What I’ve Learned from Creative 1:1s in the Design World 🪄

Marcia Dellarosa
Amazing Together
Published in
6 min readAug 6, 2024
Image created with Midjourney

As a designer early in my career, I only had 1:1 meetings with my leaders when I started working in remote companies. I wish I could have discovered their value earlier. Now, I realize how impactful it is to cultivate a thriving creative environment and support the growth of your designers through regular 1:1 meetings. These sessions are not just routine check-ins, but pivotal moments to inspire, mentor, and align your team with the broader vision. Here, I’ll share some ideas and best practices that have worked for me over the past five years. The goal behind each of these 1:1 meetings is to boost creativity and foster professional development, especially when your team is working 100% remotely.

Key Strategies for Leading Effective Meetings

  • Personalized Feedback: Tailor your feedback to individual needs. You’ll need to delve deeper for some members on certain points, while for others, a simple reminder might suffice. Work on your attention to identify who each team member is.
  • Time Management: Be mindful of others’ time. Avoid being late to meetings and ensure that each session is productive and respectful of everyone’s schedules. Not everyone needs a 45-minute meeting; identify what suits each of your team members best.
  • Professional Development: Identify opportunities for growth and development. Once a month, review their career path, bring metrics, results, and insights, and create action items from them.
  • Creative Freedom: Encourage innovation and creative thinking. Discuss new skills, software, or areas for exploration to keep their creative side always engaged.
  • Trust Building: Strengthen the relationship and trust between you and your team members. Since we spend a lot of time working, it’s important to know how your team members are doing and what’s keeping them up at night.
  • Documentation: Keep a record of each meeting. Find the perfect tool, such as Small Improvements, Personio, Notion, or Lattice. This will help both parties take and share notes, track progress, and prepare for future discussions.
Or at least, for me 😉.

Best Practices for Effective 1:1 Meetings

1. Prepare Ahead of Time

  • Review Prior Notes: Revisit notes from previous meetings to track progress and follow up on action items.
  • Set an Agenda: Outline key topics to discuss, but keep it flexible to allow for organic conversation. Ask the team member to share their points ahead of time too, in case you need to research or delve deeper into any of their points.
  • Gather Feedback: Collect any relevant feedback from peers or project stakeholders that can provide a holistic view.

2. Create a Comfortable Environment

  • Choose the Right Setting: A quiet, comfortable space can foster open dialogue. For remote teams, ensure both of you are in a private and quiet environment with a stable internet connection. Make sure this is a safe space for both parties.
  • Minimize Interruptions: Ensure there are no distractions. Silence your Slack, company chats, or any other potential distractions. You must be focused on the meeting.
  • Find the Perfect Time: If you already know you’ll be having this meeting after a full day of meetings, your energy for this meeting will be close to 0%. Avoid scheduling this meeting over lunch. Find the ideal time that works for you and your time zone.
  • Rescheduling Availability: Be transparent; if you won’t be able to fully attend, consider the option to reschedule. Also, offer this to your team members. It’s preferred to find a new slot if the original schedule isn’t working now.

3. Start with Open-Ended Questions

  • Kick-Off Conversations: Begin with questions that invite open dialogue. For example, “How do you feel about this week’s workload?” or “Is there anything you’d like to discuss today?”
  • Encourage Reflection: Ask questions that prompt reflection, such as “What’s been your biggest challenge this week?” or “What’s something you’re proud of?”

4. Dedicate Time for Personal Check-Ins

  • Life Outside Work: Make space to discuss their personal life. Ask questions like, “How are things outside of work?” or “Is there anything on your mind that’s been keeping you up at night?”
  • Celebrate Personal Wins: Acknowledge and celebrate their personal achievements, such as celebrating with friends or achieving a personal challenge like moving, a fun getaway, or a wedding.
  • Provide Support: Offer support and understanding if they are going through a tough time. Showing empathy and care can strengthen your relationship and boost morale. Remember that we are humans first. ✨

5. Focus on Growth and Development

  • Identify Strengths and Areas for Improvement: Focus on the last wins, and provide constructive feedback that highlights both strengths and areas for growth. But also, reinforce the learnings and how to address them in case they face it again.
  • Set Development Goals: Collaboratively set SMART (Specific, Measurable, Achievable, Relevant, Time-bound) goals that align with their career aspirations.
  • Discuss Training and Learning Opportunities: Recommend courses, workshops, or conferences that can help them develop new skills.

6. Encourage Creative Thinking

  • Brainstorm Together: Use this time to brainstorm ideas and solutions for ongoing projects, design processes, or company matters. Encourage out-of-the-box thinking.
  • Celebrate Wins: Acknowledge and celebrate their creative successes, no matter how small. All victories matter. 🔥
  • Provide Resources: Share books, articles, or tools that can inspire creativity and innovation.

7. Build a Culture of Feedback

  • Two-Way Street: Encourage designers to provide feedback on your leadership and the team’s processes. This can lead to valuable insights and improvements.
  • Regular Check-Ins: Schedule these meetings consistently. Weekly or bi-weekly meetings can ensure continuous support and guidance.

8. Follow Up and Follow Through

  • Action Items: Summarize key takeaways and action items at the end of each meeting.
  • Accountability: Hold both yourself and your designer accountable for following through on commitments.
  • Track Progress: Make sure the meeting notes are always updated so you can regularly review progress on goals and projects to ensure they stay on track.

1:1 meetings are more than just a managerial task; they are a strategic tool to nurture creativity and drive growth within your design team. By preparing thoroughly, creating a comfortable environment, focusing on development, encouraging creative thinking, building a culture of feedback, and following up diligently, you can transform these meetings into powerful catalysts for innovation and professional growth.

Are you not leading 1:1s yet?

No worries, you can still incorporate all the points mentioned earlier into your meetings. By doing so, you’ll ensure that your sessions are productive, supportive, and aligned with the goals of fostering creativity and professional growth.

Reflecting on My Journey

Consider these strategies as personal learnings from my recent years, during which I had the privilege of leading a diverse team of individuals from over 14 nationalities in remote workspaces. This journey has been a delightful learning path, filled with moments of celebration for each member’s wins as if they were my own. Feeling proud of how far they have come is my everyday mantra. I continually strive to unlock their full potential while fostering a collaborative and inspiring creative environment. To me, each one-on-one meeting is a meaningful moment where we celebrate, learn, and review how we can improve. This approach consistently paves the way for a more motivated, inspired, and high-performing design team.

Let’s continue fostering a nurturing, growth-oriented, and positive creative workspace. Lead by example, but always be ready to learn.

👉 Are you looking for guidance and mentorship? Connect with me or directly book a mentorship session with me on ADPList.org. Let’s embark on this exciting journey together!

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Marcia Dellarosa
Amazing Together

Design Director with 12+ years in the industry, building purpose-driven brands and boosting creative teams globally. http://marciadellarosa.com