How to Align your Team on Strategy

👋 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,

Hope you’re having a beautiful summer.

These next two July weekends I’m so lucky to be visiting friends who have places in the Hamptons. As much as I’m obsessed with New York, getting out of the city and into nature is so grounding and energizing.

Plus, getting to spend time out there is very expansive for me since my husband and I are manifesting a place of our own out east at some point (which, honestly, feels a little vulnerable to share, but here we are!).

Today we’re on our third team building newsletter. After talking hiring and onboarding, this week we’re covering how to align your team on strategy.

We’ll talk about:

• How to flow mission, vision, and values into strategy and execution

• How to translate your strategy into your team’s everyday work through OKR’s and regular check-ins

• How to teach your team how to get stuff done and create feedback loops for reflection and iteration

Bonus:  Scroll down to the ‘Highly Recommend’ section for my summer book recommendations, because rest and relaxation are key to sustainable success.

Also… you’re invited!

To a talk I'm giving on burnout, bravery and alignment, in NYC on July 30th.

In last week’s newsletter, I opened up about how I’m facing my fear of being seen in order to grow my impact at Within. So, this is me going for it before I feel ready, fears, imperfections and all.

I’ll be sharing my honest story about founder burnout, walking away from success that no longer fit for me, and the messy journey of building a life that feels truly aligned.

If you’re in the city, I’d love for you to join! Grab a ticket here.

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

HOW TO ALIGN YOUR TEAM ON STRATEGY

Scaling a startup isn’t just about having the right strategy. 

As a founder, it’s your responsibility to also make sure every person on your team understands:

• Where you’re going

• How their work connects to it, and 

• How they can move forward with clarity, autonomy, and accountability

When I was transitioning from a doer into a leader at my last startup, The GIST, one of the most important learnings for me was how to create a structure to support my team’s advancement of our strategy. 

So that their time was being spent on the most important priorities, in the most efficient ways. So that they were receiving the support they needed if they ran into roadblocks and were continuously learning and getting better.

Based on my own operating experience, the work I do with my clients, and my research in this area, I’ve compiled my five steps to creating alignment that’s not just strategic, but energizing and empowering.

1. START FROM THE TOP: MISSION, VISION, AND VALUES

Your mission, vision, and values are the foundation. Don’t just stick them on a slide—operationalize them.

• Introduce them early and often (especially during onboarding).

• Use them to guide decision-making, performance reviews, and how you celebrate wins.

• Reinforce them at all levels—from company strategy to how you give feedback.

When your team knows why they’re here and how you do things, they can act with clarity even in the face of ambiguity.

2. CONNECT STRATEGY TO EVERYDAY WORK

Strategic alignment doesn’t happen by accident. It takes intentionality to ensure it flows down through the organization.

The cascade:

• Company strategy → annual focus areas and directional bets

• Quarterly milestones → break strategy into measurable priorities

• Team OKRs (Objectives & Key Results) → clarify how each function supports those priorities 

• Projects & tasks → owned by individuals and executed week to week. These ladder up to OKR’s.

Use an OKR tracker to illustrate:

• What are the quarterly objectives (O)

• How are those objectives being measured (Key Results = KRs)

• Who owns that key result 

• What’s the status of the key result (on track, complete or at risk)

• Any notes on progress 

This makes measurement and ownership of the objectives that ladder up to strategy abundantly clear. 

Every team member should be able to answer: “What’s the company focused on, and how does my work contribute to that?”

Feel free to make a copy and adapt this OKR Tracker Template for your own company.

3. BUILD A CADENCE OF CLARITY

A predictable rhythm of check-ins ensures strategy doesn’t sit in a document, it lives in your culture and stays fresh in your team’s mind.

By empowering your team with a big picture understanding, it creates more opportunity for autonomy and emphasizes impact rather than how things get done.

Here’s my recommended cadence:

• Quarterly Strategy Meetings (Full Team):

  • Zoom out. Reconnect to mission, reflect on progress, reset OKRs, and align cross-functionally.

• Monthly Team Reviews:

  • Department-level. What’s working? What’s stuck? How will we integrate learnings next month? What do we need from other teams?

• Weekly Prioritization (1:1s or Team Standups):

  • Align on top priorities and remove roadblocks.

• Async Weekly Update (Optional):

  • A Friday Slack check-in or Notion post that asks:

    • What did I accomplish?

    • What’s next week’s priority?

    • Where do I need support?

    • Who do I want to acknowledge or thank?

Feel free to use these Team Meeting Agenda Templates and adapt them for your company.

