee Expression

Talk more than you listen. Early on in their careers, new managers often make the mistake of dominating the conversation when facilitating one-on-one conversations with their direct reports. Make a habit of allowing your employees the space to talk and be heard, as well as sit in silence. “Can you tell me more?” is one of the most powerful questions you can ask during a meeting with a direct report. This simple question shows that you genuinely care what your staff has to say and that you’re making the time and space for them to be heard.

Dr. Kyle Elliott, Founder and Tech Career Coach,

9. Set Actionable Goals Together

I recommend setting actionable goals together during the one-on-one. We identify specific objectives and create a plan to achieve them. This not only ensures alignment between individual and team goals, but also holds both parties accountable for progress. Setting clear goals helps make these meetings purpose-driven and results-oriented.

Ian Sells, CEO, Million Dollar Sellers

10. Frame Feedback as Growth Opportunities

I’ve found that framing feedback as opportunities for growth can be a powerful way to motivate and engage your direct report. Rather than focusing on what they did wrong, try to highlight areas where they can improve and provide them with the tools and resources they need to succeed. For example, if they’re struggling with a particular task, offer them additional training or support to help them develop the skills they need to excel. If they’re having trouble with time-management, suggest strategies that can help them be more productive and efficient. By approaching feedback in this way, you can create a positive and supportive environment that encourages your direct report to take ownership of their development and work towards becoming the best version of themselves.

Luciano Colos, Founder and CEO, PitchGrade

11. Have a Plan of Action Ready

The best way to run an effective one-on-one is to have a plan of action. Have a list of things that the person is doing well, as well as areas of opportunity. The next step would be to meet with the associate and discuss how you, as a manager, can support in the areas of opportunity so that the associate feels that they are able to grow and learn without the fear of being judged unfairly.

Tazeen Raza, Executive Coach, Tazeen Raza

12. Encourage Direct Report’s Ideas

Encourage your direct report to contribute to the conversation. I’ve seen a lot of managers lead their teams based on their viewpoints only. I don’t subscribe to this management style because it stifles your interpersonal relationships with staff. Your one-on-one will be twice as effective if your direct report feels welcome to share their ideas with you. It makes for a more collaborative environment where people feel free to use creative ways to solve problems. I’m certain you’ll notice a difference in the quality of your meetings using this approach.

Michael Nemeroff, CEO and Co-Founder, Rush Order Tees

13. Be Kind but Direct in Feedback

Simply holding regular 1:1s makes your team four times more likely to be engaged in their work, but maximizing effectiveness can help you get even more out of the process. 

One major mistake many leaders make is sandwiching negative criticism between two praises. Though the aim is to soften the blow of the criticism, you’re more likely to water down your message and make potentially significant sharings seem inconsequential.

Be kind but direct when giving employees feedback, and focus on what needs to happen next rather than blame. If a behavior needs to change, talk about how that looks going forward and ask how you can best support the employee. When you direct these conversations in a future-oriented way, you’re less likely to cause them to spin out on feelings of shame.

Robert Kaskel, Chief People Officer, Checkr

14. Prepare Thoroughly for Targeted Guidance

Effective one-on-one meetings with direct reports are greatly enhanced by thorough preparation. This readiness enables a more focused and productive discussion, eliminating the need for time-consuming recaps. Understanding your direct report’s recent achievements, challenges, and goals empowers you to offer targeted guidance, showcasing your commitment to their success. This approach fosters trust, strengthening your professional relationship as your direct report sees your dedication to their development. Consistently preparing for these meetings allows you to take a proactive stance, streamlining information exchange and maximizing the opportunity to align, connect, and support your team’s growth and success.

Travis Willis, Director of Customer Success, Aspire

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