👋 Hi my name is Roslyn, I’m a 2x founder and executive coach. I help founders fall in love with building their companies again. Learn about working 1:1 here.

Reader love: “Quickly becoming one of my favorite reads!”

Hi there,

It’s peak summer! 

I hope that you’re able to step away from your laptop a little more, to soak up the beautiful weather outdoors, the time with friends and family, maybe even a new adventure.

In the spirit of doing less, I have a short and sweet newsletter for you today. 

In today’s 3 minute read, we’ll get into:

• How becoming a coach to your team, instead of simply a manager, can free you up for your next level of leadership

• How to run high impact 1:1s with your direct reports, from casual check-ins to formal performance conversations

• How to go from manager → coach

Before we jump in, I want to invite you to tomorrow’s Sana Sana Social where I’ll be giving a talk on how my founder burnout was the catalyst for building a life of alignment.

If you’re feeling a little burnt out, like you’ve lost your spark, or like you’re meant for more than the life you’re currently living… this talk is for you. Join us. 💚

Alright, let’s dive in.

Where we go deep on the outer work or the inner work of building a startup.

How to Run High Impact 1:1’s

When I was a leader at The GIST, 1:1s quickly became one of my favorite parts of the job. It makes sense—today, as an executive coach, I spend much of my time meeting with clients one-on-one to support their goals, growth, and challenges.

Great 1:1s work the same way. The more you approach them as a coach guiding a leader—rather than a manager directing a report—the more your team will grow into leaders of their own outcomes, learning, and problem-solving.

If your goal as a founder is to spend less time in the weeds and more time on the strategy, innovation, and big-picture thinking that will take your company to the next level, you need a team that acts like owners—not just employees waiting for instructions.

Done well, 1:1s aren’t just check-ins on projects and tasks —they're containers for clarity, growth, and unblocking.

Here are the basics of running high-impact 1:1s.

1:1 CADENCE FRAMEWORK

Design your cadence with intention, not obligation:

• Weekly (Optional): Light, tactical check-ins for priority-setting and support
  

• Monthly: More spacious time for development, reflection, and relationship-building
  

• Every 6 Months: Formal performance and growth conversations (with mutual prep)

Consistency > frequency. Choose a rhythm that supports open, ongoing dialogue.

MONTHLY 1:1 CHECK-IN AGENDA

A strong monthly 1:1 blends strategy, development, and connection.

Use this loose structure:

1. OPEN WITH CONNECTION

• “How are you, really?” (Make space for the whole human.)

• “What’s giving you energy lately—inside or outside of work?”

• How do you feel your work/life balance is? What would you change, if anything?
  

2. CHECK IN ON WORK & PROGRESS

• What are you most proud of this month?

• What’s felt challenging?

• What’s blocking progress, if anything?

• Do you have any questions that, if answered, would help you in your day-to-day?

3. DEVELOPMENT & GROWTH

• What skills are you excited to build?

• What projects would you like to work on or be more involved in?

• What else can I be doing to help progress your career?

4. FEEDBACK & VALUES ALIGNMENT

• Where am I being clear or unclear as a manager?

• How do you feel your work is connected to our values and strategy?

• Share feedback from your end, too—through the lens of values, care and supporting their growth.

Tip: Praise in public, but save meaningful developmental feedback for private, safe spaces like 1:1s.

5. CLOSE WITH APPRECIATION & ACKNOWLEDGEMENT

• “Here’s something I’ve noticed and appreciated about your contribution.”

• “What’s one thing you need more or less of from me right now?”

Resource:

• Here are 121 useful questions you can use in your 1:1’s. If you don’t know what to talk about in your 1:1’s, this is a GREAT resource.

PERFORMANCE CONSERVATION (BIANNUAL)

Performance reviews should be held every 6 months and are a chance to go deeper than the monthly 1:1s and should be clear, kind, and actionable.

Try this structure:

1. REVIEW OF PAST GOALS & PERFORMANCE

• “Looking back at the goals we set last quarter, which ones feel fully achieved and which are still in progress?”