4. TEACH HOW THINGS GET DONE

A big part of strategy execution isn’t what gets done, it’s how it happens. 

That’s why creating clarity around process, ownership, and decision-making is so important.

• Document “how we work” (e.g., how we scope projects, run meetings, or make decisions).

• Use guardrails to empower autonomy without micromanagement.

  • (e.g., “You can make any decision under $1k or that doesn’t affect another team.”)

• Coach instead of control. Guide your team on the why and the outcome, but let them find their own best how.

• Encourage experimentation and learning—progress beats perfection.

5. KEEP FEEDBACK AND TRANSPARENCY FLOWING

A team that’s learning and integrating feedback is a team that can grow their impact over time.

• Encourage regular feedback loops across functions.

  • Bonus: check your team’s user guides for how they like to receive feedback.

• Normalize reflection and iteration. (“What did we learn? What would we do differently?”)

  • Frame mistakes and failures as opportunities to learn and improve.

• Make room for courageous conversations, not just execution.

• As the leader, normalize that it’s okay to say “I don’t know, but let’s figure it out together”.

Alignment isn’t about control. It’s about clarity, trust, and continuous course-correction.

What’s one takeaway you have from this deep dive that you’d like to try implementing this week?

Have a question about team building? Drop it here and I may respond in a future newsletter.

FOR YOUR SUMMER READING LIST

When I went through founder burnout two years ago, the thought of reading anything other than easy, entertaining fiction felt exhausting to me (no thank you business or self-help books).

So today I’m sharing a few of my faves for all of your summer beach read needs. Or for taking a 15-minute nervous system break during your workday!

Because remember, not everything you read needs to be “productive”. You’re allowed to read something for the pure pleasure, escape and relaxation of it all.

I’ve said it many times and I’ll say it again: Rest is a key ingredient to sustainable success.

FAVES

• Romantic Comedy: Anything by Emily Henry. If you’re looking for fun, emotionally layered romantic comedies, look no farther than Great Big Beautiful Life, Book Lovers, People We Meet on Vacation or Beach Read. Her female protagonists are witty, relatable women who find themselves in enemies-to-lovers or friends-to-lovers dynamics that make for the steamiest romances.

• Murder Mystery: Louise Penny’s Inspector Gamache series is made up of beautifully written, deeply human mysteries set in the fictional Quebecois village of Three Pines. She blends the charm of classic whodunits with profound philosophical and emotional depth — I kid you not, Inspector Gamache is a personal role model to me because of how honorable, emotionally intelligent and courageous he is. If you’re someone that likes to binge books there are 20 currently out so you’re all set for a while lol.

• Drama: Any Liane Moriarty book. They are smart, emotionally insightful, often page-turning dramas that get into the messy realities of marriage, motherhood, friendship and secrets. Also if, like me, you’re someone that likes seeing your favorite books adapted for TV, you can watch Big Little Lies (my favorite), Nine Perfect Strangers, Apples Never Fall and The Last Anniversary.

• Romantic Fantasy: After reading all of Sarah J. Maas’ books (she has 3 series and is best known for A Court of Roses and Thorns), I can confidently say her Throne of Glass series was my favorite. It’s an epic fantasy saga filled with magic, romance, evil and rebellion — centered around a fierce heroine who evolves from broken survivor into a powerful queen.

• A close second for me in this category was Rebecca Yarros’ The Empyrean (often referred to as Fourth Wing, the name of the first book) which is a fast-paced fantasy that blends romance with dragons (lol) on the backdrop of a cutthroat war college. Fourth Wing is getting adapted to screen too this year. I cannot wait. 

HONORABLE MENTIONS

• Dune by Frank Herbert, a sci-fi classic. Side note, I think reading this book made the movie way more understandable and enjoyable than it otherwise would’ve been.

• Elin Hilderbrand books, including “The Perfect Couple” which was adapted by Netflix, for easy beach reads.

• Anything Taylor Jenkins Reid for fun and entertaining (Carrie Soto is Back is a great one for tennis season!).

• Pineapple Street by Jenny Jackson was fun and easy and I especially liked it because it was set in my neighbourhood (Brooklyn Heights)! 

• Carola Lovering. I quite liked her books, which I would categorize as psychological dramas (even though the Tell Me Lies adaptation was admittedly weird). My fave was Too Good to be True.

What would you add to this list? Reply and LMK. 😊

• You’re invited! Join me at Sana Sana Social’s July 30th gathering 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’re interested in, 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 being here! It means the world to me.

With love,
Roslyn 💚