• “Where did you feel most in flow or energized while working toward these goals?”

• Anchor the discussion in specific outcomes and metrics, not just general impressions.

• Celebrate wins before moving to areas of improvement to build psychological safety.

2. REFLECTION FROM EMPLOYEE 

• “What are you proud of? What didn’t go how you wanted?”

• “Which of our company values do you feel you embodied most in your work?”

• “What support from me or the company would have helped you achieve more?”

• Send the list of reflection questions a few days before the meeting so they can gather examples and think deeply.

• Encourage employees to bring concrete stories or data points to make the conversation more meaningful.

3. MANAGER FEEDBACK

• “When you think of our value [X], where do you feel you’ve been strongest? Where could you stretch further?”

• “Can I share an example where I think you made a really positive impact?”

• Use SBIS (Situation, Behavior, Impact, Suggestion) to keep feedback specific and actionable.

• Pair constructive feedback with clear next steps or coaching offers, not just observations.

• Use company values as a mirror:  Instead of “You’re not collaborating enough,” try:  “One of our values is ‘we win together’. I’ve noticed some missed moments of cross-team collaboration. Can we talk about that?”

• Give feedback that’s clear and compassionate.

• Address the behavior, not the person’s worth.

4. GROWTH AREAS & FUTURE ASPIRATIONS

• “What skills or experiences do you want to build in the next 6–12 months?”

• “What projects or roles excite you most for your future here?”

• Help them connect growth areas to company goals—this makes development feel purposeful.

• Share opportunities for stretch projects, mentors, or training that can support their aspirations.

MUTUAL COMMITMENTS MOVING FORWARD

• “What do you need from me to feel most supported this quarter?”

• “What commitments do you want to make to yourself, to me, and to the team?”

• End with clear next steps and timelines—write down commitments so both sides have accountability.

• Reinforce shared ownership: “Here’s what I’ll commit to, and here’s what you’ve committed to.”

CREATE A COACHING RELATIONSHIP

Great managers don’t just assign tasks, they coach teammates into leaders.

That includes:

• Asking powerful questions vs. giving answers

• Helping teammates connect their work to mission, vision, values and strategy

• Supporting nervous system regulation during tough moments

• Believing in their highest potential, and offering honest feedback and opportunities for development so that they can get there

• Attuning to and mirroring their emotions, so they feel seen, safe and understood

• Celebrating wins and helping them see their strengths more clearly

• Creating secure attachment

Your goal is to help each team member see themselves as a leader—of their role, their work, their impact. Coach from curiosity, not control.

TIPS FOR HIGH IMPACT 1:1s

• Block time to prep: review notes, reflect on feedback themes

• Track takeaways: use a shared doc to capture goals, feedback, follow-ups

• Don’t skip the human connection: people want to feel seen, not just “checked in on”

Honor differences: not everyone opens up the same way. Build safety first. (Refer to their “user guide” once in a while to see how they like to communicate and give/receive feedback.

Prompts for your own reflection.

1. What do I stand to gain if I can empower my direct reports to become leaders? What do they stand to gain?

2. What are some of the ways I can evolve from being a manager into a coach in my 1:1’s?

3. What’s one takeaway I want to implement in how I run my 1:1’s?

• You’re invited! Join me at Sana Sana Social’s July 30th gathering (aka tomorrow!) where I’ll be giving a talk on burnout, bravery and living in alignment.

• 1:1 Coaching: I help founders fall in love with building their companies again. If that sounds like something you need, you can book a free coaching consultation.

• Ask a Founder Coach: Got a question about team building? Drop it here and I may answer it in a future newsletter.

• Let’s be friends: If you want to see more of the BTS of building Within and receive more tips and ideas on building with integrity, connect with me on LinkedIn and Instagram.

• Finally, tell me how you liked this newsletter. I read every piece of feedback.

Thanks for reading today’s newsletter.

With love,
Roslyn 💚